Amazingly, in 2008, not even that long ago, Myspace was the top social network platform. While Facebook was rapidly making progress, Twitter was still in its early days, and Instagram, Snapchat and TikTok were still just gleams in the eyes of their founders, Myspace was the place to go.

So what happened?

Like any story, it’s complex. But one key issue was a lack of product focus. Myspace didn’t know what it wanted to be. You can see that in the image above. Was it a place for friends? A place for music? A place for games or videos? It ended up being a place for everything, and it did none of it well.

Myspace didn’t have an obvious idea of what it wanted to be or accomplish, and could never decide on the best way to get there. That’s not surprising. If you don’t know where you’re going, it’s hard to figure out the best path. And within a few years, Facebook dominated social media. Which should never have happened. When you have an existing network, maintaining it should be the simple part. But they weren’t able to do that.

And the rest is history.

So how can we avoid becoming Myspace? The secret (or not-so-secret) ingredient is to define clearly what you are trying to do — within your company and within your product. Myspace didn’t fail for lack of experimenting, but for lack of clearly defining what they needed to do to be successful and then executing well on those things.

A great tool for avoiding this issue is OKRs. I’ve used OKRs in almost every team I’ve been in. There isn’t anything magical about an OKR itself, but the principles and the process make them extremely successful. So let’s take a closer look.

A Little OKR History
For those unfamiliar, OKR stands for Objective and Key Result. The objective is a high-level, aspirational goal you are trying to achieve, and the key results are how you are going to measure your success. That’s it. They are meant to be collaborative, open, and transparent. They are also meant to push you, your team, and your organization. So they’re not necessarily a good fit for every situation, but more on that soon.

We consider Andy Grove the father of the OKR. He created them at Intel in response to the more limited goal management styles that existed at the time, such as MBOs (management by objective) and KPIs (key performance indicators).

MBOs were centrally planned and trickled down the hierarchy. Unfortunately, that may still sound familiar. And Grove considered KPIs numbers without a soul. While we still like KPIs in the right context, you can’t push yourself with KPIs alone.

Why use OKRs?
If you read Measure What Matters, you’ll become familiar with the four OKR superpowers: focus, align, track, and stretch.

Focus
The most important feature of an OKR is that it allows you to focus on the most important work. It explicitly calls out what you are focusing on, and by its nature, what you are not focusing on.

This is powerful for teams and organizations. You shouldn’t have a laundry list of OKRs. Just like you can’t prioritize every product feature as the most important, you can’t prioritize every initiative or every goal as the most important. You need to focus.
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Steve Jobs famously said, “innovation means saying no to one thousand things.” And he meant it. When he returned to Apple from his time in the wilderness, he cut their product line down significantly. He focused the company so they could deliver fewer things, but better products as shown below.

This became very salient for one of my teams. We had a long list of priorities and had been reordering it for a while. As I introduced the OKR framework, I asked the team to focus on one thing. What was the most important thing to accomplish? It was a change in thinking for many. They were used to changing priorities according to the loudest voice, which would happen every few weeks. We eventually agreed on a key outcome to focus on for the quarter. We’d prioritize all the work around that and deliver.

It was difficult in the beginning. I had to remind everyone of our focus, both on the team and outside. But the outcomes were outstanding. Rather than incremental changes over long periods of time, we delivered meaningful change in a quarter. Once the broader organization saw what that kind of focus could do, it wasn’t so hard to sell everyone on the idea from then on.

Align
OKRs are a tool for empowerment and alignment across a team and organization. Remember the MBOs above? Executives would create objectives and hand them down to employees, who would then be accountable for parts of them. You can probably see multiple problems with that.

OKRs are a top-down and bottom-up process. Yes, executives and leaders should have OKRs if your company is using them. And you should be able to see their OKRs. You and your team should also have OKRs, and everyone should see them as well. The purpose is to allow everyone to see what everyone else is working on so we can align up and down and laterally.

We talk a lot about the up and down part, but not nearly enough about the lateral alignment. If other product teams have OKRs or goals that impact my group (or vice versa), it’s important we’re aware! Or if marketing or sales have specific objectives that are going to take some work from product and engineering, we should probably collaborate on that!

If this sounds like a messy process, you’re right. It is highly collaborative and hands-on. Teams will often spend lots of time working on their goals and objectives, but we need to spend a meaningful amount of time working across groups to align on goals and results.

Track
If you’ve ever been part of an annual planning process, you’re probably familiar with the weeks or months that go into putting together detailed plans, the meetings and discussions and presentations, and the agonizing over budgets and details. And after it’s all done, everyone quietly puts those plans away for the year until it’s time to revisit them next year.

That’s not how OKRs work. It’s probably not how annual planning is meant to work either. We use OKRs to track our progress continuously. And to hold us accountable.

I use a Fitbit along with some other health tracking apps. I like to monitor my progress and set goals for myself. I check in regularly with my progress so I can course correct (most often) or celebrate (less often).

The same idea applies to OKRs. If you set an OKR at the beginning of a quarter and check in at the end of the quarter, you’ve done it wrong. It’s a good start, but by that time there is nothing you can do. The tracking is best done weekly, checking your progress so you can make actual corrections and take action to achieve your goals by the end of the quarter (or time period). Hopefully, it will also give you a reason to celebrate throughout the quarter.

Stretch
Finally, we use OKRs to stretch. Don’t use an OKR for something like “keep satisfaction above 90%”. If you’re happy with where you are, that’s not a place for an OKR (more on that later). OKRs should push us, our teams, and our companies to higher heights. If it’s easy, and not without a chance of failure, we’re not stretching enough and it’s not an OKR.

I recall an OKR meeting we had where one team laid out their proposed OKRs for the quarter. They sounded reasonable, but nothing about them seemed out of reach. We were still early in the OKR process, and it sounded like the team had taken the work they had planned to do, put it into an OKR format, and was content.

It’s not enough to set OKRs for what we know we can do. We need to push ourselves, our teams, and our organizations.

Who should use OKRs?
You should. Your team should. Your organization should.

Every product team I’ve come into hasn’t been using OKRs. Neither has the organization. But you don’t need the entire company to start. I’ve always started with my product teams and product organizations, and the company has come along after.

You should start using OKRs wherever you are. If that means starting with yourself, great. What do you want to accomplish? How will you know when you’re successful?

If you’re a product manager, create OKRs with your product team. One of the biggest changes I’ve made on every product team (and product organization) is to incorporate OKRs into the process. What do we want to accomplish as a group? How will we know we’re successful? How will that help our company and how can we show it? This will change the conversation for you and your team. It elevates the discussion from the features you’re building to the outcomes you’re driving. And the glorious thing is that you don’t need anyone else to even be using OKRs. Others will see your success and want to adopt them, but you can start right now.

Your company should also use OKRs. This one may be out of your control if your company isn’t currently using OKRs, but I’ve helped organizations start using OKRs after introducing them to my teams. And I’ve pushed for them in other places, even when they haven’t been implemented.

OKRs may not be the end-all, be-all solution, but they are powerful tools for individuals, teams and companies. And in every situation I’ve seen, groups will be better off using them than not.

When to use OKRs?I always start with annual OKRs, or at least annual strategic initiatives and objectives for my teams or organizations or products. It helps me think about the bigger picture of what I’m trying to accomplish and what success will look like as we build up over the course of the year. That’s not to say that I’m married to any specific plan, but it helps to visualize where we’re going. I also tie them up to company level goals or initiatives to ensure that I’m aligned with where my company is going and what we’re focused on.
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From there, I break down quarterly objectives and key results. Quarterly OKRs are pretty standard, since it is a long enough timeframe to get work done, but also short enough to make course corrections as needed.

Besides annual and quarterly OKRs, it makes sense to focus OKRs on product areas that will benefit the most. I’ve alluded to this above, but not every product or initiative will benefit equally from an OKR.
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In a discussion at a conference, Christina Wodtke gave a splendid example of when to use OKRs based on types of products and where they fit into a BCG matrix. For high growth products, it makes sense to use OKRs to push yourself further with them. But for products that are in maintenance mode, either because you are sun-setting them (dogs) or because they are simply cash cows and you are going to continue to let them do their thing but you don’t expect to grow them, the better course is to monitor them with KPIs.

​How to use OKRs?
Shift To Outcomes
Rather than starting with what you want to do, start with what you want to accomplish. Stop talking about features and start talking about outcomes.

On my teams, I always try to shift the conversation away from features to the outcomes we want to achieve. Features are the means by which we get there, but a feature may be effective or it may not. We can’t be married to any particular feature. We have to love the problem and the goal, and find a way to achieve it. We also need the flexibility and the space to achieve that goal.

This can be a mindset shift for many organizations. I refer to it as product thinking or a product mindset. And it can often take time. Many companies are more accustomed to focusing on a list of features or projects for each team. And possibly setting goals based on that. But that is backwards.

I’ve gone through this many times with teams. You may be familiar with it as well. If you start with features or projects, you’re coming at it backwards. You need to start with the objectives. Start with the OKRs!

Quarterly OKRs
Once you’ve shifted to an OKR style of planning, you must actually implement it. Quarterly OKRs are the most common. If the entire company is starting, it will usually start with leadership teams or department heads and move down. If you are starting with your group, well, it starts with you!

Don’t expect it to be easy or smooth. OKRs are difficult and take time. You need to put in time and thought before, and then expect debate and discussion. You should set aside several hours initially for all of this. If you have a large group with lots of OKRs, you may need more. Don’t skip past the discussion and debate. It’s important in shaping the best OKRs. You want to create good goals and good measurements that you and your team can get behind, so take the time to do it right.

Regular Cadence
In her book, Radical Focus, Christina Wodtke gave the simple matrix below to show how to implement OKRs effectively into your weekly cadence.

Each Monday you should review your OKRs (the fewer, the better) and how things are progressing. You should check in on your priorities for the week in order to achieve your goals with your objective, and anything you need to do in the next month. And your health check are the KPIs or metrics that you don’t want to let slip as you reach toward your bigger goals.

The key is to make the check-in part of your weekly cadence. Start Monday with what needs to be done and end Friday with how things went. It is critical to success, and harder than it seems.

​Common OKR mistakes
Too many OKRs or key results
I recall one leadership meeting I narrowed my OKRs down to three. I had more critical things I wanted to focus on, but more than that would be too many things to focus on in my opinion.

OKRs were new to the company though, and not everyone shared my opinion. So some leaders came in with eight or nine OKRs. And we debated. Everything they had on their list was important. And I left some important things off of mine. Who was right?

I didn’t budge. I knew if I added more than three objectives I’d take too much focus away from what was important. And I wanted my team to focus. Fortunately, we agreed focus was more important than including everything, though I still think that some lists remained too long.

If you have too many objectives or key results, you can’t focus on what is important. The fewer objectives and key results you have, the better you focus on what is important. The more you and your team can rally around the goal. And you can more easily say no to things that distract you from your mission.

If everything is an OKR, nothing is.

Tasks as key results
Another mistake I’ve seen frequently is making your task list into your key results.

For me, this results from having an output as an objective rather than an outcome. In one example, the objective was something like “replace all the old phones”. Then the key results were a list of milestones like “order new phones”, “replace phones in area one”, “replace phones in area two”, etc.

Your OKR shouldn’t be a task list. It shouldn’t be a maintenance item. OKRs are about driving meaningful change for your business and your users. Why are you replacing phones? What impact should it have? How can you measure it? And if you don’t have a good way of measuring it, should you find one? Lots of areas need better measurements, and OKRs can be a good way of shedding light on that. And if that’s not the case, should you be using an OKR here at all?

Never reviewing
It’s so easy to set goals and never review them. We create a plan and then never revisit it. We simply hope for the best.

OKRs are meant to help us track our progress. And not just quarter to quarter, though that is an improvement over the annual planning process. We should track progress continually. We talked about it above. Including OKRs in our weekly planning process is critical to their success.

I’ve found the most success including OKR status checks into existing team meetings. If you are part of a scrum team, you likely have bi-weekly meetings at the beginning and ending of sprints. Those are excellent times to review sprint goals and OKR statuses.

If you are part of a larger team, you probably have some weekly meeting or bi-weekly (fortnightly) meeting. Add OKR status reviews to those meetings. Check progress and see how things are going.

Trying to copy XYZ company
No two companies are the same. I’ve used OKRs at multiple companies now and every company does them differently. Google does them in Google’s own style. You don’t need to be Google. Be your own company. Find your rhythm.

You will flounder for a bit. But you will find the style unique to your organization. Learn from the books and articles and things that others have done. Learn from others who have used OKRs in other places. And then take all of that and don’t feel bad for not being perfect. That’s not to say you shouldn’t try to be good at OKRs or use good principles, but you don’t need to be Google or Intel.

OKRs aren’t a silver bullet, but they are a great tool to empower teams and change the mindset of your organization. Rather than focusing on features, they help you focus on the outcomes you want to achieve, and empower the groups and organizations to achieve those outcomes. They take some practice, and will require giving up some centralized control, but the results will be better outcomes for your business, your users, and your employees.

In The Hitchhiker’s Guide to the Galaxy, one of the strangest and arguably coolest phenomenons is the Babel fish. It is a small, yellow fish you place in your ear that feeds on your unconscious mental frequencies. In return, it then excretes back into your mind a telepathic matrix from the conscious thought frequencies and the speech centers of the brain. Basically, all of this allows you to understand instantly anything said to you in any language. Which comes in handy when traveling the universe and encountering many civilizations speaking unfamiliar languages.

While we’re not necessarily traveling across the galaxy or running from Vogons, our businesses still need the equivalent of this translation and coordination: a mechanism to ensure that all the various groups and disciplines within our organization are speaking and understanding each other. And that we are hearing and understanding the outside voices of our users, customers and industry.

That is the essence of product management. To ensure understanding across groups. To coordinate. To solve real problems.

How do we accomplish this? How do we gain this understanding, coordinate, and translate across teams and across our company? Product managers do this by focusing on 5 key areas:

1. Discovery & Research
2. Strategy & Roadmaps
3. Partnership & Communication
4. Prioritization & Tradeoffs
5. Delivery, Launch & Go-To-Market

Discovery & Research
Product management begins with understanding. And that is what product discovery and research are — the ongoing practice of understanding user needs, business needs, and market trends to decide what to build.

For a brief history, back when software was still being packaged into CDs or DVDs and being shipped to stores, product discovery and research looked very different. Much of the research and discovery was done upfront out of necessity. If you were a product manager, you had to figure out what would get built and go onto the DVD before it shipped.

Unfortunately, many of these practices have never gone away, even though we don’t package most software into a box any more. The idea of gathering long lists of requirements up front, passing them to engineering teams, building large projects, and then hoping that it all works out once it gets to customers.

Good product managers should not be gathering long lists of requirements for modern software, though. Or passing lists off to development teams. Or waiting for feedback from users. The miracle of modern software is that all of this can and should be done in the shortest increments possible. We should work constantly on understanding users, our business, and our markets, continuously adding to our dataset to make better decisions. We should work closely with our development teams so we all have a shared understanding, rather than “toss over the wall” lists of specs. And we should get regular feedback from users and stakeholders. Monthly, weekly, daily. As frequently as you can so you can add that knowledge to the dataset you’re building.

Discovery and research may often feel like it is easy to put to the side. As I’ve worked with a variety of product teams, I’ve seen how easy it is to dedicate far more time to execution and delivery than to research and discovery. Often product managers will look at their impossibly busy schedules and feel forced to make that tradeoff. Getting things out the door always feels more urgent than building an understanding of markets and users. But that is trading the long-term for the short-term. The best product teams and product managers find the right balance, investing in the future while delivering in the present.

For a deeper dive, see my upcoming article Product Discovery: The Beginning of Good Product Development.

Strategy & Roadmaps
Once product managers have done discovery and research, understanding their users, their business and their industry, their role is to set the strategy and roadmap for their product.

Strategy
The product strategy should align with the higher product vision of the product organization. We won’t get too much into that here, but this vision should be compelling and long-term (think 3–5 years). And the strategy of each product should support it. Your product strategy also needs to align with broader business goals and strategy.

As a product manager, it is your job to set the product strategy for your product, together with your product leadership. We’ll talk more about this below, but you shouldn’t be looking to executives or stakeholders to do this for you. You will need their input, and depending on your company, you may have to balance stronger opinions with your own, but working with your product leader you should create the strategy.

Think of the strategy as a way of achieving the vision, so 1–2 years in horizon. It is fundamentally about how you’re going to achieve the goal of your product, whether that is 10Xing the business or doubling revenue.

One of my favorite tools to solidify the strategy for a product is to use a future press release. This is a tool made popular by Amazon and written about by many others. I’ve used it myself with splendid success. More on that in another article to come soon.

Roadmap
From the strategy, you should create a strategic roadmap, which tells the story of how and why you are working toward the long-term strategy of your product.

Roadmaps are not feature lists. They discuss ideas and direction, so features may be part of that, but the focus should be on the outcomes you’re trying to achieve and how the features may get you there, not on a list of features. Roadmaps also are not timelines or project plans. They are meant to give the direction, but we’re not ready to commit to specific dates or items because we’re determining what will get us to our strategic outcomes.

So if that’s the case, what should be the focus? Roadmaps should be about inspiring participants, communicating the strategy, generating discussion and gaining alignment. The focus should be on the outcome you’re trying to achieve with your product, how you intend to get there, and why that’s important.

For more thoughts on roadmaps, you can see my article on Product Roadmaps: Love, Hate (& Hate).

Partnership & Communication
Product managers are essential in partnerships and communication across an organization.

Communication is literally one of the top traits of a good product manager, so this should be no surprise that it is a key role. But product managers are uniquely positioned to facilitate partnerships and communication both within a department, a company, and outside an organization.

First, the very nature of the role is one of coordination within a product development team and across stakeholders and customers. So you should be building relationships and communicating relentlessly. This starts with your vision, strategy and roadmap, as we discussed above, and continues with prioritization, tradeoffs and delivery as we’ll discuss below.

Second, your role is to create the best product experience for your users and to deliver value through that for your business. You can’t do that alone. You literally need your users and your business partners as part of that equation. So partnering with them, building the relationships you need, and communicating frequently are all critical parts of the role of product managers.

Finally, you need to be an excellent partner and listener. It’s not enough to go out and evangelize your product. You also need to hear and understand your users and stakeholders. That’s the other side of partnership and communication. Don’t forget it.

Prioritization & Tradeoffs
One of the most troublesome parts of product management is prioritization. Frankly, it’s one of the most troublesome parts of life. Because we often have to choose between many good options and make tradeoffs with incomplete information. But it is a critical part of the role.

Prioritization is much more than just choosing the order of the backlog though, or what feature to work on first, though those are important aspects. For a deeper dive, see my article Prioritization: Choosing is the Hardest Part.

At a high level, prioritization comprises:

1. Establishing a vision and strategy
2. Understanding the context
3. Gathering inputs (qualitative and quantitative)
4. Ranking your priorities using any number of frameworks and gut checking your assumptions
5. Deciding on priority
6. Aligning and realigning

Like I said, prioritizing features on your roadmap is only one part of the bigger picture. There are a number of frameworks and methods for doing that, all of which have good attributes, so it will often depend on your company and context which will work best. I’ve used many as a product manager and product leader, and as long as you don’t outsource your prioritization to a framework since that doesn’t work, you’ll be fine. Remember, they are tools, not solutions.

Also, you are responsible for gathering the inputs and translating that to action. Stakeholders from marketing will have one perspective. The engineering department will have another. Sales will have yet another. None of them are wrong and all will be urgent and important. Everyone will need to understand the inputs, the framework for deciding, and why we’re prioritizing the way we are (see communication above). It will not be easy. Hopefully, you didn’t think it would be.

Delivery, Launch & Go-To-Market
Finally, everything above will be for naught if you don’t get your product to market and into the hands of users.

Depending on your company, delivery, launch and go-to-market may fall squarely on the shoulders of the product manager. Or it may be a shared responsibility with other groups like project managers or product marketers or sales or other groups. Regardless, it is your product, and you need to get it to your users. So it is your responsibility, no matter who else is helping or sharing in the burden.

After so much work to do discovery and research, create a compelling strategy and vision, partner with stakeholders and users, and make the necessary tradeoffs, it is almost tragic how often I’ve seen teams falter at the finish line. Don’t drop the baton at launch! Make sure you put as much time in preparing a successful launch and go-to-market strategy as you have put in preparing a great product or feature.

I’ve learned this lesson the hard way myself. Several years ago, as we created a new experience in a product we were building, we were incredibly excited about how much more intuitive it was and how great it would be for users. But when we launched it, it fell flat. We had failed to involve our support team and our training teams (we thought we wouldn’t need them since it was so good), but our users were not prepared for any changes. So we had to step back, get training in place, and then move forward again. What should have been a big step forward was delayed because we faltered with our launch strategy. I didn’t let that happen ever again.

While not exactly Babel fish (and we’ll leave the theological arguments aside, and whether product managers will eventually cause more wars than anything in the history of creation — see The Guide for more), product managers are the key to unlocking and translating real problems into real opportunities for our businesses and our users.

According to Captain Kirk, “Intuition, however illogical, is recognized as a command prerogative.” Would Spock call that illogical? Maybe. But that is part of what made Kirk and Spock such a great duo throughout the Star Trek series and movies. There is logic and emotion tied to what they do, with both of them representing either side, sometimes to an extreme, and other times surprising us.

But that is often what they needed to make their missions successful. Quick, emotional decisions vs. deliberate, thoughtful action. The push and pull.

Product managers and UX designers make up two of the three key members of a product team leadership trifecta (the other member being a technical lead). Most times, the overlap between the UX designer and the product manager will be significantly higher than with the technical lead or engineer, so finding the right balance in the relationship is critical. We talk about this in a recent podcast episode you can find here.

With that in mind, what can we do to better support each other, deal with issues, and ultimately build the best products and user experiences for our businesses and our customers? How can we create the right push and pull?

The Ideal Structure
Ideally each product, user experience, or vertical (depending on the size and focus) would have a dedicated product manager and UX designer. For larger companies or products, we could break this down to smaller components where product managers and UX designers focus on large features within the product, but the concept is the same.

This allows the right level of focus on identifying the right problems to solve, the right ways to solve them, and the right business opportunities to pursue from a product perspective.

Dealing With Less-Than-Perfect Scenarios
Unfortunately, we have to play with the cards we’re dealt. And often we don’t get to have a dedicated product manager or UX designer for every opportunity, customer journey, or even product.

You’ve probably been there. You may be there right now. As a product manager, you may not have a dedicated UX designer for your team. I’ve experienced that scenario throughout my career as organizations are usually slower to adopt user experience design as a formal practice. Even now as I’m building up the UX team at our company, we have more product managers than designers and likely will for a while.

Here, it’s critical for product managers, and everyone on the product team, to step up and own as much of the UX as possible, filling in gaps and extending the abilities of the designers wherever possible. The ultimate goal is to infuse design thinking into everything we do, so this is a step along the way, albeit without all the necessary support, but since we’re designing a user experience regardless of whether it’s intentional, we might as well be thoughtful and deliberate about it.

In an even more extreme scenario, a team may not have a dedicated product manager or product designer. While someone will fill those roles, it is critical to the success of the product, the success of the user, and the success of the company to dedicate the right mind share and the right people to those tasks. Product management and UX design are not part-time jobs for anyone. Helping leaders see that and understand the value so we can move toward more ideal scenarios is key.

Combining Forces
Regardless of the structure, whether ideal or less-than-ideal, the best user experiences and business value come from combining forces. Like joining our powers and using our planeteer rings to summon Captain Planet (you’ll have to look it up if you missed the Captain Planet cartoons of the early 90s), we can create incredible things through a focused, joint effort.

Generally, product managers bring expertise in valuation, prioritization, and business process. Product managers should be well-versed in all aspects of their product, their industry, their users, and their business, but most product managers are especially adept at wrangling the business and user problems and finding solutions and value. It’s the core of product management and why many of them are doing what they are doing.

UX designers bring a different, and much needed, perspective to product development. By focusing more on the user experience, they ensure that the product isn’t just solving a problem, but is doing it in a desirable way. UX designers come into the craft from a variety of backgrounds, but their focus on the overarching user experience, the interaction, the visual design, makes the product not only functional, but appealing.

None of this is to say that product managers don’t want appealing products or that UX designers aren’t focused on business needs, but product managers and UX designers tend to have differing areas of expertise, slightly different focuses, and different perspectives.

This push and pull within the product makes it great. If you focused solely on making a product valuable to the business, it may be profitable but it would likely be a terrible product. And if you focused solely on making a product visually appealing and a great experience for users, it would be an excellent product, but may not be valuable at all for the business. So we need to combine forces, find the balance, and create the right dynamic to create excellent experiences.

Better Collaboration
UX Designers Supporting Product Managers
How can UX designers better support product managers? We all operate under significant constraints. Almost no product manager wants to go to market with a crappy product or a crappy UX, but often there are tradeoffs that they are considering within the business, for stakeholders, and for users. So understanding those constraints is useful in better supporting product managers as a UX designer.

Product managers are often under technical, business, and time constraints, among many others. And while none of those are excuses to cut corners, we often have to made a tradeoff in one place to gain ground in another, at least for a time. Without the full picture, that may appear equivalent to shoddy work, but context is key, which is why understanding the scope and building trust is paramount.

When I was working as a product manager on a key product for our company, we fortunately had a UX designer that embodied these ideas. She understood the business and its needs. She had a good grasp of the technology. And she understood many of the time limitations we were often under. So when I came to her on a particular urgent request, we didn’t have to do the rounds. She was able to help the development team with designs and user flows that satisfied an urgent business need that they got to work on quickly.

Product Managers Supporting UX Designers
For product managers, you need to trust your UX designers. Trust that they have good reason for the choices they are making and have the data and research to back it up.

Product managers are naturally very opinionated, especially about their products. Whether it is the language on a page or the placement of a button, the PM will have an opinion. But a talented designer will do you one better. She will have the research to tell you why the language should be a certain way or the button placement should be in a certain location.

Feel free to ask and to verify. But do it in the spirit of trust and collaboration.
A few years ago I was working with a team who was debating the question of button placement. The PM felt it should be in one location based on their experience even though the designs had it in a different spot. So the designer did some usability testing and found that the button placement performed best as he had designed it.

Definitely question. Definitely test. But have trust.

Keys to Success
When it comes to successfully working together, the best product managers and UX designers in my experience have all done a few things that have made a massive difference for their interaction and their teams.

Define Your Roles
When working together, especially as a product manager and product designer, it is critical to define your roles and your interaction. Have a conversation about how you will work together, what you will focus on, how you will interact, etc. How you work together will be critical for your team’s success, so take some time to figure it out. Everyone is different and every relationship will be different with different strengths and different needs.

As a product manager, I loved design and spent significant time on mockups, prototypes, etc. Partly out of necessity because there was more work and not enough designers, and partly because it was an area of interest for me. That was a discussion I had regularly with the designers I worked with. Other product managers don’t focus as heavily on those things, so having that understanding is important. Some designers are far more technical and venture further into the realm of product management, wanting to understand the business and technical aspects of products more than other designers, who focus more heavily on visual or interaction design. Neither is right nor wrong, but having a shared understanding of this is important.

Collaborate Constantly
Once you’ve defined your roles, you need to collaborate constantly. You should meet together regularly to calibrate and ensure that you are staying in sync.

Ideally the product manager and UX designer will work in lockstep. But like I mentioned above, the circumstances won’t be ideal. So you need consistent communication.

As a product manager/UX designer duo, how often are you meeting together? And I don’t mean how many meetings are you in together. How frequently are you actually sitting down and meeting one-on-one to discuss your products, work in progress, upcoming priorities, etc? The most successful interactions I’ve had were when I was doing this regularly with my UX counterparts.

Evolve Together
Finally, allow yourselves room to evolve together. Just as you will iterate on your product, iterate on your relationship and your roles. Things will change, and you will need to change as well.

That is why the first two keys are so important. Once you’ve created a shared understanding of your roles and are communicating frequently, you will be able to change and evolve as needed, both for your product and for your business.

Early in my career, I was working with a designer on a few small products for our company. I wanted to get more into design, but the organization had a pretty strict process for everything. However, we both realized that we wouldn’t get much done if we followed that process and that we wouldn’t learn much either. So we found the areas we could flex the rules a bit, and as our business needs changed, we could help move things along as well. It became an incredibly productive partnership as we both learned and evolved.

Product managers and UX designers aren’t Kirks or Spocks in my experience. We all bring some level of emotion and some level of logic. But it is that push and pull that creates the right dynamic for success.

By working together as a team, a product manager and UX designer can combine forces to create the best product and best experience for users and their business. The circumstances will never be ideal, but by defining your roles, collaborating and evolving together, you can create the magic that will make world-class products.

2020 is off to a raucous start. I don’t think any of us would have predicted things to play out quite this way. Even when I wrote about the shift to remote work a few months ago, I didn’t think the need for all of us to move quickly to remote work would happen so fast. But here we are.

As social distancing becomes the norm and teams, organizations, and entire companies move quickly to remote work, there are several things we can all do to smooth the transition and make it seamless for our teams, customers, roommates and family members. While I mean this to be helpful during the quick transition to remote work, the same principles apply for any transition to remote work.

Individuals
As individuals, there are several steps we can take to stay productive, keep things moving along for ourselves and our businesses, and help everyone around us keep their sanity.

Define Boundaries
Physical. Defining some physical boundaries will make the transition to remote work easier for you and roommates/family.

For those of us fortunate to have dedicated offices or work spaces, this is easier. But even with a dedicated office, you may need to redefine the physical boundaries now that you’ll be home more often. I know that my office gets used frequently for building marble mazes and other games, so now that I am working from home, my office has to be dedicated to work.

If you don’t have a dedicated office, defining a place for work will be helpful in establishing a routine and creating space and separation for work. If that’s a corner of the apartment or bedroom, or even the kitchen table during the day. It will be important to define the space for work, get it set up so you can be effective, and get everyone on board.

In his book Atomic Habits, James Clear talks about the power of establishing the right context by establishing predictable circumstances:

“Habits thrive under predictable circumstances like these. Focus comes automatically when you are sitting at your work desk. Relaxation is easier when you are in a space designed for that purpose. Sleep comes quickly when it is the only thing that happens in your bedroom. If you want behaviors that are stable and predictable, you need an environment that is stable and predictable.”

Temporal. Creating boundaries around your time will also be critical. Working remotely, especially if it’s new, can be a big change. It’s easy to lose yourself in things going on at home since you’re there, but it’s just as easy to let work bleed into your home life since there is no longer a boundary.

So setting up a schedule for your time “in the office” is just as important as it was before. It can be flexible, and likely will have to be since you’re also dealing with lots of other things (and during a pandemic, there’s a good chance you’ve got kids at home and many things to worry about). But keeping a good schedule will ensure you can continue to get important work done and also keep your home life somewhat normal.

Mental. Mental boundaries will probably always be the most difficult. It’s hard enough to define mental boundaries between work and personal life as it is, right? How do you not take your work home with you when it’s right there, all the time? How do you not take the stress of home to work when they are in the same place?

Creating physical and scheduled spaces will be helpful in getting some mental space. But allowing yourself some head space will also be critical. This will be a time for change. Give yourself some time to adjust! Take breaks. Take a walk. Be sure to clear your head regularly and find the right mental balance. Creating a routine, which we’ll discuss next, will also help with this.

Create (or maintain) a routine
If you’re shifting to remote work, either temporarily or more permanently, create or maintain your routine. As someone who has worked from home frequently, the most productive days I’ve had are the ones I’ve maintained my standard routine for work. That means getting ready like usual, even getting dressed like I’m heading to the office, and then stepping into my office and starting my work day.

I’ve even heard of people “commuting” to work by leaving their house, walking around their neighborhood, and then arriving back at work. I think it’s a great idea. Creating a ritual to get you in the habit for work will set the right tone. It is critical for success, especially as you transition from being in the office to being remote. I’ve found that transition periods are usually times when my routine slides, and that is when my productivity also slides. So maintain your routine if you want to stay productive.

Communicate relentlessly
We take communication for granted when we are all in an office together. We can always pop in whenever we need or schedule a quick time to catch up or meet. When we’re not all in the same space, that becomes more difficult, so we can’t take communication for granted.

Fortunately, the tools are all readily available. We just have to use them. That may mean changing some of our habits. But it is very doable. While we can’t just pop in for a quick chat, we can pick up the phone for a quick call. And we should do Zoom calls or video chats to keep face time.

We also need to keep records of discussions we’re having. So posting Slack messages, keeping meeting notes updated, and keeping everyone in the loop frequently is key. Over-communicating, especially in the early phases of the transitions, is critical. It is better that everyone feel like too much communication is happening than to feel like too little is happening. So don’t be afraid to communicate frequently.

Focus and Prioritize
So much of our work today has become urgent, lower importance items that take up tons of time. From emails to meetings to low-value tasks. As you shift to working remotely, especially if it is for a short period, take some time to seriously assess the high value items you can do. Prioritize that work.

The unfortunate fact is that many businesses will suffer as the economy turns. So we all need to focus our efforts on the highest value tasks we can perform and ensure that we are delivering value for our companies, our customers and our users. The more we focus, the more value we can deliver. And the more non-essential we can cut out.

Managers
As managers and leaders, we are now in the position to manage remote teams, whether or not we were ready for that. Hopefully, if you’re a leader, it is something you’ve been considering or have experience with. If not, welcome to the party!

Communication
Communication with your team will be the single biggest success factor through all of this. Communication about ongoing work, expectations, changes that are happening, etc.

As a leader or manager, you need to stay apprised of what is happening with your team. It won’t be as easy as walking around an office to get a feel for what is going on. Your team members can’t just pop in either. It will require effort on everyone’s part. And as a leader, you set the tone for the team. So set a standard of communication, especially early on by having regular chats with team members. They need not be long or comprehensive, but just ensure that you’re staying updated.

You will also have to strike a balance. You’re not trying to manage every aspect of your team’s work either, at least hopefully that won’t be the case. So you’ll likely need to find the right cadence. Communicate that to your group. Let them know that you will be finding the right balance and you’ll all be working together. You’re all in this together.

Expectations
Next, be sure to set clear expectations with your team. When will you be having meetings? When will you expect people to be available? What will communication look like? How will you handle issues as they arise? You may not have all the answers immediately, but starting to set clear expectations will avoid so many issues down the road.

In past teams, we set the expectation that we do video calls, video on for everyone so we can all see each other. That set the tone for the team so there were no questions.

In our current situation, we’ve set the expectation that team members have kids at home and that we are okay with that as a group. If kids pop into calls, that isn’t a surprise or issue for us.

As a leader, have these conversations with your team. Outline expectations and then document them so everyone is aware. You can keep documenting things as you go.

Documentation
And that’s a great segue to documentation. Documenting discussions, decisions, meetings, etc., will be even more than ever before. If you haven’t been in the habit of documenting things, this will be quite the change. But it will be a good change and a good habit to create.

Taking notes doesn’t have to be onerous. You can rotate the responsibility around the team so it isn’t a burden on any one person, or have someone dedicated to the task. You’ll want to ensure you note important decisions and action items so you can follow up in the future and so anyone who wasn’t able to be part of the conversation can catch up quickly.

Creating team documentation is an important key. With everyone remote, even for a short period, there is less ability for the regular interactions and so it is even more important to write down team norms, helpful hints, and other useful bits of information. Product management, for example, is learned much more by apprenticeship. But when everyone goes remote, there is obviously much less opportunity for that in a traditional sense. So we have to communicate more and write down as much as we can to help newer members of our team continue to learn their roles.

Metrics
With the turmoil and chaos surrounding everything right now, it would be wrong to expect performance of teams and organizations to be unaffected. As leaders, we should acknowledge that there is so much more happening than we can fully get a handle on. It is tough and may get tougher still. So let’s help our people do the best they can. That is our main purpose.

With that said, we all still want our companies to be successful (I hope). As leaders, we can’t manage by butts in seats. Hopefully that isn’t how you’ve been doing it, but that won’t cut it in a remote world. Therefore, we need to focus on the metrics that matter most. How can we ensure that our teams are delivering value? Find those metrics, make them obvious, and work with your teams to align your goals against them. And measure your success by them. Hint, it won’t be hours worked, lines of code delivered, or emails answered.

One ongoing practice for my team has been to set a few goals at the beginning of each week for the most important things to accomplish and then report back on those goals. I also do the same. More on that in another article. But it helps keep the focus on what is most important and ensures accountability.

Moving to remote work can be a huge benefit for many people and organizations. As part of a larger strategy, it is great. When it happens suddenly because of sudden events such as pandemics, it can seem like a strain initially. However, with the right steps, it’s not only manageable, but can be just as effective as being in the office. By creating the right boundaries and expectations, focusing on the right priorities, and communicating relentlessly as individuals and leaders, we can continue to be successful as teams and companies.
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And as we manage the transition, hopefully we can incorporate remote work as part of our larger strategy going forward.

Hopefully, your team or company won’t ever get hit by the “blizzard of the century” that keeps you all out of the office for a week, but you never know.

Years ago I was scheduled to fly to the east coast just as a superstorm was about to blow through. I wisely postponed that trip and dodged what was a nightmare for weeks. Many people couldn’t travel to work, and many office buildings were without power (or running on backup generators) for days. I’m glad I wasn’t stuck in a hotel room without power for a week.

Those kinds of events can shut down teams, companies, and even industries. A major storm, a natural disaster, an outbreak, or just life. A few storms like that have inspired us to prepare our home with things like a backup generator and emergency supplies so we’re prepared for a snowpocalypse.
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But what about getting our teams and companies ready? Fortunately, we don’t have to be doom and gloom about it, because the benefits are massive, and we can have them today.

The future of most knowledge work will be distributed and remote. As companies become more global and as connectedness shrinks the distance between people, going into an office to do the same thing you can do at home or at the coffee shop down the street will become an antiquated notion. In many places it already is. But this trend will continue to speed up and engulf organizations that have been slow to move.

And this future may come much sooner than you think. While the culture of an organization may not change overnight, you never know when some unforeseen circumstance may force everyone in your group or company to be remote for some period, like the superstorm that hit our team years ago. Or like the major disease outbreaks that are causing huge issues today. The coronavirus has caused tens of thousands of workers in China to work remotely as it has spread rapidly across the world.

Having been at organizations and offices across the spectrum of remote work, I’ve learned some key lessons about how to make your team or group the most effective no matter where you are on the spectrum. Whether your work is primarily or partly remote, you’re in the main office and interact with remote workers, or you’re part of a remote group far from the company headquarters, there are several steps we can all follow to improve the productivity of our teams and prepare ourselves and our groups to be remote friendly.

1. Define Your “Why”
As an organization, clearly define why you are shifting to more remote friendly work. Is it to remain competitive and attract the best local talent by allowing flexibility? Is it to expand your talent pool by hiring beyond the local market? Is it to lower costs? To diversify talent? To expand globally? Some combination? Those are all good reasons, so you should be able to articulate among them why you are becoming more remote friendly.

You need to have a clearly defined “why” and be transparent. There are likely benefits to your current employees, but it may also unnerve if you don’t communicate what you’re doing. With adding global talent, existing employees may wonder if their jobs will go away. You need to address that. Besides addressing concerns, if you don’t have a clear strategy, you won’t know if you’ve achieved your goals. If lowering costs is the goal but you never define that, how will you know you’ve been successful?

By having a defined “why”, you can incorporate this into your ongoing practices. Your employees shouldn’t be thrashed around by whims of new leaders or changing environments, so defining your remote working strategy ensures that everyone — from employees to leadership — understands what to expect and can get on board. Remember, many people make important life decisions based on company policies, so we should be thoughtful about how and why we do things.

2. Change Your Mindset
The next key is to change your mindset. If you are a manager or team lead, this will be a critical step.

Way of Working
While we once considered remote working a perk, we need to look at it as a way of working and a way of life now. Remote work is a requirement, not a fringe benefit. It’s not just a bonus which also means that it isn’t something that we can give and take away like a ping pong table in the break room. This is especially true for workers who are transitioning fully to remote work. And this trend will only continue. While not every employee will work remote full time, most employees will work remote at least sometimes.

Value over Outputs
Being in the office has long been a proxy for measuring productivity. That may have made sense 50 years ago when much of the work you needed to do had to be done in the office because that is where the documents were or the computer was. But with the connections we have today, everything is accessible everywhere, if we like it or not.

Rather than managing to perceived outputs such as time in the office, we need to shift to managing to outcomes and value. You’re right that measuring how much time someone is in the office is easier. But it may have zero correlation to the value being delivered. Someone could easily be in the office for 10 hours per day while delivering no real value. Likewise, someone could be in the office for 1–2 hours in a week and deliver significant value to the business or customers.

Watch Your Language
“Sh*t.” — Iron Man

“Language.” — Captain America.

That’s not the language we’re referring to here, though you may want to watch that as well depending on your work environment. What we mean here is watching how you talk about work. It's easy to forget how different it can be for our remote colleagues, especially anyone who is remote full time.

Be sure to be inclusive. It's easy to talk about how great it is to be together in the office, or how great face-to-face communication is. However, that can feel hurtful, especially if someone is remote full time. These kinds of comments are especially difficult if they come from leaders. If someone is remote or part of a remote office, they already feel somewhat isolated. Therefore, comments from leaders that further exclude them only widen the divide. As leaders, especially with remote workers, we need to ensure that everyone understands that we value their work and their contributions regardless of where their desk is located.

Cultural Shift
Being a remote friendly organization will be a cultural shift. This will probably take some time. But being transparent about it and shifting your mindset will make the transition much smoother for you, your team, and your company.

3. Think Remote First
In recent years there has been a shift in software development to “mobile first.” This has meant that design and development should focus first on making an excellent experience on mobile devices and then take that to the desktop.

The reason for this is twofold: First, it is much harder to get something right on a tiny screen. There is not a lot of real-estate to work with so you have to be very conscious of what you do and what makes it onto the screen. Second, people have shifted to using mobile devices as their primary source. Since we’re no longer tied to desktops for most of the functionality we need, we expect to do everything on our cell phones and tablets. And rightly so.

We need to take the same approach to remote work. We need to think remote first. The reasons are very similar to the thinking with mobile first: First, it is harder to get it right. In-person is easier, so shifting to remote first is a challenge. Second, many people are shifting to this mindset for their own work. Similar to being able to access anything on our mobile devices, the expectation for work is following suit. We should be able to expect the ability for people to be mobile.

Make Every Meeting Remote Friendly
At one company I worked for, I was in the main office and we had a few remote team members. At first, this was challenging since most of us were in the office. We defaulted to focusing on the group in the office. But this didn’t allow for broad participation. So we shifted our focus.

We started by ensuring that every meeting had a dial-in and I started bringing a camera to connect the room and remote folks. As we got comfortable with this format, I realized that getting people into a conference room was unnecessary. We could shift our meetings to be entirely remote for everyone. That meant that team members could stay at their desks if they needed, or work from home without having to worry about meeting schedules for the day.

Make it a regular practice to make meetings remote friendly, and you’ll see a big change in your ability as a team or department.

Get the Tools
A key to making this shift work is ensuring that your groups have the right tools. Today, there is no shortage of excellent tools to use for communication. Slack for chatting. Zoom for online video calls. Microsoft Teams for either of those. A host of other options exist. There is no excuse not to leverage these tools, whether on a small scale or across an enterprise, to allow everyone access to team collaboration.

One of the key benefits of being in a conference room is often the white boarding or brainstorming that can take place. However, I’ve found excellent tools that allow for that same collaboration done across offices or remote employees. My favorite is Lucidchart, which allows many people to edit at the same time. I’ve used it as an online board for writing ideas in real time, and a board for sticky notes that an entire team can contribute to. This has been awesome as we’ve created user story maps, brainstormed ideas, or gone through similar exercises as a product or development team.

Document Discussions & Decisions
One of the biggest changes to remote friendly work is documenting meetings, discussions, and decisions. This is critical because you need to ensure that everyone is aware of decisions being made whether or not they were present. And when teammates are remote, whether full time or just on and off, you need to have good documentation that everyone can refer back to.

I’ve found that this is just good practice. Whenever I’ve gotten away from the habit of documenting discussions, meetings or decisions, it has come back to bite me. Several months ago we were in discussions on team structures. The conversations were all in person and were moving quickly. Unfortunately, we didn’t write much down. So when some questions arose later on, we had nothing to refer back to other than our memories of what we had discussed. Which were an imperfect record. I kicked myself for not writing the decisions we were making as we went. This would have been even more difficult if some of the team had been remote and wouldn’t have been available to talk in the office. Don’t make the mistake I did. Write things down.

4. Ensure the Right Fit
Hire the Right People
Hiring the right people is a key to anything, and that holds true here as well. If you’ve got a team of people that you can’t trust to work remotely or unsupervised, you likely have bigger issues.

So hiring folks who you can trust is critical. Teams should think about that in making hiring decisions, from the managers to the team members. You should think through the questions:

• How will our interactions be if one of us is remote?
• Can we be confident this person can get their work done without significant supervision?
• Are there any barriers that may cause issues if we are all remote?

Ideally, a team should be able to function whether or not everyone is in the same place. But even if your ideal is complete co-location, be prepared because not everyone will always be in the office. If you plan around that, especially with having the right people, you’ll be able to continue to deliver quality work as a group, even if the situation isn’t ideal.

Find the Right Balance
We also need to understand that remote work isn’t for everyone, and to be successful we need to properly support teammates who will work remotely or in remote offices.
Jessica Pamdeth a staff engineer for WGU, recalls her time working for IBM when they shifted to remote work for the engineering teams:

“When IBM sent us all to work remote, about half the folks started looking for new jobs right away. Not everyone has a good space in their home for working. Perhaps they have young kids at home every day, or their place is just too small for a dedicated workstation. Maybe they can admit to themselves they don’t have the discipline. Or they just prefer the interaction with coworkers every day.”

Regardless of the reasons, full time remote work may not be for everyone, so it is important to understand that. Everyone seems to have varying degrees at which they can productively work remotely. As a manager, it’s important to understand that and find the right balance for your team and your organization.

5. Set Expectations
Once you’ve created your remote friendly workplace, it’s important to set the right expectations for your team and organization. The level of formality will vary depending on the situation, but it is important for your employees and their development to help them understand how they can progress, especially if they are remote.

Promotions
In one of my previous roles, one of the most senior members of the organization was a remote employee. And she was a phenomenal employee. But because she was remote, they limited her in moving into a VP role. While she essentially ran the entire department in that capacity, they refused to give her that promotion, which was unfortunate.

It’s important to be clear how far employees will advance and be promoted in remote roles. Will they be excluded from management roles? Should they be? You may not have all the answers to these questions yet, but think through them. If you will exclude remote employees or expect them to move to your main office for big promotions, you may end up losing out on some of your best talent. Is that something you’re willing to do?

Asynchronous Communication
How do you expect employees to communicate? This is a broader question and is often overlooked when most employees sit in the same office or in the same time zone. But it gets more difficult as employees stretch across offices and time zones.

Allowing employees to have focus time is critical, especially in knowledge work. So setting the expectation that most communication (except for urgent matters) will be asynchronous may be a great idea. That way everyone can handle communication when it fits their schedule rather than when the Slack notification hits their phone or laptop.

No Second-Class Citizens
When we were setting up the Salt Lake office for Goldman Sachs, many people in New York and London viewed it as a second-tier office. A place where they could send crappy work they didn’t want to do so they could focus on sexier projects. It took some time to get everyone away from that idea, but we eventually did.

If you’re setting up a remote office or remote workers, don’t do it with the view of second-class citizens or a place to send your shit-work. That will be a way to get a lot of disgruntled employees quickly. You want full teammates. It will be better for your team and your company in the long-term. Even if they are less expensive in other locations, that doesn’t mean they are less valuable.

6. Give Teams Autonomy
Once you’ve got the mindset, the tools and the people in place, it’s time, especially as a leader, to give teams autonomy to find their cadence. Not every team functions the same. Humans are complex, and our interactions are complex. Leaders at high levels should allow their teams flexibility to find the right cadence. Allow the leaders within groups and teams to find the right solutions. Let go of some control and let your people find the solutions that work!

For people to do their very best work, it often means they need the right environment, free from distractions, to immerse themselves and perform at their peak. Modern offices are notoriously bad environments for this type of work. They are full of distractions, from meetings to phone calls to quick questions. By focusing on value delivered and allowing employees to work wherever they can deliver that value best, we can continually move in the direction of becoming remote friendly.

For team leads and team members, it is critical to show the value that you’re delivering to your organization. If you will not be measured by the hours you’re in your chair in the office, you need to make it easy to show the actual value you’re providing.

7. Promote Face Time
None of this is to say that face-to-face interactions aren’t important. Humans are social creatures. It’s in our nature. We will not change hundreds of thousands of years of evolution with modern technology and we shouldn’t pretend to. We need time together as a group. So it is important to bring remote people together periodically to create those uniquely human bonds.

This is especially important if most of the team is located in an office with a few remote members. In one of my roles, I was in a remote location while the rest of the team was (largely) in New York. I made a point to travel out there every few months to work in person. Most teams I’ve worked on have had a similar policy, but it’s important to make sure that remote teammates join the team periodically, especially during important events such as product launches or celebrations. This is particularly important for teammates who are the lone remote members of the group, or in the minority. It is easy to feel isolated when you’re the one far from the team, and it is easy to forget how difficult that can be when you’re not the one who is remote.

To make face-to-face time more meaningful, you can maximize the usefulness of your team’s time together by focusing on shared experiences. This means rather than continuing with business as usual, ensure that you’re taking time as a team to build relationships by solving problems together, cooperating on shared goals and maximizing interactions.

8. Make the Effort & Commitment
Ultimately, it comes down to making an effort and commitment. Many people think co-location, especially of development teams, is the only option. I disagree. I’ve seen high-performing teams that are largely remote. And poorly performing teams that are co-located. It comes down to the team and the effort. I wrote about this in another post, Co-Located vs. Remote/Distributed Teams: What Works and Why. While it takes more effort to reduce the social distance of a distributed team, with the right leadership and the right tools, the team can bond and perform just as well as a co-located team.
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On teams that are remote or have remote members, it takes an extra effort to keep everyone involved. But that effort becomes second nature with some practice. Calling folks up to chat for a few minutes may seem strange at first, but becomes normal quickly. By changing the mindset of the team, remote work can quickly become a default that is easy to manage and easy to execute.

Becoming remote friendly will be critical for businesses and teams to succeed. But the benefits will be huge. Businesses will access a global talent pool, or at least a far larger talent pool than just the local one. For many companies, this will mean great employees and lower costs.
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The benefits to employees will be huge too. As we shift from the mindset of being tied to a particular location to do all our work, we will be much more free to find the time and place that best suits our productivity and passion.

Like any good product person, I have a lot of whiteboards for writing out ideas and brainstorming. That includes a big whiteboard in my office at work. It also includes two whiteboards in my home office — one on the wall and one I can move around as needed. Excessive? Maybe a little. But it comes with the territory.

When I’m not using the extra whiteboard at home, I set it behind the door and let my kids color on it. They enjoy that. I try to convince them to draw out lean canvases of product ideas too, but they’re not there yet. Baby steps.

Often the whiteboard will get filled up with scribbles and artwork and I’ll just leave it for a while because I think the drawing is pretty cute, either intentionally or unintentionally. Like one that my daughter drew on the left below. I’m not entirely sure what it is supposed to be, but she was really feeling her inner artist when she was drawing it and it kind of speaks to me in a cute kid way, but also in a deep, existential way.
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So I kept it around for a long time without erasing it.

Likewise, my son loves to build. So Legos or marble mazes or other contraptions of different sorts will often occupy the table in my office. His most recent marble maze is pictured above on the right.

He’s pretty proud of that one, so it, too, has been up for quite some time.

The problem with leaving marble mazes fully constructed or whiteboard pictures un-erased is that there isn’t any room for new pictures to be drawn or new mazes to be constructed. Sure, the ones that are there now are great. But what about the new ideas? We don’t know what great new thing might come into existence if we give it some room! And even clearing some space just for the creativity to happen is critical.
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So much to my kids’ dismay, I took down the marble maze and erased the whiteboard. Some tears were shed, it’s true. But now there is room for something new. Which is incredibly exciting.

We often get stuck in the same rut regarding our own creativity, and we rarely even realize it. This is especially true when things are going all right. It’s easy to see when you’re in a rut when things are going poorly, but it’s much more difficult to see you need a change when things are going okay.

Maybe you’ve reached a local maximum. The best you can expect given certain inputs. But is that where you want to settle? What about the global maximum. Why stand on the tallest hill that’s close by when there are much higher points not that far away?

Erasing our Own Whiteboards
I think we’ve all been a similar situation. So what can we do to get our creativity flowing again? How can we stretch beyond what we’re doing now to something much greater? How can we take ourselves, our jobs, our products to new heights?

Read Extensively
One of the lowest cost, lowest effort options is to simply broaden your reading list. From books to articles to newsletters. I’d even include podcasts in this category.

Find material that broadens your thinking and challenges you. The key is to read both inside and outside of your field.

In one of my favorite books of the year, Range: Why Generalists Triumph in a Specialized World, David Epstein addresses this at length. The entire book is a deep dive into the importance of getting out of your field to expand your vision (and well worth your time if you haven’t read it yet), but I’ll use the example of Johannes Kepler here to illustrate the point.

Kepler had accepted the Copernican model of planets orbiting the sun, but there was little else to explain motion in the heavens. So he drew on ideas from other areas such as boats in whirlpools, magnets pushing and pulling, optics of lenses, etc. There was no field of astrophysics until Kepler invented it, so he drew on lessons from other fields to guide his thinking.

“In an age when alchemy was still a common approach to natural phenomena, Kepler filled the universe with invisible forces acting all around us, and helped usher in the Scientific Revolution. His fastidious documentation of every meandering path his brain blazed is one of the great records of a mind undergoing creative transformation. It is a truism to say that Kepler thought outside the box. But what he really did, whenever he was stuck, was to think entirely outside his domain.”

I’ve found that reading extensively is one of the best ways to think outside my domain and get exposure to areas that I may not otherwise see. It helps to erase some of barriers I put in place with my professional experience, and allows me to see things through different lenses.

Get out of the Office
Nothing curbs creativity and narrows our vision more than spending all our time in the office. You may not even notice it until you finally pull yourself away from your desk and actually get out.

If you’re a product manager or UX designer, you need to be getting out of the office to meet with customers weekly. If you’re in another role, especially creative roles, you should be getting out of the office weekly as well. Make it a habit. Make it a priority.

Meet people. One great way to get out of the office is to simply go have lunch regularly. I try to schedule lunch with former coworkers or other people I know at other companies at least a few times a month. It’s nice to catch up with old friends and it helps get perspective on things happening outside of your company.

Find mentors. It’s also a great idea to have some mentors. If you don’t already, I suggest putting in some time to find some. And then have a chat with them periodically. I’ve had a group of both formal and informal mentors for some time, and as I’ve taken on more leadership roles I’ve worked to expand this group. It helps to have people you can turn to for advice and insight outside of your company.

Go to conferences and meetups. I love conferences and try to take my teams to at least a few each year. Not only is it a great chance to get out of the office as a team, but you get to hear from industry experts, meet lots of other professionals, and turn your mind to something other than the immediate issues you’re facing in your day-to-day role. And that is such a huge key to being able to bring new thinking to your challenges. Meetups can often be a “mini-conference” where you can listen to a presentation and grab lunch, with some of the same benefits as a longer conference without the same time or financial commitment.

Do things other than work
One of the best things you can do to “clear the whiteboard” and open up your mind is to do something other than work. This includes taking time both during the workday and ensuring that outside of work you have hobbies and interests that allow you to engage your creativity.

Personally, I make it a habit every day to take a walk outside to clear my head and stretch my legs. It gives me a chance to get away from my computer, email, Slack, etc., and just think for a little while. I’m fortunate now to have a nice little pond by my office that I can walk around. For several years these walks have been around parking lots and some neighboring streets since that’s what was available, but that hasn’t deterred me.

Outside of work it’s also incredibly important to have interests and hobbies that engage you. Referring back again to the book Range:

“Rather than obsessively focusing on a narrow topic, creative achievers tend to have broad interests. This breadth often supports insights that cannot be attributed to domain-specific expertise alone.”
“Compared to other scientists, Nobel laureates are at least twenty-two times more likely to partake as an amateur actor, dancer, magician or other type of performer. Nationally recognized scientists are much more likely than other scientists to be musicians, sculptors, painters, printmakers, woodworkers, mechanics, electronics tinkerers, glassblowers, poets or writers of both fiction and nonfiction.”

Challenge Assumptions and Processes
It’s easy to put processes in place and then allow them to stay in place for a long time, if not indefinitely. That’s why it’s critical to constantly be challenging our assumptions and processes, both personally and professionally.

I’ve been woodworking for years now. One thing I make and sell is shaving sets, which I’ve linked if you’re interested in seeing more. I finish each item with multiple coats of super glue, which I polish to a nice glossy finish. I created a process early on where I put on a coat, sanded it, polished it, and then repeated the process about 10 times. I did that for a while. Until one day I questioned my process. Could I do it better? Did I need to sand and polish between coats? I experimented and found that I was wasting time and material and should just be putting on 10 coats and then doing my polishing. It sped up my process significantly. But I never would have made that change if I hadn’t challenged my process, which had been working just fine for me for a long time.

How many processes are like this in our organizations? How many times do you hear things like “that is how we’ve always done it” or “this works for us, that other thing wouldn’t work here.”

We should, as a habit, periodically reimagine all of our processes and assumptions from the ground up. If we were to start over, how would we do it now? Over the past several years as I’ve come into several new roles, this is where I’ve always started and it has yielded tremendous, if difficult, results. We won’t always have the luxury to start over, or implement every change, as I know firsthand, but this is the mindset that will help you continually drive innovation for yourself, your team, and your organization.

Run Experiments
We build good product development on experimentation. To understand what will work and what isn’t, like scientists, we have to constantly be running experiments. When I was a product manager responsible for specific products, this was a huge part of my role.

In one of my products, we theorized that we could improve the user experience by simplifying the flow and the design of one of our products. So I created some working prototypes and we set out to test that assumption. Unfortunately they didn’t work the way we expected. But we learned some valuable lessons on what might work, which informed the next set of experiments and decisions, just as you’d expect. And eventually we got to a better design and user experience.

We should take the same attitude toward experimentation in our companies and individually. Eric Ries, in his book The Startup Way, talks about taking many of the startup principles he discussed in The Lean Startup and making them part of general business culture.

“Continuous transformation — an organization’s ability to test and learn from experiences related to its own structure and processes, promoting the best proven techniques across the enterprise, limiting or discarding the rest — is what will give this organization the ability to thrive in the modern age.”

It’s this kind of ability to adapt and evolve that allows modern companies to keep pace with competition, especially startups that are doing the same. But it is not an easy thing to do, especially at a company or organizational level. Erasing the whiteboard — reimagining the very things that got us to where we are — can be difficult, if not impossible. But that’s often the difference between companies that thrive (or survive) and those that don’t.

Individually, we can adopt the same mindset. Continuous transformation is the goal, and ongoing experimentation is the key. We have to disrupt ourselves, our routines, our comfort to find what will work and what will bring success.

This is often an easier mindset to have early in life, when we feel like we may have the freedom to explore a bit more and experiment with our talents and things we like. But eventually we lose that mindset and feel that we have to have everything figured out and determined. Which is why continually experimenting individually is critical.

For example, when it comes to fitness, experimenting with different workouts and routines is critical to progress. If you’ve trained or exercised, you’re likely familiar with “the plateau” — the time when you no longer see progress. It’s easy to hit a plateau by sticking with a familiar routine because you’re constantly working out the same muscles. Your body adapts and you no longer need to get stronger to do that particular exercise. That’s why you need variation. Often it may take some experimenting to find what will work best, but breaking out of the routine is key.

This is the same idea for cognitive and professional pursuits. We’ve got to break out of the routine, experiment with the new, and break past the plateau.

Make a Big Switch
Ultimately, erasing the whiteboard is the goal so we can unleash our creativity. And that may mean we need to make a big switch.

In one of my favorite books about creativity, Creativity Inc., there are numerous stories about creativity (obviously) and unleashing creative potential. One story about Finding Nemo is particularly relevant.

In the creation of Finding Nemo, Andrew Stanton pitched the entire story which everyone loved initially. The movie would have a series of flashbacks from Nemo’s father, weaving the story of Nemo and his father. But when the storyboards were put together, it was confusing. The braintrust at Pixar lobbied for the story to be more linear, and when Andrew did that, making a big switch to the movie, it became not only much clearer, but Marlin (Nemo’s father) became a much more sympathetic and likable character.

Sometimes we have to make a big switch, tossing out a big portion of our ideas to get to something much better, like the case with Finding Nemo and almost every other Pixar movie.

Years ago I witnessed the benefits of a big switch in my family. My dad had been working the same job for a long time. He was very good at it, and it had become comfortable and familiar. He liked the fact that it was comfortable and familiar, so it took some prodding for him to make a change, but I remember as he moved into a new role there was a massive shift. He was much happier at work, and it made him happier everywhere. It brought a renewed engagement that comes with a new role, and a new excitement. It cleared the whiteboard of everything he had been doing and started things anew.

Sometimes it takes a big shift to get things started again. I’d argue that it’s even necessary to plan on big shifts periodically. In your career, you’ll be best served by reimagining your role periodically, whether that means moving to a new job or simply changing positions or taking on massive new projects or responsibilities. But even within our roles, we can make these big shifts as we challenge the processes we have in place, experiment with what works and learn about new and better ways of doing things.

One of the best ways to foster creativity is to start with a blank slate — erase the whiteboard and start fresh.

This can be a hard thing to do. At our companies, we often face a myriad of entrenched processes that have often served us well. Individually, we may be in a similar situation. What we’ve done so far has worked well. Why should we abandon it now?
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But often the best thing for a system, whether an office or ourselves, is to inject a little randomness, cut things down to their core, and start to reimagine. You’ll be surprised with what you come up with.

ProWritingAid
I do a lot of writing. I’ve been doing a lot of articles and blog posts, working on a book, doing an MBA, and just enjoy writing for work and for fun. ProWritingAid is a grammar checker, a style editor and writing mentor (pulled that from their site). I checked out a bunch of writing tools and it was the one that most closely aligned with what I wanted and needed. And it has been excellent. I’m amazed how I got along without it for so long. I don’t think I could go back to not having a tool for editing my writing, whether emails or documents or blog posts. It is worth every penny.
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Echo Auto
I was fortunate enough to get to beta the new Echo Auto, which puts Alexa in your car in a nice little package. I was super impressed by the whole setup. It syncs seamlessly with my phone, is unobtrusive in my car, and allows me to use voice commands and other things that I didn’t have available in my not-smart car. I’d say it even works better than the integrated system we have in our truck, which is pretty cumbersome. I imagine newer cars and infotainment systems won’t need Echo Auto, but it’s been amazing to get into my car and have it just work to play music, podcasts or audiobooks.

Daylio
Daylio is a daily micro journal and mood/activity tracker. I started using it at the beginning of the year and have been pretty religiously using it every day since. I love keeping track of activities and how they impact my mood. I also love jotting down some notes about each day. I’m a journal keeper and it has been amazing to scroll through each day to look at the highlights from the week.

Eufy Smart Scale
I mentioned getting a smart scale at the end of last year, and it has proved to be a key life changer this year. Being able to track weight (and other metrics) over time has made it so much easier to understand the impact of choices and to monitor health. It’s become part of my fitness routine and has made me a healthier person. Looking back at various times in my life, I realize how much I wasn’t controlling my lifestyle and the negative impact that was having on my. This has been part of a big change that I’ve made, and it has made it easier.

Fitbit Versa
Along the same lines as a smart scale, my wife gave me a Fitbit Versa this year, and it has continued my fitness progression in a significantly positive way. I’ve been a Fitbit user since they came out with their first wristband, so it shouldn’t be too much of a surprise. But the Versa has almost taken the place of other smartwatches. The only problem is that it doesn’t fully take the place of a smartwatch yet, so that leaves me with my Fossil smartwatch and my Fitbit. I don’t mind it, but it leads to many people asking questions.

Ring Security
​We invested in a Ring Security system late last year. It was dead easy to set up and install, which was a good start. It went well with the doorbell we already had and gave some extra peace of mind. We added a floodlight camera to the backyard as well. Later in the year, there was a string of car thefts happening all around our city. There were a couple in neighborhood, and it was right about the time we got a new truck and had to park it out on the street for a few weeks before we could rearrange the garage to get it to fit. So we added another Ring security camera to our driveway, both as a deterrent and a way to catch anyone who broke into our cars if it happened. Fortunately, it didn’t, but we’ve become huge fans of Ring for how integrated it all is, how easy it is to set up, and that you don’t have to buy into a long-term security system to get what you need or want.

So that’s the list for 2019. There were several other products that almost made the cut as well. The ones above I use almost every day in some way. But there are others that are just as good that maybe don’t quite see as much use. The Echo Show 5 is a great little device. I’d probably take that over Echo Dots now, and I’ve got one in my office. It’s the perfect size and has all the functionality you need. If you enjoy making ice cream, a Whynter upright ice cream maker should be on your list. We’ve been using one for a few months and are making far better ice cream than Cold Stone. I also got the new Galaxy Note 10+ a few weeks ago. It’s been amazing so far, but since I’ve only had it for a short period of time I kept it off my 2019 list.
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It was a great year for apps and gadgets. I’m excited to see what 2020 will bring.

I began 2019 with the goal of reading a book a week. And here in the final week of 2019, I’ve finished reading 52 books (see the full list below). So this is, first and foremost, a humble brag post about that, as are all articles on favorite books (we won’t kid ourselves, right?). But secondarily — a very, very distant second mind you — I populate a lot of my own reading lists with recommendations from others. So I find these articles really useful personally.
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This year’s reading list included everything from history to science fiction to product management and business books. Some classics, some new releases and some new favorites. But I wanted to highlight the best books of the year, some of which I’ll add to a few of my upcoming lists on must-reads for product managers and product leaders.

Range: Why Generalists Triumph in a Specialized World
Since I was young, I’ve been torn by my varied interests, but also the need I constantly felt to specialize. I remember this becoming especially acute in high school where I was very good a range of things, but didn’t feel that I was the best at any particular thing.

Range: Why Generalists Triumph in a Specialized World is a kind of vindication for my younger self, putting into words what I always felt: that exploring a range of opportunities and becoming good at a variety of things would ultimately be a successful path. There was no need to give up every sport to focus solely on one. Or give up every interest to become the best at a single venture.

“Our greatest strength is the exact opposite of narrow specialization. It is the ability to integrate broadly… In the wicked world, with ill-defined challenges and few rigid rules, range can be a life hack.”
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Specializing early can be extremely detrimental in most areas, excluding a few well-defined skills like golf or chess. Gaining broad experience, and this book was a fascinating look into why that is. I could go on and on about it, but the best thing you can do is go read it.

The Three-Body Problem
We probably don’t realize just how fortunate we are to be in a stable orbit around our sun. This book explores an alien world that faces a three-body problem as it orbits two stars, constantly facing periods of stability and instability, and the adaptations they have to make to adjust to that.

Of course, Earth becomes intertwined with them eventually. It is set against the backdrop of the Chinese cultural revolution, which admittedly I was not that familiar with, so the whole book is fascinating and one of the best science fiction books I’ve read.

Deep Work: Rules for Focused Success in a Distracted World
Cutting out distraction and focusing on the most important tasks has been a critical theme for me over the past few years, and Deep Work is one of the best books on the subject. It has become a book I reference often and one that I will go back to re-read to keep the lessons fresh in my mind. Because I drift back into my distracted habits when I know I want to focus on the most important things, especially since I know that they will pay off the most for me.

“The ability to perform deep work is becoming increasingly rare are exactly the same time it is becoming increasingly valuable in our economy. As a consequence, the few who cultivate this skill, and then make it the core of their working life, will thrive.”

Antifragile: Things that Gain from Disorder
I had read Fooled by Randomness and The Black Swan while I was still working on Wall Street, but I took some time this summer to read them again and then finally read Antifragile and Skin in the Game.

Antifragile to me was the best book of the group. It brought together all the ideas and showed why they are so important.

Basically, we live in a complex system. Each of us is a complex system. The number of variables in a complex system is almost infinite. The more we try to control that type of system and manipulate it, the more we mess it up. That’s why simplifying is often the best course. If nature made things a certain way, we should think hard before we change it. And we should also seek ways to make ourselves antifragile, often by allowing (and injecting) randomness and uncertainty rather than trying to eliminate and control it.

“Antifragility is beyond resilience or robustness. The resilient resists shocks and stays the same; the antifragile gets better.”

The whole book is really a revelation on complexity, randomness and embracing uncertainty in our lives.

The Innovators: How a Group of Hackers, Geniuses and Geeks Created the Digital Revolution
I didn’t read as much history or as many biographies this year as I normally do (I have a long list waiting for me in 2020, so next year’s list will probably have quite a few). But this book was excellent.

It walks through the history of the digital revolution, discussing the main players and companies and how they all built on each other. It is a fascinating history, especially for those of us who didn’t live through it.

Creativity Inc.: Overcoming the Unseen Forces that Stand in the Way of True Inspiration
I find myself referencing this book more and more in articles I’m writing and in conversations. It not only gives the history of Pixar, which is fascinating but also gives a great look into the Pixar process and what they do to make such great movies.

Pixar is probably one of the most creative companies there is, and they’ve created an amazingly creative culture. As a product leader, I pull lessons from Pixar regularly as our teams need to also create amazing products and user experiences.

“Making the process better, easier, and cheaper is an important aspiration, something we continually work on — but it is not the goal. Making something great is the goal.”

The Gods Themselves
This is another classic science fiction novel by Isaac Asimov. It again involves worlds intertwining, aliens, scientists, twists and turns. Earth seems to have found the answer to its energy problem, and almost no one wants to ask any questions.

“It is a mistake,” he said, “ to suppose that the public wants the environment protected or their lives saved and that they will be grateful to any idealist who will fight for such ends. What the public wants is their own individual comfort. We know that well enough from our experience in the environmental crisis of the twentieth century. Once it was well known that cigarettes increased the incidence of lung cancer, the obvious remedy was to stop smoking, but the desired remedy was a cigarette that did not cause cancer. When it became clear that the internal-combustion engine was polluting the atmosphere dangerously, the obvious remedy was to abandon such engines, and the desired remedy was to develop non-polluting engines.”

Extreme Ownership: How U.S. Navy SEALs Lead and Win
I’m a sucker for Navy SEAL stories. I’ll admit it. They are just so badass. So you couple that with leadership principles and I’m all in.

Even if you’re not a diehard fan, this is a great book. The core message of extreme ownership is one that leaders need to take to heart. Anyone in a leadership position, formal or informal, needs to feel extreme ownership for their product and team to produce the best outcomes.

“Leaders must own everything in their world. There is no one else to blame… the most fundamental and important truths at the heart of Extreme Ownership: there are no bad teams, only bad leaders.”

What You Do Is Who You Are: How to Create Your Business Culture
As I’ve been focused the latter part of this year on building a new product organization, I’ve been thinking a lot about team and culture. This book is an interesting look at various cultures and how they were built. From gangs to samurais to slave uprisings. I don’t know that you’ll get more eclectic examples than this book, but it makes for a good read and comes together nicely.

“Your culture is how your company makes decisions when you’re not there. It’s the set of assumptions your employees use to resolve problems every days. It’s how they behave when no one’s looking…Culture is a strategic investment in the company doing things the right way when you’re not looking.”

Team of Teams: New Rules of Engagement for a Complex World
Leadership needs to take a systems thinking approach in our complex world. And that is what this book is about. Rather than try to control everything, leaders need to empower teams to make decisions. We need to push the authority and tools down to those closest to the decisions.

“The temptation to lead as a chess master, controlling each move of the organization, must give way to an approach as a gardener, enabling rather than directing. A gardening approach to leadership is anything but passive. The leader acts as an ‘Eyes-On, Hands-Off’ enabler who creates and maintains an ecosystem in which the organization operates.”

Full list of books from 2019:

• The War of Art
• The Three-Body Problem
• Radical Focus: Achieving Your Most Important Goals With Objectives and Key Results
• Parallel Worlds: A Journey through Creation, Higher Dimensions, and the Future of the Cosmos
• Einstein’s Relativity and the Quantum Revolution
• Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs
• Infinite
• Don’t Make Me Think, Revisited: A Common Sense Approach to Web Usability
• The Theory of Everything: The Quest to Explain Reality
• Powerful: Building a Culture of Freedom and Responsibility
• Chaos: Making a New Science
• Simply Said: Communicating Better at Work and Beyond
• Split Second
• Eon
• What If?: Serious Scientific Answers to Absurd Hypothetical Questions
• Team of Teams: New Rules of Engagement for a Complex World
• The Gods Themselves
• Origin Story: A Big History of Everything
• Junk
• You Are a Badass
• Outcomes Over Output: Why customer behavior is the key metric for business success
• Algorithms to Live By: The Computer Science of Human Decisions
• Thinking in Bets: Making Smarter Decisions When You Don’t Have All the Facts
• Deep Work: Rules for Focused Success in a Distracted World
• Lean UX: Designing Great Products with Agile Teams
• The Innovators: How a Group of Hackers, Geniuses and Geeks Created the Digital Revolution
• The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success
• All the Myriad Ways
• Range: Why Generalists Triumph in a Specialized World
• Fooled by Randomness: The Hidden Role of Chance in Life
• The Black Swan: The Impact of the Highly Improbable
• Antifragile: Things that Gain from Disorder
• Skin in the Game: The Hidden Asymmetries in Daily Life
• Heart of Darkness
• Artemis
• Extreme Ownership: How U.S. Navy SEALs Lead and Win
• Indistractable: How to Control Your Attention and Choose Your Life
• The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers
• The Power of Vulnerability: Teachings of Authenticity, Connections and Courage
• The Mythical Man-Month: Essays on Software Engineering
• Dune
• Creativity Inc.: Overcoming the Unseen Forces that Stand in the Way of True Inspiration
• Dune Messiah
• Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity
• Children of Dune
• Talk Like TED: The 9 Public-Speaking Secrets of the World’s Top Minds
• The Dispatcher
• What You Do Is Who You Are: How to Create Your Business Culture
• The Fourth Turning: What the Cycles of History Tell us about America’s Next Rendezvous with Destiny
• The Startup Way: Making Entrepreneurship a Fundamental Discipline of Every Enterprise
• The Hive
• You Have 8 Seconds: Communication Secrets for a Distracted World

If you’re like me, you’ve probably experienced a variety of terrible one-on-one meetings.

As an employee, maybe you’ve seen the calendar reminder pop up and you’ve rolled your eyes, hoping that your manager will cancel or something else will come up. Or when the meeting actually happens, it quickly devolves into a boring status update. Or maybe you’ve been in a different situation where you really need to talk with your manager and are looking forward to finally getting a chance during your one-on-one meeting, only to have it canceled for the umpteenth time.

As a manager, you’ve probably maybe you’ve viewed these meetings as good opportunities to get status reports or “touch base.” Or maybe a quick chance to check in and then check it off the list so you can get onto other things, without giving it much thought.

Given how ubiquitous one-on-one meetings are, why are they so bad? And what can we do to make them not suck?

The Purpose of One-on-One Meetings
But before we can dissect why these meetings suck, we need to better understand the true purpose behind the meetings. Why are we having them in the first place? Or why should we be having them?

1. Coaching/Feedback — One-on-one meetings should primarily be about coaching and mentoring. They are a prime opportunity to give feedback, review goals, evaluate progress, and help employees continue to progress in their careers.
2. Team strengthening — These meetings are also a chance to strengthen the overall team by uncovering and addressing any underlying issues that may be happening. As a manager, this is a great opportunity to have frank and open conversations that may not happen elsewhere. The health of your team may depend on it, so don’t squander these meetings.
3. Brainstorming (Jam Sessions) — I’ve found one-on-one meetings to be a unique place to bounce ideas off of both managers and employees in a way that doesn’t happen in other meetings. These meetings can be incredibly useful brainstorming sessions for new ideas. I use the analogy of a jam session, since they can be less structured and more free-flowing and creative.
4. Rapport Building — Finally, one-on-one meetings build rapport between managers and direct reports. These are key relationships in the workplace, and need to be continuously cultivated. You should never assume that simply because there are lines on an org chart that there is some sort of automatic relationship with no effort.

Why They Suck
I’ve already touched on a few of the reasons, but let’s dive into why these meetings suck.

1. Status update meetings — way too often one-on-one meetings devolve into status updates. I get it. Managers are busy and it is a great time to get status updates and dive into the work that is happening. I’m guilty of this. And while a one-one-one meeting can be a good place to touch briefly on that, it’s not the right place to take up time on tactical items.
2. Lack of purpose — When there is no clear purpose to the meeting other than it is something that we “should” do, then it becomes something that gets put on the calendar and then becomes a status update meeting, or a something very similar. Without a clear purpose or agenda, the meeting devolves into suckiness quickly.
3. Lack of discussion — And when there is no real purpose other than to have a meeting and you burn through status updates and other tactical topics, you’re often left with not much else. Which can be awkward. And no one likes a meeting where there isn’t great discussion and it’s just two people sitting awkwardly in a room with little to discuss. Ugh.
4. Lack of direction — Finally, if there isn’t clarity who will direct and own the meeting, then there won’t be any clear direction for the meeting.

All of these things can be fixed, and I’ll discuss how we can address them below.

How to Make One-on-One Meetings Rock
I originally was going to say “how to make one-on-one meetings not suck”, but that felt like a low bar that, even though it kept with the theme of the article, really didn’t get us to the point I want to be at. So let’s make these meetings rock. Let’s make them something to be excited about and to look forward to. I love them as a manager. I’ve loved them (at times) as an employee. It would be great if everyone could look forward to them as an opportunity to grow and develop.

Make Them Regularly Scheduled
One-on-one meetings should be regularly scheduled. Most of us get that already. You must find the right cadence for your group. It may be every week, it may be every other week. You should meet with your direct reports that often. If you can’t, take a hard look at whether you have too many direct reports or other responsibilities and need additional help.

For non-direct reports, it’s a great idea to also regularly schedule some time.I’ve done this with folks and also had managers a few levels above me schedule time with me monthly to check in. It is highly appreciated. It is very helpful.

Finally, while you can’t always get out of the office, take time occasionally to move your meeting out of the office. Grab lunch or coffee or simply go outside. It’s nice to get a change of scenery and it helps make the conversation more personal every once in a while.

Show Up and Fully Focus
As a manager, now that you’ve got your meetings scheduled, show up on time and don’t make a habit of canceling them. Most folks understand if you need to move things occasionally. But if you make a habit of it as a manager, it will give the impression that you don’t care about your employee.

I had a manager many years ago who not only wouldn’t regularly schedule one-on-ones, but whenever I would schedule a meeting with her, she wouldn’t show up. No notice or anything. So I’d have to reschedule and reschedule to even get her to acknowledge it. It was more exhausting than you can imagine. And when I gave up trying to get time with her, I got in trouble for that too. Don’t be like that.
In the meeting, both as an employee and a manager, focus your attention. That may mean closing your laptop and putting your phone away unless you need it for your agenda or notes. But if you do need it, close down Slack or Teams or Outlook or whatever else might call your attention. Because it is too easy to get consumed if you don’t. This is time to focus attention, not to answer emails.

Have a Loose Agenda
Create a shared agenda and keep it in a place where you both can edit it to prepare for your meeting. I’ve used a variety of tools for this, so anything from OneNote to Evernote can work. You just need somewhere you can both access it and make changes.

As an employee, you should be driving these meetings. Your manager is there to help and guide you, so take advantage of that. As a manager, you should be letting your employees direct. They may need some help, so establish an outline if they need. It can follow something like below.

Life Updates: Some might view this as small talk, but I mean it to be actual real talk. Take time to actually get to know each other and what is going on. This goes both ways. Remember, this meeting is about establishing rapport. It’s a two-way street.

Status Update: I know I said these meetings aren’t about status updates. To avoid devolving into a status update, I suggest actually posting a status update somewhere else. Maybe wherever you’re storing your shared agenda. That way the manager can have visibility into what is going on without having to take up too much time in this meeting. But we all know that it will likely be a topic of discussion here. So let’s just add it to the agenda, time box it, and get it out of the way.

Career Focus: This should be much of the meeting. This is a chance to review goals, check progress, and talk about next steps for progression. Remember, this is a strategic meeting. It should be focused on the long-term. Way too often we set goals at the beginning of a year or quarter (since we’re required to in whatever HR system we use) and then forget about them until we have to review them for annual reviews. Sound familiar? Of course it does. But it doesn’t have to be that way. It shouldn’t be that way. We should be setting meaningful goals and then we should review them regularly together to see how we’re doing. This is a great opportunity to do that.

Feedback/Coaching: The one-on-one meeting also offers managers the opportunity to regularly coach and mentor their employees. However, feedback should be ongoing and real-time. These meetings should be more of a chance to review feedback from the week and see how it’s gone. As a manager, I shouldn’t save my feedback from last week’s meeting until my one-on-one. I should give it immediately, good or bad. And then we can talk about it again when we meet in our one-on-one to see what progress has been made.

Jam Session: Finally, one-on-ones offer the chance to bounce ideas off each other. As an employee, it gives me the opportunity to get feedback on ideas I may have. As a manager, it gives me the opportunity to get feedback on ideas for the team or organization from individual employees. The setting is perfect because everyone can be much more open than they otherwise may be in a bigger team setting. We can talk about important changes that may be coming up or other items that may be on our minds.

Prepare and Take Notes
To make these meetings meaningful, it is important to prepare ahead of time. Having and creating and agenda is one key part of this. The one-on-ones where I’ve had agendas have always been more organized than the ones where I haven’t. Why? Because it has forced me to prepare beforehand. So prepare an agenda.

Give yourself a few minutes to get ready before as well. This is just good advice for any meeting, but especially for one-on-ones. These aren’t meetings that you can bluff your way through or just show up to. You need to put in some time, look over your agenda and notes, and be ready for. That goes for both managers and employees.

As I just mentioned, you also need to take some notes. Take notes during the meeting. This goes for managers and employees again. You’ll both likely have takeaways and to-dos. So write things down. Put the to-do list in the agenda so you both have access to it and can see it! That way you won’t be starting from scratch in the next meeting. You can pick up from where you left off and have a meaningful conversation.

As an employee, I’d suggest you prepare to share some success or win. It will start the meeting off on a great note and get the energy up. Even if you’ve got some bad news for the meeting, sharing wins is a good place to start. It can be personal or professional.

As a manager, I’d also suggest you prepare something to share as well. I had a manager who always had an interesting story to share when I met with him. It usually had nothing to do with work, but was just an interesting fact or story that he had learned that he wanted to share. It was a nice way to start a meeting. Find something that fits your personality and go with it.

Ask Good Questions and Ask for Feedback
Ask good open-ended questions. This goes throughout the meeting. It may help to kick things off by asking a question to start. There are a number of sites that offer good questions. But it is helpful to have a number of questions ready to ask throughout the meeting as well. Some examples include:

• What do you like best about your job?
• If you could change something about what you do, what would it be?
• If you could change something about what I do, what would it be?
• What has you most concerned about our team right now?
• If you could have any one superpower, what would it be?

Finally, wrap things up by asking for feedback. Both as an employee and as a manager. There are always areas to improve, so be open to ways to improve them.

To make this successful though, be ready to offer feedback. And that is where it gets difficult. So you need to think of ways that your employee or your manager can improve. And then be willing to share. Which can be uncomfortable. But is so necessary.

I had a manager who would always ask for feedback at the end of every meeting. He was a great manager, and I rarely had anything to offer. But he would always press the issue. It was tough because he only would occasionally let me off the hook without giving feedback. I’ve adopted that same practice now. I know that I have many areas for development, and I expect others to offer candid feedback.

One-on-one meetings have the tendency to suck if you don’t put some effort into them. But they don’t have to. We can make them awesome with a little work. It just takes some preparation, thoughtfulness and feedback. But by putting in the work, we can get so much more out of the time we put in. We can grow as employees and as managers. And in turn, we can see incredible returns within our teams and organizations.

Like many of you, I’ve struggled at times to describe to friends and family what I do for a living and what product management really is. It is especially hard to describe to anyone outside of technology. And to kids. Which can be frustrating, especially since I’ve been doing it for over a decade (whoa) and certain folks (hey mom!) still have no idea what I do. But for those of us who’ve been here a while, we should really be better at simplifying what we do.

Some of you may be here to better understand product management in general. Others may want to better describe what it is to friends and family, or to simplify it to start the conversation for other reasons. Or maybe you need to present what you do at career day and need some ideas. Regardless, I hope this helps.

Product Managers Are Builders
For our 6-year-old, a simple example that has seemed to work well has been the example building a home. Especially since he got to see our new home as it was being built from the ground up. I’m simplifying a bit here, but it let’s go with it for a moment:

The builder is a key person in the construction process. He works with the family to understand the kind of home that they want. Where they want the kitchen, where they want the bedrooms, etc. He works on understanding their needs and then helps build a home that is great for them. That’s his job.
Once he understands the family’s needs, he then works with the teams of people who build the home to make it all happen. The cement truck that pours the foundation, the guys who build the walls, the people who put in the kitchen cabinets, the people who put in the carpet to make sure it is just what the family needs.
That’s very much like what a product manager does as well, except rather than with homes, she does it with software — applications on computers or phones. She works with users to understand their problems and then she works with teams of engineers to create features to address those problems or needs. All of the cool games on your phone or tablet have a product manager that works on them. She is the builder who understands what makes them fun to play. Then she works with the engineers (those are the people who know how to write the code to tell the tablet how to make the monkey swing on the branches and how to make the music play) to build the application so you have a game to play.

Product managers, like builders, work with customers to understand their needs and create solutions to problems. There are certainly some nuances to that we miss, but I think the builder analogy gets to the heart of the idea.

Going Deeper
Of course, we’re not 6-year-olds, so we can take this a few levels deeper (though hopefully that is helpful in any conversations you may have with your kids). And while the analogies are not perfect, as no analogies are, they illustrative of product management in many ways.

Product Managers Are Architects
Let’s stick with our building analogy for a moment, but take it a step further and make it a bit more technical. Let’s talk about architects.

If you’re like me, the first thing you think of when you think of an architect is a big table with drafting paper and rulers where they can sketch out a detailed drawing of their next skyscraper. They’ve got the big vision for a grand building. Maybe the next Empire State Building. And that is certainly part of their job.

But another part of it is all the details. Because that skyscraper or house or school has to have ventilation and plumbing and electrical systems, and all of that has be taken into account in the architectural design. They also have to think about the building codes and fire regulations and zoning laws, etc. So while the architect certainly has to think about the big picture and beautiful end result they want to achieve, they also have to go through all the details of how to get there.

Product managers are architects in the same way. They have a big vision about the software product (or products) they are building. They want their app to be the next Instagram or Fortnite. They have a long-term roadmap that shows the way to get to something big. But they are also focused on all the little details as well. Things like “adding better error handling” to timeout messages. Or speeding up the login page so it shaves a second or two off the time it takes you to log in. All while building out the experience within the building that will eventually lead to the bigger vision.

Product Managers Are Small Business Owners
Many people have written about product managers as CEOs of their products. I even dove into that debate a while back with 6 Ways the Product Manager is the CEO. I like the analogy of a product manager as a CEO, but I like the analogy even more of a small business owner.

A business owner isn’t nearly as lofty as a title, which makes it more apt for a product manager. A business owner often has to be scrappy, especially when you think about a small business owner. If you own the local bakery down the street, there is a good chance you wear a lot of hats. You probably have a team of people working with you in various roles, especially as you’ve grown, but you know the business inside and out. You are ultimately responsible for its success. You’ve delegated responsibilities and trust your team to execute, but you know the buck stops with you.

As the business owner, you are also keenly aware of the financial impact of the decisions you make and how they impact your business. Opening an hour earlier has certain costs and certain benefits, and you analyze both sides. Adding items to the menu as well. Maybe you’d love to expand your bakery and offer a wider array of services to your customers based on their feedback, but you’re always carefully analyzing the feasibility and desirability of doing that, experimenting continuously before committing significant resources.

These characteristics tie in nicely to product management. Product managers own their products just like a small business owner owns their business. Product managers generally aren’t the boss or manager of the people on the team, but they own the experience of the product.

If customers are having issues or requesting features, the product manager analyzes why that is and what the solutions might be, never stopping at simply “adding something to the menu” because someone wanted it. They work to understand why they wanted it to address the underlying issue. And like a true owner, they have to understand the cost associated with adding features. Because everything they do has a costs and benefits associated with it, and they understand that.

Finally, product managers wear a lot of hats in their roles, just like small business owners. They are scrappy, often moving from talking with customers one minute to checking on their teams the next minute to making sure that their application is functioning fine the next minute. They are truly small business owners, entrepreneurs within their own worlds.

Product Managers Are Guides
If you’ve ever booked a trip somewhere with a guide, you likely know of some benefits you get. First, they are experts in areas you are not. Second, they allow you to maximize your efficiency. They put in a lot of work for you, so you can focus on the areas you’re more concerned about, like seeing the sites. Finally, they create the plan and can adjust as needed based on the needs of the group, the conditions at hand, and changes that arise.

A good tour guide is an expert in the area they are taking people. They can communicate the map and itinerary so that everyone is clear what the plan is. They also understand the group they are working with. Each group is different. A tour group of 30-year-olds differs immensely from a group of 70-year-olds and a good tour guide will adjust accordingly.

My mom has worked as a tour guide in southern Utah for several years now, and I can attest that anyone who is fortunate enough to go on a tour with her is getting all the above-mentioned benefits. Few people are as avid about the outdoors as she is, and she knows all the national parks like the back of her hand. That includes all the hiking trails, which ones are easiest, which ones are hardest, where the crowds are most likely to be at what times, etc. So whenever one plan doesn’t work, she can adjust to another without missing a beat.

We were recently on a family vacation to one of the national parks and availed ourselves of her expertise. We had young kids in our group, so we wanted some easy hikes to see some things. She pulled out the map and laid out a plan for us, showing us a couple things we could see along the way and then what we could do if it parking was a problem. It was great. We could do a couple easy hikes that everyone enjoyed and quickly move from one area to the next without trying to figure out what we should do next. My mom knew what we wanted to do and got us to it so we could get to enjoying the park.

Like a good tour guide, a good product manager is an expert guide for their product.

A good product manager is an expert in their product area. Like a tour guide, a product manager has to know the terrain to guide others through it. So product managers have to become deeply familiar with the software they work on, whether that is applications for phones or software for computers, etc. While that doesn’t mean product managers have to be as technical as software engineers, it means they often have to be technically fluent depending on the product and area they work in.

A good product manager minimizes the time to value. Like a good tour guide, good product managers bring efficiency to software development. Yes, you can travel to a foreign country and find your way around on your own without a guide. And yes, you can build software without a product manager or someone in that role. But chances are you may end up wandering around quite a bit more than you need to. If you’re on vacation, that may be fine. If you’re building software on a budget in a business, that may not be the route you want to take. A product manager reduces the time to learn what is the right thing to build for your customers and your business.

A good product manager can create a plan and adjust that plan as necessary based on the needs of the product and the needs of customers, stakeholders and the business. Just like a guide builds an itinerary and adjusts it based on the group and what happens with the weather and the crowds, a product manager builds a roadmap and a strategy for their product based on their outlook for the business and customer needs. Then, as the product evolves, along with the business and customers, the product manager also evolves the roadmap to account for those changes. It is an ever-evolving and ever-changing strategy. The plan we put in place will never be the plan that we fully execute.

Product managers, like architects, business owners, and guides, wear many hats in their roles in software development. They help create the vision of a product, they own it from start to finish and the have responsibility for the team that is delivering it, and they help guide customers, users and the business all along the way.

Product manager is not an easy role to describe because it is always evolving and changing. But that is largely what draws so many people into product management — the fact that is always moving and changing.

Ultimately, a product manager coordinates the many moving pieces, ensuring that the overall experience remains cohesive and ultimately solves the right problem for the user in a way that makes sense for their business.