Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After

by Matt Lemay

I’ve been surprised at how quickly a team can be turned around with a simple and transparent acknowledgment to the tune of “Yes, I don’t necessarily agree with this decision—but we work for a company with a lot of moving parts, and we won’t always agree with every decision that gets made. I do think that we have some great opportunities here to make sure that this work solves a real problem for our users, and I’m excited for us to explore those opportunities together.”

Earlier on in my product career, I was ill-equipped to handle the emotional side of the job. So much of product management is leading without authority, which means repeating yourself a million times over—something that requires an inordinate amount of patience and confidence. Lacking both patience and confidence, I’d take refuge in product and engineering team meetings—“product therapy,” as we’d call it. During these meetings, I found myself commiserating with my team over difficult stakeholders, not being appreciated enough, and everything else that was/is part of the job. At first, these meetings seemed like a safe space to say what I needed to say and to get things off my mind. The us-against-them, David-versus-Goliath mentality felt invigorating. It gave me a sense of purpose, like if I couldn’t succeed in moving a product idea forward, at least I had the support of the people. In the end, none of this worked out well. The safety of the moment was fleeting, but the frustrations were kindling for a longer-burning fire of emotions. It’s easier to say this looking back, but I fueled a lot of these fires out of a need to soothe my own ego, rather than accepting what I could control and moving on. The in-the-moment trauma bonding was addictive, and gave me the sense of a higher mission. While I have remained friends with some of my coworkers, I see in some instances that apart from the negativity we shared, we really didn’t have much in common. Being a product person requi...

But when there’s a fundamental mismatch between what the business wants and what your team wants, you can’t resolve it by ignoring the business in the name of “protecting” your team.

Several years ago, I was tasked with putting together a new roadmap for a company where I worked as a product manager. I spent countless hours slowly getting buy-in from all parts of the organization, hearing people’s concerns, making adjustments, and putting something together that seemed both impactful and achievable.

After the meeting where our leadership team collectively agreed to this roadmap, one senior stakeholder pulled me aside. “You’re such a creative person,” he said, “I’d love for you to present a more creative option the next time we all meet.” Oh, heck yes! I put my “creative person” cap on and spent the better part of the next week putting together something truly awesome—the plan that I had really wanted all along. The day before the next week’s roadmap meeting, I sent that senior stakeholder an email, which, to the best of my recollection, was approximately 10,000 pages long. It detailed my plans for a brave new direction and thanked him for unleashing my creativity. I slept very well that night, confident that I had the blessing of one of the most senior and important people in the organization. The next day’s meeting was, in short, a bloodbath. No sooner did I begin to present my great new idea than another senior stakeholder jumped in with, “Wait, I thought we had already agreed to a roadmap last week? What the hell is this?” To my great shock and indignation, the very senior stakeholder who had asked me for a more “creative solution” then began berating me for taking the project so thoroughly off course. I threw my arms up in exasperation and did my best to fight back tears. How could he do this to me? I was very angry about this for a long time. But in retrospect, I made no less than two huge mistakes in the way I approached that fateful meeting. First: I essentiall...

The solution here is pretty simple: nothing that you are telling a senior stakeholder in a “big” meeting s...

Navigating company politics can seem like a lot of work—and in most cases, it is a lot of work. However, it is critical for you to remember that your success ultimately hinges not on your ability to make stakeholders happy but rather on your ability to make users happy.

Here are a few tips for staying user centric even as you navigate company politics:

Let your users make the case for you. Remember that you are ultimately building a product not for your stakeholders but for your users. If you are doing the work of regularly talking with and getting feedback from your users—which you absolutely should be—you should have plenty of information at your disposal to bring your users’ needs to life as you present options to senior stakeholders. If you find that you don’t have a clear sense of why your users might need a thing you are proposing to build, you probably shouldn’t be proposing it in the first place.

Connect user needs and business goals. It is not uncommon for product managers to find themselves feeling like they are advocating for “what’s good for the user” against executive mandates to build “what’s good for the business.” But the biggest problem in this scenario is not an imbalance between user needs and business goals, but that these two things are perceived as being at odds with each other in the first place. If you feel like you are caught in a tug-of-war between business goals and user needs, the solution is not to pull harder, but rather to make sure that a clear and positively correlated relationship has been established between the needs of the user and the g...

Flip the script and ask senior leaders about users. If you’re looking to encourage user centricity throughout the organization, ask your senior leaders what they know about the needs of your users. Make it clear that your goal is to help them deliver value to users and meet the goals of your business. Invite them into a conversation in which you are collaboratively exploring multiple solutions to a well-understood user need, rather than debating a single, predetermined solution.

Senior Stakeholders Are People Too Last but not least, remember that senior stakeholders are people too. They have their own concerns keeping them awake at night, their own battles to fight, their own hopes and ambitions and frustrations. Your interactions with them may seem very important and significant to you, but they are likely preoccupied with lots of other things. Keep this in mind when you feel like you aren’t getting the recognition or validation that you want from senior stakeholders, or when you are convinced that senior stakeholders are purposefully withholding information from you. Odds are they’re just really busy, and the information you think they’re withholding may very well be information that they themselves simply don’t have.

Let’s look at three common scenarios you are likely to encounter as you work with senior stakeholders.

Executive: I just saw the work your designer is doing. I don’t like the colors, and it doesn’t look anything like the product I signed off on!

What’s really going on The executive in this case feels like he’s out of the loop. Something is moving forward that he doesn’t recognize, and it implicitly threatens his sense of authority and control.

What you might do First, you might want to straight-up apologize. If the executive is seeing something that feels new to him, then something about the way you are getting product ideas and designs approved is not working as well as it could. Explain to the executive that you never want anything to feel like a surprise or catch him off guard. Ask what you can do to make sure that he can see works in progress on a timeline that makes sense for him.

Patterns and traps to avoid

This is the exact thing you signed off on. The only differences are purely cosmetic! Because you are speaking with somebody whose power and authority greatly exceed your own, you likely do not want to go into litigation mode. What is the real issue here? Is it the changes themselves, or the fact that this executive is seeing something that seems new to him?

I sent you the updated mock-ups last week and asked if you had any feedback, and you never responded! Anything short of affirmative and specific buy-in is not really buy-in. If your updated mock-ups were one of 10,000 messages to hit somebody’s inbox and you received no response—or even a generic “looks fine” response—you might as w...

OK, we’ll change the colors to whatever you want. If you read the executive’s comment carefully, you might notice that he is not actually asking you to change anything about the product. He is essentially describing a communication problem, not a prod...

Yeah, well, that’s just, like, your opinion, man. Even if “the colors are all wrong” is just an opinion, you’re better off not going down this road. Getting into a battle of opinions with anybody—let alone a senior stakeholder—is a bad move in the best of circumstances...

Executive: I know that your team is already working on something this week, but I’m really excited about that other feature we discussed a few days ago. Do you think you could find a little time to work on this as well?

What’s really going on On the surface, this might seem like an executive trying to sneak her own pet projects into your team’s tightly scoped work plan. But if you take this executive at her word, her motivation is excitement, not sabotage. If an executive is taking the time to come to you and express her excitement about a specific feature—even if it’s one that you are not currently planning to build—this is a great opportunity for you to better understand her priorities and how they align with your team’s priorities.

What you might do Have an open and transparent conversation about what makes this specific feature so exciting to the executive and why it was not prioritized by your team as part of the current week’s work. Maybe this executive was part of a high-level conversation that potentially shifted your organizational goals and you simply are not aware of that conversation. Or maybe this executive is really just super excited about this idea and is not aware of the specific goals against which your team is executing. Be open to the possibility that the feature that this executive is suggesting might actually be more important to the organization than what your team is building.

Patterns and traps to avoid

Yes! Immediately agreeing to a request like this not only undermines the existing processes your team uses to prioritize work, it also sets up the executive for disappointment when the actual thing you deliver doesn’t live up to the abstract idea in her head. Unless you have taken the time to fully understand why this feature is being requested, you are in no position to promise anything.

No! If an executive has taken the time to come to you and share their excitement about a specific feature, there is almost certainly an important reason. Even if you ultimately plan to stand firm on your team’s original priorities, take the opportunity...

Maybe. We’ll see how much time we have. The fundamental question here is not whether your team will have time to work on the new feature, but rather why this executive is so excited about the new feature in the first place. If you make this merely a matter of capacity, you are missing out on a critical opportunity to bett...

Executive: Listen—I’ve been doing this for a long time, and I just need you to trust me when I say that I know that this feature is going to be a big success. OK?

What’s really going on Executives are people too, and there are times when they get just as defensive and exasperated as you do. The difference is, they are able to trot out a more dressed-up version of “because I told you so,” whereas you almost certainly are not. There will be times in your career when you find yourself talking to an executive who would rather give you opaque marching orders than slog through the work of finding common ground—especially when you’re dealing with an executive from outside your immediate team who may not be familiar with your day-to-day work or experience.

What you might do By the time somebody reaches an executive position, they likely have many perceived wins under their belt, and those perceived wins have shaped their experience and expectations in ways that are always good for you to understand. One approach I’ve found particularly helpful is to say something to the effect of, “I’m super excited that you think this feature is going to be a win for us—help me understand your thinking here so that I can make sure I execute against this in a way that will continue to build on the success we’ve had so far.”

Patterns and traps to avoid

Whatever you say, boss! If the feature you build fails, it is very unlikely that this executive will say, “I was the one who insisted that this feature would be a success, so its failure is totally my fault.” It is much more likely that this executive will find some minor flaw in the execution and insist that “this whole thing would have been a huge success if they had just done it the way I told them to!”

Well, I think that this feature is going to fail. Unless you have built a very strong relationship with this particular executive, you are very unlikely to get much out of an opinion versus opinion battle. Even if you do think that this feature is going to fail, both you and the executive are almost certainly working with an incomplete set of information. Your job is to get as muc...

Sorry, but I’m not going to build something just because you tell me to. From the executive’s position, they are likely not telling you to build something “just because they tell you to.” They almost certainly have their own reasoning, and it is your job to understand that reasoning as best as you can, even if you don’t f...

Working with senior stakeholders is a particularly challenging and high-stakes part of a product manager’s job. There can be times when these stakeholders—especially founders and executives—seem to have an incredible amount of control over your fate and destiny. But remember, executives are people too, and they can fall into the same traps of self-doubt and defensiveness that you do. Help them make the best decisions they can, learn from their experiences, and stay patient and curious.

When working with senior stakeholders, don’t set out to “win.” Help empower them to make great decisions and demonstrate that you can be a valuable and supportive thought partner.

Come to terms with the fact that you won’t always get the answer you want from senior stakeholders and that this is not a reflection on you personally.

Don’t try to “protect” your team from senior stakeholders by talking about how ignorant, arrogant, or out of touch these senior stakeholders are. Instead, openly acknowledge the constraints within which you are working an...

Never surprise a senior stakeholder with a big idea in an important meeting. Socialize ideas slowly and deliberately in one-...

Don’t let company politics drown out the needs of your user. Let user needs guide your decision-making, and bring the user’s perspective t...

Take every opportunity to connect business goals with user needs to reinforce the busines...

When senior stakeholders ask you questions like “Can this be done by Tuesday?” take their questions as actual que...

When confronted with a swoop-and-poop, don’t try to litigate the details of past conversations. Look for opportunities to diagnose and address the underlying issues so that the swooper-p...

If a senior stakeholder suddenly wants your team to work on something different, find out why. There might have been an important high-level ...

Remember that senior stakeholders can get defensive and exhausted, too. Stay ope...

In many ways, talking to users seems like it should be the easiest part of a product manager’s job. I mean, how difficult can it be? Find some users, talk to them, and before you know it, you’ve got the whole “user centricity” thing in the bag. But talking to users can actually be the most difficult thing for a product manager to learn. Why? Because many of the behaviors that can help a product manager successfully work with stakeholders are exactly the wrong behaviors for learning from users.

When working with your stakeholders, you want to draw compelling connections between high-level strategy and executional details. You want to present options, explain trade-offs, and empower your stakeholders to make the best possible decisions they can. And when it comes time to make those decisions, you want specific and affirmative commitment to a path forward.

When talking to users, your goals are very, very different. Your job is not to explain, to align, or even to inform. Instead, your job is to learn as much as you can about their goals, their needs, and their world. Returning to our third guiding principle, this means immersing yourself in your users’ reality, rather than dragging them into your company’s reali...