The first time my dad met his future father-in-law, he was invited to join in for a friendly game of after-dinner poker. My dad, much like myself, is not somebody who has generally excelled at competitive rituals associated with male bonding. He also, much like myself, is not very good at cards. However, in this particular situation, he wasn’t too concerned about his skill level. My dad’s goal was not to win the poker game, but rather to make sure that his potential future father-in-law won the poker game. From what both of my parents have told me, this worked quite well.
I’ve thought about this story many times during my career as a product manager, especially when I’ve found myself sitting in meetings with people who have much more organizational authority than I do. In most high-stakes meetings—as in some high-stakes poker games—“winning” doesn’t necessarily mean the same thing to everybody at the table. And when you are working with senior stakeholders, the best way to “win” is often to help somebody else win.
In theory, working with senior stakeholders should be no different from working with anybody else in an organization. In practice, this is rarely the case. For better or worse, senior stakeholders often wield the power of “because I said so.” They can override your priorities. They can shift goalposts when you’re midway through a project. Or, they can shift goalposts after you’ve finished a project, and then fire you for failing to meet your new surprise objectives. Senior stakeholders will always win the poker game. Your mission, should you choose to accept it, is to ensure that your business and your users win along with them.
In this chapter, we look at some real-world strategies for working with senior stakeholders, a challenge often referred to in business parlance as “managing up.”
Occasionally, somebody will ask me if I think there is a situation in which a product manager simply cannot succeed. I always have the same answer: a product manager cannot succeed if there is not clarity among senior leaders about a company’s strategy and vision.
Though this can sound a bit fatalistic, it is downright empowering if taken the right way. Basically, this means that your job is to push upward for clarity at all costs. If you don’t have that kind of clarity, there is no way for you to succeed in your role. Which also means that, if you don’t have that kind of clarity, you have literally nothing to lose.
A lack of clarity about company strategy and vision might arise when multiple senior stakeholders are pushing and pulling for their own strategy and vision. Perhaps one senior leader sees the company pivoting, whereas another feels that it is important to stay the course. Perhaps there are multiple senior stakeholders implicitly competing for their boss’s job, each working to sabotage and undermine the others. As a product manager, it is all too easy to become collateral damage in somebody else’s quest to vanquish their organizational foes.
In many cases, though, the challenge is not that there are competing visions for the company, but rather that there is no vision at all. Showing up to work every day with no real goals or strategy to work against can feel liberating—you’re free to do whatever you want! If the developers on your team want to spend three months refactoring code, sure, we can do that! But any true vacuum around vision is only temporary. At some point, somebody is going to step into that vacuum and ask you why you’ve been doing what you’ve been doing. And if you don’t have a good answer, that person will likely not have a lot of faith in your ability to succeed as a product manager.
In keeping with our guiding principle of “no work beneath, no work above,” this means that you must be willing to step up and work towards defining the company vision if nobody else will. If there are senior stakeholders pushing competing visions for the product, go as high up in the organization as you can to get a clear sense of what goals you should be executing against. If you have a CEO or a departmental leader who won’t commit to goals or clearly articulate a vision for the product, do everything within your power to get some face-to-face time. And then let that person take full credit for the vision that you helped create. Remember, CEOs or departmental leaders are going to win one way or another, and you are much better off if they win by the rules that you created together.
When product managers fail to push upward for clarity, they tend to retreat into building cohesion within their own team at the expense of their team’s connection with the organization as a whole. Early on in my career as a product manager, when a request came in from senior leadership that felt unreasonable, my first thought was always, “Oh no, my team is going to blame me for this.” In an attempt to emerge blameless, I would end the conversation with senior leaders as quickly as possible, go back to my team, and say something to the effect of, “Can you believe how those idiots are jerking us around? WELP, I guess this is what we’ve got to work on now. *Cough* NOT MY FAULT.”
In the moment, this can feel like the only way to keep the trust and respect of your team while also placating senior stakeholders. But in the long term, it never works out. The second you go to your team and say something like “our boss is an idiot,” you have effectively ruined your team. They will begin to see any and all requests that come down from senior stakeholders as arbitrary and unreasonable. The time and energy they spend working on projects that align with organizational goals will feel like grudging concessions to the powers that be. And the time and energy they spend working on projects that do not align with organizational goals will feel like “sticking it to the man.” They will see your role as protecting them from senior stakeholders, rather than connecting them with senior stakeholders. And you will have backed yourself into a corner where the trust and support of your team hinges on you dutifully performing this role. In the interest of protecting and defending your team, you will have set them up to fail on the organization’s terms.
So, what do you do when a directive comes down from senior leaders that doesn’t make sense? You manage up for clarity. You explain to those senior leaders why it doesn’t make sense, what trade-offs are at play, and what the downstream implications of their demands might be. Treat them like partners, not like idiots. If you feel that their suggestions don’t align to a clear vision or set of goals, help them articulate that vision and define those goals. When you go back to your team, take ownership of the decisions that were reached. Don’t blame the suits. Explain why these choices were made, share your point of view, and tie it back to goals and vision. Even if your team is frustrated in the moment, you are setting them up for success on the organization’s terms, rather than pretending that you will somehow be able to win on your own terms.