One of the topics that come up a lot in the CPO Bootcamp is the relationship between the product leader and their manager. It can be the CEO, the CTO, or a business unit manager, but by definition, they are almost never product people. This relationship is complicated as is, since both the product leader and the manager try to lead the company in a certain direction, and in a product company this is done through the product itself. I have written about it a lot – what to do when your CEO has a new product idea, how to say no without ruining the relationship, and other specific dilemmas that you are probably facing. 

In the last coaching session of the CPO Bootcamp, D., the VP Product of an established startup, said that he once got advice from someone who told him that it is his job to keep his boss happy. D. was puzzled since many of the topics we touch in the CPO Bootcamp are meant to challenge the way the company management sees things, and that is not necessarily aligned with keeping them happy. I thought this conflict brings an interesting perspective on this topic as well as some insights that are worth highlighting. 

Your Boss Needs to Be Pleased

Let’s start with an obvious truth that needs to be told: your boss needs to be happy with your work and the value you bring to the table, otherwise you won’t stay there for too long. Sometimes, in our effort to bring our professional truth to the surface, we forget that. When stated clearly it sounds almost obvious though.

But what is it that makes them happy? It’s not always easy to know since they are not product people and can’t guide you the way you used to be guided in previous positions. One of the hardest things in your role is that you now need to manage yourself at a level that you most likely never did before. This includes being proactive and initiating early things like roadmap planning: we all know that it’s coming, yet we are almost always surprised when we are asked to define it. As a product leader, you should think about it before you are asked to do so, and ideally should drive this effort yourself and not only when asked. Another example is identifying gaps in the strategy or execution that no one else sees, and work on closing them – by yourself or as it mostly happens by aligning with other leaders and driving the company to make hard decisions.

What executives (your manager included) typically want from you is full accountability. They want you to solve their problems, not create new ones for them to solve. So while it is indeed part of your job to call out everything that is not working, make sure to not just leave it there for them to solve, and make it yours to close.

But You Can’t Afford to Be a Pleaser

The one thing you can’t do though is to do what your manager asks you to do simply because they said so. It sounds counterintuitive because I just said that it is your job to keep them pleased. But if you look into it, you will see that there is actually no contradiction there.

Think about your own employees (if you never managed people, think about the people you buy services from). Is what you want from them to always say yes and do as they are told? Most likely no. And it’s not just that you are fine with them saying no every once in a while, you want them to do that. You want them to challenge your thinking because it makes you a better thinker. You want them to highlight the things that are not working because if you miss them it is your results that will be impacted. So not only you are fine with them not being pleasers, being pleasers is actually a bad thing.

Another example of this is with any service provider you have. In my case, it can be my accountant or my graphic designer – anyone that you hired because they are professionals. Whenever I tell them to do something other than what they suggested, say I got a design from my graphic designer and suggested a change to it, if they just say “ok” and do it I am not happy. In fact, I am terrified. Because I can’t know if they are doing it only because it is me who pays their salary, or because they think – with all their professionalism – that this is the right thing to do. I hired them for their professional experience, and while I have an opinion (especially on things like design and product, by the way, anyone has an opinion and that’s ok) I don’t want it to be automatically accepted if it’s not the right thing to do. Don’t confuse your manager’s legitimate need to participate in the discussion and understand how you think with an intent to override your decisions.

Here is a magic trick that will help you balance doing what is good for your managers and what you believe is good for the company: instead of trying to do what they want, ask your managers how you can help them. It immediately positions you as their partners in the mission (which you truly are) and opens the discussion to things that you might not have thought of. Once they know you are on their side, you can call out almost any problem you see, and they will know you mean good.

As always, explain why you are doing things to keep reminding them that, but don’t revert to saying yes to something you don’t believe in just because you couldn’t convince them. Only do so if you truly believe it doesn’t matter and isn’t worth the effort. Otherwise, you will find yourself in a passive-aggressive mode (“let’s agree to disagree, but I’ll do it anyway since you are the boss”), and that anyway doesn’t count as pleasing.