My husband and I went on vacation to a hotel in northern Israel over the weekend. During our stay, he pointed out to me the many tactics the hotel uses in order to lead guests to behave in a certain way. For example, to make sure we sit in a specific dining room section, they would only set the tables there. Another example is that the juice glasses are usually small, because juice costs money. While the juice itself is unlimited, if we take several glasses, the hotel staff won’t clear them from our table. The glasses remain in front of us for everyone to see, making us conscious of how much we drank (and what other people might think about it).

The hotel staff is not our managers, and they would never tell us not to get more juice. Despite having authority, they wouldn’t use it on us, but they could influence how we behaved nonetheless. Obviously, these measures won’t work with everyone, but it only has to work with a majority of guests in order to save a lot of money.

The same thing happens in managing up: while you’re not your CEO’s manager, you still need to manage them in a way. If you don’t do that, your connection with them could suffer, and you might get frustrated as a product leader. You may think you are mostly expected to follow their orders, but this could result in you ending up not doing what they need you to do. Remember that what they ask you and what they really need from you are two different things.

Your CEO Is Not the Problem

Relationship difficulties between the product leader and the CEO often come up in my CPO Bootcamps. Usually, the product leaders complain about their CEOs, saying that it shouldn’t be handled this way or that their CEO needs to act differently. They emphasize how uncomfortable it is for them. 

While it is, indeed, uncomfortable, and they have my full empathy, this is a very common situation, and most likely your CEO is not the problem. Most CEOs are assertive yet reasonable people, and there is a certain way to work with them well. Blaming your CEO for the problem is an easy way out, which prevents you from taking action and responsibility in the matter. Most people cannot replace their CEO, and even if they move to another company, it would not solve their problems because other CEOs would most likely act the same way. When you say or even feel that the CEO is the problem, you are left helpless.

But as I said earlier, the problem itself is real because it’s often in the nature of the relationship: The CEO doesn’t see the details at the level you see them and rarely understands how you operate, think, or work, especially if they do not have product background. At the same time, they may have other factors that you are unaware of, or additional information that paint a different picture for them. 

If you’re in a product company, this problem could even get worse since your role as a product leader is in many ways to lead the company alongside the CEO, which could increase the friction. Therefore, finding the right balance between your roles becomes even more critical for both of you.

As a product leader, it is your responsibility to manage this relationship and make it productive. To accomplish this, you must first let go of any notion that the CEO should be the one to change. Instead, you need to focus on ways to make it work, and there are many ways to do that. 

Side note: It may be necessary to move to a new company if you are 100% sure the CEO is the problem, but if there is any way you could work with them, give it a try. From my experience, there is a lot you can do to change the relationship. I had the privilege of working with many product leaders who had a complicated relationship with their CEOs, and after a quick process, we were able to create a significant transformation. 

Leading to a More Productive Conversation

When your CEO comes to you with requests, you will often see them as commands rather than instructions, but it is usually not their intention. In most cases, they seek your input, but it might come across as a demand, if they don’t express it well.

Try to put yourself in their shoes and think about the relationship with the people you manage. Is everything you tell them a direct order? Usually not. You manage intelligent people, and you want them to think. The same goes for you and your CEO.

Keep in mind that the CEO wants your perception even if they don’t ask for it explicitly. If there is a real problem with what they want to do, they surely want to know that, and it is your obligation to tell them. Remind yourself that even if it doesn’t seem so, making all the decisions by themselves could be terrifying for your CEO, and they hired you to help them, not to be their yes-men.

They might not always agree with you, but you need to keep in mind that (1) they won’t be able to agree if you don’t share your considerations, and (2) the discussion you have with them is crucial, so even if they disagree, it’s not the end of the road. You can take the discussion to another level by sharing your reflections and tradeoffs, which could lead to a more productive conversation.

Give Your Recommendations the Right Way

Working with a CEO correctly includes providing them with your alternatives, the pros and cons of each choice, and your recommendation. Don’t skip this last part, because speaking up is the only way to give your CEO a chance to accept the direction you want to take them in. On the other side, a recommendation alone is usually not enough for them to take action. It is your responsibility to explain why you prefer option A over B and give them all the necessary information to make the right decision, based on your suggestions.

The best way to build trust is by allowing them access to your thoughts, but leaving the final say to them. It also shows the CEO you gave it thorough consideration and didn’t just go with your gut feeling while opening the conversation to additional – potentially better – alternatives. The discussions could lead you both to better understand your initial decision or open a different option you hadn’t considered.

If you want a particular outcome, there are many ways to get there. The first thing is understanding the stand you take in the matter and then stating it clearly. You can’t expect magically for your CEO to understand what you think, and you need to help them help you by giving them a good, clear recommendation. Also, make sure you do not come across as defiant since you want to avoid provoking objections.

When you make your recommendation, though, make sure it is one that your CEO can actually accept. For example, I had a participant in one of my CPO Bootcamps, a VP Product in a mature startup, who did extensive research into their pricing model. He realized that their pricing should change, allowing the company to become more profitable over the long run, but they will suffer significant losses in the short run.

When he suggested the new model to the CEO, it was rejected. During the CPO Bootcamp, we looked at it from the CEO’s point of view and realized that this was a proposal he simply could not have said ‘yes’ to. 

Most CEOs would have a problem with significant losses in the short term, which could cause them to either tell you ‘no’ straight to your face or otherwise leave them with a problem they need to solve on their own. It truly is a difficult situation to solve. But if you genuinely want to work well with your CEO, you need to take on the hard work and reach them with a mature solution to the problem, which takes into consideration everything there is to take, including conflicting interests, and thus could result in a ‘yes’. It was only when the aforementioned VP Product took the CEO’s consideration into account that he was able to come up with a creative suggestion that would work for everyone. It was the only way to get to a ‘yes’.

Remember that you need to help them solve their problems, not create new ones. This is true also when you escalate things to them – you must be clear about what kind of help you need, not just tell them you have a problem and let them figure out what to do.

So here are the guidelines to put in front of you at all times:

1.     Make sure you fully understand the CEO.

2.     Ensure the CEO knows you understand them by asking if you got it correctly. This will help build trust.

3.     Get back to them after considering all the options, show them how you thought about the problem, and explain the tradeoffs and alternatives.

4.     Make a recommendation they can say ‘yes’ to.

The last part is the most challenging of course since you are the one to do the heavy lifting and solve a complicated, sometimes conflicting, almost unsolvable matter. But that is why they hired you as their product leader. There isn’t always a simple solution, but it’s much easier to find it once you know where the CEO is coming from, consider their needs, and make an educated and explainable solution. Hey, we never said it was easy, but that’s all the fun, isn’t it?