G. was a great product manager who worked for me. He was super sharp, always kept all the details in his head, and knew immediately when the dots didn’t really connect together. The developers loved him. Other product managers loved him. Salespeople loved him. But when it came to working with executives, G. couldn’t nail it. Time and again I saw him frustrated by how much they don’t get it, and time and again I had to convince upper management that he wasn’t a lost cause.

G. knew that this was his weak spot. His previous managers already identified that. He really wanted to work on it. But no matter how hard he tried, it didn’t seem to work. Since G. was such a great product manager, when there was an opportunity to work on a huge project with high visibility into senior management, I encouraged him to take it. Both he and I knew that this would require him to overcome any barriers he had up until now and work well with the executive team, or else the entire project would fail. And that’s exactly what he did.

Throughout the project, I saw him growing his capabilities in this area until he became an expert. His growth was so significant, that when I prepared the session about working with executives for the CPO Bootcamp, I asked G. for his lessons learned on this topic. Before he gave me his actual lessons learned, he surprised me with a thank you note.

He said that many managers before me tried to work with him on this topic, but only I succeeded. He went further to mention exactly how I managed to do that, and that’s what you are going to read further in this article. 

Provide Ongoing and Timely Feedback

Last week I talked about the beginning of the growth journey, which is to make sure your product manager wants to grow, and make sure you focus them on the very specific areas that they need to grow in. But no matter how much your product managers want to succeed, giving them onetime feedback isn’t going to do the trick. It needs to be of continuous focus both for you and for them, and you need to give constructive feedback frequently and regularly.

When G. mentioned that he knew exactly how I helped him grow where other managers failed, he mentioned exactly that. He said (I didn’t even remember I did that) that I used to talk to him for a few minutes after important meetings, pointing out exactly the point where he lost the executive’s attention, for example. G. said that this was the first time he actually understood why he was failing. From then on the path to success was much clearer and G. needed less guidance to march in it on his own.

When you give feedback, make sure it is timely – given as shortly after the occasion you are referring to as possible, specific – give the example of what went wrong, and explained – talk about why it was wrong and what was the impact.

Surface Alternative Behaviors

Oftentimes people understand what they are doing wrong, but they are so used to working this way that they simply can’t think of any other option. Make sure that your feedback conversation ends with your product manager knowing what they should do the next time this happens, and not only what they did wrong this time.

For a starter, once they understood what they did wrong, ask them what they would do differently from now on. If the answer is lacking, you can give them your own examples, and suggest how you would approach it if you were in their shoes. 

If you were the one to suggest the alternative behavior, you need to ask them again what they would do differently, since otherwise they might still be left with “it’s a nice idea but I don’t really know what to do”. Help them embrace it by making it their own. Once they said out loud that they would do something, it’s harder to back off, even when it’s not their default behavior.

Let Them Clean Up Their Mess

When there’s a gap between the level you need your product managers to be at and the level they are truly at, you will be constantly disappointed. They will fail to meet your expectations, by definition. Since product management is such a central part of the company, their failure will have an impact, and this impact is under your responsibility.

Many managers I work with do the most natural thing – and that is to take over when things don’t work. When the product manager communicated something to management that is not aligned with what you wanted to say, naturally you will want to write a clarifying email. When your product manager isn’t lean enough and brings a huge scope to the table, the most natural thing for you to do would be to decide what needs to be left out. When they prepare a presentation that isn’t good enough, it is very tempting to simply write it yourself.

This is a very natural tendency, but it is deadly to your product manager’s ability to grow. If you have young kids, think about it this way: when you want them to learn how to get dressed in the morning by themselves, you have to let them deal with it. It takes a ton of time. They wear it all wrong and need to start over again. They start doing other things while you are sitting there, late for work. It is so much easier to just dress them up yourself. It will get the job done both better and faster. But they would never learn how to do it themselves this way.

When you take over the work of your product manager, not only you don’t let them develop the skills that they need to do it well the next time, but you also send a message that you don’t trust that they can do it, simply because they failed once. But you knew they would fail, or otherwise, you wouldn’t need to work with them on their professional growth, right?

Don’t back off from your commitment to their growth the second they mess up. Messing up is part of the process, and to make it a mess that was worth it, make sure you make it a real learning opportunity for them.

Give them the timely, specific, and explained feedback mentioned above, make sure they understand what to do differently the next time around, and send them to have another attempt if possible. If damage control is needed, work with them on doing it right. You can guide them, but they need to own the consequences and stay at the front. This will not only make them remember it better for the next time, but also send a message to the entire team that you trust them and that they don’t shy away from their responsibility in the matter.

Handhold Them When Needed

In some cases, the gap that they need to close is so big that they wouldn’t know how to do it even if you explained it to them. Once they tried on their own with the proper feedback from you a few times, and still aren’t quite there, you might want to handhold them – temporarily – a little tighter. 

Note that handholding isn’t the same as taking over: you are not doing it for them, you are escorting them as they do it themselves. You might give examples, but eventually, they remain in the front and you guide them in the back. The ownership of the task remains theirs, and the success would be theirs too.

The reasons for handholding can vary: it could be that the person is junior and never did it before, it could be that the gap they need to close is too big, or that the project at hand is too important to let them fail. Whichever the reason is, make sure you are doing it because you want them to succeed and not because you don’t trust them, and explain it clearly and transparently. You should also explain that it’s temporary and include the path to them doing it independently. For example, you might say that you want to do the first one (presentation, email, report, meeting) with them so that they understand what you mean, and they will do the next one on their own. For damage control, you might explain that you want to make sure they know how to fix it, and once you are aligned they can continue independently. It sets the ground for you to step in without stepping on their tows, and sends a clear message that you still expect them to succeed regardless of everything that happened up until now.

Remember: expanding one’s comfort zone isn’t easy. It takes time, lots of practice, and the proper patience and persistence to succeed. Start this journey knowing that it would not happen in an instant, and make sure to stick to your commitment to your product manager’s growth even when things get rough along the way.

Do it until they succeed, or until you realize it’s not going to work. Next week I’ll talk about how to distinguish between the two.