I have been coaching the CEO of a highly successful company for several years. He mentioned that he was struggling with a problem. In meetings with his senior team, he would throw ideas around and then come in the next day, and people would be implementing them. Sounds great; however, he did not intend for them to implement it. He considered them to be just brainstorming ideas.

Also, he had a habit of playing devil’s advocate in the meetings. Whenever someone threw out an idea, he would look at the downside and point out ways it might not work. His team was frustrated and reluctant to bring up their suggestions. He told me that he thought their ideas were fantastic, but it was just the way his brain worked. That he was driven to avoid mistakes. He was not particularly risk-averse. He just asked the difficult questions to give himself confidence that the idea would work.


This miscommunication was creating some friction. I recommended he put together a memo called “working with me.”

I asked him to outline what people should understand about how he thinks and works. He was incredibly thoughtful in this exercise and gave a superb overview of how to best work with him. Here are a few of the things he mentioned.

Just because I have an idea does not mean it’s a good one. Until we discuss the idea and all feel that it is on track, don’t start implementing it.


If I bring up an idea, I would like you all to push back on it. Look for where I could be wrong. Point out the weaknesses in the concept. Please help me make it better.

When I push back on your ideas and try to poke holes in them, it’s not because I don’t think it’s a great idea. It is just the way my brain works. I always look for the downside. I want to explore what might go wrong in order to make the idea the best it possibly can be. Please continue to bring up ideas and understand that I’m not attacking you. I’m attacking the idea to convince myself that it will work.

I’m not particularly eager to make decisions on the spot unless it’s absolutely necessary. I prefer to think things through for a day or two, discuss it more, and then I will be more comfortable and confident in making the decision.

Sometimes it may look like I’m not paying attention in a meeting. I’m just in deep thought. Ask me a question or point out that I am not engaging, and I will refocus on the discussion.

I don’t show a lot of emotion. Even though I might be very excited about something, it can be hard to tell. Don’t look for how I react. Listen to what I say. I will tell you when I am excited, concerned, confused, or upset. You won’t see it on my face.

He listed many other things that would help the people on his team understand how to interpret his behaviors. This ended up being a very powerful tool that the rest of his team also did. The level of psychological safety, candor, and trust went through the roof. They are now one of the most cohesive and high-performing teams I’ve had the pleasure of working with.

Perhaps you might consider writing a “working with me” memo for your team.

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