Can’t Read Your Boss’s Mind? Ask Madeleine

Hi Madeleine,

I have a great job that I love in a fast paced, entrepreneurial young company.  We are a small shop, so for some projects I work directly with the CEO. I’ll call him Rob. 

My problem is that Rob seems to expect me to read his mind. He rarely gives me any specific direction.  If I try to go it alone, he finds fault with my approach.  But if I try to explain the situation so he can advise me, he gets frustrated and testy with me and says, “Oh forget it, I will just do it myself.” 

Everyone has been under a lot of pressure to perform. I know I can do better with just a little extra direction but I don’t know how to get it. 

Not a Mind Reader

Dear Not a Mind Reader,

You have perfectly described the classic CEO of a fast paced, entrepreneurial start up.  Wildly energetic, visionary, creative leaders make big cognitive leaps and connect dots that others don’t. They are rarely able to slow down long enough to think through their own thought processes, much less take the time to articulate them as step-by-step directions for someone else. Often this type of person simply can’t understand that what is obvious to them is not obvious to everyone else. This can be extremely frustrating for employees and, in some cases, has been known to actually derail the growth of an organization. People like Rob are successful in the long term only if they can depend on people like you to be the bridges between them and the rest of the world.

The good news is that it isn’t personal. He doesn’t seem to be holding your mistakes against you, so he must know he needs you.

The key to being successful in this situation is to make it easy and quick for Rob to give you clear direction.  Just asking “What should I do?” will put him on tilt, as you have experienced, so meet him halfway. When you are unsure how to proceed, stop and check in with Rob. I suspect he prefers texting and is okay with any hour of the night or day.  Give him a brief, brief, brief outline of the situation and the ways you think you could respond to it as two or three multiple choice options.  If one is spot on, he will text you back “C” and will maybe add some quick additional thoughts.  If you are completely missing the boat, he may pick up the phone and explain how. But you will have at least thought it through to the point that he doesn’t have to start at square one with you, and you will likely get you what you need to move forward.

It sounds like you are having a lot of fun, and I hope this approach makes it even more so.

Love, Madeleine

Got a question for Madeleine? Email Madeleine and look for your response here next week!