What Your Boss Really Thinks About You?

Do you ever wonder what the boss really thinks about you? Finding out can be a difficult and delicate task. While most people fear the overly blunt, critical boss, an overly nice or evasive boss can be just as frustrating.

When I worked at Microsoft, I hit my metrics each year but got no sense of when I might get promoted. When I’d ask for feedback, my boss would just tell me he had my best interests at heart. Needless to say, I left Microsoft after a few years of employment. Looking back, I might have stayed and it could have worked out if I was better at communicating with my boss.

Now that I run my own company, I see that some mangers fear they will anger employees or hurt their feelings if they are too open. Some worry that the person will go to HR and cause a big kerfuffle.

Based on my corporate experience, there are ways to draw out a reticent boss. The most important is acknowledge up front that you have weaknesses. This makes it easier for a manager to open up because there is less fear the employee is going to explode in rage or dissolve in tears. The best thing you can do is to say you’ve had a tough time with a problem and would like the boss’s help figuring it out. This sends a message of “It’s OK to give me feedback because I know I’m not perfect”. Addition questions include:

• What would you do differently?

• How do you think I can make this better?

• What would it take for you to be really excited about this?

Perhaps the trickiest part of doing this is to ask these questions in a nuanced way that suggests you know there is room for improvement. Practice with a trusted co-worker, friend, or loved one.

Regardless of the answer, thank the manager for whatever feedback you get. Even if you think it is mean or off-target such as “It must have been a real risk for you to share that with me. I really appreciate it.”

The best approach for advancing your career is to solicit the feedback early. There should be no surprises in your monthly/quarterly/yearly review. Tell your boss you want prompt, frequent feedback. This shows you are results-oriented and take responsibility for your career. If you need any advice or wish to discuss a specific scenario, please send me a LinkedIn message and we can connect offline.