Give feedback to your boss?

This is a delicate situation, so let’s turn to Kim Scott, author of Radical Candor, a book that teaches us how to care personally while also challenging directly. 

Scott says, “It’s not your moral obligation to criticize your boss if it will cost you your job.”

Yet, some bosses are unaware of how their behavior affects others, and some would welcome constructive feedback that helps them…if their safety is maintained.

Yes, their safety. 

Put yourself in their shoes. Why would your boss’s emotional safety be at risk if you ask them to change their behavior? 

Scott recommends testing the waters first. If you sense receptivity, move slowly.

Ask your boss for guidance before you give it, she advises, and rather than critique the criticism, or accept bland praise, “focus on rewarding candor if you get it and on embracing discomfort if you don’t.”

She next counsels us to ask permission to give a boss guidance, saying something like: “Would it be helpful if I told you what I thought of X?” 

"If the boss says no, or that it’s not your job, then just let it drop and polish up your resume! If your boss says yes, start with something pretty small and benign and see how they react. If they react well and reward the candor, keep going. If they don't, give up immediately or assume ill intent. Try again carefully, but if you get the same reaction the next time, it may be time to move on. You deserve a better boss."

This may seem harsh, but Scott reminds us that the ability to be candid with your boss is crucial to your success: 

"If you manage people [or even if you don’t], you inevitably will wind up responsible for executing decisions you disagree with, which can feel like a Catch-22. If you tell your team you do agree with the decision, you feel like a liar or inauthentic. If you tell your team you don’t agree with the decision, you look weak, insubordinate, or both."

And yes, all the other rules of giving observational feedback still apply.