Your Boss Expects You to Be Perfect All the Time? Ask Madeleine

Dear Madeleine,

I am smart, I work hard, and I am a pleaser. These qualities have made me very successful. I am now a senior manager in a fast-paced, high-pressure service business.

My problem is that I have created a monster in my boss. She is so used to my pleasing perfection that she pretty much expects me to be perfect all the time now—which, of course, is impossible.

Any teeny infraction gets a comment now. Here’s an example: She asked me for an outline for a report to the board and gave me the deadline. I don’t usually miss deadlines, but I was traveling that day. My five-hour flight was delayed and the internet on the plane didn’t work, so I sent the report as soon as I landed (about 11:45 p.m. in her time zone).

In my mind, I met the deadline with fifteen minutes to spare. I expected to hear “Well done—you got it in!” Her response? “How do I get you to submit your work before five minutes to midnight?”

This is driving me crazy. How do I get her to cut it out?

Not Perfect

Dear Not Perfect,

Your boss’s behavior does indeed sound frustrating—and for a pleaser, every little criticism can feel like being poked with a sharp pencil! In short, the way to get her to cut it out is to tell her to cut it out. Nicely. But let’s rewind and think this through.

It sounds as if you have been telling yourself a story about how you have both gotten into this muddle together. I suggest a reframe. Ask yourself if the story you have made up about this situation is really serving you. Then you can go to your boss and say, “So here’s what has been happening, and this is the story I have made up about it. I am hoping we can change this dynamic.”

Is it possible the story you have created is based on other relationships you have had in the past? Most of us interpret situations based on previous experience, so that may be at play here. In this case, I think there is a new story available to you—a much simpler one about the lack of explicit expectations and clear agreements.

You interpret a deadline as midnight on that date. It’s possible that your boss assumes everybody interprets a deadline as the end of the business day. When you talk to your boss about her criticisms, tell her it is your goal to please her and make her job easier. But to do that, you need her to be crystal clear about her expectations—all of them—so that you can be sure to never disappoint her.

The next time she makes a snide comment that catches you off guard, point to where the discrepancy was between your understanding of the expectation and hers. You are allowed to stand up for yourself, and you should. She can be more disciplined about clarity, and you can say “ouch” when you feel it.

I don’t necessarily agree that you have trained your boss to expect perfection, but I do think you may have led her to believe you have a thicker skin than you have. Let go of the whole “perfect” story – and rewrite it about how unspoken expectations and assumptions can catch all of us wrong footed.

Love, Madeleine

About the author

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

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