How to Criticize Your Boss (and Not Get Fired)

How to Criticize Your Boss (and Not Get Fired)

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I think I’m pretty good at taking criticism, but it didn’t come naturally.

20 years in business — as an underling, entry-level worker bee, manager and CEO — taught me that criticism is important to every position in a company.

While some only care what their superiors think of their performance, it’s often been feedback from people “under” me in an organization that has proven the most valuable.

With that in mind, and assuming your boss isn’t a total psycho, here are a few lessons I’ve learned about how to give a leader criticism so that it’s well-received, embraced and effective.

1. Ignore my Angry Resting Face.

Angry Resting Face (to use the politer version of the term) is when your neutral, everyday face comes across as irritable or angry without your intending it.

I’ve been told that I have this condition, and I suspect that it’s not that uncommon among bosses in general. Don’t let it deter you.

Psychologist Christopher Olivola says that we “put so much weight on [a person’s facial cues] that we end up ignoring other, more useful pieces of information.”

This more useful information includes what you know of me from our interactions together, and what you’ve observed during my interactions with others. If those cues have been positive overall, focus on them versus my mug.

2. Wait until you feel calm.

I’ve never had a good experience speaking from a place of anger. Satisfying in the moment, maybe, but usually I feel embarrassed and regretful afterward.

Waiting 24 hours for emotions to pass can help you decide if a matter is important enough to make a big deal of in the first place. Whether it is or isn’t, they’re precious hours and you should take advantage of them to cool down.

Approach me when you feel clear, calm and confident. We’ll have a better talk, and we’ll accomplish more in the bargain.

3. Warn me in advance.

If you feel comfortable trashing me in person, schedule a sit-down. Here’s the thing, though: Be sure to warn me in advance that I’m about to receive criticism.

It isn’t fun to think, “Hey, So-and-so wants to chum,” and then settle in for an intimate discussion about how much I suck. It’s not like you have to submit an agenda for the meeting — just so long as it doesn’t feel like a surprise attack.

This isn’t something you have to schedule through a secretary. Write me an email: “Hey, there’s something I want to address that’s been bothering me. Maybe I’m mistaken, but I want to get it off my chest.”

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4. Don’t beat around the bush.

Be as nice to me as you can, but don’t hold back. Once you’ve made the decision to rip me a new one, say everything that you need to say.

No matter how harsh it may seem, spell it out plainly. If your critique is thorough and respectful, chances are great that I’ll learn and grow from the experience.

On the other hand, if you’re overly cautious for the sake of my feelings, it’ll not only waste both our time, it’ll leave me with the impression that you pulled your punches.

5. Give me space to process.

In most cases, I’ll see the error of my ways within the span of our meeting. But if we separate without finding a resolution, give me at least 24 hours to get back to you.

Our failure to immediately resolve your concern is not a reflection on you. I may just need time to ponder.

If I don’t get back to you within 24 hours, feel free to give me a nudge. Schedule another sit-down and we’ll rehash it.

6. Write it down.

If you need to get something off your chest, but you’re just too damn nervous to talk to me face to face, try writing me a letter.

A letter is more personal than an email, and taking the time to compose one can put you in an excellent frame of mind for discussing delicate subjects. Just keep it short and sweet and stick to the main issue.

Feel free to point out one or two things you like about me, too — I’m as fond of a compliment as anyone else.

7. Be prepared to be right, wrong or both.

My business partner once told me that he was worried about an unhealthy attitude that seemed to be developing in our new California office. We talked about it multiple times.

For days, I racked my brain wondering who the source of his concerns could be. Finally I turned to him and said, “Hey! You’re not talking about me, are you?”

Yes. Yes he was. Turns out that I’d made a few comments that, while technically true, could also be interpreted offensively. I was correct within my paradigm, and he was correct within his.

We’re trained from infancy to frame the world in terms of either/or, but in something as complicated and messy as a human life, that standard usually never holds.

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About the Author — Levi King is co-founder and CEO of Nav, a free way for business owners to manage their entire credit and financial life. King is a six-time entrepreneur who has started successful businesses in the manufacturing, hospitality, retail financial services, and franchising spaces. He has accessed financing more than 30 times and founded Nav to provide small-business owners with a resource to help ease the process.

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