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A great blueprint for dealing with terrible bosses

30 years ago Jim VandeHei — co-founder and CEO of Axios — got leadership feedback all wrong. Now, he has the ideal blueprint so you can get it right.
Monochrome portrait of a smiling man with short hair, framed by abstract patterns and images of chess pieces, symbolizing strategic boss feedback.
Credit: Jim VandeHei / jeshoots / Unsplash / Big Think
Key Takeaways
  • Before voicing your concerns about a leader, preparation and planning are everything.
  • Be measured and respectful — choose explanation over accusation.
  • Embrace great bosses, but try to fix bad ones: if nothing changes, quit if you can.
Excerpted from JUST THE GOOD STUFF by Jim VandeHei. Copyright © 2024 by Jim VandeHei. Used by permission of Harmony Books, an imprint of Random House, a division of Penguin Random House LLC, New York.  All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.

It’s hard enough to give candid feedback to a friend or subordinate. Giving it to your boss is one of the most difficult things to do—and can get you booted if you botch it. 

Why it matters. Very few of us make it through life without running into a moronic, mushy, or mediocre manager. But there are ways to raise concerns directly, safely, and effectively. 

I botched my first stab at it, quite spectacularly. I was at Roll Call, in the mid-1990s, when a fellow journalist, Ed Henry, was put in charge of the newsroom. A few of us thought he was wrong for the job, so I impulsively went to the bosses, winged it with no forethought, made it way too personal, pitched myself as an alternative, and . . . lost. Ed’s boss listened politely . . . and then sided with Ed. He remained editor. 

I did everything the Jim of today would counsel young Jim not to do. Now, thirty years later, having watched others do this well and poorly, I see a clear blueprint: 

Sharpen your thinking. What exactly is the boss doing that’s making it harder for you or others to thrive? 

Do a gut check. Discuss your issue with a friend, family member, or mentor—ideally someone not involved at your company. Lay out your concerns without hyperbole, then lay out dispassionately the defense your manager might make.

Write it down. I am a big believer that you can be more precise and measured if you put your concerns in writing. Be respectful. Be direct. Say you appreciate the chance to share your unvarnished thoughts.

Explain, don’t accuse. You put someone instantly on the defensive if you hammer them or question their character. Be very specific, clinical, and unemotional in how you frame your concerns.

Offer solutions. No one wants to hear someone simply bitch about problems or grievances. Offer specific solutions or alternative approaches.

Lock arms. Make it plain that you want to be part of the solution. People who feel isolated, backed into corners, or judged typically retaliate or hide.

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Follow up. Ask for a follow-up conversation, in person, after they have digested your note, to discuss the next steps. How they respond will give you a very strong indication of whether the situation is fixable.

Give ’em a chance. Change is hard. Watch to see if a correction is made. If not, politely but directly remind them of your note and chat. 

TRUTH BOMB. Just because someone gets power does not mean they deserve it. A lot of bad or talentless people rise to management by bootlicking or tenure. 

Confront reality. Most middle managers, in my experience, are hard to change. If someone does not listen to you respectfully or refuses to change, be ready to live with the status quo . . . or quit. 

The bottom line. Great bosses are like firm—but unconditionally loving—parents. Embrace them. Bad ones are like duplicitous ex-boyfriends or -girlfriends who suck the life out of you. Try to fix it. But if nothing changes, run if you can.

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