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Don’t make this one big mistake when dealing with a difficult boss, a career coach says

January 25, 2026
in News
Don’t make this one big mistake when dealing with a difficult boss, a career coach says
Kyle Elliott is sitting on a chair holding a phone.
Elliott advised being careful who you vent to when you have a difficult boss. Courtesy of Kyle Elliott
  • Kyle Elliott, a career coach to tech employees, often helps clients who have difficult bosses.
  • Clients venting to their bosses is one of the biggest mistakes he sees.
  • Venting to a career coach instead of a friend can also be a misuse of time, he said.

Kyle Elliott, who’s been a full-time career coach since 2017, spends his days helping tech employees solve their most challenging work issues.

He’s noticed a common problem among clients: difficult bosses, including micromanagers.

One key mistake employees make when they’re trying to fix a problem, Elliot told Business Insider, is venting to the wrong person — particularly your boss.

It makes sense to push back against a difficult boss when their behaviour or expectations are disrupting your work, said Elliot, who is based in California. But venting to them will rarely make the situation better, but nearly always damage trust, he added.

Even if you have a good relationship, it would be more appropriate to vent to a friend, family member, or career coach. They can also help you brainstorm solutions.

“Your boss is not your therapist. You want to come to them with solutions, or at least a clear sense of how they can help you improve the situation or the working relationship,” he said. “If you want a promotion, you want your boss to view you as someone who is thoughtful and solution-oriented, not someone who complains.”

When you organize the feedback session with a difficult boss, choose a private setting, such as in a 1-1 meeting, and interlace constructive feedback with positive remarks about things they do that you like.

Venting to your career coach is a waste of money

Another common issue Elliott encounters is clients misusing their time with him by ranting about their struggles with their boss and what’s frustrating them, he said.

“They often believe they must provide extensive context in order to receive effective coaching, but this isn’t true,” he said.

“You can vent,” Elliot added, but “it’s a very expensive venting session.” While it may feel cathartic, you’re better off airing your frustrations to a friend and using your paid coaching session to outline what you can change, such as what battles with your boss to choose, or how to communicate better with them.

“Coaching is about empowering you, not venting about your manager. Your boss isn’t in the coaching session. You are,” he said.

Read more of Elliott’s tips for dealing with a difficult boss.

Read the original article on Business Insider

The post Don’t make this one big mistake when dealing with a difficult boss, a career coach says appeared first on Business Insider.

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