What If My Boss Is the Problem? 2 Things to Try First

So many people come up to me after a keynote or workshop and say, “Alex, that’s great. But what if my boss is the drama? Like, my boss is the nightmare.”

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It’s one of the questions I get most often. Research suggests that about half the time, you’ll have a less-than-stellar boss. Some of us use that as an excuse to check out and stop getting results.

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First, I’m sorry you’re struggling with this. Working for someone you feel doesn’t trust you is exhausting, and it follows you home.

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Before we label your boss the villain, though, I want to offer you two things to try first. They’ve helped me in my own career, and they’ve helped the people I coach every week.

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The short answer: If you feel like your boss is the problem, start by dropping the judgment and getting down to the facts. Then sit down with your boss and map out three things: what a great working relationship would look like, what you’re willing to do to get there, and what they could do to support it. Most “nightmare boss” stories get a lot smaller once you do both.

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Step 1: Watch for judgment

Judgment is the root cause of nearly all the drama in the workplace.

The moment we start judging, we stop helping. We’re no longer working on the problem; we’re building a case against someone. Every bit of energy we put into that case is energy we’re not putting into making the situation better.

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So when you catch yourself thinking “my boss is impossible,” pause. That thought feels like a fact, but it isn’t. It’s a story.

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Get down to the facts

Here’s the kind of story I hear all the time:

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“My boss is a micromanager. They treat me like a child. They’re constantly checking on my projects. They don’t value me, and they don’t trust me.”

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That’s a lot. Now let’s separate the story from the facts:

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• “They’re a micromanager.” Fact: they check on projects.
• “They treat me like a child.” Fact: they check more often than I’d like.
• “They don’t value me.” No evidence yet.
• “They don’t trust me.” No evidence yet.

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Strip it down and the fact is this: I have a boss who checks on my projects more often than I prefer.

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Notice how much smaller that is? When you take the time to stop judging and get to the facts, reality is a lot less harsh than it first appears. And a smaller problem is one you can actually solve.

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Ask: What would great look like?

Once you’re working with the facts, the question changes. It’s no longer “How do I survive this boss?” It becomes “What could I do to help? What would great look like?”

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With a boss who checks in more than you’d like, that’s one simple conversation:

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“How can I build trust in my work so you feel you need to check on it less often?”

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That question does a lot of work. It tells your boss you’re not fighting them. It invites them to tell you exactly what they need to see. And it puts you in charge of the outcome instead of waiting for them to change.

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Step 2: Try the three-sheet conversation

Here’s a technique that has helped me more than once in my career. Grab some time with your boss, ideally somewhere different from your usual one-on-one, and bring three sheets of paper.

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1. Sheet one: What would great look like? Write it out as a list. If this were going perfectly, what would our working relationship be? What would an awesome back-and-forth look like?

2. Sheet two: What I’m willing to do. “That’s what I’m hoping for. Here’s what I’m willing to do to lean into it.” Be specific: earlier updates, fewer surprises, flagging risks before you’re asked.

3. Sheet three: The invitation. “What could you do to support that?” This is an ask, not a demand. You’re inviting your boss to meet you in the middle.

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The order matters. Lead with the picture of great and with your own part in it. That shows you’re not judging them; you’re trying to make things better. Only then do you ask for their part.

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This often clears things up fast and gets you working with your boss in a whole new way.

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Try these two things before you call it

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So if your boss feels like a nightmare, try these two things before it’s officially confirmed:

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1. Drop the judgment and get to the facts. The story is almost always bigger than reality.

2. Have the three-sheet conversation. Show what great looks like and what you’ll do, then invite your boss to meet you there.

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You can’t control your boss. But you can control whether you add to the drama or help clear it.

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Want more tools for building accountability and ditching the drama at work? My new book, How We Could, is a national bestseller. Follow me on LinkedIn, Instagram, and TikTok for new ones every week.

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Frequently asked questions

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What should I do if my boss is the problem?

Start by separating judgment from facts. Write down what your boss actually does, not what you think it means. Then ask your boss what great would look like, and offer what you’re willing to do to get there.

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How do I deal with a micromanaging boss?

Ask directly: “How can I build trust in my work so you feel you need to check on it less often?” Then deliver on what they tell you. Frequent check-ins usually drop once a boss sees consistent, proactive updates.

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What if my boss doesn’t trust me?

Check whether that’s a fact or a story. A boss who checks in often may be anxious about the outcome rather than doubting you. A direct conversation about what would build trust gives you a clear path forward.

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How do I talk to my boss about our working relationship without it turning into a fight?

Lead with what great would look like and what you’re willing to do first. Then invite them to share what they could do to support it. Leading with your own part shows you’re trying to help, not blame.

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Who is Alex Dorr?

Alex Dorr is a leadership expert and CEO of Reality-Based Leadership and the author of the national bestseller How We Could. He teaches leaders and teams how to eliminate workplace drama and get back to doing great work.