A story about a guy who was irritated with his boss

This is a story about a guy named Josh, who was irritated with his boss.

Josh was a very thoughtful leader. Smart, curious – and nice. He also had ambitious business strategies and personal goals. But every time we talked, we got sidetracked by a usual suspect: intense irritation with his current boss.

Every time we talked, we’d end up in a rabbit hole, with Josh analyzing the same problems in a loop. He felt frustrated being excluded from meetings and confused about his role. And he left weekly check-ins with his boss feeling deflated and miserable.

So we set aside strategies and stretch goals, which frankly weren’t going anywhere. And we focused on one simple thing: improve the weekly meetings between Josh and his boss.

I agree that sounds very dull.

But since most of us encounter bosses and other people who irritate us, I’ll press on.

I asked Josh to describe a typical meeting with his boss. He explained how he provided a detailed update across a variety of complex subjects every week for nearly an hour. Then I asked him to think about what made him feel awful during the past few meetings.

In his characteristic way, he became very quiet as he replayed the meetings in his mind. After a few silent minutes, he said it happened when he asked his boss for role clarity and to include him in meetings, often in the very last minutes of their check-ins. His boss became defensive and argumentative every time, compounding Josh’s frustration.

I repeated back what I heard, not quite able to hold back a small grin: “So after listening to your unscripted, detailed update for nearly an hour, you push your boss for more direction on how to do the job you just updated him on?”

To Josh’s credit, he laughed and admitted he’d never thought about it that way.

Of course, it’s normal to want role clarity and to be included in meetings. 

But it’s often a narrative that lands poorly. And for Josh, it backfired every time. That’s because his boss really didn’t have any answers. His own role was just as uncertain. And when Josh thought about it, he admitted he was waiting for his boss… to be a better boss.

Is this irritating? Sure.

Is it fair?


But now we were clear on the dynamic. And that meant that Josh could change his approach to these testy meetings.

First, Josh prioritized how he felt, which directly impacted his work. He could continue to feel frustrated and terrible. Or, he could be irritated – and still choose to feel OK.

Next, we defined what ‘improvement’ meant for these meetings. Here I intervened with a constraint: the ONLY goal for these meetings was for Josh to leave feeling at least as good as he did at the start.

This is a magical constraint. It forces us to focus. In Josh’s case, it put him 100% in charge of success for these meetings. What his boss said didn’t matter. Success for Josh meant he left his boss’ office feeling OK.

Finally, Josh committed to prepare before these meetings, so he would arrive feeling calm, curious, and alert.

What first seemed like a dull task became a fun experiment.

Could Josh handle a confusing and messy situation with a person who really annoyed him? Of course.

And just to make sure, he created a list of three things he would do for every meeting.

1. Prepare
2. Be succinct
3. Ask for input

And this short list, neatly printed in the upper left corner of his notebook, soon became a mental model for Josh – and a mantra: Prepare. Be Succinct. Ask for input.

Prepare. Be Succinct. Ask for input.

Josh’s list is pretty great.

Be prepared meant preparing an agenda with only 3 topics, which Josh sent to his boss before they met. Any more than three topics derailed the meetings.

Be succinct meant keeping his updates brief and articulate, which he practiced by planning what to say ahead of time – avoiding  the technical details that drove his boss nuts.

Ask for input meant Josh prepared to have a conversation. With his boss. He even practiced simple phrases and questions to keep his boss engaged, “Here’s how I’m thinking about that. I’d love to hear your thoughts.” and “What do you think?”

I wish I could tell you that Josh’s boss recognized him as the amazing leader he is.

But that was not the goal of his experiment.

Nor is it the moral of this story.

No, Josh’s boss continued to irritate him regularly. But his new approach improved the conversations with his boss a lot. Even better, he left these meetings feeling as good as he had at the start. And while his boss didn’t always remember to include Josh in key meetings, other people sure did.

carolyn solares
I help people navigate irritating situations at work.
(My brother calls me a workshrink.)

Work with me at murphymerton.
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Photo by Vladimir Kudinov on Unsplash