How to Talk to a Difficult Boss (Who Just Won't Listen)

🪨 The Impasse 

My client, Kasvi, came into our session feeling frustrated, angry, and rejected.

Her boss had shut down her suggestion for improving team output—offered in good faith to support the team’s performance.

Instead of openness, she hit a wall: “That’s my problem to fix,” said the boss tersely. (Translation: “Stay off my turf.”)

The thing is, Kasvi doesn't want her boss’ job—she just wants to do her own better, more effectively. 
So she asked me:
“How can I convince my superior to change their perspective?”

She had plenty of reasons why the boss was wrong—monopolizing decisions, heading for (yet another) burnout, and ignoring input. Colleagues had complaints too.

🐺 The Scared Animal 

As I listened, the picture of the boss that emerged was familiar—
An overachiever on high alert. Someone afraid of making mistakes, losing status, or falling behind.
A nervous system locked in defense mode.

And here’s the thing: scared animals—humans included—don’t respond well to push, pressure, or critique.

Kasvi hesitated to re-approach. That earlier pushback felt like personal rejection.

And that’s what we humans do sometimes—we take "no" personally. (Been there, done that too often myself).

But when we do, we lock ourselves into a perceptual impasse. A deadlock where people get stuck in conflicting viewpoints, unable to move forward because each believes their perspective is the only valid one.

We stop stepping forward, stop iterating, stop experimenting with different reframes and approaches. 

So I offered her a reframe:

💃🏾 Don’t Battle. Dance.

By the way, I'm in Switzerland right now. Yesterday I facilitated an interactive negotiation workshop for open science researchers, using the metaphor of negotiation as a dance. (You can read the recap HERE on LinkedIn) 

Engaging a difficult boss is also a kind of a dance.  
Kasvi had stepped onto the metaphorical dance floor (offered a recommendation), got her foot stepped on (encountered pushback), and pulled back ("Ouch! I never want to that again.") 
But now, it was time to try a different step—
One that would help her move toward her goals and invite her boss into partnership.

Step One: Regulate

First, she needed to regulate her own nervous system—to come into the conversation calm and grounded.
She chose to take a walk through her local botanical garden before reengaging her boss. That moment of stillness would help her bring ease into her body—and into the room.

When you’re calm, you’re not just more effective. 

You can also see more clearly: Everyone has their own reasons for saying no.

Even when we don’t understand or fully agree, we can choose to stay in the dance.

Step Two: Pace, Then Lead

An “I’m-right-you’re-wrong” stance with someone already on high alert? That’s like squaring up to a cornered dog—it can easily backfire. 

Instead, we pace. Then lead.

Here’s what I walked Kasvi through:

• Establish common ground.
  Focus on the shared challenge, not who’s to blame.

• Mirror what you agree with.
  If her boss says, “The loss of users is a problem,” she might reflect: “I hear that engaging users is a top priority.”

• Match tone, pace, and priorities.
  If the boss says, "Whatever we do, there's no room for error," she might reflect: "Yes, we want to do this carefully and get it right the first time." 

• Then lead with an invitation.
  “As we're on the same page about priorities and doing it well, would you be open to a few ideas to help reduce errors and increase efficiency?”

Step Three: Invite the Dance 

This is the moment my client shifted from waiting or withdrawing to stepping forward with openness and leadership energy.

And leading this kind of self-advocacy?
It’s absolutely possible for you, too.

With practice—and the right support—you can build the strength, flexibility, and calm presence needed to move through workplace tension with clarity and confidence.
If you’re navigating a tricky dynamic at work and want to explore new ways to lead, influence, or advocate for yourself…

Let’s talk.

Click here to book a free consult with me.
In a complimentary, hour-long conversation, we'll look at what’s getting in your way and how coaching can help you move through it, powerfully and on your own terms.

See you on the dance floor,
Jamie

P.S. Guten Tag from beautiful Beatenberg, Switzerland! 

I have the extremely good fortune of participating in Open Science Retreat. Negotiating and advocating for your career growth can feel so heavy sometimes, so I asked the workshop attendees to join me in a funny group photo (I'm in the pink sweater with jazz hands). 

It's a dream come true to be hanging out with big-hearted, big-brained dreamers and doers from around the world! 

Don't have FOMO. You can: 

• Read the recap of the workshop HERE on LinkedIn. 

• Listen to the podcast episode with Dr. Joyce Kao and Dr. Heidi Seibold, my coaching clients who organized this retreat HERE. 

• Or watch previous negotiation webinars on my YouTube HERE.