How to Coach a Difficult Leader (Without Calling It Coaching)
TL;DR:
Some leaders don't need more feedback. They need containment, clarity, and quiet coaching disguised as “doing the work.” If you work in communications, you're probably already doing this. Here's how to do it more intentionally.
A Brief Case Study in Insecure Leadership
Let me tell you about a former boss who accidentally trained me in coaching insecure leaders.
He’d hired me to lead internal communication, then regularly met with senior leaders without me, made decisions about my function, and handed me execution plans afterward. When the work landed well, it was framed as a “team win.” When information was missing, I usually found out through back channels.
Things came to a head over writing.
Within my first 90 days, I built and launched a news hub on our intranet, complete with an editorial calendar and a steady publishing cadence. I also introduced a feature-style series highlighting employee career journeys.
My boss instructed me to open every article with the subject’s name, title, tenure, location, and job responsibilities. I disagreed, explained why that structure hurt readability, and used a more engaging lead instead.
That’s when he lost it.
Red-faced. Fist pumping. Shouting, “Why aren’t you taking my feedback? This is good feedback.” The call ended with him announcing he would approve every piece of content going forward, then abruptly signing off with, “Just do what I tell you.”
Only later did another pattern become impossible to ignore.
During periods of organizational change, he increasingly relied on me for emotional support. When our global CEO announced their departure, he called four times in two hours. Not to discuss messaging. To process his anxiety about leadership instability.
At that point, it was clear the issue was never about writing.
It was about control.
At the time, I stayed calm and logical. I explained my rationale. I focused on the work. And I unintentionally made things worse.
What I know now, thanks to coaching training and hindsight, is that I was responding to surface-level behavior instead of what was driving it. When leaders feel threatened or defensive, logic rarely lands. Curiosity does. Which brings me to the real reason you’re reading this.
If you work in communications, you’re often the closest thing difficult leaders have to a thought partner. Whether you want that role or not.
You can’t force leaders into coaching. You can, however, coach them quietly through how you show up in moments of tension.
Here are a few “clandestine coaching” tactics you can use every day.
4 Quiet Coaching Moves for Difficult Leaders
1. When a leader goes off on a tangent
This usually signals anxiety, not strategy.
Try asking:
“How does what you are sharing connect to the communication outcome we are aiming for?”
You're not shutting them down. You're anchoring the conversation.
2. When a leader becomes argumentative or defensive
Once emotions spike, justification backfires.
Shift to rapport instead:
“It sounds like this is frustrating.”
or
“I’m noticing a strong reaction. Can you help me understand what’s driving that?”
Understanding lowers the temperature. Defending raises it.
3. When feedback is vague or slippery
“Make it better” isn't direction. It's a feeling.
Ask:
“Can you give me an example of you're hoping to achieve here?”
This helps them think more clearly without putting them on the spot.
4. When opinion is presented as fact
You know the line: “Everyone wants to know this.”
Try:
“How do we know?”
or
“What input led you to that conclusion?”
This invites evidence without turning it into a power struggle.
The leaders who are hardest to work with are often the ones who feel the least secure. They react instead of reflect. They cling to control instead of trusting expertise.
You can't fix that.
What you can do is slow the moment, surface what's really happening, and guide the conversation back to clarity and outcomes.
