What Does High-level Coaching Sound Like?
image: Alexandre Boucher Doup via Unsplash
I’m often asked what high-level coaching looks like. Perhaps the better question is what does the impact look like, or better yet, what does it sound like?
Here’s a recent LinkedIn post by a media CEO that might provide some context:
Last week something unexpected happened.
My girlfriend and I were driving to San Antonio for her show, and I had my monthly 2-hour call with my business coach.
Normally, I’d throw in my AirPods and keep it private. But I couldn’t find them, so I put the call on speaker.
If you’ve ever had a great coach, you know these conversations aren’t light. Mine gives me tough love and practical guidance, and I get brutally honest about what’s working, what’s not, and the mental load of leading two businesses.
When I hung up, my girlfriend turned to me and said: “That was awesome.”
She’s heard me talk about work before, but she had never sat through the equivalent of a two-hour business therapy session. She got to hear me unfiltered—the wins, the frustrations, the accountability challenges—and it gave her a whole new appreciation for the weight I carry.
Even more meaningful, she started thinking about how she could better support me as my partner.
We spent the rest of the drive debriefing—not just about business steps I need to take, but about how we show up for each other. It ended up being one of those rare connecting moments you can’t plan for, but you don’t forget.
As leaders and entrepreneurs, we focus a lot on business support systems—but our personal ones matter just as much. Sometimes it takes an unexpected moment, like a missing pair of AirPods, for the people closest to us to truly see the load we carry.
A beautifully powerful testimony to impact, and in a real-world context.
What strikes me most about this story is how coaching ripples outward. The coaching conversation wasn’t just about revenue targets, decision frameworks, or the next bold move — it was about humanity. About one person daring to speak honestly about the weight of leadership, and another person — their partner in the coaching relationship — getting a rare window into that hidden terrain. That’s what high-level coaching sounds like: not jargon, not performance theater, but truth spoken out loud.
Coaching at this level often has a double impact. First, it equips the leader with clarity, courage, and perspective for the complex systems they steward. But second — and often more quietly — it deepens the leader’s capacity to connect with those who matter most. The boardroom and the living room are not separate worlds. When a leader brings more self-awareness, resilience, and candor into their leadership, it inevitably spills into their closest relationships.
This is the paradox of high-level coaching: what begins as a conversation about strategy or leadership challenges often ends up being about identity, connection, and the kind of human being you want to be on the journey. And that’s why it sounds so different. It sounds like laughter breaking through a tough truth. It sounds like silence while someone gathers the courage to admit what’s really at stake. It sounds like possibility — something loosening inside that makes space for a new way forward.
When you listen closely, high-level coaching sounds a lot like life being lived with greater honesty, responsibility, and love.
