Becoming Coachable: A Primer for Executive Coaching That Actually Works
The Coaching Mindset That Sets Exceptional Leaders Apart
Many senior leaders I work with come to coaching later than they should.
Not because they aren’t ambitious. But because by the time they’ve reached the C-suite, they’re used to being the one with the answers.
That’s precisely why Becoming Coachable — by Scott Osman, Jacquelyn Lane, and Marshall Goldsmith — is such a valuable read. It’s not just a book about coaching. It’s a playbook for how high-performing, high-context leaders can actually get better through coaching.
In an era where stakes are high, boards are demanding, and the pace of scale is punishing, the right coaching relationship can be a multiplier. But only if the leader is ready to meet it.
Coachability isn’t a trait — it’s a strategic skill
Becoming Coachable makes a powerful argument: coachability isn’t something you either have or don’t. It’s a strategic choice — a learnable capacity rooted in self-awareness, humility, and intentional growth.
For experienced CEOs and senior executives, this can be a hard pill to swallow. You’re operating at a level where feedback is scarce, your inner circle may be overly deferential, and your instincts are deeply ingrained. Coaching, when done well, doesn’t just reflect back what’s working — it helps uncover the hidden assumptions, mental models, and leadership blind spots that are holding you back.
This book names that tension directly — and gives executives a clear path through it:
Coachability at the senior level isn’t about being open-minded in the abstract. It’s about being willing to surface the uncomfortable truths about how you lead — especially when the company’s scale or complexity has outgrown your current leadership patterns. It requires a level of strategic humility: the ability to hold both your authority and your blind spots in the same frame.
And in a high-growth environment — where you’re simultaneously managing investor expectations, board dynamics, and team culture — that mindset becomes a differentiator. Leaders who can examine their own defaults, rather than defend them, tend to build more enduring companies.
Coaching that works: what it looks like in practice
I’ve coached founders who’ve taken companies public — and I’ve coached leaders mid-flight in high-growth, high-pressure environments. The pattern is remarkably consistent:
The most successful coaching engagements don’t start with goals. They start with permission — for the leader to slow down, step back, and interrogate their own operating system.
I’ve seen dramatic transformations happen when an executive stops trying to “perform coachability” and instead gets curious. Curious about what’s not working. Curious about the ripple effects of their leadership. Curious about how they might evolve — not to prove something, but to unlock something.
That’s the mindset Becoming Coachable invites.
How to choose a coach who can help you evolve
One quiet insight in Becoming Coachable is this: the right mindset will only take you so far if you’re not working with the right coach.
Too many senior leaders pick coaches the way they pick vendors — resume-first, reputation-driven, looking for credentials instead of fit.
But executive coaching is not a transaction. It’s a relationship built on trust, challenge, and accountability.
What to look for:
Someone who can engage with your leadership substance, not just your psychology.
Someone who knows how to hold both space and edge — empathy without deference.
Someone with enough context to understand your world — and enough distance to help you see it differently.
It’s not about finding the most impressive coach. It’s about finding the one who can help you see what you can’t yet see — and grow into what you’re capable of becoming.
Mindset shifts for leaders considering coaching
Whether you’re stepping into coaching for the first time, or re-engaging after a break, here are three powerful mindsets to hold:
Measure outcomes by mindset shifts, not just milestones.
Coaching is not consulting. It’s not about fast fixes or tactical advice. The real ROI often shows up in how you think, decide, relate, and lead over time.
Your coach isn’t your cheerleader — or your therapist.
The best coaches hold up a mirror, not a megaphone. Expect discomfort. Expect challenge. Expect to work.
Make space for the work.
Coaching only works if you treat it like a core part of your leadership, not a side task. The insight comes between sessions — in the pattern recognition, the journaling, the experiments you run.
The right mindset unlocks the real value
Becoming Coachable is a must-read not because it makes the case for coaching — but because it makes the case for how to be coached.
In a world that rewards speed, certainty, and output, it’s a quiet invitation to slow down, soften your stance, and sharpen your leadership.
I spend a lot of time thinking about coaching — both the dynamics that make it work and the mindset that unlocks its power.