A paradox of outfits, from a recent photoshoot.
When people think about coaching, they often think about questions.
Good and clever and insightful questions. The kind of questions that unlock thinking and move a conversation somewhere useful.
And yes — these certainly play a big part in coaching.
But if coaching were only about asking questions, AI could do most of the job. (And frankly, it’s getting scarily decent at that.)
What really separates people who are coach-like from those who are merely asking questions is the being of coaching, not just the doing.
And since teaching this work – first while developing The Coaching Habit and then in the decade since it was published – I’ve noticed that the people who embody coaching well wrestle with a set of tensions or paradoxes.
There are four paradoxes that I’ve narrowed it down to.
But before we get into them, a reminder that today is the last day to save $100 on Bring Out Their Best, my coaching course, where you’ll learn how to embody this being of coaching.
1. The paradox of you: Humble Confidence
The first paradox sits in how you show up.
To be helpful in a coaching conversation, you need confidence. You need the willingness to step forward, use your voice, and trust that you have something worthwhile to bring to the interaction.
But the confidence that works best here is not bravado, nor is it the performative version that dominates social media.
It’s confidence paired with humility. And the humility I’m talking about is more honest.
It’s the ability to recognize both the places where you’re strong and the places where you’re still learning, and to hold those realities with a lightness rather than defensiveness.
When humility and confidence sit together like that, something useful happens.
You show up grounded but not timid, confident but not arrogant.
2. The paradox of you and them: Fierce Love
The second paradox sits in the relationship with the other person.
Coaching is an interaction between two human beings, and the quality of that relationship shapes everything that follows.
The approach that’s most powerful here is something I call fierce love.
The “love” part is about genuine care. You want the other person to succeed. You want them to grow and learn and step more fully into their potential.
But the “fierce” part matters just as much.
You care about the person, and you care about their growth. And sometimes caring about their growth means asking the question that’s a little uncomfortable, naming the pattern that’s been avoided, or inviting them to step beyond what currently feels doable.
It’s support and challenge, held together.
3. The paradox of the process: Light and Grounded
The third paradox shows up in how you manage the conversation.
When you’re being coach-like, you’re helping shape the process. But at the same time, you’re not controlling the thinking.
Because the goal isn’t to lead the other person to your answer. The goal is to create a structure that allows them to discover their answer.
So there’s a constant balancing act happening. You provide enough structure to keep the conversation purposeful and useful, but you also allow enough freedom that insight can emerge in unexpected ways.
Too much control and the conversation becomes disguised advice.
Too little structure and the conversation drifts into pleasant but unproductive wandering.
The craft of coaching lives somewhere between those two extremes.
4. The paradox of the outcome: Care and Don’t Care
The final paradox sits in how you relate to the outcome of the conversation.
Of course you care about what happens. You want the shift to occur and progress to be made.
But if you hold that outcome too tightly and become invested in a particular answer or direction, you subtly start steering the conversation toward what you want.
And when that happens, curiosity begins to shrink.
You care deeply about the outcome of the conversation because you care about the person and the impact they can have.
But at the same time, you recognize that the other person owns their choices, their actions, and ultimately their results.
Your role is to create the conditions for better thinking. What they do with that thinking is theirs.
These four paradoxes are simple to name, but they’re subtle to practice.
And learning to hold these tensions — rather than collapsing into one side or the other — is where the real work of bringing out someone’s best begins.
That is what you will do inside Bring Out Their Best.There are three cohorts available (one starting March 24th, and two in September). You can save $100 on any of these cohorts when you register today before 11:59pm ET.
