Every Leader Needs a Circle

Years ago, a coach and friend shared a simple truth that has stayed with me: every leader needs a circle.

A circle is a small group of people who see you clearly, stretch you deeply, and stand beside you quietly when the weight of leadership feels heavy.

The best board directors and leaders I know have a circle — a handful of trusted people who help them lead with clarity, humility, and courage. Here’s who you need in yours:

1. A Confidante

This is the person who lets you take off the armour.
They know the full story, the wins and the wobbles, and they love you anyway. They’re the one who listens without judgment, then tells you the truth when you’re about to trip over your own ego.

For board directors, this might be a peer in another organization, someone who understands the stakes and the solitude of governance. It’s not about venting; it’s about recalibrating.

2. A Coach

A coach isn’t there to make you comfortable; they’re there to help you grow.
They ask hard questions, hold up the mirror, and don’t let you settle for good enough.

For aspiring directors, a coach can help you clarify your board value proposition and presence. For seasoned directors, a coach helps you evolve and to shift from doing to influencing, from leading to guiding.

Growth doesn’t stop at the board table. It just gets quieter, more internal and that’s where a coach becomes indispensable.

3. A Wing Person

Every director needs someone who sees what they can’t see yet.
A Wing Person has peripheral vision. They notice the opportunities (and risks) you might be missing. They whisper to you, “Look over here, there’s something you haven’t considered.”

This might be a fellow director with a different lens, a governance professional, or even a sharp-eyed colleague in your professional circle. They help you stay adaptive in a fast-changing world.

4. A Contrarian

This is te brave soul who doesn’t agree with you.
A Contrarian is a gift. They challenge your thinking, force you to sharpen your logic, and make sure your conviction isn’t just confirmation bias in disguise.

Good governance depends on this energy. Every board needs it. But so does every leader. It keeps you honest, curious, and grounded.

5. A Mentor

And finally, the steady hand on your shoulder.
A Mentor is someone who’s been there before, who knows when to hold the line and when to read the winds and pivot.

They won’t tell you what to do, but they’ll help you see the bigger system you’re operating in. For board directors, a mentor helps you navigate not just the what of governance, but the how. The subtleties of influence, timing, and tone that separate the good from the great.

Building (and Tending) Your Circle

Circles aren’t built overnight. They’re cultivated through trust, shared values, and time.
And like a good board, a healthy circle evolves. People come and go. The roles shift as you do.

But here’s the truth: no one leads well alone. Whether you’re an aspiring director finding your voice or a seasoned chair mentoring others, your circle keeps you anchored and expanding at the same time.

So ask yourself:
Who’s in your circle?
Who’s missing?
And who might need you in theirs?