Ben Cashion
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FEBRUARY 20254 min read

What CEOs Actually Need (It's Not What You Think)

Hint: it's not another strategy session.

board meeting

When a CEO calls me for the first time, they almost always lead with a business problem. Revenue has plateaued. The executive team isn't aligned. They're facing a decision that could define the next decade of the company. These are real problems, and they matter.

But within the first few conversations, something else almost always surfaces. Beneath the strategy question is a leadership question. And beneath the leadership question is a deeply personal one.

The Loneliest Job in the Building

Being a CEO is isolating in ways that are hard to explain to anyone who hasn't done it. You carry information you can't share. You make decisions that affect hundreds of families. Your direct reports need you to be confident, your board needs you to be strategic, and your family needs you to be present — and all three are competing for the same finite resource: you.

What most CEOs actually need isn't another framework or another offsite. They need someone who gets it. Someone who's sat across the table from leaders carrying the same weight, who can ask the questions they've been avoiding, and who won't flinch when the conversation gets honest.

Beyond the Sounding Board

A lot of executive coaching positions itself as a "thinking partner" or a "sounding board." And while there's a place for that, it often stays at the surface. The CEO talks, the coach listens, everyone feels good, and nothing actually changes.

The work I do goes deeper. It starts with a diagnostic — not a personality assessment or a 360 review, but a comprehensive understanding of who you are, how you lead, what's working, and what's getting in your way. We look at everything: your team, your business model, your decision-making patterns, your relationship with your board, and yes — your life outside the office.

What Changes When You Get It Right

When a CEO gets the support they actually need — not just strategic advice, but genuine formation — the ripple effects are extraordinary. They make better decisions, not because they have more data, but because they have more clarity. They build stronger teams, not through new org charts, but through deeper self-awareness about their own leadership patterns.

And perhaps most importantly, they stop carrying the weight alone. Not because the weight gets lighter, but because they've found someone who understands it — and who can help them carry it in a way that's sustainable for the long haul.

If you're a CEO reading this, you probably already know whether this resonates. And if it does, a conversation is the best place to start.

Ready for Formation Work?

If this resonates, let’s have a conversation. Thirty minutes will tell us both whether there’s a fit.