Ben Cashion

CEO Coaching

Your company needs a better version of you. Let's build that.

THE WORK

Most CEOs I work with aren't in crisis. They're in a season where the job has outgrown their current playbook — a growth inflection, a team that needs rebuilding, a decision with no clear answer.

They don't need a cheerleader or a sounding board. They need someone who understands the weight of the role, asks the questions they've been avoiding, and helps them build the leadership capacity the next chapter demands.

That's what I do. One-on-one, over 12 months, built entirely around your world.

THE PROCESS

How We Work Together

01

Deep Diagnostic

Before I start coaching, we understand everything. One-to-one, I learn your business, your team, your leadership style, and what's actually working—and what's getting in your way. Not what some generic process assumes is the real picture.

Everything that follows is shaped by what we find here.

02

Custom Design

From the diagnostic, I build your engagement around the 5–10 priorities with the highest leverage. No preset curriculum. No one-size-fits-all. Your plan draws from 100+ tools and frameworks developed over 30 years of coaching—assembled specifically for your situation.

03

12-Month Formation

We meet consistently over 12 months—not because change takes that long, but because formation does. We return to your core priorities again and again until they're wired into how you lead. Language sessions, curated resources, and experiences with other leaders who get it.

AREAS OF FOCUS

Where We Typically Go Deep

Every engagement is different. These are the challenges that come up most:

Executive team composition and dynamics
Strategic pivots and major business decisions
P&L management and financial clarity
Vision casting and organizational alignment
Scaling leadership capacity for growth
Board relationships and governance
Succession planning and legacy
Personal sustainability and avoiding burnout
BROADCAST

Tools and Experiences

You'll leave with frameworks you can use long after we stop meeting. One example: The Five Tasks — a tool developed by my business partner Steve Graves that cuts through the noise and clarifies what a CEO should actually be spending time on, tangible to understand and hard to argue with.

Beyond frameworks, I create experiences — introductions to other CEOs navigating similar terrain, curated dinners with leaders who can speak into your situation, and connections that remind you that you're not the only one carrying this weight.

Ben Cashion in conversation at a leadership summit
NEXT STEP

Start With a Conversation

A 30-minute call will tell us both whether this is the right fit. No pressure, no pitch — just an honest conversation about what you're facing and how I might help.