Executive Coaching
for the Long Game
Focused partnership for leaders who want to grow — not just succeed.
Built Around You
You didn't get here by accident. But the skills that built your company aren't always the ones that take it — and you — to the next level.
I work one-on-one with CEOs and family offices to get underneath the surface. We start with a thorough diagnostic — your leadership, your organization, your financials, your strategic goals — and build a coaching engagement around the 5–10 priorities that will actually move the needle.
This isn't motivational. It's strategic. We work on real decisions, real dynamics, and the kind of personal growth that shows up in how your team performs and your business runs.
Two Ways I Serve
CEO Coaching
Your company is growing. The question is whether your leadership is growing with it. I partner with CEOs to diagnose and strengthen your most critical challenges — strategy, cash, key financial metrics, team alignment, equity retention, and navigating any headwinds.
We go deep on what matters, skip what doesn't, and build the kind of leadership capacity that compounds over time.
Family Office Advisory
Wealth creates complexity in relationships, in decisions, in legacy. I work with ultra-high-net-worth families to navigate generational transitions, governance, generational dynamics, and the values that need to carry forward.
From governance and generosity to expectations and stewardship, we help families become their next stewardship and values-sent generation.
True change doesn't come through epiphanies. It comes through formation — the slow, intentional work of weaving new patterns into how you lead and live.
— Ben Cashion
What Leaders Say
“Ben is an effective and insightful strategist who integrates some of the best leadership development and organizational strategy content into a formative coaching experience. Our work together provided a rich tapestry of experiences, fresh perspective, and critical problem solving.”
Matt Farmer
President, National Christian Foundation, Kansas City
“Ben guided our executive team through a pivotal season of clarity. He helped us shape a vision for evolving from a single-entity company into a holding company built to develop leaders who build great businesses.”
Erin Kiefer
President and Owner, Kiefer Sage, Inc.
“Ben’s insight, steady guidance, and willingness to help me process complex challenges have been invaluable as I’ve worked to transform my company. The results speak for themselves: our 4-year CAGR is +44%.”
James Harris
Founder & CEO, High Impact Analytics
“Leading from the front line, it was pivotal to spend time with Ben out of the trenches. Our conversations were dispassionate and strategic—in service not merely of holding the line, but of taking ground.”
Carsten Pedersen
CEO, Martin Bionics
Let's Start a Conversation
If you're navigating a season that calls for outside perspective and sustained support, I'd welcome the chance to hear what you're working through.