Two founders sat across from me, exhausted. They'd already worked with three coaches. Nothing changed.

"We keep having good conversations," one told me, "but we're still stuck in the same place."

This wasn't about effort; both founders were smart, committed, and willing to do the work. The problem was simpler and more frustrating: None of their previous coaches could actually address what was broken.

I see this constantly in my practice. Founding teams invest serious time and money in professional support, follow the advice diligently, and end up exactly where they started, just more articulate about their dysfunction.

The issue is a training mismatch. The coach they hired—however credentialed and experienced—simply wasn't equipped to fix their specific problem.

After years working with founding teams at every stage, from bootstrapped two-person operations to late-stage companies with hundreds of employees, I've mapped three distinct practitioner types in this space. Each brings specific capabilities and each has predictable blindspots.

Understanding these distinctions before you hire someone could save you months of spinning your wheels.

You've probably met this person. They built something meaningful, exited or didn't, learned hard lessons, and now help others navigate similar terrain.

Their advantage:

Context. When you describe how your latest funding round is creating weird tension, or how bringing on advisors changed the power dynamic between you and your cofounder, they immediately understand. No translation needed.

According to the 2025 ICF Global Coaching Study, 85 percent of coaching clients consider coaching certification and credentials essential. But depth varies wildly. Some former operators pursue serious psychological education. Others complete weekend certifications. None demand the same number of supervision hours as a licensed therapist.

When your challenges are primarily strategic—how to structure equity, whether to bring on this investor, how to divide operational responsibilities—these practitioners excel. They've navigated similar crossroads and have battle-tested frameworks.

Their limitation:

Building a successful company doesn't automatically teach you how human psychology works under pressure. Most operators I meet assume interpersonal problems are actually structural problems in........

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