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.
The Business Veteran Turned Practitioner
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 disguise.
Sometimes they’re right. Often they’re not.
When founding partners start avoiding each other, when someone consistently shuts down in important conversations, when the same argument keeps surfacing despite clear agreements—these are psychological patterns, not governance issues. They require different tools.
Research from the University of Sydney found that 25-50% of people who seek coaching show clinically significant anxiety, stress, or depression symptoms. Business veterans typically lack training to recognize this. They keep offering operational solutions to emotional injuries. If that happens, the team wastes valuable time and resources.
Optimal application:
Partnership is fundamentally healthy but operationally misaligned
Challenges are genuinely strategic, not emotionally driven
Industry-specific knowledge matters to you
Clinical Practitioners Entering the Startup Space
More therapists are recognizing that partnership dynamics translate across contexts.
Their advantage:
Clinical practitioners understand something most coaches miss: how people actually change behavior. They’re trained in attachment theory, nervous system regulation, conflict de-escalation. They know how to work with people who’ve stopped trusting each other.
Their therapeutic frameworks—Emotionally-Focused Couples Therapy, Gottman Method, Imago relationship therapy—were built specifically for repairing damaged relationships. When founding partners can’t be honest anymore, when someone’s considering walking away, when patterns repeat despite good intentions, clinical training matters.
The financial equation differs too. Many practitioners charge hourly therapy rates rather than monthly coaching retainers. Some accept insurance. This fundamentally changes accessibility, especially for bootstrapped founders watching every dollar.
When your partnership has experienced genuine relational wounds and is a romantic partnership, therapeutic expertise becomes essential. Strategic advice won’t heal relational wounds.
Their limitation:
Clinical training programs don’t teach business. Understanding couples therapy doesn’t automatically translate to understanding cap tables, board dynamics, or why fundraising creates specific partnership pressures.
Some practitioners grasp venture building through years of self-education. Others remain perpetually behind the curve, requiring founders to explain their industry context every session. That’s unhelpful and unproductive for everyone involved.
Optimal application:
Financial constraints limit your options significantly
You’re capable of bridging business knowledge gaps yourself
Clinical-level relational support is needed (e.g. teams who are dating or married)
Coaches With Psychological Expertise
This category is smallest and hardest to find. These are people with legitimate psychological training who’ve also spent meaningful time working in startup environments.
Their advantage:
They work in the overlap. When you’re describing tension around your product roadmap, they simultaneously hear the strategic question and notice the emotional charge underneath it. They understand these aren’t separate problems.
Their training allows multi-level intervention. They can help you build better decision structures while also addressing why one partner consistently feels dismissed. They see how psychological patterns create business outcomes.
Studies published in Human Resource Development Quarterly demonstrate that the practitioner-client relationship significantly predicts outcomes. Research shows that coaches understanding both business environment and relational dynamics outperform specialists on most measures.
Practically, this means working with tactical disagreements rooted in divergent working styles, while simultaneously addressing underlying patterns around control, visibility, and emotional safety. They engage the full system.
Their limitation:
These practitioners typically won’t just hand you operational answers. They’re not building your financial models or designing your org chart. Their focus stays on the partnership itself—how you collaborate, how you repair ruptures, how you create space for difficult truths.
They also tend to cost more than therapists while being harder to locate than business veterans. The combination of psychological depth and operational literacy remains relatively uncommon.
Optimal application:
Your challenges exist in the messy middle between business and relationship
You want to prevent future breakdowns, not just resolve current crises
You recognize strategic problems might have psychological foundations
Diagnosing Your Actual Problem
Before hiring anyone, you need clarity on what’s genuinely broken.
Most founders I meet describe their symptoms as issues with roles and responsibilities, communication, ownership, or performance. But symptoms aren’t root causes.
I recently worked with founding partners who’d spent eight months debating their sales approach. One insisted on enterprise deals. The other advocated for product-led growth. They were deadlocked.
Except the deadlock wasn’t actually about sales strategy.
Through our work together, it emerged that the enterprise advocate felt increasingly sidelined as their company scaled. His cofounder consistently interrupted him in leadership meetings, made decisions without consultation, and dismissed his expertise in front of the team. The sales debate was his last stand—proof he still had influence.
Once we named the actual issue of feeling erased, needing recognition, and wanting partnership rather than hierarchy, the sales strategy resolved immediately.
This pattern appears constantly in my work. Arguments about hiring timelines mask conflicts around risk tolerance. Debates about product features hide power struggles. Disagreements about company culture reflect unspoken value differences.
This is precisely why practitioner background matters. The most expensive mistake isn’t hiring the wrong practitioner. It’s spending months with someone skilled at solving Problem A while you actually have Problem B, implementing excellent advice that never touches your real issue.
Everything you’re building rests on whether this partnership works. That deserves more than checking credentials and hoping for the best.
Figure out what’s genuinely broken. Then find someone trained to fix precisely that.