Executive Coaching FAQs
Coaching is a high-trust relationship — and it’s important to know what you’re getting into. These FAQs answer the most common questions from founders, CEOs, and senior leaders about how coaching works, what to expect, and whether it’s the right fit for you. If you’re exploring coaching for the first time — or looking for a partner who can match the complexity and scale of your role — start here.
Who are your typical clients?
I work with people who lead others—founders, CEOs, and senior leaders at companies, funds, and institutions. Many are first-time founders scaling quickly or managing teams for the first time. Others are seasoned leaders running large, complex organizations. What they share is a commitment to growth—not just getting through the hard stuff, but learning from it and leading better because of it.
What kinds of things can coaching help with?
Most of my clients are navigating a period of transition or complexity. The coaching often begins with a tactical challenge and expands into deeper leadership work. Common focus areas include:
Scaling leadership alongside a growing company
Co-founder or team dynamics
Executive presence and board relationships
Decision-making under pressure
Navigating exits or acquisitions
Managing burnout, self-doubt, or imposter syndrome
Clarifying purpose and long-term direction
Do you charge per session or on retainer?
I work on a retainer basis. This creates the consistency and flexibility required for high-impact coaching — without forcing important conversations into a clock or calendar. Engagements include scheduled sessions and direct access between them for time-sensitive decisions.
Can I expense coaching through my company?
Yes. In nearly every case, coaching is expensed through the company and treated as a professional development investment. It’s a strategic resource — not a personal perk — and is often covered as part of an executive’s leadership or growth budget.
Do investors and boards value coaching?
Absolutely. Investors and board members consistently look favorably on CEOs and senior leaders who work with high-quality coaches. Strong coaching builds stronger companies — it improves decision quality, deepens self-awareness, and accelerates leadership maturity. It’s an investment in the business, not just the individual.
Do you offer sliding scale pricing for nonprofit leaders?
In select cases, yes. I’m open to sliding-scale arrangements for nonprofit leaders doing complex, high-stakes work — especially when the engagement criteria align with how I work with founders and senior leaders in the private sector. If you think that might be you, feel free to reach out.
How often do I meet with a coach?
Most clients meet with me weekly or bi-weekly, depending on what they’re navigating and how much space they need to think. The cadence can flex — but the container is consistent. I’m also available between sessions for timely conversations when the stakes are high.
What’s the difference between coaching and therapy?
Coaching is future-facing and action-oriented. It’s about decision-making, leadership behavior, and how you show up under pressure. Therapy often looks inward to address past wounds or clinical concerns. Coaching meets you at the edge of your current challenges — and helps you grow into what’s next.
What if I’m not sure coaching is the right fit?
That’s completely normal. If you’re curious but unsure, the best next step is a brief conversation. I work with a small number of clients at any given time, so fit matters to me as well. I’m happy to explore whether this kind of work is what you need — and if not, I’ll point you in a better direction.
How do we get started?
It usually begins with a short call to understand what you’re navigating and whether I can help. If it feels like a fit, we’ll talk through structure, cadence, and goals — then get started. There’s no pressure. The goal is to get to clarity, not close a sale.
What’s your coaching background?
My coaching is grounded in both research-based methodologies and lived experience leading at the highest levels. I’ve founded, scaled, and taken companies public. I’ve run global teams, built international businesses, and invested in hundreds of startups. I’m also a certified coach and a Fellow at the Institute of Coaching at Harvard Medical School. But more than credentials, it’s the combination of real-world leadership and deep partnership that defines this work.
What makes your coaching different from therapy or consulting?
This isn’t therapy, and it’s not consulting. Therapy looks to the past. Consulting often provides answers. Coaching is a different discipline. It’s a structured partnership designed to expand your leadership capacity — helping you see more clearly, make better decisions, and lead with greater clarity and impact.
What’s your approach to confidentiality?
Confidentiality is foundational to this work. Everything we discuss stays between us, unless you explicitly decide to share it. This boundary creates the trust and psychological safety needed for honest conversations and real growth — especially when stakes are high and visibility is constant.
What happens in a typical coaching session?
There’s no one-size-fits-all format — but most sessions center on what’s most pressing or most meaningful to explore. That might be a difficult decision, a challenging team dynamic, or a longer-term pattern in how you lead. Some sessions are tactical. Others are more reflective. The goal is always the same: helping you think more clearly and lead more effectively.
Do you offer 360 feedback?
Yes, when it’s useful. I offer tailored 360s using a mix of interviews and thematic synthesis — not generic surveys. These are best for clients seeking deeper feedback from peers, reports, or board members. We decide together whether it’s the right move based on your goals.
How do I know if I’m ready for coaching?
Coaching works best when you’re open to slowing down — at least a little — to reflect on how you’re leading. You don’t need to have all the answers. You just need to be ready to ask better questions, challenge your assumptions, and grow with intention. If you’re navigating a pivotal moment, coaching can be a powerful tool.
I’m already successful — do I need a coach?
Most of my clients are high performers. They don’t work with me because they’re falling short. They work with me because the stakes are high, and they want to lead at their best — with more clarity, less noise, and a stronger foundation for the long haul.
Can coaching help if I’m feeling stuck or burned out?
Yes. It’s more common than most leaders admit. Coaching won’t solve it overnight, but it can create the space and structure to get underneath what’s really going on — and rebuild your energy, clarity, and capacity from the inside out.
Is coaching worth it for early-stage founders?
Absolutely. The early stages are intense. You’re learning fast, leading for the first time, and making decisions that set the trajectory of the company. The earlier you build your leadership muscles, the stronger your foundation for growth.