If you’re reading this, chances are you’ve been thinking about working with a CEO coach but haven’t quite taken the leap. Maybe you’ve heard about coaching from peers. Maybe someone on your board recommended it. Or maybe you’re simply feeling the weight of leadership and wondering if there’s a smarter, more strategic way to carry it.
As someone who has coached dozens of CEOs, I get it. Starting a CEO coaching program can feel a bit like walking into the unknown. You’re probably wondering: What happens in a session? Will this actually help me? Is this worth my time?
Let me walk you through what that first coaching session looks like and how it can lay the foundation for the kind of growth that transforms not just your business, but you as a leader.
Why CEOs Consider Coaching in the First Place
Before we get into what actually happens in the first session, let’s talk about why most CEOs even get to the point of considering a coach.
If you’re like most of my clients, you’re successful, smart, and surrounded by people who look to you for answers. But even CEOs hit walls. They may feel stuck. Overwhelmed. Isolated. Pressed for time. Unsure how to take their company, or themselves, to the next level.
You’re used to solving problems, but when you’re at the top, who’s helping you grow? You can’t talk to your board about your deepest fears, you can’t share your doubts and concerns about the company with your management team, and most people at home don’t know how to support you.
That’s where a high-impact CEO coaching program comes in. My role isn’t to give you generic business advice or micromanage your calendar. It’s to create a confidential, high-trust environment where we can have the conversations you can’t have anywhere else and to challenge and support you in becoming the best version of yourself as a leader.
What to Bring to Your First Session
I often tell new clients: you don’t need to bring anything formal to your first coaching session—but you do need to bring honesty.
Come ready to talk openly about your biggest challenges, your blind spots, and the things that keep you up at night. You can show up with bullet points or just a jumble of thoughts. That’s totally fine. I’ll guide the conversation.
Some CEOs arrive with a clear agenda:
- “I need help thinking through a merger.”
- “I’m struggling to get buy-in from my leadership team.”
- “I want to scale, but I don’t know where to start.”
- “I constantly feel overwhelmed.”
Others show up saying, “Honestly, I don’t know what I don’t know and that worries me.”
Both are completely valid. The first session is about meeting you where you are, not where you think you should be.
What Happens During That First CEO Coaching Session
Here’s what you can expect during your first session with me, step by step:
1. We Build Rapport—Fast
Trust is the foundation of any effective coaching relationship. So before we dive into strategy or leadership frameworks, we take the time to connect. I want to know who you are—not just as a CEO, but as a person.
I’ll ask you to walk me through your leadership journey:
- What’s your company story?
- What’s your personal mission?
- What do you love about being a CEO, and what drains you?
- What do you really want to accomplish in life?
This part alone is incredibly revealing.
2. We Define Your Core Challenges
Next, we identify the biggest issues you’re facing today. This might be external, like market shifts or competitive pressures. Or it might be internal, like team dynamics, decision paralysis, cash flow or burnout.
Together, we zoom out and look at the full picture. What’s working? What’s not? What feels stuck?
This is where the real clarity starts to emerge.
3. We Explore Strategic and Leadership Goals
Every great CEO coaching program is built around meaningful goals. In your first session, we’ll begin identifying what success looks like for you both personally and professionally.
Some clients come in focused on business strategy:
- “I want to double revenue in 18 months.”
- “I need to position for acquisition.”
- “We’re pivoting, now how do I lead through that?”
Others are focused on leadership itself:
- “I need to become a better communicator.”
- “I feel reactive, not proactive.”
- “I want to be more intentional with my time.”
Whatever your goals are, we start shaping them here.
4. We Begin the Real Work Right Away
Even in our first session, we often tackle a real issue you’re dealing with right now. That might mean helping you navigate a tough conversation with your COO, thinking through a board relationship, or identifying a key bottleneck in your decision-making process.
The idea is simple: give you immediate value and insight.
I don’t just ask “What do you think you should do?” I will tell you what I think you should do. You already know the answer, you just want validation that you should do it.
How Most CEOs Feel After That First Session
Let me share something I hear all the time from new clients:
“That was the first time I’ve had a conversation where I could be completely honest without judgment.”
Most CEOs operate in high-stakes, high-pressure environments where they’re expected to have all the answers. It’s rare for them to have a space where they can just think out loud, ask tough questions, or admit doubts.
That’s what the first session gives you. A mental exhale. A moment of clarity. A feeling that you’re no longer doing this alone.
You’ll likely walk away with:
- A better sense of where your real challenges lie.
- A stronger vision of what leadership growth could look like.
- A genuine sense of partnership with someone who gets what it’s like to sit in your seat.
What Happens After the First Session?
After that first session, if we both agree it’s a good fit, we’ll create a customized coaching plan.
This plan outlines:
- The frequency of sessions (typically weekly).
- Your short-term and long-term goals.
- Key focus areas (strategy, leadership, communication, time mastery, etc.).
- Specific outcomes you want to achieve.
Each session builds on the last. As we progress, we’ll shift from reacting to challenges toward building systems, habits, and perspectives that scale with your business—and your ambition.
This isn’t about fixing symptoms. It’s about enabling you to become the kind of CEO you want to be.
How a CEO Coaching Program Evolves Over Time
You might come in focused on one issue, but over time, the coaching relationship becomes a catalyst for broader transformation.
Here’s how a typical CEO coaching journey unfolds:
Months 1–3:
- Immediate relief as you offload pressing concerns.
- Identify blind spots and set clear goals.
- Start making faster, more confident decisions.
Months 4–6:
- Strengthen team dynamics and improve communication.
- Build strategic systems to free up your time.
- Begin shifting from reactive to proactive leadership.
Months 6–12 and beyond:
- Lead from a position of clarity and calm.
- Expand your company’s strategic advantage.
- Experience personal growth, increased self-awareness, and deeper fulfillment.
Throughout, I’ll challenge you not just to think bigger, but to act with more intention, more courage, and more precision.
Is Coaching Right for You?
If you’ve read this far, chances are something here resonated.
Maybe you’re not 100% sure you need a CEO coach. That’s okay. You don’t need to be in crisis to benefit from coaching. You just need to be ready to grow.
A great CEO coaching program isn’t about fixing you, it’s about unlocking your potential. It’s about having someone in your corner who’s been in the boardroom, who understands the stakes, and who’s committed to helping you win.
If you’re still weighing whether now is the right time for a coach—or even what questions to ask yourself before starting, watch this short video where I explain how to evaluate your readiness, what to consider before hiring a coach, and how CEO coaching can drive meaningful personal and professional growth.
So if you’re feeling unsure, curious, or quietly excited, I invite you to take the first step.
Let’s Talk
I offer a complimentary initial conversation—no pressure, no obligation. Just a chance for us to connect and see if coaching is the right next move for you.
I’m Glenn Gow, The CEO Success Coach. With 25 years as a CEO, five years in venture capital, and 10 years of coaching CEOs, I’m here to help you succeed. I’m also a Harvard MBA, a board member, and an AI expert.
I offer a complimentary 60-minute coaching session to qualified CEOs. You’ll get valuable insights from our time together and decide whether you’d like to continue with coaching. Why not give it a try? Go here: glenngow.com/apply
