Why CEO Coaching Isn't What You Think
CEO coaching exists to solve a problem most people don't understand: the more successful you become as a founder, the fewer people can actually help you. This article explores what effective CEO coaching actually looks like..
The moment everything changes
There's a moment every scaling founder faces. You're sitting in a board meeting, presenting metrics that look great on paper, fielding questions you can answer confidently. Then someone asks a question that hits differently: "What's keeping you up at night?"
And suddenly you realize: everything.
The product roadmap you're not sure about. The VP of Engineering who's brilliant but can't communicate with anyone. The funding runway that looks fine until you model the aggressive hiring plan. The co-founder relationship that's gotten weird since you became their boss.
But here's what you can't say in that room: you have no idea if your decisions are right anymore. The stakes are too high, the information is too incomplete, and everyone is looking to you for certainty you don't feel.
This is exactly why CEO coaching exists. Not for the reasons most people think.
What CEO coaching actually is (and why most definitions are wrong)
If you Google "CEO coaching," you'll find a lot of corporate speak about "leadership development" and "strategic thinking." Most of it is written by people who've never sat in the CEO chair during a scaling crisis.
Here's what CEO coaching actually is: it's having someone who's been where you are, who you can be completely honest with, and who has no agenda other than helping you figure it out.
CEO coaching isn't executive coaching scaled up. Executive coaching helps functional leaders get better at their function, better communication, delegation, performance management. CEO coaching not only should help you in these areas, it should also help you navigate the unique psychological and strategic challenges of carrying ultimate responsibility for everyone and everything.
The real value isn't advice, it's experienced perspective on decisions that feel impossible.
Think about it: every professional athlete has coaches. Multiple coaches. The better they get, the more coaching they need. But somehow we've decided that running a venture-backed company, which is arguably more complex than any sport, should be done without coaching.
This is where most founders get stuck. Not because they lack intelligence or drive, but because they're trying to navigate unprecedented complexity alone.
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The scaling paradox nobody talks about
Here's the counterintuitive truth: the more successful you become, the fewer people can help you.
In the early days, you're surrounded by other founders going through similar challenges. You can grab coffee with someone who's six months ahead of you and get real advice. Your investors are hands-on because their money is at risk too.
But as you scale past Series A, something changes. Your challenges become more unique. The stakes get higher. The people around you have never done this before either, because you're all figuring it out for the first time.
Your team looks to you for answers. Your board gives you advice, but they have their own agendas. Other CEOs at your stage are too busy (and often too competitive) to be truly helpful.
You end up making the biggest decisions of your company's life with less real support than you had when the decisions were smaller.
Why founder experience matters in coaching
I get asked why I focus on venture-backed CEOs. It's not elitism, it's specificity.
The challenges of scaling a venture-backed company are different from other leadership challenges. The pressure is different. The timeline is different. The stakeholder dynamics are completely different.
When you're growing 300% year-over-year with a board breathing down your neck and a runway that forces aggressive hiring, you need someone who's felt that specific type of pressure.
I've raised over $150 million across multiple companies. I've built teams from 0 to 250+ people. I've had the fundraising meeting where everything went wrong. I've had to shut down a company and lay off the entire team. I've had the acquisition call that changed everything.
This isn't about credentials, it's about pattern recognition. When you describe a situation to me, I can often see where it's heading because I've been there. I can help you avoid the mistakes I made and the mistakes I've watched other founders make.
The three CEO coaching conversations that actually move the needle
Through working with 50+ venture-backed CEOs, I've found that breakthrough moments happen in three types conversations:
The "what should I do?" conversation
These are the strategic decisions where the path isn't clear. Market timing, product direction, team structure, fundraising strategy. The decisions that feel 51/49 and could go either way.
One Series A CEO was torn between expanding to the US or doubling down on European growth. Everyone had opinions. Through coaching, we mapped out resource requirements, risk factors, and success metrics for each path. The focused European strategy led to their Series B at 40% higher valuation six months later.
The "how do I do this?" conversation
You know what needs to happen but not how to make it happen without breaking everything else. Having a difficult conversation with a co-founder. Managing an unreasonable board member. Restructuring without destroying morale.
A Series B CEO needed to transition their technical co-founder out of the CTO role. The relationship, the team dynamics, the technical continuity, everything was at risk. We developed a 90-day transition plan that preserved the friendship, maintained technical momentum, and actually improved team performance.
The "am I crazy?" conversation
When you're considering something bold that everyone thinks is risky. When you need someone to reality-check your thinking before you make a bet-the-company decision.
One CEO wanted to pivot their entire go-to-market based on what seemed like limited data. Through coaching, we stress-tested the hypothesis, identified key assumptions, and designed controlled experiments. The pivot worked and became their primary growth driver.
The magic happens when you have someone who can have all three conversations with full context and no agenda.
CEO coaching for London founders and beyond
Based in London but working with venture-backed founders internationally, I've seen how the challenges of scaling are universal, but the solutions need to be specific to your context, culture, and market.
Whether you're navigating UK fundraising dynamics, building international teams, or scaling across multiple markets, the principles of effective CEO coaching remain the same: systematic skill development with accountability and measurable outcomes.
My systematic CEO coaching approach
My CEO coaching approach is built around the reality of venture-backed scaling, whether you're based in London or building globally:
Foundation phase (Month 1-2)
Comprehensive assessment of your current situation and challenges
360-degree feedback from team, co-founders, and board members
Identification of decision patterns and blind spots
Personalized development plan aligned with your company's timeline
Ongoing coaching
Monthly strategic sessions for big decisions and long-term thinking
Tactical support for real-time problems and difficult situations
Direct access for urgent decisions between sessions
Custom frameworks and tools specific to your challenges
Quarterly evolution
Progress assessment against original goals
Strategy adjustment as your company and challenges evolve
Recalibration of focus areas for the next quarter
The goal isn't dependency, it's developing better decision-making patterns that make you more effective over time.
When CEO coaching creates the biggest impact
CEO coaching isn't most valuable when things are going badly. It's most valuable when things are going well but you know they could go better.
The optimal time is when you have space to think strategically rather than just fighting fires. Typically during these transitions:
Pre-Series A to Series A: Moving from product-market fit to repeatable growth
Series A to Series B: Scaling team and processes for the first time
Series B and beyond: Managing complex stakeholder dynamics and organizational challenges
But honestly, the right time is whenever you recognize that the decisions you're making have gotten bigger than your experience base. When figuring it out as you go is no longer sufficient for the stakes involved.
The ROI of CEO coaching: Why it pays for itself
Example outcomes from recent clients:
Average 25-40% improvement in decision speed
One avoided bad hire at VP level saves £75,000+ in costs
Improved fundraising narrative can impact valuation by millions
Better team retention reduces recruitment and training costs significantly
The Harvard Business Review found that companies return between $4 and $8 for every dollar invested in executive coaching. For scaling startups, the multiplier is often higher due to the leverage effect of CEO performance on overall company trajectory.
But the real ROI isn't just financial, it's making the whole job more sustainable. You make decisions with more confidence, navigate difficult situations more effectively, and feel less isolated because you have someone who genuinely understands what you're going through.
Book your complimentary CEO coaching strategy session →
Key questions answered
Q: How is CEO coaching different from having advisors? A: Advisors give periodic advice. CEO coaching provides systematic skill development with accountability and measurable outcomes. It's transformation, not just guidance.
Q: I'm working 70-hour weeks. Where do I find time for coaching? A: Coaching saves more time than it takes. Most clients reclaim 5-8 hours weekly within 60 days through better delegation, faster decision-making, stronger accountability (achieving better results with less). You'll also boost energy and fulfillment by focusing time on the right activities. We meet just 1-3 hours monthly, scheduled around your existing commitments.
Q: Is CEO coaching only for struggling founders? A: My best clients are actually doing well, they want to do exceptionally well. High performers understand that small improvements create massive leverage.
Q: How do I know if I need CEO coaching? A: Simple test: Are you the bottleneck in your organization? Making the same decisions repeatedly? Working harder while the company grows slower?
View complete CEO coaching FAQ →
Client stories: What actually changes
"The 360 feedback revealed blind spots I couldn't see. Within three months, my relationship with our board completely transformed, and we closed our Series B ahead of schedule." — Series A CEO, London fintech startup
"Asher helped me navigate the technical co-founder transition without destroying our friendship or technical momentum. It's the conversation I couldn't have with anyone else." — Series B CEO, AI startup
"Having someone who's actually been through an acquisition was invaluable. The emotional and strategic complexity isn't something you can learn from books." — CEO, successful exit
The choice every scaling founder faces
You have two paths:
Path 1: Keep figuring it out alone. Learn through expensive trial and error. Hope you make more right decisions than wrong ones.
Path 2: Get systematic about developing decision-making skills. Learn from patterns instead of mistakes. Have experienced support for the moments that matter most.
The founders who choose systematic CEO coaching don't just build bigger companies—they actually enjoy the journey more.
Ready to stack the odds in your favor?
The best time to start CEO coaching is before you desperately need it.
The second-best time is now.
What you'll get from our complimentary strategy session:
Clear identification of your biggest decision-making bottlenecks
Specific frameworks you can implement immediately
Honest assessment of whether CEO coaching makes sense for your situation
Actionable insights regardless of whether we work together
No sales pitch. No pressure. Just a founder-to-founder conversation about scaling challenges and proven solutions.
If you're building something important and want to stack the odds in your favor, let's talk.
Asher Ismail specialises in CEO coaching for venture-backed founders scaling from Seed through exit. Having raised $150M+ and scaled multiple companies from 0 to 250+ people, Asher combines hard-won founder experience with systematic approaches to help CEOs develop the decision-making skills their companies need.Scaling a company is one of the most exhilarating — and most demanding — journeys you can take.
