I almost spit out my coffee.

“You pay him $2000… for a 45 minute call??”

“Yeah. Every week. And I’d pay more if I could meet with him twice a week, honestly.”

I, meanwhile, find it hard to justify spending $120 an hour for my vocal coach for singing lessons. But the truth is, it does make sense. I would not be able to correct my pitch and even be aware that I was not “speaking from my diaphragm” if it weren’t for having a coach.

Similarly, my friend was a Founder and CEO of a Series B startup that was edging on 50 employees. And he was claiming that the coaching was worth it for him (and the startup) despite it costing $50K a year.

Do Founders and CEO’s really get that much value out of a coach?

What leaders actually buy when they hire a coach

• A private, objective sounding board. You get a confidential space to test decisions, surface blind spots, and talk through hard problems without internal politics. Coaches are hired for proactive development and for transition support; many leaders use them as an ongoing thinking partner.
  
  

• Structured reflection and measurable progress. Modern coaching isn’t a remedial fix; leaders treat it as a developmental investment with clear business outcomes.
  
  

• Decision quality and follow-through. Good coaching focuses on how you think, not just what to do, which improves judgment and adaptability under pressure.

Quick check: What’s the one decision you’re sitting on today that would benefit from a frank, off-the-record conversation?

Why founders, especially, lean on coaching

• The role loads you with competing demands. You’re expected to project confidence while navigating uncertainty, move fast without being reckless, and stay open with the team while holding the line. That tension is built into the job.

• The emotional load is high. Surveys show large shares of founders report poor mental health, high stress, and anxiety; identity often fuses with the company’s performance. Coaching gives you tools and space to separate person from role and make cleaner calls.

• Internal support has limits. Co-founders and reports bring power dynamics and emotional entanglements. An external coach gives confidential, unbiased feedback when you’re considering a pivot, a key hire, or a board move.

Prompt: Where do you censor yourself with your co-founder, exec team, or investors? Write down one topic you avoid and why.

What changes with a coach

• Sharper decisions. You clarify priorities, weigh options, and choose with more conviction, especially under uncertainty.

• Scaling yourself. You delegate, set decision rights, and shift attention from firefighting to strategy.

• Cleaner team dynamics. You address avoidance patterns, improve the cadence of communication, and hold people to standards.

• Observable business effects. Multiple studies link coaching to higher goal attainment, resilience, engagement, and performance.

What coaching covers for founders (typical scope)

• Personal resilience and burnout prevention

• Decision frameworks and thinking traps

• Hiring, exec alignment, and org design

• Board/investor communication

• Deliberate pivots and market shifts

These show up again and again in founder coaching programs.

Question: If you had two extra hours a week freed from decisions others could make, what would you apply them to?

When coaching won’t help

Coaching doesn’t work when someone refuses accountability or is stuck in rigid blame patterns. Readiness to reflect and change is non-negotiable.

How CEOs pick a coach (and what you should look for)

• Fit and trust. You need psychological safety to talk about strategy and doubt. Many executives prefer external coaches for objectivity and confidentiality.

• Relevant context. For founders, pick someone who “gets” startup pressure, fundraising, and team scaling; for corporate execs, expect 360s, stakeholder interviews, and assessment tools.

• Structure and measurement. Agree on goals, cadence, and how you’ll track progress over time.

• Budget. Executive coaching rates vary widely. Expect a broad range on an hourly basis.

A simple 90-day starter plan

Weeks 1–2: Define 2–3 outcome goals and the decision areas where you want leverage. Schedule recurring sessions.
Weeks 3–6: Map decision rights, create a weekly decision log, and practice one feedback script until fluent.
Weeks 7–10: Install a leadership cadence (1:1s, staff, OKR reviews), with clear agendas and owner metrics.
Weeks 11–12: Review outcomes against goals; refine next-quarter focus and adjust cadence.

Try this self-coaching script today

1. Goal: What outcome do I need in the next 30 days?

2. Reality: What facts am I avoiding?

3. Options: What are three viable paths and the tradeoffs?

4. Will: What will I do this week, by when, and how will I know?
   (Use it in your next 1:1 with yourself.)

Quick FAQ

Is coaching for big-company execs different? Yes. Corporate coaching tends to go deeper on specific competencies and formal stakeholder work; founder coaching spans more areas because the role is broader and resource-constrained.

How often do sessions run? Many engagements start bi-weekly, then shift to monthly, with a plan for outcomes and measurement.

What will we talk about? Decision quality, team performance, your calendar, and the hard conversations you’re postponing, plus the personal habits that support all three.

If you’re coach-curious: book two chemistry calls, bring one live decision to each, and compare which conversation helped you think better. Then commit for 90 days and measure the before/after on decisions made, delegation, and time on strategy.  

So, should you get a coach?

Yes… we think so.

But it’s expensive, isn’t it?

At the end of the day, what you want out of a coach is a sounding board, structured reflection, and sharper decision-making.

We’ve built out an AI coaching assistant that we think does a really good job as a coach. Give us a try, and let us know what you think.