How to find, hire, and get the most from an executive coach

Executive overview

Leadership coaching has shifted from a remedial fix to a strategic investment — the best time to hire a coach is when things are going well and you want to go further. Most leaders struggle to know where to start, who to approach, and what to expect.

Start by interviewing three coaches with different backgrounds. That process alone accelerates self-awareness before any formal engagement begins.

The core insight: coaching is not about fixing failure — it is about unlocking potential at the moments that matter most.

When coaching delivers the most value

• Leaders at inflection points — major transitions, market disruptions, rapid company growth — gain the most from coaching.
• Coaching is equally valuable when things are going well; building on success compounds returns faster than recovering from failure.
• Two common entry points: navigating a specific problem (behavioural, relational, strategic) or identifying blind spots you cannot see yourself.
• Leadership is isolating — people below you filter what they share; a coach gives you unfiltered perspective.
• A 360-degree feedback process, though often uncomfortable, is one of the few ways to see yourself with full candour.

How to find the right coach

• Interview at least three coaches before choosing — diversity of background (e.g. therapy-trained, former executive, traditional coach) reveals different approaches to the same problem.
• Chemistry calls serve double duty: you assess fit, and the coach assesses whether they can genuinely help you.
• Come prepared with the one thing you most want to work on — not a list of five.
• Be honest about your preferences: cadence, level of involvement, what success looks like for you.
• Openness matters more than preparation; arrive ready to hear things that challenge your current thinking.

Experience vs certifications

• Experience coaching (ideally five to ten years) is more predictive of effectiveness than certification alone.
• Certifications signal seriousness and baseline training — useful when vetting less experienced coaches.
• At the highest level, coaches often discard formal frameworks and operate from deep intuition built over decades.
• Elite coaches spend less time with clients, not more — their value is in getting to the issue fast, not in hours logged.
• Mid-range coaches are often excellent mirrors, helping leaders reflect and identify what needs to change.

Format and cadence

• Most executive coaching happens virtually; in-person meetings are the exception, not the norm.
• Weekly sessions typically run one hour; bi-weekly sessions run two hours.
• Weekly cadence suits issues requiring close accountability; bi-weekly works better for strategic, longer-arc work.
• The coach and coachee set cadence together — there is no universal correct answer.

Making the business case for coaching

• Companies are the primary beneficiaries of executive coaching — frame any budget conversation around value creation, not cost per hour.
• Know the budget before meeting coaches; tell them upfront to avoid wasted conversations.
• One study of Fortune 500 companies found a 529% financial return on investment from coaching; when employee retention is factored in, that figure rises to 788%.
• For a high-value leader at a critical inflection point, the return is dramatically higher than the average.
• If your organisation has not budgeted for it, asking for coaching signals ambition and commitment — not weakness.

Slow is smooth, and smooth is fast

• Executives default to speed; coaching requires intentional deceleration, especially at the start of an engagement.
• Taking turns slowly — in driving and in leadership — produces more control, not less progress.
• A coach positioned outside the day-to-day pressure can see when slowing down will create better decisions and stronger outcomes.
• The instinct to charge ahead is often the exact thing coaching needs to interrupt.

What changes over time

• The authors once believed some leaders were simply uncoachable; they now believe anyone can develop coachability — it is a journey, not a fixed trait.
• All meaningful organisational change originates with a leader; great leaders often create change invisibly, by elevating everyone around them.
• A flourishing leader does not maximise personal visibility — they create conditions for others to operate at their best.
• Coaching accelerates the shift from self-focused leadership to leader-as-multiplier.