How to Hire an Executive Coach

A Practical Guide for Founders, Executives, VPs, Senior Leaders & Department Heads

Most leaders spend more time researching a laptop purchase than evaluating an executive coach.

Anyone can call themselves a coach. No license required.

Most leaders don't know what to evaluate. So they default to what a coach's website says, a few LinkedIn posts, or a warm referral from someone whose situation looked nothing like theirs. Then six months later they have a lot of notes and good ideas but no significant behavioral changes or different results.

The easiest way to hire an executive coach is to request a free session to work on your biggest challenges right now. You'll know within 55-minutes if that coach can actually help you or not. We offer a no-pressure first coaching session for free.

Coaching works when you show up willing to examine what you're actually doing, not just how others are getting in your way. Most leaders arrive with a clear story about why their situation is difficult with their board, the team, the company, the market. Here's the truth: you can't change them. But you can change yourself and how you lead them. Good coaching starts by looking at what you're contributing to the situation, which requires a deeper kind of willingness to change.

You don't need to have everything figured out. You don't need a polished development plan. You need to be genuinely curious about your own patterns and skill level and be willing to act on what you uncover in your coaching sessions.

If you're coming to coaching because you know something needs to change and you're ready to do the work to figure out what and how, you'll do well with a great coach.

Coaching Question: Which are your biggest problems right now? How long have you been trying to figure those out? What are they costing you daily (in frustration, time and money)?

Coaching is pattern recognition. The more leaders a coach has worked with across different role levels, industries, and types of organizations, the more precisely and quickly they can figure out what's really happening with you and what's required.

Ask the coach to walk you through what a typical engagement looks like from day one to the last session. You want to understand how goals are set, how progress gets tracked, and how you'd both know if you're delivering on your desired results.

At HPO, we start with your goals and desired outcomes, including what success looks like. If your company is investing, we ask your manager or HR to add their goals for the engagement. Then we assess your current reality across 10 domains, your current performance, goals, and developmental requirements, so we both know exactly where you are before coaching starts. Then we dig into your challenges, diagnose and define your problems clearly, craft practical action plans, and support you through execution, including skill development, mindset shifts and a toolset you can use throughout your career. We coach you to build skills, improve communication, and deliver better results, faster. At 90 and 180 days, we reassess to measure what changed and what to focus on next.

Coaching only works if you are willing to tell the truth. Most leaders have very few relationships where that's fully possible: your direct reports have stakes in how you perform, your peers are in some degree of competition with you, your manager evaluates you, your partner has limited bandwidth for another hour of work talk, and you can't be completely honest with your board about a lot of things.

Half of CEOs report feeling lonely in their role, and 61% say it hinders their performance (RHR International / Harvard Business Review). A coaching relationship is a rare relationship with confidential conversations where you can be brutally honest to say exactly what you think and feel, and use that to strategize, work through problems with an unbiased advocate to help you see your blind spots, identify your handle difficult issues and develop your leadership skills.  

Good coaching is focused exclusively on you, your reality, goals and challenges.

A first conversation that feels more like a sales call than coaching is telling you the sale is more important to the coach than your goals and challenges.

A lot of people call themselves coaches and engage in mild bullying to just "follow their system," without fully understanding the nuances, needs, and challenges you're facing and how to address those effectively.

A great coach opens every session with your goals and challenges, then immediately starts helping you assess the situation, diagnose and define problems, build practical action plans and identify and quickly develop the skills needed for you to execute effectively. They earn your trust quickly (by acting in your best interests) and regularly add more value than they are charging.

"How do you hold clients accountable between sessions?"

We track commitments you make in every coaching session and review them at the beginning of the next session. We don't hold you accountable. Our job is to help you become more resourceful and hold yourself accountable more often. We dig into what you did, what worked, what still needs addressing and how to execute effectively, given your reality, challenges, goals and stakeholders. If you didn't make progress, we dig into why and next steps to get you back on track quickly.

"Who is your best client, and who doesn't get results with you?"

The best clients are clear on what they want to change, willing to examine their own role in the problems they're facing, and committed enough to do the work between sessions. Leaders who don't get results either want to spend the sessions venting about other people, or they want the coach to solve problems for them.

"Who has access to what happens in our sessions?"

Everything we discuss in coaching is 100% confidential. If your company is paying for coaching, our agreement is clear: our coaches may only share whether you have attended the coaching sessions that you scheduled and if we believe you're responding well to coaching or not. Everything else is kept completely confidential. You may share anything you feel comfortable sharing with your manager or HR.

Most leaders wait until something is clearly not working. By then, the first month or two of coaching usually focuses on triaging high-stakes issues, meaning you're in reactive mode, which is the hardest state to develop leadership skills in. 86% of organizations that calculated the ROI of coaching made their investment back, with average returns of 5 to 7 times the cost. (ICF / PwC)

The leaders who develop fastest hire a coach before problems are obvious. They're performing well, but want to hone the skills they need to perform better. The best case for coaching is: six months from now, I want a much better reality and better results, I want to think, decide and lead differently, and I'm not going to build that capability by working harder or figuring it all out on my own.

Coaching Question: What do you want your reality and results to be in 6 months? What are you doing and learning right now to build toward that?

You now know what to look for: depth of experience with leaders at your level and organizations your size, a structured engagement with change measured over time, a relationship where honesty is possible, and a coach who can respectfully name problems directly rather than shielding you from them.

The fastest way to give coaching a try is to request a High Performance Executive Coaching Test Drive.

A coach worth hiring will immediately help you assess your situation, define your problems clearly, and start building a practical path forward. If that doesn't happen in the first 55 minutes, you need a different coach.

Should I hire an independent coach or go through a coaching firm?

For an individual founder, executive, VP, senior leader or department head hiring for themselves, an independent coach with a verifiable track record at your level almost always produces a better engagement and better results. Independent coaches stake their coaching practice reputation on helping you get results. Large coaching firms tend to hire less experienced coaches and require them to follow standardized methodologies with varying results. The best coaches at large firms tend to leave and build independent practices once their track record is strong enough to build an independent business. Coaching firms make more sense when HR is buying coaching for dozens of leaders and needs consolidated relationship management, reporting and billing. You need a coach informed by deep operational and strategic experience who can be your advocate, challenge you, see your blind spots, and tell you hard truths to help you grow and deliver better results, faster.

Does a coach need to have held a leadership role themselves?

Experience at your level matters. A coach who has never led through a difficult reorganization, managed a team through significant conflict, or navigated the political issues of a senior role is learning on your dime. When you describe what’s happening in your organization, you need a coach who already understands the terrain and can quickly orient to your reality. You should look for a coach who has spent serious time with leaders at your level, seen the specific patterns you’re struggling with, and can quickly help you diagnose and define problems and devise action plans that are tailored to your goals, challenges, skills and reality.

Can I bring current, live work problems into coaching sessions?

Yes, and you should. Bring your biggest challenges, like difficult stakeholder relationships you have to navigate, an important decision you’re struggling with, or a team challenge that keeps producing subpar results. Good coaches will help you understand the patterns beneath those challenges and equip you with the mindset shifts, skills and tools to address them and deliver better results, faster.

What does it mean that executive coaching is unregulated?

Anyone can call themselves an executive coach, which makes hiring the right coach a little harder. Look for coaches with proven track records. Request a free initial coaching session before signing a contract to experience the coach’s thinking and the quality of their questions. Evaluate their coaching by changes in your thinking, decisions and actions.

How do I know when I’ve found the right coach?

The right coach makes you think harder and helps you work through some of your biggest leadership challenges in the first conversation. Every coaching session is focused on your goals and challenges and builds ambitious but realistic action plans that you can execute immediately. Great coaches will help you develop stronger root cause analysis skills, ask you tough questions you wouldn’t have thought to ask yourself, help you build action plans tailored for your reality, and identify and develop the skills you need to generate better results and advance your career.

What happens in the first coaching session?

We offer a no-pressure first coaching session at no cost to founders, executives, VPs, senior leaders and department heads who are seriously considering executive coaching. In that first session you bring your biggest leadership challenges and we’ll coach you just like one of our long-term clients. If you’d like to experience great coaching, our High Performance Executive Coaching Test Drive is a free 55-minute 1:1 executive coaching session. Request yours today.

The High Performance Executive Coaching program (HPEC) is a 4-month, 8-session 1:1 executive coaching engagement for founders, executives, VPs, senior leaders, and department heads who want to build healthier, more productive, and more profitable teams. HPEC leverages the mindset shifts, skills and tools from the High Performance Leadership Operating System, tailored for the unique stressors, reality and challenges of senior leadership. Includes a baseline, 90-day and 180-day assessment to track what changed and what to focus on next.