Hiring a coach is like hiring any other vendor, so the usual rules apply. However, hiring a startup or growth-stage CEO coach has some unique twists you should consider.
Generating a List
You should meet at least 2-3 prospective coaches before selecting one. Unfortunately, the startup coaching market is inefficient in the sense that it's hard to acquire quality information readily. Some of the best coaches don't have websites, and plenty of mediocre coaches are brilliant at SEO. As a result, your best bet is to tap your network (investors, advisors, other CEOs, and executives) for recommendations.
Evaluating Coaches
Coaching success is the result of the strength of the relationship. Checking for that rapport and connection is critical. Coaches also look for a good connection, so the standard in the industry is for coaches to do 30-60 minute initial meetings with prospective clients at no cost. These are sometimes called "chemistry" calls.
As I discussed in the article "Why First-Time CEOs Derail and How You Can Prevent It," you should dig into both the coach's technical and adaptive coaching skills, in addition to checking for a sense of connection. Before interviewing coaches, consider what you want to accomplish in coaching. For example, if you're a first-time founder, you probably have crucial technical learning to do around executive leadership skills. If you're an experienced executive transitioning to entrepreneurship, you may be facing more adaptive challenges, for example, making difficult behavioral changes or reframing your mindset about how you show up as a leader. In either case, you'll likely confront both challenges and want a versatile coach who can help with both types of challenges.
The crux move is ensuring you check for the full range of skills while evaluating coaches.
When you're evaluating technical or instructional coaching skills, consider looking for the following:
Skill simplifying and explaining leadership techniques so they can be easily applied in the real world.
A curated library of frameworks, methodologies, and techniques that address a wide range of situations.
An approach to leadership that is consistent with your values and how you want people to lead in your company.
Openness to adapting that approach to your unique needs and situation.
Experience coaching leaders in similar companies and a history of success in this work.
A track record of operational leadership roles in successful companies that provides an experiential understanding of leadership.
When you're evaluating adaptive or inquiry-based coaching skills, here are some factors to consider:
Do you sense chemistry with the coach—connection, relatability, and rapport that will make you comfortable opening up?
Does the coach listen well, pay close attention to what you say, and ask probing questions that force you to think more deeply?
Is the coach willing to challenge you and push you to be the best version of yourself?
Do they understand the dynamics of working within a high-growth startup and the unique challenges leaders face in that context?
Do they see you as a whole person, not just an executive?
Do they seek to understand the dynamics of the team and company you work within and how those dynamics impact your leadership?
Can they help you connect your personal growth and the business outcomes you want to achieve?
Has the coach received formal training and certification in this style of coaching?
Don't hesitate to ask for real-world examples of both coaching styles. Coaches should have a high bar for confidentiality. It's critical, so don't expect a prospective coach to name or reveal specific details. However, you should be able to hear anonymous examples.
If you're looking for a coach who can combine technical and adaptive coaching, check that the coach is aware of the dynamics that come from combining these approaches. It's worth exploring how they handle these different roles. (Note: They may not use this terminology, so you'll need to dig a little.)
Unlike hiring for a critical executive role, your coach is a significant but relatively low-risk hire since they won't be building a team or function within your company. After the first few sessions, you'll have a sense of whether it's working, and you can always make a change if it's not. So, trust your gut and don't overthink the hire.
Paying Your Coach
Generally, there are two standard ways that coaching is packaged. The first is that the coach charges a fixed rate, often up front, for six months of biweekly sessions and usually a 360-degree review.
The other approach is for the coach to charge a monthly retainer for monthly, biweekly, or weekly sessions. In this case, they usually charge separately for a 360 review if they offer that service. In the month-to-month approach, some startup coaches will take a mix of cash and equity for long-term engagements. Feel free to ask about pricing and terms in the initial chemistry call. Prices can vary widely.
The best coaches are an investment, and the ROI can be very high. What is more critical to your company than your success as a leader?
I became a coach partly because of my incredible experiences working with coaches. I was also inspired by the times I failed to get the right coaching and suffered from a lack of support. I hope you have a wonderful journey with your coaching experience. Please comment with your thoughts, experiences, and suggestions regarding hiring a coach.
Note: Confidentiality and respect for privacy are paramount in my coaching practice. The insights and advice shared in this post are based on my general experiences and knowledge and do not represent the situation of any specific individual or company.