How to Interview an Executive Coach So You Don’t Hire a Navel-Gazing Guru or an Overbearing Drill Sergeant

executive coach reads over new material for interview
Photo By Andrea Piacquadio

If, tomorrow, I had to make a purchasing decision about a new chainsaw for clearing brush, an exotic emu pet for my back yard or an herbal medicine practitioner for my aching back, I wouldn’t know where to start. Since my wife is the mechanical one in the family, and the other dads in my neighborhood knock on our door all of the time to borrow her power tools, I’d trust her to make the right call on the chainsaw.  Perhaps Yelp could assist me with the emu and pain relief? 

Despite the ubiquity of executive coaching the past twenty years, the majority of senior leaders, business owners and up-and-coming influencers like you have yet to experience what coaches have to offer. How can you discern if a coach can get you where you want to go, and if they will ultimately be worth the expenditure of your most precious resource: time. 

As a coach of almost two decades, I’ve been interviewed hundreds of times by prospective clients. I greatly respect those who do it cautiously and with intention, because I know that my lived experience, business specialties and occasionally sarcastic personality are best suited for a specific band of leaders who are facing a limited set of challenges.  When searching for your best coaching match, I advise you to look beyond LinkedIn profiles and testimonials on websites, and take the kind of rigorous approach you would if you were hiring a lynchpin employee for your own company. 

The following lessons are derived from the executives who expertly interviewed me over the years, especially the ones who DID NOT HIRE ME, because their process revealed that I wasn’t the right advisor for them, given their unique style and obstacles.

You’re Not Paying for Time, You’re Paying for a Destination

Begin by dispensing with the notion that you are paying a coach an hourly rate to meet with you. You are buying results! When you hop into an Uber, you’ve agreed on the precise destination and the exact cost of getting you there. As a naïve Texan, every time I grab a cab in NYC, I’m sitting in the back seat watching that meter racking up my bill, thinking, “Is this really the shortest route to get to my hotel?”  I want to pay for arrival at a destination, not the tenths of miles I spent in the seat.

Coaching is only valuable if the coach helps you get to your destination.  You should spend at least one or two FREE discovery meetings with a potential coach articulating 3-5 measurable goals or destinations you want to go as a result of the coaching.

·      “I want to craft a one-page strategic plan for my department.”

·      “I want to grow in emotional intelligence as manager, as measured in my next 360 review.”

·      “I want to make a wise decision about whether go to market with this new product.”

·      “I want to manage my time and priorities at work so that I increase my quality family time by 50%.”

·      “I want to be named the successor to our company’s CFO within a year.”

Now, coaches aren’t magicians with a wand to wave to make you CFO next year or turn you from a toad into a prince. The client does the real work, and circumstances may intervene, but the coach guides the path. That’s why you, after you’ve scribed the 3-5 destinations, need to start asking the coach some behavioral interview questions. 

·      “Tell me about a time, you helped a client build a strategic plan that ended up exceeding performance expectations.”

·      “Without naming any names, tell me about some clients who had been criticized for their Type A personalities, and ended up softening their approach after working with you.”

·      “What are some of the analytical approaches you’ve used in the past to help clients make big decisions?”

Past performance with similar clients is usually a predictor of success on your particular coaching plan.  If the coach doesn’t help you draft your destinations, and can’t demonstrate real stories of how they’ve helped in similar situations, you may want to ask the cab to pull over.

Can I Trust Them?

Trust is the nourishing lifeblood of the coaching relationship. My incredibly wise colleague, Dr. Monica Scamardo, defines trust as “your willingness to be vulnerable to another person’s words, decisions or actions.” For coaching to be transformational, you’ll have to be vulnerable. Disappointments at work. Frustrations with your team. Failures. Hopes about the future.

From her research, Monica points out there are three primary components that cause you to trust someone. All of these must be at least partially established in your initial meetings with a future coach.

1.      Competence – Do they have the knowledge, skills and experience to understand the different moving parts of my world, and offer insightful counsel?

2.      Character – Are they driven by strong values? Do they follow through and do what they say they will do?

3.      Benevolence – Do they show authentic care and concern for me? Do they see who I can become? Is their sales pitch more concerned with closing me than deciphering my needs?

As mentioned above, I think you need at least one or two hour-long meetings with a coach in order to establish the early foundations of trust. I realize that many coaches would object to that kind of initial investment, but I’ve always been grateful when my investigating clients have insisted upon it.

Get Beyond the Catchphrases, Ask about the Tools

Every coach has a toolkit. Tools are frameworks, assessments, checklists, readings, experiences and templates the coach will either utilize during your sessions or assign you as fieldwork in between meetings. Most coaches accumulate their tools from other sources, which is completely legitimate. Some work within strategic frameworks like EOS. Others create their own tools. 

In your discovery process, once you have enumerated your destinations for the engagement, then ask your coach to describe which tools they will be using to help you achieve your goals. A Hogan Assessment of your leadership behaviors. A weighted decision tool. An OKR template. A chapter from Brené Brown. Steven Covey’s Important-Urgent matrix. A Nine Box scorecard for your team members. 

You don’t need to recognize or approve every tool. The point is that executive coaching is much more than Socratic dialogue to help you solve your own problems. Your coach must possess the right tools to match your aspirations.

10X+ ROI on Your Time and Money

You’re about to expend a not-insubstantial amount of time and money to work with a coach for the next 4-12 months. Do enough diligence inquiry about destinations, trust and tools to determine the expected payoff and the likelihood of attaining it. Coaches cannot offer ironclad guarantees of results, but before I send a formal proposal to a new client, I always ask myself three questions. “1. Am I the right advisor to help this person with these unique opportunities and problems? 2. Do they trust me? 3. Given my experience, toolkit and abilities, can I deliver at least 10X return on their investment?” 

The stakes are high for executives. Sometimes you are making decisions that affect the success of many people, millions of company dollars or many years of your own life. Ask the right questions to find the best coaching partner. At Emergent Execs, all of our coaches are willing to do the initial discovery work for free to ensure you feel confident moving forward, or we’ll happily connect you to someone in our field who is a better fit.

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