How to Pick a Career/Executive/Leadership Coach

Photo by Cory Woodward on Unsplash

I am a full-time professional coach. Previously, I was a design leader in technology and had spent 22 years in corporate, both as an individual designer and then leading teams working in startups, design firms, and a variety of large companies including Disney and Facebook. I currently support leaders in tech corporations and startups work through challenges where they feel stuck.

But that’s not the story I want to share today. I’m currently seeking a new coach to support me, and I’m outlining my personal experience with coaches in the past, and the current process I’m going through while seeking a new coach. I’ve had a life-long deep yearning to learn and keep growing myself. I was once described by a colleague as the most curious person they’ve ever met.

About a decade OK, the first time I sought out a coach was to fix a problem. I was working as Head of Design and General Manager of the San Francisco office for a digital consultancy with engineering roots. I had been told that while I was a brilliant, passionate, hard-working leader, the other execs in the company had trouble working with me because of my communication style. I had the reputation of being a difficult person, and I worked with my coach to identify what really mattered to me and how to adjust my range of working with others. I didn’t really know what I was doing in terms of finding a coach — I simply asked some colleagues for referrals, and ended up working with the first coach I talked to. I lucked out — we had great chemistry.

When I started working at Facebook, every manager was assigned an executive coach. I didn’t have a choice and it felt like a nice bonus perk where Facebook Learning & Development helped me become a better manager. She was an OK coach, but it felt like we were following a template and we never really connected About six months later, I was lucky enough to be nominated to a women in leadership program where a cohort of 12 of us were supported by 4 coaches. We workshopped together for a week where I was able to experience coaching from all of them. After the week, I bonded with one of them and immediately requested to have her become my executive coach. I stayed with her for 3 years, and unfortunately, when I left Facebook also had to stop working with her as she only worked for corporate clients.

As I left the corporate world to start my own business, I knew that I needed help. As part of my coaching certification program, I needed to select a coach. My experience of all the seasoned coaches who had led many classes was that while I loved coaching, I had a fierce rebel streak that was slightly nauseated by the cookie-cutter inspirational-poster-style of positivity that was natural to many coaches. I was drawn towards the non-nonsense, sarcastic, challenging coaches. This time, I was wiser in picking a coach—I had complimentary 1-hour coaching sessions with three coaches I admired, and after checking the chemistry of the sessions, ended up picking a coach I adored, David Darst.

I’ve had three coaches in 2020— David Darst, Rich Litvin (through a business coaching mastermind), and Rosy Elliott who is supporting my partner and I in co-creating our future lives together. And now as I look ahead to who I want to be and what I want to create in 2021, I realize that I’m yearning for a long-term coaching relationship to support growing myself and my business.

Having talked to many clients who had never worked with a coach before, I’m demystifying the process and breaking it down into four steps: 1. Name the Pain, 2. Ready to Dream, 3. Investment in You, and 4. Dating and Chemistry.

1. Name the Pain

What’s the particular challenge that you’re facing right now? What’s different about it? Most of us address challenges in our same default mode how we’ve always handled them our entire life. For me, I tend to be cerebral— I write lists of pros & cons, try to imagine multiple outcomes, and also consult my close friends. This approach tends to work well for binary decisions such as Should I accept this job offer? Should I negotiate for a bigger salary? Should we move to Montana?

Yet sometimes you get to a place of stuckness for months if not years and can’t easily see a way out. My challenge right now while looking for a new coach is that I’d like to spend time with more self-growth and learning, both for how to be a better person, and also how to fully embody this better person in my business, whether in service of coaching clients, or other consulting projects. It’s something I’ll work on for the next years and likely the rest of my life, however, in these early transition years of starting a business—I’ve heard that the first three years are critical—I’d like a guide who’s been through this to help me along the way.

My clients, who are all incredibly high-performers, tend to ask for help with the following pain-points:

• I’ve just leaped into a new professional phase, and I need help developing my leadership to rise to the level of challenge. The skills that have gotten me here won’t get me there. Professional phases vary from being in the C-suite for the first time, starting a new job and wanting things to be different, inheriting new teams across multiple countries, or managing a team for the first time.

• I am driven, smart, and have high expectations. And there’s a problem when I apply these high expectations to the people around me— people call me difficult and my relationships suffer. (more reading at How to Work with Difficult People… When You’re the Difficult Person)

• Many flavors of career transitions. e.g, I am currently interviewing / looking for a new job and I want help figuring out what’s a good fit for me. Or I’m working in corporate with a side-hustle that’s my startup or own small business—help me make the leap to quit.

• I’ve always been a high performer and have spent years being successful in my career. Now something feels missing and I’m stuck. I’m looking for something to be different, but am not quite sure what.

What pain are you dealing with? How acute is it? Most clients have tried reading books, talking to friends, and working through these issues using their default tools. But it’s not working. This is likely a trigger to seek outside help with a coach.

2. Ready to Dream

As you’re pondering working with a coach, and you’ve already identified the problem, spend some time considering if it’s the right time. To work with a coach and make changes, you have to be willing to dream. You’ve got to be ready to open up, think long and hard about what you really want, how your life could be different, and how big and fulfilling life will be once you start to address the pain.

And sometimes people aren’t ready to dream big. Perhaps there’s not enough time right now because it’s too busy with the end of year sales rush. Perhaps you don’t have enough time to focus on dreaming when you’re barely holding it together balancing the schedules of two working parents while also being a teacher for your distance learning kids. Perhaps you’re at full capacity as a caretaker for loved ones.

Another distinction to make is the difference between working with a therapist or a coach. About a third of my coaching client, also have a therapist. When I’ve worked with a therapist, it’s typically been to look backwards and process past or current trauma & grief that has occurred. While there is a huge variance between therapy practices, often therapy is looking backwards to make sense of the past and of present emotions / reactions to the past. Processing the past is needed before there’s enough activation energy to be ready to dream.

3. Investment in You

If you know what your challenge is, and you have the capacity to dream, next consider what you’re willing to invest to create change in your life. One of the teachers in my coaching program was a seasoned Israeli coach in his late 60s. He’d successfully run a couple of IT companies before switching gears to become a coach in the last decade. As we were scheduling some time to chat, he casually mentioned that his entire month of March was blocked for some learning & growth programs, and when I pressed for more information he matter-of-factly shared that he had an annual 10,000 euro budget for his learning. My jaw dropped! I’d never known of anyone budgeting for personal growth before. It inspired me to create my own budget because of course I value growth and change; and how better than to learn than from other experts.

The other investment I talk to clients about is time. Coaching sessions aren’t simply navel-gazing conversations to discuss issues and come up with insights. Instead, much of the learning happens in between the coaching sessions when clients follow through on an action plan of experiments that are co-designed. Applying new behaviors into day-to-day situations and learning from them helps cement new behaviors and ways of being in the world. How much time are you willing to invest in reflection and running experiments to see how you could do something differently?

Consider how much you’re willing to invest in yourself to grow, to achieve a bigger dream and to eliminate pain in your life. How much money would it take for you to take your problem seriously and want to work on it. I’ve spent $15K for one of my coach’s 7-month programs and another of my coaches charges $400/hour. There’s a range of prices and coaches — what investment of both time and money are you willing to to put in to create change?

4. Dating and Chemistry

Finally, if you’ve thought about steps 1–3 and you’re ready to get started, consider it a process of dating and chemistry. There are a lot of coaches out there and each coach has a distinct style, area of focus, and way of serving her clients. The only way to see if this may be a good coach for you is to get out there and start dating. Every coach will offer complimentary sample sessions where you get to know each other and see if there’s the click of chemistry and resonance. You’re looking for if this person truly gets you and can help you see & become a better version of yourself. My recommendation is to talk to 3–5 coaches and explore which one you’d like to be in a longer term relationship with.

One of my good friends, recently called me up to ask for advice as she’d talked to six different coaches and couldn’t decide who to work with. She told me about each one and gave me pros/cons and wanted help making a decision. I told her not to settle, that she should keep looking and eventually there will be a feeling of amazement of fuck yeah!— I must work with this coach. She kept on dating and several people later found a coach who felt like magic to her.

Bottom Line

Many people haven’t gone through the experience of looking for a coach before so I thought I’d pull back the curtains and share a bit of my 4-step process — 1. Name the Pain, 2. Ready to Dream, 3. Investment in You, and 4. Dating and Chemistry.