How to Interview an Executive Coach (or a Doula)

Bethany Crystal
Jan 22 · 5 min read

I hired an executive coach the same month that I hired a doula. As it turned out, these were pretty similar tasks. So, I thought it might be helpful to share some reflections about how I approached this process and a couple of questions that might help you, too.

First off, let’s start with some basics.

What Are They?

Executive Coach: Someone who coaches career professionals on their personal and professional development. Often, they serve as a “mirror” to their clients, reflecting back on themes or ideas that might be hard to see for yourself.
The Goal: Help you identify areas of self-awareness, identify any blindspots, and coach you through behavioral changes to help you “level up” your leadership skills.

Doula: Someone who coaches women through the process of giving birth. They stay by your side throughout the entire process of labor and delivery, offering a mix of coping mechanisms, motivation, and hands-on techniques until the baby is born.
The Goal: Help you and your partner manage through all of the sensations and stages of giving birth, including navigating relationships with the hospital or medical system.

How Coaches & Doulas are Similar:

  • They are both *really* up in your personal business.
    I can think of few other professions where you hire someone with the explicit task of seeing you at your best and at your worst. Exec coaches have a penchant for asking just a few more personal questions than you might feel comfortable answering, stripping away your “professional mask” and leading to a level of vulnerability that might feel foreign to you in a work context. And doulas will quite literally see everything…the way you contort your body in discomfort, the fluids you excrete from multiple orifices, the tears you shed. They may hold the unique honor of being one of the few people on the planet who may ever hear you moo like a cow in pain. Given all this, trust in both relationships is paramount to your mutual success.
  • There’s a spectrum of philosophies.
    Like any people-centric profession, there’s a wide range of approaches. You might speak with coaches that insist on mindful meditation or poetry readings at the start of each session, or with coaches who ask you to create a “business plan” for your personal development that they hold you accountable for. One doula I interviewed would only agree to work with me if I committed to meeting with her on a weekly basis for the four months leading up to my birth so we could form a stronger spiritual connection and bond. As a result of these gradients, the “personality fit” is key in both contexts.
  • Both relationships require work on your end.
    Yes, you are hiring someone to help you execute a task (“help me be a better leader” or “help me get this baby out!”), but neither one can do that work alone. With exec coaching, you need to be willing to be open-minded in your approach to professional development, challenge your own assumptions, and practice some new behaviors. Similarly, at the end of the day, no matter who else is in your hospital room, you are the only one who can push that baby out of your body. In both contexts, friction develops if you fight against your coach’s methods or practices too much. In other words, you need to first want their help in order to benefit from their help. It’s a two-sided street.

Interview Questions for Your Exec Coach (or Doula)

When going about my search for an executive coach and a doula, I interviewed about 4–5 people in each category. Going in, I thought it might be helpful to create a consistent framework of questions to help me navigate the nuances of different personalities. While this evolved over time as I spoke with more people, here are the three questions that helped me the most. In either context.

Question 1: What makes your practice or philosophy different from others?

This is probably my favorite question to ask because you get two valuable pieces of information all at once. First, you get to hear — in their own words — what they believe to be their unique value proposition. Second, you get to hear how they reflect on their peers or competition in the space. Often, I’ve noticed the way people react to their peers (whether it’s competitive, collaborative, or isolating) exposes a lot about their personal philosophies and overall character.

Question 2: What does a session look like? What’s happening? How is it structured?

In professions like coaching where the “deliverable” is so abstract, it can be hard to pinpoint what exact you’re looking for in that initial conversation. As a pretty literal person, it helped me to break through the layers of abstraction and try to get them to visualize with me what a session or our experience might look like. By painting a picture together (including things like where we meet what the room looks like, what we talk about, and what the process looks like), I was able to imagine each relationship a bit more clearly. As an added bonus, if I found someone unable to walk me through this “paint the room” exercise with me, I knew that we might not share a similar enough vocabulary to effectively work together.

Question 3: What have your most successful client relationships had in common?

It’s impossible to ask a coach or a doula to predict how exactly things will go for you by the end of their engagement with you. Sometimes, the thing you went in to get coached for morphs into an entirely new problem. And many times, as new mothers know, despite all best intentions, you need to throw your birth plan out the window. So I tried not to ask too much about my success, but instead asked about what they observed about successful previous client relationships. Do most of their clients establish a regular texting relationship? Is there a degree of “homework” or “prep work” needed on the part of the client in order to create a solid working relationship? And, in the case of my doula, how involved were the partners of her clients in the birth process? And what did this look like? Just like the “painting the room” exercise, this question often helped me to listen for subtle cues about their current client base and help me decide for myself if I felt aligned with (or removed from) their operating mode.


Pulling it all Together

By this point, I’ve been working with an exec coach for about three months and had two or three conversations with the doula that I ultimately chose.

While we’re clearly still in the thick of the process, I do believe that I chose well in both cases. In both relationships, I feel a deep sense of commitment in the relationship. And even though both individuals often ask me to explore new processes (in the case of my coach, a new way of thinking; in my doula’s case, a new way of helping me relax my muscles), I am willing to play in these new spaces because we are starting from a foundation of trust.

At the end of the day, whether you’re looking for a coach, a doula, a business partner, a romantic partner, or someone else, I imagine that’s what it all comes down to the most.


Originally published at Dry Erase.

Bethany Crystal

Written by

GM @USV, alum of @StackOverflow and @NorthwesternU, board member at @CompSci_High and @NUalumni, co-founder of #BeyondCodingNYC

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