When I give advice to executives looking for a coach, I typically break it down for them into these straightforward steps on how to structure their search. This is Part 3 of my series on executive coaching based on insights from 80+ interviews with executives and coaches, focused on how to find a coach. Check out Part 1 for a rundown of the results and data, and Part 2 for what I’ve learned as a coach so far.

Establish Your Groundwork

One of the most commonly neglected steps in running an exec coach search is taking a few minutes to sit down and reflect on what you’re hoping to get out of the executive coaching experience.

Step 1. Write down your goals

Write down what your goals are for executive coaching.

Prompts:

  • What are your goals in working with an executive coach?
  • Imagine 6 months has gone by and you have had a positive and successful experience with executive coaching, what’s different about your life?

With goals, try to be more specific about what your goals are and where you hope to affect change. Here are some examples:

  • Needs improvement (Symptom identified)
    • I want to improve and get better as a human
    • I want to get promoted
    • I feel stressed and anxious
  • Good (Topic identified)
    • It’s my first time leading a cross-functional team and I want to improve as a manager
    • I want to work on my executive presence
    • I want to get better at managing my time
    • My cofounder and I have been having a lot of conflict and I’d like that to stop
  • Better (Topic and specifics)
    • It’s my first time leading a cross-functional team and I’ve received feedback that I need to step up in communication and cross-functional coordination
    • I need help scaling leadership skills, examples where I’ve felt I could use help include ____.
    • I want to improve my ability to tailor my communication by audience, like ___.
    • My cofounder and I need help getting aligned in our communication, team management style, and vision for the business

With success metrics, it can be a little more amorphous but it is helpful to imagine a situation or outcome you’d like to see improve.

Step 2. Establish your learning style

Write down the style of learning that resonates best with you. This is a helpful way to understand the situations and learning modes you respond best to.

Prompts:

  • How do you learn best? Structured or unstructured? Hands-on or frameworks? Do you enjoy homework and pre-work?
  • How do you prefer to be held accountable to your work?
  • Reflect on a time you’ve tried to institute a new habit or lifestyle change (e.g., diet, waking up early, completing a long-term project, learning something new). What has worked and what hasn’t?

There is no right answer here. For example, some people enjoy homework and highly structured curriculums (e.g., a bootcamp class), while others prefer unstructured discussion-oriented styles (e.g., a seminar). Here is an example of a potential response:

  • I learn best with a lot of examples and the hands-on relevant experience. I dislike courses and prework because I don’t have the time and it’s discouraging when I fall behind. My best experience was with a workout routine, when I worked with a trainer and they responded to my feedback and held me accountable with a scheduled time on my calendar.
  • I love frameworks and it’s how I see the world. I really want to have a structured, challenging curriculum and have some measure of how I’m doing and progressing. I want a lot of extra work like book recommendations. My best experience has been with taking external seminars where there’s a speaker who leads us down a structured path.

Step 3. Define your budget and timeline

It’s helpful to assess your resources before embarking on a coach search.

Prompts

  • How much are you willing to pay?
  • Does your employer offer a benefit or program to help cover the cost?
  • How much time do you realistically have to dedicate to coaching work? (Both # hours per month, and # months)

For coach pricing data, you can refer to my earlier post. TLDR- coaches can charge anywhere from $150-3000+/hr. With most sessions paced at twice a month, this means $300-6000/month, a huge spread! I would advocate thinking this through and budgeting for at least 6 months. It is also a helpful conversation to have with your company.

The other factor beyond money is time. Coaching is typically a longer-term commitment to work with someone. How much time do you have in your life to meet with someone on a monthly basis? If you are someone who craves structure and homework, do you have the ability to put in the amount of effort right now? If there’s something coming up in your life like a new child, role change, or new commitment, that’s helpful to consider too.

Running a Coach Search

Step 4. Curate a list of potential coaches

Now that you’ve done your pre-work, you should be able to run a coach search. I would recommend going down several paths:

  • Referrals – ask your network!
    • I’ve seen people do a general post on social media to ask their network, or ping people they know/respect. When you do ask, pro-tip: include the context of what your goals are so they have a better understanding of the type of work you’re looking for.
  • Coaching marketplace
    • Lots of options here. I know and am a fan of Skye, an excellent service for matching coaches. There are also service like Prismaticco for founder coaching, and b2b solutions like Torch as well.
  • Social Media or Search for content
    • Who are the top thought leaders in your goal area? Are there coaches there? The type of content that they write can be a great insight in whether they will be a good fit to work together.

The overall goal in the list creation is to get to a small subset of coaches (under 5) where you feel strongly that they have goal-coach fit. This means that the coach’s specific background or expertise is a match for the goals that you have. Often, your network will throw out any coach they happen to know, without regard for the specific area that you’re looking for help in. These can be false leads even if they have had a positive experience.

Step 5. Interview at least 3 coaches with a curated set of questions

I recommend reaching out with the goal of having 3 conversations. This may sound like a lot of work, but isn’t the decision to spend several hours working closely with someone kind of a big commitment? Finding a great coach fit is a lot easier if you have something to compare it to.

When you interview coaches, I suggest preparing a list of questions to ask based on the reflection you did earlier. There is again no wrong set of questions, but here are some examples you might come up with:

  • Describe what a typical session looks like for you. What are some examples of topics that people bring you?
  • If I bring you my goal of (x) with context, what are some ways you’d think through working this together?
  • How structured or unstructured are you? How will you help hold me accountable?
  • Tell me about your background in (x).
  • etc.

I always advocate for a standardized set because it will be easier to reflect and compare coaches later. The goal of the interviews is to:

  1. understand their coaching approach and style
  2. understand whether their background and experience areas fit with your goals
  3. get a sense of their “vibe” – your level of connection to them, their credibility to you, the ease of communication

Of this list, the last “vibe” part is in my opinion the most important. The ability to establish a close, trusting relationship is key to a successful coaching outcome.

Step 6. Do you really need a coach?

I always encourage everyone to consider whether coaching is the right fit for them. When it comes to personal development and learning, there’s a whole world of options out there! There are books to read, podcasts to listen to, courses to take, mentors to ask, friends to engage with, journals to write, and so much more. Coaching is one of the more time (and capital) intensive ways to learn, and while it does have its unique advantages, it’s worthwhile to consider whether it’s the best tool for the job.

Prompts:

  • If you were to do something today to accomplish your goal, what would it be? And do you need a coach to do so?
  • What are your alternatives to coaching?
  • Knowing what you know about yourself, is coaching the best option?

I often like to explore with potential clients what they’ve done already to try to reach their goals. I also ask them what they think they’d want to do to work on it.

Step 7. Pick a coach!

Now that you’ve walked through all the considerations, pick a coach and good luck!

Want more content like this?

My understanding of the business of coaching is constantly evolving, but getting the opportunity to talk live to 80+ executives and coaches has helped sharpen my perspectives. I’m glad to be able to share some of my insights and welcome feedback if you have any! Please subscribe if you’re interested in hearing more.