A Freelancer’s Journey of Interviewing 12 Coaches

Jānis Lanka
5 min readSep 16, 2019

Some of my friends have had very clear goals right from the get-go the second they graduated college. Not me. I chose to go with a blissful entrepreneurial flow and it gave me some of the most amazing experiences. “Living by default” is how my life choices would best be described — making a yearbook in high school landed me on a team responsible for designing yearbooks in college, which put me on radar to receive a tech scholarship, which got me a meeting with a digital agency from Canada, which gave me a summer internship the following year, which inspired me to co-found a digital agency in Lithuania, which led me across the Atlantic to join the Vancouver 2010 Winter Olympics ecommerce team, and so on.

But this story really started when realizing that “what got me here won’t get me there” and recognizing that most blocks in my future life will be due to my own mind. And since I’m a “verbal thinker” — something I found during one of my sessions that has got me into trouble in both my personal and professional life — I needed someone who is able to guide my thinking, identify my thinking patterns, show me where I’m off, and guide me to a better frame of mind.

Unlike my friend Scot, who just went to the first coach he talked to, I’m of the more pragmatic persuasion and thus inquired for a few more recommendations. Recommendations came out of the woodwork, and suddenly I discovered that the coaching business is a lot more popular than I ever imagined. Just like with therapists, you immediately understand that you’re in the minority who doesn’t have one yet! I ended up with quite a list and it’s just in my personality to do a thorough analysis…and with that kind of attitude, I needed to interview them all!

So here’s what I learned after interviewing 12 coaches…

1) Sharpen your story on why you’re looking for one

Your 20s are filled with discovery and new experiences, figuring out what type of career you’d like, travelling, meeting new people… But in your 30s you need to start focusing and enhancing that direction and set the foundation for the next decade.

There are different types of coaches — transitional, business, executive, life, and probably a few others. So you have to have a very clear idea of what you’re looking for. Don’t seek out a coach that covers it all — I find that the more focused they are, the better they will be able to focus you.

I found that after each introductory call, my story was becoming clearer of what exactly I was looking for. Understanding their vocabulary and coaching specifics helped me to use the correct words and shortcuts in conversation. After a few calls, I was fairly fluent in the lingo but I had to “dumb it down” to evaluate coaches on an equal level regarding what words they used with newbies, how they explained basic concepts, etc.

2) Define a method of evaluation

I created a system that evaluated everyone on the same scale. Think of the elements of the future relationship that are important for you and evaluate each on a five-point scale. For example, here are attributes that were important to me:

  • Questions — How well did they ask good questions to understand me better?
  • Banter — Did I see myself having a conversation with them at their level of energy?
  • Language — Did I understand them or were they dropping all sorts of complex jargon?
  • Business knowledge — What was their business savviness and how entrepreneurial have they been before? Would they understand the freelance world?
  • Authority — How well would they be able to keep me accountable, and would I take them seriously?

3) Ask for a complimentary session

Sure, I was able to weed out a bunch of the candidates based on our informational session, but I still had four strong candidates to choose from! In addition, it’s a really big ask to commit to such a large purchase based only on a single phone call. Luckily, I found out that some offered a complimentary session, so I asked the others for one — they all agreed. During a complimentary session, they helped me to focus on one of the topics I was interested in. This call truly gave me the best insight about how further interactions would go.

Considering that this was a complimentary session, one coach suggested for me to donate money to a charity of my choosing. Took me by surprise, but I realized it’s a nice nice way to acknowledge their time investment in you, and a great way to start a good relationship.

4) Record all the sessions

My interview process was not very intensive and spanned over several months. There were too many details to remember, and ultimately all these sessions were starting to merge into each other and it was difficult to recall the difference between the second and sixth coach interviewed. Luckily, having already had experience interviewing people, I decided early on in the process to make an audio recording of my calls that I was able to revisit.

Record audio if possible (so long as it is legal within your state/provide/country) as it helps to go back and review it, reference it, etc. There are several ways to do so:

  • Phone apps
  • Conference platforms, such as Zoom or Uberconference
  • Loudspeaker and audio recording on your smartphone

5) Consider cheaper options

Some of you will be scared away by the pricetag. This will also take you away from possible billable client work. After all, you are taking an hour-long call, and possibly another 15–30 min recording notes and switching context to another client. Most coaches will prefer a 3-month commitment (every two weeks), so the costs add up.

During my research I learned of a few ways to reduce costs:

  • Offshore coaches — Your coach doesn’t have to be in your city. In fact, they can be a digital nomad living somewhere cheaper, and thus able to offer a lower rate.
  • Communication via instant messaging — Not all coaching has to be done over a phone call, and not all of us can think on our feet and be available for live conversations.
  • New coaches who need their certification hours — To be a certified coach you need to gain a certain amount of hours, and some are willing to give you a really good rate, possibly even grandfather you into that rate for life!

Everyone has their own reasons as to why they need help from a coach — help with a big transition, be a better boss, figure out what to do with the rest of your life, the list goes on. Coaching borrows elements from both consulting and therapy and the reality is, once in a while we need someone with a mental crowbar to open up our brains and help us make sense of that chaotic spaghetti factory. And to find the right match who can do that, you will need to put forth a bit of effort on your side.

Was it worth interviewing all 12 of them? You certainly don’t need to do that. Has my current coaching been worth it? Absolutely. I need to “wrestle” with someone through this, and a coach is perfectly suited for the task.



Jānis Lanka

Building a better internet, one digital brick at a time.