My Experiences with Professional Coaching

It’s after work, before the holidays in 2016 and inside the Lever office in downtown San Francisco, I’m hanging out with my friend Jen, catching up and venting about work. I’m telling her about some hard decision that I didn’t have enough validation on when she suggests, “You know, one thing that’s worked really well with our team is professional coaching.” She explains how she helped her team find the best coaches, the benefits of coaching, and referred me to Christina and Blue Door Partners.

So a week later, I’m dialing their number, not knowing what to expect but open to being challenged.

“Hiiiiiiiii”, says Christina. “Hey, this is Ryo. So, what happens now?”

Fast forward a year, and I’ve been able to work on a bunch of longstanding challenges like,

  • Saying yes too much
  • Taking work too personally
  • Not giving people enough space for their own feelings
  • Not being assertive, authoritative, charismatic, inspiring, vulnerable, or strategic enough
  • How to be a more supportive partner
  • Upcoming challenging social situations
  • Recovering from breaking someone’s trust

Looking back at it, it’s hard to believe I covered all of that. When I started the coaching experiment, I didn’t expect much. But I ended up getting a lot out of it. So, I’m writing this post for anyone who hasn’t explored coaching as an option for personal improvement because I didn’t know what to expect when I started.

Before going into what coaching actually involves, I admit that it seems silly. But when you pay a couple hundred dollars to work with someone to do silly things, you start to pay more attention to both the task and its intended value.

The initial coaching work consisted of exercises like:

  • Inner Voices - Have you ever lost control of your inner monologue? This exercise involves writing a paragraph describing the inner voices in your head. A Saboteur voice that comes up whenever there’s uncertainty. A Practical voice that focuses on what to do next. An Appreciator voice that comes up to reflect on positive situations. etc. These voices are then revisited throughout future coaching sessions to improve recognition and understanding of how you feel.
  • Strengths/Weaknesses - Another part of understanding yourself is appreciating your strengths and admitting your weaknesses. Writing a paragraph about one’s own strengths, and then acting them out in a physical motion representing the strength, and doing an investigation on weaknesses can bring themes to recurring challenges.
  • Improv - How awkward is it to do improv exercises alone and over the phone in a glass conference room that all your coworkers can see and hear into? Very! That’s why I take my calls in the back room. Based on the value I got out of the coaching improv work, I even ended up taking a class at a local theater, BATS.

From there, the sessions followed a common pattern.

  1. Biggest Challenge - The beginning of every session started with a question: “What do you want to work on?”. There’s a significant chunk of value attached to having someone ask you this question. After going through a couple sessions, I realized that in the rush to get things done, it’s easy to ignore the harder challenges that have no easy answers. But they don’t go away. They’re on the back of your mind, collecting in a pool which eventually gets distracting, irritating, then unavoidable. And having someone ask you that question helps empty that pool.
  2. Exploration - Going deeper into the topic through a series of Powerful Questions. Alternating between questions, and having Christina reflect back on me her observations of how I answer. Having a great coach allowed me to have a mirror on both my external projection and internal perception. A coach is supposed to help you find your own answers (although I did from time to time get straight advice, which was nice too).
  3. Homework - identifying actions that can be taken in the next week to either explore or improve the issue. The homework would be reviewed at the beginning of the next session. The pressure to actually follow through with the homework was valuable.

Every 2 weeks, we’d have a 30-minute session following the above structure. The meetings felt like a pocket of intense inner reflection, in a sea of external responsibilities and priorities. And having the support from someone you know you can share everything with feels great.

If you’re interested, Blue Door Partners offers individual coaching in addition to Pop-Up Coaching where they come on-site to run individual coaching sessions for companies. We’ve had a great experience offering the service to our employees as a perk to improve wellness and professional growth. In addition, it’s a smart idea to set up initial introductory sessions with a couple coaches and see who gels with you. Yelp is great for this.