“You’re worth it.”
These three words, stated by one of my close friends over late-night cocktails, launched a transformational chapter of my life: working with an executive coach to super-charge my personal and professional leadership.
More on that in just a bit…
Backstory: Why I Hired A Coach
I hired an executive coach so that I could transform myself as a professional.
I ended up transforming not only my career, but many other parts of my life.
Originally, I hired a coach because I was seeking mentorship. I’d transitioned from working in marketing communications to joining a company in a business development role. I was eager to learn from someone experienced in the field. When I was unable to find a well-suited mentor, I chatted with a colleague who mentioned that he was working with an executive coach.
I was only familiar with the idea of executive coaching in passing, but was piqued by my colleague’s choice to, essentially, “pay” for a mentor. And I figured it could be even better than a mentor, because the relationship and the exchange would be clear: pay to engage a coach, and in exchange the coach and coachee will have regular, dedicated time together. It seemed worth exploring.
I wasn’t totally sure what to expect from a coach. I figured they’d be an objective voice of reason, a listening ear, and an experienced professional who could suggest tools or strategies to help me up my game.
Coaching, Entry Level
I worked with my first coach for one year. She had previously been my client when I freelanced as a copywriter, so I was familiar with her work as both a therapist and a coach. I reached out to her, we met to discuss why I wanted to engage a coach, and then we set a plan to meet once per month for hour-long, in-person sessions.
During our sessions, we talked through goals, discussed what notable things happened at work over the previous month, and agreed to the “homework” that I’d work on leading up to our next session. Sometimes I cried. Sometimes I vented. She asked a lot of really good questions. She challenged my assumptions. She helped me see through the fog of some tough career circumstances.
This format and level of coaching was helpful as I transitioned into my new role at work. The monthly cadence gave me accountability for my goals, and I added a few new communication tools to my toolkit.
After approximately a year, we both sensed it was time to transition. I had accomplished most of the goals I originally established.
Coaching, Leveled Up
I met my second coach serendipitously.
I was not actively searching for another coach when I met Miriam Meima. I sat a few seats down from her at the opening keynote event for Boulder Startup Week. I was instantly magnetized to this woman because of her grounded presence—she had a joyful charisma. I knew I had to meet her.
A mutual friend introduced us, and I asked Miriam to grab coffee. When we met a couple days later, I learned that she was a leadership coach. During our conversation, I got a sense of her philosophy and approach. She later emailed me her coaching process and the retainer model commitment. It was a level of financial, and mental, investment that terrified me. It felt like moving up to the major leagues.
During the weeks that I spent carefully considering this decision, I was with my friend, Matt, talking about the opportunity to work with this coach—and feeling intimidated by the cost and commitment required to work with her. Matt said something so simple, and so shocking to my system: “You’re worth it.” And he meant it. It was his direct, unflinching call to action that pushed me over the edge.
The next day, I signed the retainer with Miriam and embarked on what would become a year of intensive self-work.
How Coaching Worked
This time around, I had a clearer sense of why I wanted to engage a coach (again).
Before our first official session, Miriam invited me to complete a worksheet that outlined my initial goals, which we went over during our first call. I met with her every two weeks on a video call, eventually slowing to once per month after our first few months of working together. We had regular communication between video calls, through phone, Voxer, text, and email.
Most of our sessions consisted of her asking brilliant, challenging questions, and me laughing, crying, and thinking through those questions, aloud, with her. She never told me what to do. Instead, she invited me into new ideas and possibilities.
I had homework between video calls, which ranged from journaling, to practicing new tactics at work, to reading and video content. The goals we set during our first session were either achieved or changed as the months progressed.
I kept a journal dedicated exclusively to coaching. I made my own notes, I took notes down during our sessions, and I pasted in Miriam’s notes that she’d email to me after each session. This created a body of work that I continue to reference to this day.
The throughline of this experience was a blend of introspection and practice. It. Was. Hard.
What I Got Out Of Coaching
I got so much out of coaching. I unpacked past work-related baggage, much like my experiences in therapy. I examined my behaviors, learned patterns, unhelpful habits, and my ways-of-being.
Coaching took me beyond common career questions such as, “What’s the best way to run an effective meeting?” to bigger questions along the lines of, “What stories around money do I carry from my childhood that now impact how I negotiate for compensation and raises at work?” Coaching took my leadership from the smallness of tactics to the bigness of strategy.
I grew more from one year of coaching with Miriam than almost any other single year in my life. Miriam’s compassionate, no-nonsense commitment to helping me identify my strengths and move more fully into my life’s work changed my life.
For example, I was completing my master’s thesis during the year I worked with Miriam, and I learned a mind-melting lesson about my approach to big goals that I’d never realized. Miriam made this observation: “You feel more inclined to move forward when you feel far from the summit.” Hey now. What?!
When I started my thesis, I could easily find motivation and energy to research, read academic books, develop my thesis committee, and build a plan to knock my graduate degree out of the park. But the closer I got to finishing my thesis, the more I procrastinated and developed a level of internal stress that bordered on combustion.
Somehow, getting closer to the “summit” of finishing my master’s degree terrified me. I was scared equally of failure (what if I couldn’t successfully defend my thesis research?) as I was of success (what if my thesis research actually has a life beyond a degree?). I was dreading achieving one of my life’s big goals.
As it turned out, that was true of many goals I set for myself. “You feel more inclined to move forward when you feel far from the summit.” So, through the coaching, I learned tactics and strategies to feel inclined to move forward even as I got closer to completing big goals. I learned ways to build momentum and recognize my procrastination habits. (And I did finish my thesis!)
Through coaching, I became more curious. More apt to consider multiple sides of a problem. More centered in stressful situations. I developed more confidence. I formed an executive presence that I’d previously been unable to grasp. I softened some of my rough edges. I sharpened some dull skills.
At a high level, this is what I got out of coaching:
- Feedback—with candid honesty
- Tools—especially interpersonal communication and leadership
- Frameworks & mental models—an “over the horizon” vision
- New perspectives—to pull me out of my old ruts
- Support—to keep a trusted baseline
- Inspiration—going for the unreachable
If You Want to Hire a Coach…
I’ve had friends and colleagues ask me how to find, select, and work with a coach. Here are my suggestions:
Ask for referrals from friends or colleagues. There are many different styles of coaching, and each coach will approach the work with their own models, theories and practices. Look at their website or social channels. If their language and style resonates with you, it’s worth reaching out to them to learn more.
I’m now a leadership development coach, and would love to chat with you about coaching. I’m also fortunate to be in community with many other sharp coaches and happy to make recommendations — send me a note.
Meet with them once.
Any coach worth their salt will offer an initial complementary consult, in person or over video/phone. Take advantage of this, and speak with two or three of the top coaches you uncovered in your research. Ideally, you want to have chemistry and a mutual connection with each other.
Have ideas about why you want coaching.
Before you meet with coaches, make a short list of why you’d like coaching. Is it to become a better manager? Navigate a career transition? Set better professional goals? Develop interpersonal communication skills? Your coach will guide you through a process to understand your goals once you start your work together, but it sure doesn’t hurt to consider your “whys” early in the process.
Be ready & open.
The most useful coaching will take you to raw, vulnerable places. Be emotionally & intellectually ready and open to doing the hard work. And be ready to change. (This is often the hardest part!)
Commit time & resources.
The best results will come from meeting with your coach frequently and consistently, at least as you start. Coaching requires a time investment, including the coaching sessions themselves, as well as the work you do on your own. It will also require a financial commitment, which varies from coach to coach. I thought of my coaching as an investment not too different from paying for a college degree. It certainly was a worthy education. (And to be honest, coaching equipped me with tools I never learned in college—but wish that I had.)