Six lessons from working with executive coaches

Coaching is not just for athletes.

Photo by Alejandro Escamilla on Unsplash

I used to ask myself: How can I get better? But as an entrepreneur, the real challenge became scaling my abilities alongside my company's growth.

"So many thoughts. I really want someone on the outside to talk to. Like a mentor. Someone who can coach me through all the thoughts in my head and help me get a handle on our fundraising." — Journal Entry from 2016-01-24

After four years of running a startup, my company got acquired, and one of the first "luxuries" I got at our new home was an executive coach. Looking back, it's been a pillar helping me evolve into the COO role and to scale at the acquiring company — where we continued to fix the engine while the plane was flying.

I had a lot to learn since I was always new to what I was doing — that's what happens when you've only worked in executive positions at startups. I was used to figuring things out on my own, which was rewarding. Still, sometimes I thought I would scale faster from having someone to show me the ropes and coach me through managing people (up, down, sideways) at scale, thinking organizational systems for 18+ months ahead while also making daily progress towards our short-term goals.

During my startup journey, I benefited from informal mentors and company advisors who helped me along the way, but no one kept me accountable for my growth on a continuous basis.

Without a coach or extreme rigor, you stop growing. Below, I'll take you through my own coaching journey with the accompanying lessons learned along the way.

Lesson #1: Ask your network for recommendations

My first coach was shared with the CEO of my acquiring company. He had followed the coach on Twitter and was impressed by their thought leadership. Since I was clueless about finding a coach, I seized the chance to work with someone trusted.

In addition to fostering a safe space where I could discuss the things I was too afraid or insecure to bring to light elsewhere, my first coach asked me about my intention and personal development areas:

"I want to grow in both the improvement areas I'm aware of and those I'm unaware of. I want you to help me identify those and push myself to grow and change my mind and attitude where I've become "stuck." — My intention when starting to work with my first coach.

"Becoming more efficient by doing the most important things first, building rapport with the team, and adapting to change much faster." — My personal development areas when starting to work with my first coach

Over six months, we met bi-weekly for one-hour sessions, with zero to no communication in between. Although the coaching helped me through my first termination conversations and overcoming insecurities in the new role, it felt very transactional, and I experienced a lack of clear drive for outcomes. This may have been partly because I didn't research their coaching style or clarify my own needs from the start.

After working with my 'hands-off' first coach, I realized I needed someone more proactive to challenge and hold me accountable for my goals.

Lesson #2: Do a discovery session with several coaches before deciding which one to use

I met my second coach at a networking event a few years earlier. I didn't have the money to pay for coaching at the time. He had been following up with me over the years (proactive), and as the stars aligned (having funds), he offered to do a free 'discovery' coaching session. Afterward, he emailed me the high-level discussion points and my action items—to get a flare of how he followed up and was proactive between sessions. 

My advice for anyone looking for a coach is to focus the discovery sessions on either the challenge/growth area you have in mind OR challenge the coach to help you identify them through the conversations. You're often getting great results just from these free 30-60-minute sessions!

Additionally, I recommend asking:

• What is your coaching style?

• What are your areas of expertise?

• How do you measure success?

• What are your fees?

Looking back, coaching costs vary widely based on location and industry, ranging from $500 to $12,000 monthly. Some may offer hourly rates. Platforms like BetterUp can be an affordable option to consider for getting started.

Lesson #3: Find a coach who speaks frankly and says the things that cannot be said

My second coach emphasized the importance of aligning actions with personal values. I remember a termination where I was too focused on my own discomfort from hurting their feelings. He helped me see how I could honor my 'integrity value' and simultaneously share the detrimental news.

As a 'people pleaser' who culturally grew up to not ruffle any feathers, we also spent much time with my 'saboteur' (take the Saboteur assessment here). This was often triggered by my never-ending imposter syndrome (someone I'm today punching in the gut weekly as I'm publishing on my Substack).

"You are so committed to growth even under difficult circumstances, and it's amazing to see how calm you can remain even with so many balls in the air (personal and professional). As we discussed, sometimes you need conviction to move forward even when things aren't perfect. Toes might be stepped on, not everyone will be happy, yet you can still move forward and honor your values as best you can. And as the 360 feedback described, your team fully supports you in making that shift." — Excerpt from an email from my second coach between sessions reminding me that it's ok not to please everyone.

While my second coach was proactive and helped me stay true to what we discussed and my values, I felt two things were missing:

First, we focused too much on that day's fire and not enough on progressing toward becoming more strategic and less of a doer. Ironically, we failed to 'see the forest for the trees.'

Secondly, I often felt too busy and scatterbrained to go through all the probing and self-inquiring questions. Instead, I wished he'd sometimes just advise me what he would do based on his experience.

Related, I felt like I needed someone who would speak their mind more freely and not worry about my feelings. I needed someone to call out my blindspots and keep me accountable to them.

After we raised $60m in funding, we started rapidly growing the team. Our lead investor recommended a specific coach they used across their portfolio. I was grateful to find someone who was extremely frank, straight-shooting, and experienced in my role as COO. She helped me think through our organizational challenges with an 18+ month lens while battling today's crisis.

Lesson #4: If you're new to coaching, any coaching will be good

With new funding, we grew the team from ~40 to ~80 over six months. With many first-time managers, we looked for scalable ways to help them grow in parallel to their increased responsibilities. We tried to close the gap with the coaching platform BetterUp.

This was a massive hit for everyone new to coaching. However, those with prior experience asked for more role-specific mentorship, something the platform didn't provide at the time. 

Lesson #5: Identify what type of coaching you need now

There's a vast flare of role-specific coaches: general executive, communication, sales—you name it. I started with a generalist executive coach and ended up with a specialist operations coach. 

In hindsight, knowing that coaches aren't supposed to actually advise you what to do or share their own opinions, I should've doubled down—paired up an operations mentor with my executive coach for a dynamic duo of growth. Imagine having Claire Hughes Johnson (former COO of Stripe) as a mentor and Joe Hudson as an executive coach! 

Fast Track by First Round Capital runs a top-tier mentorship program, connecting you with mentors who are a few steps ahead in your career path. During my sabbatical, I've been mentoring with them, which has been a fulfilling way to pay forward my experiences. Although it's not coaching, it's a great way to dip your feet into what you can achieve by having someone rooting for you from the sidelines.

Lesson #6: Coaching is a journey, not a destination: expect aha moments to arrive today and years into the future

Now that I'm on my sabbatical, I no longer have a company paying for my coaching, and as a result, no coach. Instead, I've been writing on my Substack to gain clarity of thought and reflecting on my startup journey through memory and (journal) notes.

Reviewing my coaching notes, I've found more benefits and aha moments from the reflections that I'm doing now – with a clear head. There are lots of exercises that I'm revisiting now, such as:

• Defining my values

• Identifying my saboteur

• Understanding my mission

• Reflecting on my blind spots, weaknesses, and strengths

Looking back, I am incredibly grateful for the chance to grow through coaching. But coaching isn't just for startup executives and athletes. Everyone benefits from it. If you want to take your life/business/career/health to the next level, get a coach. 

What are you waiting for?

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A huge thank you to everyone who helped me get this over the finish line, either this week or back in May when I first started drafting it:

Chao Lam

,

Benny Benford

,

Maria Kim

,

Neilda

,

Tiff Willson

,

Chris Cordry, LMFT

,

Di Galeano

,

Jeff Giesea

,

Lavinia Iosub

and

Alissa Mears

❤️