The Top CEOs Embrace Coaching – And You Should Too
Learn or die.
The essence of startups.
Is this totally melodramatic?
YES!
But also…I’m not wrong 😉
Learning, scaling with your company, and growing as a leader are essential components of every successful startup story.
No one cares more about your company than you!
But the skills you needed for 0 to $1M are wildly different than the skills you need from $1M to $10M, then $10M to $50M, and beyond.
Can you grow and learn fast enough?
There’s lots of ways to learn. But do you want to know what the best CEOs do??
COACHING! (Or, as I like to say “professional mentorship.”)
I’ve been lucky enough to work with a variety of coaches over the years. They’ve been instrumental in my personal and professional development.
If you’re looking to get started or wondering what to look for or consider, here are my top 7 suggestions!
1. Identify a coaching style that works for you.
It may take some trial and error. That’s okay! Here are some different considerations, styles, and strengths I’ve seen.
Do you want tough love or positivity?
Do you like the Socratic method (question asking) or direct advice?
Do you want lots of structure or templates? Or something more fluid?
Do you want a peer group as part of 1:1 coaching?
Do you need someone on-call or only for scheduled sessions?
Do you like strong intuition or more facts and figures?
Do you want someone who can help through their network?
Personally, I realized that I do not respond well to tough love. Call me a fragile Millennial but I am critical enough of myself, I don’t need anyone else piling on. I do best with a style that’s uplifting, highly intuitive, understands sport, and strong at reframing and analyzing self talk.
But everyone is different!
I know CEOs who love being told they are wrong or want a “punch in the face” (metaphorically of course).
This is why coaching is so personal and varied.
2. Understand your aspirations.
Something I’ve noticed…on some level, you want to be like your coach. Maybe not in all ways but there is a skill set or knowledge that you’d admire and want to learn. Can you identify it?
I’ve also seen a lot of success when someone finds a coach “like them” in meaningful ways.
Maybe it’s someone from your hometown, built a company in the same industry, a similar career path, same gender or ethnicity, a fellow wellness nerd — whatever makes you feel:
They “get” me.
3. Get a recommendation from a peer. Or pick someone you know fairly well.
Peer recs are the best.
I have worked with people I’ve found randomly on the internet or met (1x) at an event but those did not last.
My favorite coach was someone I knew before they became a coach. I’ve also had peer recs that didn’t work out, but I could still acknowledge they were very good just not a fit for me personally.
If you think you don’t know anyone who is getting coached…you’re wrong! Lots of people have coaches, it just isn’t talked about much.
Ask around, starting with the people you admire most. If they don’t get coaching, they probably know people who do.
4. Go with your gut.
There’s no “right” coach. It’s kind of like a life partner — there’s someone for everyone!
What one person loves may be your worst nightmare.
If you’re deciding between a few options, pick someone you like and are excited to talk with. That is a good, easy sign for fit. Don’t overthink it or make a pro/con list!
I also think it’s valuable to work with the same coach as other people on your leadership team.
Craig Hyde and I worked with the same coach at Rigor and it was very helpful for alignment.
5. Decide who will fund.
It’s normal for coaching to be a company expense. And it never hurts to ask!
It’s (usually) an excellent use of professional development funds, especially in a startup where folks are “figuring it out” and may not have a lot of senior leadership to learn from.
Investors often want founders to get coaching! Also true for high potential team members.
If company budget is tight, paying out of pocket can be worth it.
With the right coach, you'll often see results like better job performance, new financial opportunities, or improved stress levels and life satisfaction.
6. Assess cost options and value.
Coaching engagements can range from $150/hr up to $1000/hr (or more).
Or it can be a retainer model of $1000 up to $10,000/mo (or more).
You can do trial sessions, pay upfront for a certain number of hours, and other flexible options. Most coaches will work with you (within reason) on packages and payment scenarios depending on your situation.
From what I’ve seen, price is not necessarily aligned with quality. It’s easy to think more expensive is better. Or more experience is better.
Coaching (like most things) is a skill that improves with time and effort — but also some people are more naturally coaches, helpers, talent extractors than others.
I think of it like hiring. Consider overall value.
Sometimes 2x the price = 10x the value.
But sometimes 2x the price = is 10% better (or worse). Whomp whomp.
Trust your instinct not the price tag.
7. Make a change if needed.
These things can happen:
You worked with a great coach who just isn’t doing it for you anymore.
You’ve learned all you could.
You want to try a different style.
You want to work on a different skill set than where this coach focuses.
You realized their style doesn’t work for you after all.
Whatever the reason, it’s your life, your time, your (company’s) money.
Do what’s best for you!
It is normal and healthy to change coaches over time.
Professional runners switch coaches every few years. Fresh ideas spur growth.
Now, if you’re trading out coaches very often and it’s always “the coach’s fault”…this is a pattern to examine.
As my friend Betty says, “What’s the common denominator here? You!”
But if it takes a few tries to find a good fit or you’re ready for a change, go for it. Just make sure you’re learning (about yourself!) from each experience.
Have you gotten coaching? What worked for you? What do you look for in a coach? What advice do you have for someone interested in executive coaching?
This is a great guide for CEOs (and any senior leader for that matter), but also a reminder for those of us who coach. We are not all the same nor are we a “one style fits all”. Our initial conversations should focus on fit or match to ensure we provide the most value to our clients and their teams.