Stop Settling for Mediocrity in Your Leadership Game

A step-by-step guide to choosing the right CEO coach

I just started reading Trillion Dollar Coach, a book about Bill Campbell, a prolific leadership coach in Silicon Valley who influenced the likes of Eric Schmidt, Sheryl Sandberg, Steve Jobs…the list goes on. Bill had a meaningful impact on many of the companies that have become household names over the last few decades — Google, Facebook and Apple, to name a few––and it’s clear that he was a guy any of us would have been lucky to meet.

Interestingly, many of the CEOs with whom he worked were serial founders themselves. While Google’s Eric Schmidt initially balked at the idea of working with a coach, in his first year with Bill by his side, he noted the transformative impact his presence had both on him personally and on the company as a whole.

No matter how experienced you are in your career, a strong coach can be a game changer for every executive.

We’re big believers in the power of coaching here at Pillar, and recently launched a new program that provides every founder in our portfolio with a $5,000 CEO Coach & Wellness stipend. Like all benefits we offer, the program is opt-in, but we’ve already seen that over half the founders in our portfolio have raised a hand to take advantage. Some of our firm’s team members also actively work with coaches, and have directly experienced the power of aligning with the right partner.

If you’re considering bringing on a coach, start with a purposeful approach. I navigated this path myself last year, and pulled together a few reflections on how to find the right fit.

Coaching Isn’t “One-Size-Fits-All”

Reaching out to other CEOs who you respect and admire can be a great place to start for recommendations. (I’ve also included a list of folks who come highly recommended below👇🏾.) But don’t assume that someone else’s endorsement will hold true for you. Just because one of your peers has had great success with a coach doesn’t mean you will too. Coaching is highly personal, and it’s important to connect with someone who suits your own style. Do the work to find the right match.

Understand Your Objectives

Before you embark on meeting with coaches, consider what you’re hoping to achieve. Are you looking for someone who has traveled the road ahead and can coach you on challenges lurking around the corner? Perhaps you’re struggling to wrap your head around how to achieve a specific business result, and need coaching on how to form a game plan. Maybe you’re just looking for a sounding board, someone you trust to share helpful insight and advice.

Here are just a few examples of specific ways you might work with a coach:

  • You just took on institutional capital, and are facing the prospect of managing a board for the first time.
  • You need to have a difficult conversation with a key executive on your management team and need coaching on the best approach.
  • You want to understand the motivations of each individual on your management team in order to foster a healthy dynamic.
  • You want to build a culture around operational excellence at your company, and want to learn from someone who’s done it before.
  • You want to be purposeful about scaling your company’s culture, and need guidance on how to do it in a purposeful way.

Don’t worry if you’re feeling overwhelmed by the prospect of identifying what you need––a great coach will also open your eyes to opportunities for growth that you may not have even been able to see for yourself.

Find Someone with Relevant Experience

While it isn’t always critical that your coach has walked a mile in your shoes, it’s certainly helpful, particularly if you’re sitting in the CEO seat. From fundraising and board management to leadership team dynamics to scaling culture, a coach should have enough personal context and experience to understand the types of situations and challenges you encounter daily. In the absence of direct experience, make sure your coach has experience working with people like you, and understands your professional world.

Take Your Relationship for a Test Drive

Coaching requires a high degree of trust; building a strong connection and rapport creates the foundation you need to explore topics and situations that are often deeply personal. Don’t rush into it — take time to get to know each other. Set up a 30–60 minute call with each potential coach on your list. Observe whether they listen, ask questions, are able to connect the dots and share useful insight. Make sure you vibe with your coach; you’re looking for someone who can hold you accountable and help lead you to positive change, even when it involves nudging you outside your comfort zone. You don’t want to align with someone who will tell you things you already know, rather, you want to find someone who will push and challenge you in positive ways.

Explore the Methodology

As part of your call, ask the coach about their methodology. How frequently will you engage? How will they structure your sessions? How will they interact with other members of your team? Every coach is different. Understand each individual’s approach to give you a feel for what the relationship will look like, and help you understand how to get the most out of working with your coach. Keep in mind that aligning with one coach across your entire team can often create a more powerful coaching experience, one that’s rich with context, but some coaches prefer to focus their energy on CEOs alone. Feel out the right fit for you.

Talk to References

Just like any other interview, make sure to follow up by checking references. Talk to people who have worked with the coach you’re considering. Ask how the the coach tailored their approach to each individual. Find out what worked well, and what didn’t work so well. Remember, you’re not trying to use their experience as a measure for your own potential fit, but rather, are seeking to better understand the coach’s approach and whether it jives with what you need.

A Short List of CEO Coaches

Now you’re armed and ready with the information you need to dig in. As a starting point, all of the coaches below have worked with the Pillar team, one of our Co-Founding Pillar CEOs, one of our Portfolio CEOs, or a founder we respect and admire.

  • SSCA | Stephanie Tran and Brad Spencer: Several coaches are part of this firm, which provides CEO and executive coaching. I personally work with Stephanie Tran, and one of our Co-Founding Pillars and a portfolio CEO both work with Brad Spencer. There are seven coaches in total at the firm, each with a different style.
  • Ardoudse Group | Don Arnoudse: Don was recommended to Pillar by one of our co-founding CEOs’ companies, who has known him for 25 years and has deep respect for his practice. Don works with very senior executives.
  • Working in Sync | Whit Mitchell: Whit Mitchell was recommended to Pillar with high praise by one of our co-founding Pillar CEOs, who has worked with Whit for several years as a coach.
  • Anthony Palombit: Anthony has a psychology background. He works with CEOs, executives and senior teams, and also facilitates workshops. He is very effective by phone, also teaches at Wharton part time.
  • Sam James: Sam was recommended to Pillar by the former GM of a publicly traded company in Boston. Sam has a psychology background, and brings science to his executive coaching in a non-academic way. Sam works with both CEOs and executives.
  • Reboot.io | Dan Putt: Founded by former VC, Jerry Colonna, Reboot offers coaching, 360 degree performance reviews, bootcamps, co-founder bootcamps, peer groups, internal trainings and organizational change management for your company, and plenty of rich resources for entrepreneurs, such as their podcast.
  • Results by Design | Amy Tananbaum: I worked extensively with Amy Tananbaum and the group of coaches she oversees at my last company, Intelligent.ly. Amy and her team have supported individuals ranging from early-stage startups to Fortune 500 companies, and take a highly personalized approach to coaching.
  • Catlin & Cookman| Bouzha Cookman: This group provides CEO coaching, but also hosts CEO groups for early to late-stage companies. Several of our Co-Founding Pillar CEOs and Pillar Partner, Russ Wilcox, have participated in the program, crediting the peer support they received as one of the most valuable resources and entrepreneur can tap.

One of my favorite takeaways from Trillion Dollar Coach so far is the idea that while coaches are helpful, we can’t forget that the responsibility rests with each of us to exercise our inner coach. Authors, Eric Schmidt, Jonathan Rosenberg, and Alan Eagle note, “The reality is that a formal coach will see only a fraction of the moments where you could benefit from feedback and guidance. It’s up to all of us to coach our employees, our colleagues and even sometimes our bosses.”

Aim to find a coach who helps you surface the best coach in yourself, and your company will feel the ripple effect at every level.


We’d love to hear your comments if you’d like to share a coach with whom you e had a positive experience. Let’s chat below 👇🏾