What It’s Like to Work With an Executive Coach: Lessons From 5 Business Leaders - Senior Executive
Executive and Leadership Coaching 4 min

What It’s Like to Work With an Executive Coach: Lessons From 5 Business Leaders

Senior executives share the lessons they learned from executive coaching — ranging from people management to career development. They also share how to find a coach that works for you.

by Kaitlin Milliken on January 10, 2022

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  • Over 55% of organizations use executive coaching for leadership development

  • When searching for an executive coach, look for a coaching style that matches your needs and career stage

  • Five leaders share their experiences and the most helpful lessons they learned

Many senior leaders turn to executive coaches for wise counsel on managing a company, scaling a business and professional growth. More than 55% of organizations use executive coaching for leadership development, according to a 2020 report from Chief Learning Officer. 

You can find executive coaches with a background in a variety of industries. Coaches also have experience with different aspects of people management and leadership. 

Senior Executive Media asked business leaders to share the most important lessons that they have learned from working with executive coaches. They revealed conversations focused on mentoring and management, setting career priorities and building teams.

Share your experience: Tell us what you’re working on with your executive coach.

Finding an Executive Coach: Identify Different Styles for Different Career Stages

“I’ve had the opportunity to work with two different executive coaches – [with] completely different styles. … If you are going to work with an executive coach, find one that really addresses what it is you want. So my one coach, which I worked with a little earlier in my career, he was a person who would throw on the floodlight, hand me this giant mirror, and help me see ‘Oh, wow, that’s me. Wow.’ It was a…more tough-love experience of ‘so what are you going to do with that information?’ … I’ve worked with a coach that…[was] a little bit more of a gentle reminder…and a partner with you.

At different points in your career, different things can be incredibly helpful. Find that right coach that’s going to suit what you need.”

Jennifer Reyntjes, chief people officer at Strata Oncology, a cancer diagnostics organization.

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Executive Coaching Lesson: Leaders, Choose Your Words Wisely 

“Earlier in my career, I…hired a coach to help me focus on people management. … Her name was Debbi Nissman Young… One thing she taught me is that, as a manager and as an executive, people will take your words very seriously. So be careful with your words.

Many times, something you say to someone particularly young on your team will have a lasting impact on their career. They’ll remember what you said to them.”

Paul English, founder of Kayak and Lola.com, a fintech platform acquired by CapitalOne.

Executive Coaching Lesson: How to Find Your Next Big Project

“The most meaningful coaching experience I had was in my early 30s. I had spun up a lot of different projects and opportunities, none of which were going to change the world. But they were all sucking up an enormous amount of my time. And I worked with a coach who helped me… The exercise was about going through a process to get all that stuff out of your head and be able to pick what’s the big thing that’s next for you as an individual.

[Executive coaching] is not a business [outcome] necessarily. … There may be a problem you want to solve or a capability you want to get better at.”

Scott Case, founding CTO of Priceline.com.

Executive Coaching Lesson: Build a Balanced Team 

“I talk a lot about people issues with one executive coach… … He has this quadrant method that he uses…[to determine] the types of people that you need to surround yourself with. … You have people that are your strategic people [quadrant one]. Those are the people that you are going to…be talking business strategy with. Your ‘how’ people, which are the process people [quadrant two]. They are the engine builders. They’re the ones that actually help to determine how to actually build efficiency and how to actually get the things done in the business. The tactical people [quadrant three] that come in there and just really know how to actually get those things done – they’re very data-driven, analytical people typically in that case. And there are your culture people [quadrant four].

Most people at least always fit one quadrant. Most people fit two quadrants… And that construct has really helped me and our company…make sure we’re not over-indexing on people that are only talking blue sky and not really executing on the business itself. Versus only bringing in people that are doing things but are not being driven by a centralized strategy.”

— Greg Segall, CEO of Alyce, a corporate gifting platform. 

Executive Coaching Lesson: Recognize Each Individual’s Motivations

“[My coach helped me] understand…what motivates me versus what motivates my team. … When I first started as a leader, I thought everyone is like me. Everyone is motivated by the same thing. Why wouldn’t this be obvious to someone else? The truth is, what’s obvious to us is not obvious to everyone else.”

—  Shama Hyder, CEO of Zen Media, a digital PR and marketing firm.


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