What does it take to do work you truly love — and to help others find the same? How do the best leaders build teams they’re proud of, instead of teams that simply work for them? And when it’s finally time to exit the business you built, how do you make sure you’re ready for what comes next?

In this episode of Leaders Living Their Values, host Mitchell Levy speaks with Heather Bennett, partner and managing director at Newport LLC, a national C-suite advisory firm that helps middle-market business owners grow, de-risk, and successfully exit their companies. An advisor and career coach with more than 25 years of experience, Heather is also the author of the Amazon bestseller Fun and Fulfilling Careers, One Question at a Time, and the host of The Growth Plus Exit Podcast. A mom of four and a committed outdoor enthusiast, she brings the same belief to her work and her family: lead with presence, listen first, and help people see the potential they can’t yet see in themselves.

Quotes:

• “I firmly believe what I do is a calling. I want people to be doing the work that they love, that they’re passionate about.”

• “You should be proud of the people you work with. You should be proud of your employees.”

• “Stop thinking, and just listen.”

• “It’s being able to see in them what they don’t see in themselves.”

• “It’s always about giving the right message at the right time to the right person, in the way they’re open to receiving it.”

Takeaways:

* Lead with presence — show up, listen, and ask questions before you act, whether you’re managing a team or raising a family.

* Treat your people as colleagues you work with, not staff who work for you, and take the roadblocks out of their way.

* See the potential others miss, and develop people into roles they don’t yet believe they’re ready for.

* Prepare early for your exit — plan not just the transaction, but the identity and purpose that come after it.

Timeline:

[00:04] Introducing Heather Bennett

[00:40] Why Heather sees her work as a calling

[06:26] The unexpected favor that changed her career

[07:48] Lessons learned from raising four kids

[12:24] How siblings inspire and teach each other

[14:59] Working “with” your people vs. “for” you

[16:18] Building pride and advancing your team

[20:17] Teaching leaders how to truly listen

[23:45] Timing the right message the right way

[25:33] Preparing owners for life after the exit

[28:14] The one question every founder should ask

Conclusion:

Heather Bennett shows that great leadership and great parenting share the same foundation: presence, curiosity, and the willingness to put others first. Whether she’s guiding a founder through the most important transition of their career or pointing to the potential a teammate can’t yet see in themselves, her message stays consistent — listen more than you speak, lead with your people in mind, and prepare for what comes next before you need to. Whether you’re building a team, growing a business, or planning your eventual exit, Heather’s insights are a reminder that the work we love and the people we serve are what make leadership truly worth living.

Links/Resources:

• Learn more about Mitchell Levy:

https://MitchellLevy.com

• Book time directly with Mitchell: https://mitchelllevy.com/contact-us

• Connect with Heather Bennett on LinkedIn https://www.linkedin.com/in/heather-h-bennett/

• • Newport LLC: https://newportllc.com/ma-advisory• Heather’s podcast: The Growth Plus Exit Podcast

• Heather’s book: Fun and Fulfilling Careers, One Question at a Time (Amazon bestseller)https://www.amazon.com/Fulfilling-Careers-Question-Step-Step/dp/1954263007

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