In this episode, we dive deep into the real-world challenges and profound rewards of leadership.

I’m joined by Jonathan Bennett—Executive Advisor, Professional Mentor, and Strategist—who helps leaders find clarity, confidence, and purpose amid the pressures of high-stakes decision-making. Jonathan shares insights from his own journey: from being an executive in a large hospital system, to founding and scaling a successful management consulting firm, to ultimately creating an advisory practice focused on supporting the people behind the roles.

We talk about navigating mergers and acquisitions, building psychologically safe cultures, knowing when you need an advisor versus a coach, and how leaders can carry the weight of responsibility without losing themselves in the process. This conversation is a must-listen for anyone in a leadership role—or aspiring to step into one—who wants to lead with integrity and make a meaningful impact.

Jonathan Bennett has worked with hundreds of organizations and leaders around the world. He brings a blend of deep listening, strategic thinking, and honest insight to his work with founders, CEOs, and C-suite leaders.

He’s also the author of seven literary books and a passionate advocate for inclusive, ethical leadership. Based in Ontario, Canada, Jonathan’s mission is to help leaders thrive while staying true to who they are.

Watch this episode on Youtube: https://youtu.be/EppXbxJhL40

🌐 Connect with Jonathan:

Website: clearlythen.com

LinkedIn: Jonathan Bennett

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Disclaimer

The Entrepreneurial Elevation Podcast and content posted by Kelley Beveridge is presented solely for general informational, educational, and entertainment purposes. The use of information on this podcast or materials linked from this podcast or website is at the user's own risk. It is not intended as a substitute for the advice of a physician, professional coach, psychotherapist, or other qualified professional, diagnosis, or treatment. Users should not disregard or delay in obtaining medical advice for any medical or mental health condition they may have and should seek the assistance of their healthcare professionals for any such conditions.

Transcript

[00:00:00] Jonathon opens with a powerful reminder: Celebrate how far you’ve come. Entrepreneurship is tough, and hitting a dry spot doesn’t mean you’ve failed—it just means it’s time to adjust your approach.

[00:04:00] Kelley introduces Jonathon, an executive coach, advisor, author, and seasoned leader with experience across urban, rural, and First Nations communities. He’s passionate about helping leaders tackle tough organizational obstacles.

[00:09:00] Jonathon shares how starting his career close to CEOs shaped his understanding of leadership. Early exposure to boardroom dynamics taught him how high-stakes decisions are made—and communicated.

[00:13:00] They discuss the biggest challenge for leaders: what got you here won’t get you there. Jonathon stresses the importance of learning to delegate and letting go of the “hero” mindset.

[00:18:00] Kelley and Jonathon dive into practical delegation. It’s not about dumping tasks—it’s about creating agreements and accountability so people take ownership and grow.

[00:23:00] On inner pressures: Jonathon explains how leaders carry invisible weight. It’s isolating because there’s often no safe place to share doubts without scaring boards, investors, or teams.

[00:28:00] Advice for leaders on the brink of burnout: schedule intentional reflection time, plan vacations proactively, and stay curious to keep inspiration flowing.

[00:33:00] Jonathon discusses staying connected to purpose and values. For him, true leadership means making decisions that align with your ethical compass—even when it’s hard to walk away from money or clients.

[00:38:00] They talk about impostor syndrome. Jonathon shares that even top CEOs experience self-doubt. Vulnerability and being willing to say “I don’t know” is actually a powerful leadership trait.

[00:43:00] Jonathon’s call to action: Build your own personal board of directors. Surround yourself with people who will tell you the truth and support your journey. Leadership is hard—but you don’t have to do it alone.