A Private Podcast Series for Curious Leaders

Experience the essence of the advisory, mentorship and strategy work I do. Gain practical insight you can apply to your leadership journey by listening in on six actual conversations I’ve had with real (and fully consenting) leaders. Listen anywhere! (Spotify, Apple, YouTube, etc.)

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  • Private Podcast Feed for Leaders

    Confidentiality is everything to me. So even though everyone gave their consent to record, no names are shared. And, you won’t find these episodes on streaming platforms.

  • Six, Real Leadership Advisory Sessions

    As you listening, you’ll gain  an understanding of the essence of my advisory, mentorship, and strategy work and identify whether it aligns with your needs and approach.

  • Powerful Learning & Takeaways

    Each episode will leave you with practical insights you can apply on your own leadership journey. You’ll learn from both myself and the leaders I work with as they share their stories.

Leading is an honour.
It’s also a massive challenge.

I KNOW BECAUSE I’VE BEEN THERE. 

Hi, I’m Jonathan Bennett, a founder, entrepreneur, longtime board director, and business generalist turned trusted advisor and strategist. 

After joining the C-Suite of a large hospital, I spent a decade building a management consulting company. We served over 200 organizations nationwide and became a proud B Corp. Then, in 2021, I sold up and moved on to my next adventure: serving not just organizations but the leaders who run them through trusted mentorship, advisory, and strategy services.

Now, my mission is clear: to help purpose-driven leaders go from being overwhelmed and stuck to thriving.

“Jonathan is a one-stop shop. Whether it's government relations, governance, communications, issues management, crisis communications, HR, business, politics, or the social stuff. Who knows you, knows your career, and believes in you, but who also understands all those things? Once he is invested in your success, he’s all in. I don’t know how I would have navigated my path without him.”

— Hon. Maryam Monsef, CEO, Onward | Former Minister of Women and Gender Equality, Govt. of Canada

LISTEN & LEAD WITH JONATHAN BENNETT

Deep insights from real conversations with leaders.

Every episode in this series is different, but they all have one thing in common: a focus on unlocking clarity, building better strategies, and making leadership a little easier.

  • EPISODE 1

    Social Justice & Leadership: A Founder’s Reflective Transition

    Listen in as we explore the emotional ties founders have to their businesses, the importance of defining an exit strategy, and how to build alignment between personal values and professional goals.

  • EPISODE 2

    Leading with Vulnerability: Lessons for Emerging Leaders

    Meet a thoughtful new leader navigating management for the first time, and hear an example of my professional mentorship work—supporting emerging leaders as they develop the skills and confidence to grow into their roles.

  • EPISODE 3

    A Non-profit Leader Navigates Tough Team Conversations

    Discuss psychological safety, sensitivity, and compensation with a senior communications leader trying to lead meaningful conversations with her team and prepare for a performance appraisal conversation with a valued team member.

  • EPISODE 4

    From Builder to Visionary: Constructing the Next Chapter

    Meet a seasoned entrepreneur who founded, scaled, and recently sold their company, and now has to navigate that notoriously tricky transition period during a year-long handover—and hear the lessons he’s learned along the way.

  • EPISODE 5

    How A Wellness Entrepreneur Found her Focus

    Hear me hold space for an inspiring mid-career entrepreneur who has scaled her company but, despite her growing success, grapples with a familiar challenge: how to spend less time on tasks that drain her and more time doing what energizes her.

  • EPISODE 6

    Balancing Purpose and Profit: Imagining the Next Act for a Mature Practice

    Listen as a seasoned financial advisor reflects on his career and the future of his practice. Together, we discuss balancing purpose and profit, creating meaningful connections with the next generation, and reigniting ideas that had been set aside.

BUT WHAT’S IT REALLY LIKE?

Hear Jonathan In Action

Experience the essence of the advisory, mentorship and strategy work I do. Gain practical insight you can apply to your leadership journey by listening in on six actual conversations I’ve had with real (and fully consenting) leaders. Listen anywhere!