In this insightful episode of The Leadership Toolkit, host Mike Phillips welcomes leadership expert and executive coach Jeff Oak. With over 35 years of experience leading business turnarounds, mergers, and growth strategies, Jeff shares the real-life struggles leaders face... and... how to overcome them.

From feelings of isolation and imposter syndrome to managing personal “slippage,” Jeff outlines four core challenges that leaders at every level encounter. He breaks down Vistage’s unique coaching model, the power of peer advisory groups, and why coaching the person—not just the business—is critical for lasting growth.

Jeff also explains how vulnerability builds trust and unlocks leadership potential, and why the best leaders are humble, hungry, and smart. Whether you're leading a startup or a Fortune 500 team, this episode is filled with tactical insight, emotional intelligence, and authentic stories from the front lines of leadership.

5 Key Takeaways from This Episode:

• Leadership doesn't have to be lonely—peer groups create support and connection.

• Isolation, imposter syndrome, and self-doubt are common leadership challenges.

• Coaching the individual is more impactful than coaching the business alone.

• Vulnerability isn’t weakness—it’s the foundation of trust and growth.

• Humility is the #1 trait of great leaders, followed closely by hunger and people smarts.

Get ready for a conversation that’s honest, powerful, and packed with tools to help you lead with greater clarity, confidence, and connection.

Contact Information:

GUEST – Jeff Oak

Email: Jeff.Oak@vistagechair.com

LinkedIn: ⁠⁠⁠⁠⁠Linkedin.com/in/JeffOak

Vistage: https://Vistage.com

Jeff's Site: ⁠⁠https://JeffOak.com⁠⁠

Mike Phillips
Email: ⁠⁠⁠⁠mike@TheLeadershipToolkit.com⁠⁠⁠⁠

LinkedIn: ⁠⁠⁠⁠Linkedin.com/in/LeadTheTeam⁠⁠⁠⁠

Twitter: ⁠⁠@LeadershipTLT⁠

YouTube: ⁠YouTube.com/@MikePhillips

Credits:

Hosted by Mike Phillips

Produced by The Leadership Toolkit Team

Guest: Jeff Oak, 35 year leadership expert

🎧 Watch more episodes of The Leadership Toolkit at https://spotify.TheLeadershipToolkit.com

If you enjoyed this episode, please consider leaving a 5-star review!

Make sure you share this as a resource with friends and colleagues.

Thank you for watching and listening!

Disclaimer: The views and opinions expressed by guests on this show are solely those of the guest(s) and do not necessarily reflect the views or opinions of the host, producers, or any affiliated parties. The host and production team make no representations as to the accuracy or completeness of any information discussed by guests on the show. Listener discretion is advised.

Affiliate Disclaimer: Some of the links listed go to my websites and some are affiliate links that may generate me a sales commission if you make a purchase.

In this powerful episode of The Leadership Toolkit, host Mike Phillips sits down with John Donnelly, Executive Director at Service First Mortgage Company (SFMC) and a high-performance sales leader known for building elite mortgage teams with clarity, trust, and consistent execution.

John shares his incredible leadership journey — from weathering economic headwinds in the mortgage industry to climbing Mount Kilimanjaro as a personal mission of reinvention. Learn how returning to the basics, staying teachable, and leading with intention can fuel both personal growth and professional success.

🧰 Tools of the Trade: Top Takeaways You Can Use

✅ Going back to the basics: why human connection still wins

✅ Engagement over activity: using social media with purpose

✅ Why staying teachable keeps leaders relevant

✅ How to protect your time and build high-value relationships

✅ “You lose inspiration if you wait” — the power of taking action and setting audacious goals

Whether you're leading a team, building a business, or climbing your own personal mountain, this episode is packed with practical insights and leadership fire you don’t want to miss!

Contact Information:
John Donnelly

Email: JDonnelly@sfmc.com

Linkedin: Linkedin.com/in/TheJohnDonnelly

Web: https://sfmc.com/playbig

Mike Phillips

Email: ⁠⁠⁠⁠mike@TheLeadershipToolkit.com⁠⁠⁠⁠

LinkedIn: ⁠⁠⁠⁠Linkedin.com/in/LeadTheTeam⁠⁠⁠⁠

Twitter: ⁠⁠@LeadershipTLT⁠

YouTube: ⁠YouTube.com/@MikePhillips

Credits:

Hosted by Mike Phillips

Produced by The Leadership Toolkit Team

Guest: John Donnelly, High-Performance Sales Leader, Mortgage Lender, and Kilimanjaro Conqueror

Watch more episodes of The Leadership Toolkit at: https://spotify.TheLeadershipToolkit.com

If you enjoyed this episode, please consider leaving a 5-star review!

Make sure to share this as a resource with friends and colleagues.

Thank you for watching and listening!

Disclaimer: The views and opinions expressed by guests on this show are solely those of the guest(s) and do not necessarily reflect the views or opinions of the host, producers, or any affiliated parties. The host and production team make no representations as to the accuracy or completeness of any information discussed by guests on the show. Listener discretion is advised.

Affiliate Disclaimer: Some of the links listed go to my websites and some are affiliate links that may generate me a sales commission if you make a purchase.