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

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