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Topics discussed - Revenue Operations, Customer Success, Goal Setting & Execution, Mindset, Performance, B2B Sales, Sales Training, Product Market Fit, Growth, Hiring, Recruitment, Sales Process, Business Acumen, Startups, Leadership.

Feb 24, 2025

In this episode, host Mike Simmons dives into the complexities of leadership—how to lead up to difficult leaders, work effectively across teams, and lead teams with clarity and purpose. Mike shares personal experiences, leadership philosophies, and actionable strategies to help listeners navigate leadership challenges at all levels.


Key Quotes:

  1. "Leadership starts with self. If you're looking for leadership, start with a mirror."
  2. "If you think different, you can do different. If you do different, you can be different."
  3. "Sometimes, the hardest part of leadership is managing the assumptions we make about others."

Episode Summary (50 Words):

Leadership isn’t just about managing others—it’s about self-awareness, clear communication, and building trust. In this episode, Mike Simmons explores how to lead up to difficult leaders, collaborate across teams, and inspire those we manage. He shares tools and insights to navigate leadership challenges with confidence, clarity, and a service-oriented mindset.


5 Key Takeaways:

1. Leading Up to Leadership Challenges

  • Understand your leader’s background, concerns, and goals before making assumptions.
  • Improve communication by aligning with their priorities and preferred methods.
  • If a leader is ineffective, decide if you can help—or if it’s time to move on.

2. Building Strong Cross-Team Relationships

  • Empathy is key: understand what other teams care about and what challenges they face.
  • Transparent communication fosters collaboration, even in competitive environments.
  • Align team efforts with business goals to create a unified direction.

3. Leading Your Team with Clarity

  • Get to know your team’s goals, communication styles, and career aspirations.
  • Provide opportunities for cross-functional learning to build leadership skills.
  • Lead with transparency, trust, and a willingness to adapt.

4. The Importance of Effective Communication

  • Leadership is built on clear, purposeful communication.
  • Miscommunication happens—what’s said, what’s heard, and what’s remembered are rarely the same.
  • Tools like structured feedback loops and regular check-ins prevent misunderstandings.

5. Leadership as an Act of Service

  • Leadership isn’t about control—it’s about enabling others to succeed.
  • Sometimes, leaders struggle due to insecurity; build trust to help them delegate.
  • If leadership doesn’t align with your values, it’s okay to step away.

Final Thoughts:

Leadership is a journey of continuous growth. Whether leading up, across, or down, it starts with self-awareness and service. This episode provides practical insights to help you lead with confidence, no matter your position.

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