Episode 18

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Published on:

9th Feb 2026

Mastering Uncomfortable Conversations: The Real Job of a Leader

"The real job of a CEO is to go from one uncomfortable conversation to another."

If you are procrastinating a phone call, letting a deadline slide, or avoiding an underperforming employee because you don't want to "rock the boat," you are not protecting the team—you are hurting them.

Many leaders suffer from "Nice Guy Syndrome." We think that by avoiding conflict, we are keeping the peace. But in reality, we are losing respect.

In this episode, we break down why your brain is neurologically wired to avoid these conversations and how to overcome it every time.

In this episode, you will learn:

  1. The "Nice Guy" Trap: Why trying to be liked usually results in being disrespected, and why your team actually caves accountability .
  2. The Psychology of Avoidance: How "Conditional Parenting" and the ego's need for safety cause us to procrastinate on high-value conversations .
  3. The ARC Framework: A 3-step process (Awareness, Response, Compassion) to navigate conflict without blowing up.
  4. Curiosity vs. Blame: How to start a difficult conversation so the other person doesn't get defensive (hint: be specific, not general) .
  5. The "Silence" Trick: Why you must stop talking after asking a hard question and let the silence do the heavy lifting .

💪 The Challenge for This Week:

-Identify: Who is the one person you have been avoiding? (A peer, an underperformer, or even a boss).

-Compose: How do you want your energy to be? (Curious, not accusing).

-Schedule: Put it on the calendar today. Do not wait for the "right time." .

Resources:

-Join the Conversation: Join our Leadership Mindset 2.0 community on LinkedIn or Facebook

-Get Live Coaching: Move from listening to doing inside the Growth Leaders Collective. Start your $1 trial at RMichaelAnderson.com/GLC

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About the Podcast

Leadership Mindset 2.0
Transform From Tactical Doer to Strategic Leader: The Psychology of Scaling for Executives & Entrepreneurs
Leadership Mindset 2.0 is the definitive playbook for executives and entrepreneurs ready to break free from the "Doer Trap" and scale their business using psychology and strategy.

Host R. Michael Anderson has scaled multiple software companies to the Inc. 5000 list and was named Social Entrepreneur of the Year. Now, as a 2x Executive Coach of the Year, he uses that experience to help high-performers transform from Tactical Operators into Strategic Leaders.

In this podcast, Michael blends cutting-edge neuroscience, emotional intelligence (EQ), and battle-tested business strategy to help you overcome burnout, imposter syndrome, and the "Leadership Incompetence Trap" so you can lead with clarity and confidence.

Two New Episodes Every Week which include a mix of:
• Strategy: Neuroscience frameworks & leadership tactics to start your week.
• Mentorship: Live Q&A and specific answers to your leadership challenges.
• Coaching: A fly-on-the-wall look at real, unscripted executive coaching sessions as Michael helps leaders break through their blind spots live.
• Masterclasses: Listen in as Michael and guests teach valuable leadership and management skills to a real-life audience.

Topics include: The Psychology of Scaling, Burnout Prevention, Strategic Planning, Executive Coaching, and Emotional Intelligence.

About your host

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R. Michael Anderson

R. Michael Anderson, MBA, MA has a striking combination that creates truly impactful transformation in leaders – he has the real-life business success of founding, scaling and exiting three software companies, plus the educational background of a Masters Degree in Psychology.



This combination gives him the unique ability to connect to other leaders as a peer, then teaches evidence-based leadership skills that genuinely drive behaviour and performance.