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Scaling From Operator to CEO: Letting Go of Control and Leading With Trust | Andrew Poles
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In this episode of Mind Over Masculinity, host Avik Chakraborty sits down with executive coach and 3x founder Andrew Poles to unpack one of the hardest transitions in business and life—shifting from operator to CEO. Many men are taught to prove their worth by doing it all themselves, but true leadership demands trust, influence, and the ability to empower others. Andrew shares what it takes to let go of micromanagement, avoid burnout, and build a culture where people thrive. This conversation dives into mindset shifts, sales fundamentals, and why culture will always eat strategy for breakfast.
About the Guest :
Andrew Poles is a single dad, 3x founder, and executive coach who has guided over 10,000 leaders—including at NASA, Dell, Netflix, and Epic Games. With lived experience balancing the grind of 80-hour weeks and the demands of scaling, Andrew helps leaders shift from being results-driven operators to visionary CEOs who inspire without losing themselves.
Key Takeaways :
The biggest shift from operator to CEO is moving from producing results yourself to empowering others to deliver results.
Micromanagement feels like strength but ultimately slows business growth, fuels burnout, and damages relationships.
Healthy accountability requires guardrails, clear outcomes, and regular check-ins—without over-control.
Trust means giving people room to fail safely, learn, and grow, while ensuring the company remains protected.
Sales is a science of ratios: know your funnel, your numbers, and where breakdowns occur to fix the right problems.
Fear of selling often comes from personalizing rejection—shift focus to serving the customer instead of proving yourself.
Culture shapes how strategy gets executed. Without the right culture, even the best strategy fails.
First-time CEOs should stop comparing themselves to “finished” archetypes and instead measure growth against their own starting point.
Connect with the Guest
Website: andrewpoles.com
LinkedIn: https://www.linkedin.com/in/andrewpoles
Want to be a guest on Healthy Mind, Healthy Life? DM on PM - Send me a message on PodMatch
DM Me Here: https://www.podmatch.com/hostdetailpreview/avik
Disclaimer
This video is for educational and informational purposes only. The views expressed are the personal opinions of the guest and do not reflect the views of the host or Healthy Mind By Avik™️. We do not intend to harm, defame, or discredit any person, organization, brand, product, country, or profession mentioned. All third-party media used remain the property of their respective owners and are used under fair use for informational purposes. By watching, you acknowledge and accept this disclaimer.
About Healthy Mind By Avik™️
Healthy Mind By Avik™️ is a global platform redefining mental health as a necessity, not a luxury. Born during the pandemic, it’s become a sanctuary for healing, growth, and mindful living. Hosted by Avik Chakraborty—storyteller, survivor, and wellness advocate—the channel shares powerful podcasts and conversations on:
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