207: The Seven Paradoxes of Leadership with Sumit Gupta

We’ve all been there. We thought we knew what was best, only to find out later that what we thought we knew was wrong. Even the best manager can get lost in all the leadership advice, trying to do what’s right and still somehow failing. This is because sometimes that leadership advice is wrong.

Today’s guest is Sumit Gupta. Sumit spent 20 years in software, started 2 for-profit and 1 non-profit organizations, and is a photographer. He combines his experiences as a techie, engineer, 3x entrepreneur, and leader in companies like Yahoo and Booking.com, and as a poet and photographer – to help leaders merge the science of doing business with the art of leadership.

Sumit and I talk about the seven paradoxes of leadership. These paradoxes are concepts that shift the way we think about leadership and what it takes to be a great manager. They take the typical leadership advice and flip it on its head.

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Read the related blog article: What You Thought About Leading a Team is Wrong


Podcast: https://www.deployyourself.com/podcast/

LinkedIn: https://www.linkedin.com/in/sumit4all/

Newsletter: https://www.deployyourself.com/newsletter/

Seven Paradoxes Report: https://www.deployyourself.com/7-leadership-paradoxes/

Key Takeaways:

  • What we believe about effective management is often the opposite. We call these paradoxes of effective leadership.
  • To build psychological safety, trust your team’s intentions and abilities from the start, rather than waiting for them to prove themselves.
  • Don’t blindly trust. Set up the right structure of clear expectations, values and direction. Be transparent about any concerns you have so they can be addressed right away.
  • Fear is your friend. It tells you what is at the edge of your abilities and what’s important to you. Don’t cover it with guilt for feeling that way.
  • Leadership is power through the ability to get results, not superiority. People want to follow leaders who know how to win together.
  • We can’t force people to change. The best we can do is create the right conditions and inspire others by our own actions.



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