Ep 16: The Hard Side of Leadership: How to Silence Fear and Doubt in Order to Navigate Contradictory Truths and Challenging Times

“At some level all of us in the positions we’re in have to really wrestle with that painful dark side [of leadership].”

Tired of all the podcasts that gloss over the HARD parts of leadership? In this episode of the Generous Leadership® Podcast Tricia Halsey and Matt Procter talk about the hard and dark parts of leadership, with hope that you are as hungry for real talk as they are. It’s easy to gloss up leadership and focus on all of the times when we feel like a hero. But what about all of the other times when fear, and doubt creep in and we face uncertainty? When we question our own identity and sufficiency? Maybe it’s in those times that generosity is most important because what if unreasonable generosity somehow holds an antidote?

Matt Procter. President of Improve Group

Matt Procter is the President/CEO of Improve Group.  Improve Group is based in Albuquerque, NM and works across the United States and Europe helping organizations find ways to make time an ally, rather than an enemy, while revolutionizing their buildings. From the US Military to hospitals to large companies, Improve Group works with organizations of every form. Though Matt has seen Improve Group experience fast growth (mostly despite him), become employee-owned, and allow him to be named one of Albuquerque’s 40 under Forty, he’s most proud of figuring out how to get his awesome wife Ashley to marry him…which led to getting to raise 3 awesome boys.  Normally you’ll find him drawing a new idea on a white board or running on a trail.


  • Why leadership can be so hard, the difficult side of leadership.
  • How to deal with, and lead through, fear and doubt as a leader.
  • In the moment when you’re going through really challenging times, you can’t see the benefit. But it is the challenging times that lead us to beneficial change in the future.
  • We all have to answer the question: what determines our identity?
  • It is dangerous to put your identity in the thing that you are leading. Because every organization is inconsistent in different times. The times of high success are equally dangerous as the lowest of lows.
  • How to navigate the attacks on your identity as a leader.
  • Leadership can feel isolating when other leaders are projecting that times are always good and optimistic. It’s important to surround yourself with people who can tell the truth and sit in the hard times together.
  • How to measure seemingly contradictory truths to make decisions.
  • The power of generosity to change the atmosphere and shift reality. What does generosity say to fear?

References and Resources


  • “We often think of those triumphant moments and those inspiring people and the heroes, but what about all of the other times when leadership isn’t fluffy and fun…when fear and doubt and uncertainty creep in?”
  • “Anybody who’s been through leading anything knows there is deep painful, irrational often, fear that we all deal with.”
  • “We don’t like to admit that we are weak.”
  • “Do I find my sense of wellbeing, and do I find my security, in something that is going to be inherently, probably, very inconsistent?”
  • “When you are in the moment and you are going through it and its confusing and you’re disoriented and you’re questioning all these identity level foundational things, it’s so hard to see past that to a different time horizon. But isn’t that what we spend a lot of our time as leaders doing? Trying to help ourselves and the people around us have a different time horizon than what our emotions want us to feel then?”
  • “As leaders we feel like because we put [responsibility] on our shoulders we have to do it alone and that’s the biggest lie we can tell ourselves.”
  • “One of the markers of generous leaders is that it seems that all generous leaders want to do something unreasonable. Because at some level real generosity is pretty unreasonable.”
  • “Is it possible that generosity is the great secret weapon against fear?”