EPISODE · Sep 25, 2026 · 1H 16M
Ep 015 | Unprocessed Pain Is Leading Your Team | feat. Ross Naylor-Tatterson
from The Driven Podcast · host Colt Charlebois
You've poured into people who left and kicked you on the way out, and now you lead a little more guarded than you used to. Is that wisdom, or pain you never dealt with? In this conversation, Colt sits down with Ross Naylor-Tatterson, a leadership coach and pastor, to unpack what it takes to become a leader worth following. You'll hear why agreement doesn't equal commitment, and how Ross listens to every struggling entrepreneur for three things: self-awareness, others awareness, and skills awareness. You'll hear why "without humility, it's impossible to learn," and what separates clean pain from dirty pain. Ross also shares the story of a woman who grew up in a Himalayan slum and now goes back to her village to tell the people who harmed her that their lives can change, and why he believes earning a livelihood, not education alone, breaks generational poverty. If you've been absorbing hurt from the people you lead and calling it leadership, this one is for you.ABOUT THE GUESTRoss Naylor-Tatterson leads EnLive Leaders, where he helps entrepreneurs become a leader worth following through honest conversations and small behavioral experiments. His work focuses on character and decision making. He builds leaders' skills in communication, decision making, and conflict resolution, and the organizations they serve see better quality, higher job satisfaction, stronger retention of good workers, and greater profitability. Ross is regional coordinator for Asia and MENACA with Vineyard Mission USA and pastor emeritus of the church he planted in Michigan. He was born in Australia and has lived in the United States for 26 years. He writes two weekly Substack columns, Wisdom and Pressure on Mondays and the Friday Exhale.
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You've poured into people who left and kicked you on the way out, and now you lead a little more guarded than you used to. Is that wisdom, or pain you never dealt with? In this conversation, Colt sits down with Ross Naylor-Tatterson, a leadership coach and pastor, to unpack what it takes to become a leader worth following. You'll hear why agreement doesn't equal commitment, and how Ross listens to every struggling entrepreneur for three things: self-awareness, others awareness, and skills awa...
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Ep 015 | Unprocessed Pain Is Leading Your Team | feat. Ross Naylor-Tatterson
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