How to Share: Secrets of Collaborative Leadership

The best leader is the one who has sense enough to pick good men to do what he wants done, and the self-restraint to keep from meddling with them while they do it.” – Theodore Roosevelt

I played on a tennis team when I was in my 20’s. It was a loosely organized group of women who played at the public tennis courts. We were part of a league that created matches with other teams, some of whom were the “fancy” ones who belonged to a club with a pro.

But my team had a secret weapon: our coach, Evan. A quiet-spoken man who seemed to take everything in. He’d meet with us at practice and not only run drills to improve our skills but also strategically position who should play singles versus doubles, and forehand versus backhand.

I don’t remember our records of wins and losses so it probably wasn’t that great. But I know we got better as a team and also as individuals. It was largely because of Evan. He could see our strengths and vulnerabilities and help us position them to the best advantage.

I was reminded of Coach Evan when I recently talked with John Hernandez, the Director of IT at Leisure Care on the How to Share podcast. John has an incredibly collaborative leadership style and knows how to balance giving people on his team leadership, agency, and backup when needed.

In short, he’s a very good coach for a strong team.

John told me how he landed on this leadership style and how it’s worked as his team and responsibilities have grown. We talked about how people in technology can sometimes be protective of their knowledge and not want to share. And we discussed how AI changes the game for so many people in technology and how to wrangle it as an asset, not a competitor.

I asked John about how he adapts his message for people who are less technical. He brought it back to the power of telling a story and finding key beats, regardless of the topic.

This is a great episode about how leadership, openness, curiosity translates to infectious passion for sharing – and for team building. I know you’ll love it!

Takeaways

  • John emphasizes the importance of sharing knowledge to build effective teams.
  • A collaborative leadership style fosters a culture of openness and mentorship.
  • Technology professionals often hoard knowledge due to fear of job security.
  • AI is changing the landscape of IT, enabling more collaboration.
  • Storytelling can help convey complex technical concepts.
  • Creating a supportive environment encourages team members to grow.
  • Passion for technology can be infectious and motivate others.
  • Adapting messages for different audiences is crucial in IT.
  • Building a knowledge-sharing culture can lead to better team dynamics.

Here’s a clip of John describing how he landed on his leadership style:

Here are some ways you can listen and watch this infectiously energizing episode:

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Secrets of Collaborative Leadership transcript

51: Letting Go of Outcomes: The Mindset That Keeps You Moving The Life of Try: Personal growth, one try at a time.

Expectations can inspire us to try—until they harden into a demand for a specific outcome. In this episode of The Life of Try, Wynne Leon explores how unmet expectations fuel disappointment, why that disappointment can keep us from taking healthy risks, and what it looks like to stay hopeful without clinging. From a childhood lesson about “pressing for the answer” to Alexander Fleming’s accidental discovery of penicillin, we’ll trace how openness, curiosity, and faith can turn apparent failures into forward motion. Along the way, we’ll draw from Brené Brown’s research on disappointment, Maya Shankar’s reframing of identity after loss, and spiritual wisdom about surrender and non‑attachment—so you can keep trying even when the path changes.In this episode, you’ll learn how to:Recognize when expectations are motivating you—and when they’re setting you up for disappointmentPractice openness and curiosity when a try doesn’t go as planned (and why that matters)Name and communicate your expectations to reduce “unspoken contracts”Reconnect with your deeper “why” when your “what” gets taken awayHold onto faith that trying will lead somewhere good—even if it’s not the destination you imagined.The Life of Try is a podcast about personal growth, one try at a time.What happens when trying becomes more important thangetting it right?The Life of Try is a personal growth and self‑help podcast about getting unstuck, navigating uncertainty, and choosing to try—even when it’s uncomfortable, inconvenient, or not your idea.Hosted by Wynne Leon, the show explores how real growth, reinvention, and discovery often begin not with confidence orclarity—but with a single attempt. Through thoughtful interviews, reflective conversations, and real‑world case studies, each episode examines what it looks like to keep going when doubt shows up, plans fall apart, or life forces achange you didn’t ask for.This podcast is for anyone who:Feels stuck or uncertain about what’s nextIs navigating change, burnout, or reinventionWants to live more intentionally without pretending growth is easyBelieves progress starts by trying—again and againThe Life of Try isn’t about hustle or perfection. It’s about learning as you go, surfacing what matters, and sharing what you discover along the way.If you’re ready to surf the uncertainty, outlast the doubts, and step into your own try‑cycle, you’re in the right place.Links for this episode:The Life of Try HomeLetting Go of Outcomes: The Mindset That Keeps You Moving transcriptSir Alexander Fleming – Biographical – NobelPrize.orgHow to Regulate Your Emotions and Mental Chatter When Bad Things Happen | Maya ShankarAtlas of the Heart: Mapping Meaningful Connection and the Language of Human Connection by Brene BrownPenicillin Wasn't Alexander Fleming's First Major Discovery | Scientific American
  1. 51: Letting Go of Outcomes: The Mindset That Keeps You Moving
  2. 50: How to Write the Book You've Been Meaning to Write | Dr. Victoria Atkinson (Slivers)
  3. 49: Personal Growth Pivot Points: Pause, Quit or Keep Going?
  4. 48-How to Get Unstuck: Michael Yang on Saying Yes, Resilience, and Coming Alive
  5. 47-From Stuck to Momentum: Thomas Edison’s Method for Progress (Try, Learn, Improve, Repeat)

Links for this episode:

John Hernandez on LinkedIn