Below the Waterline: What Leaders Don't Know About Their People with Tim Dittloff
Jun 17
Most leaders know their team at the surface level. They know the roles, the deliverables, the performance trends. What they don't know is what's going on below the waterline in the lives and motivations of their people. And according to Tim [LAST NAME], not knowing is how organizations quietly run aground.
Tim is a USCG-licensed merchant mariner and leadership coach who uses sailing as both a metaphor and a hands-on experience for executive teams. He joined Aaron Lee to talk about what it takes to actually know the people you lead, and why the teams that can't talk to each other on the water are the same teams that can't talk to each other in the building.
The conversation moves from the Indian Ocean to Mongolia — and picks up a Harvard Business Review line along the way that is hard to shake: hurry and care can't coexist.
Key moments
- 0:17 — "Below the waterline": what leaders miss when they only coexist with their teams
- 2:32 — The Vestas Wind: how a professional race crew ran aground in the Indian Ocean with GPS on
- 4:10 — Zach Mercurio (HBR): "Hurry and care can't coexist"
- 6:31 — The best leader Tim ever worked for: a three-star general who knew his kids' names four times a year
- 7:30 — Merle Freytag and "lack of candor can kill"
- 10:32 — How a toxic race crew became the idea for a leadership business
- 13:40 — USCG Rule 5 on the water and in an architectural art firm's org chart
- 19:00 — 5 Voices in Mongolia: three languages, one shared framework, a nurturer who finally understood his role
- 23:10 — Every role on a sailboat matters — including the "rail meat"
- 24:00 — New addition: a karate dojo and why the basics are the whole game
About Tim Dittloff
Tim Dittloff is a USCG-licensed merchant mariner and leadership coach. He works with executive teams using sailing as a hands-on leadership experience, and partners with Leaders Rising Network on 5 Voices-based development. He shares leadership insights regularly on LinkedIn.
Resources
About the show
Leaders Rising is the podcast of Leaders Rising Network, a culture and leadership consultancy based in Glen Allen, VA. New episodes drop regularly. Subscribe wherever you listen.




