Below the Waterline: What Leaders Don’t Know About Their People

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Below the Waterline: What Leaders Don’t Know About Their People

Tim Dittloff, a USCG-licensed merchant mariner and leadership coach, on what leaders miss when they only coexist with their teams, and why the crew that can't talk on the water can't talk in the building.

5 min read Jul 14, 2026 Aaron Lee C-Suite Leadership Self-Awareness

Episode 12

The teams that can’t talk on the water can’t talk in the building.

Tim Dittloff sails executive teams into open water to show them what a conference room hides: who actually knows whom, who stays silent when it counts, and whether the leader has ever gone below the surface of their people’s lives. This conversation runs from a grounded ocean-race boat to a leadership session in Mongolia, and lands on a simple test of whether you lead people or just share a schedule with them.

What Leaders Miss When They Only Coexist

Most leaders know their people at the surface. The roles, the deliverables, the last three quarters of performance. What they don’t know is what runs underneath: what their people are carrying, what they want, what would make them speak up instead of nod. Tim Dittloff calls that the part below the waterline, and he says not knowing it is how organizations run aground while everything on the dashboard still looks fine.

He has a picture for it. In the Volvo Ocean Race, a professional crew on a boat called Vestas Wind drove onto a reef in the middle of the Indian Ocean with the navigation electronics on. The charts were right there. At the zoom level they were using, the shoal simply didn’t show. Nobody was watching the water itself.

Teams do the same thing. They trust the instruments, the reports and the metrics, and stop looking at the people. Tim points to Zach Mercurio’s Harvard Business Review work on mattering, and one line from the conversation is hard to put down: hurry and care can’t coexist. A leader moving fast enough to hit every number is usually moving too fast to see the person in front of them.

The General Who Knew Their Names

Ask Tim about the best leader he ever worked for and he doesn’t describe a strategist. He describes a three-star general who saw his people maybe four times a year and still knew their kids’ names.

Presence is simple. In the few minutes you have with someone, do they walk away knowing you actually see them? The general had rank enough to skip that. He didn’t.

Tim pairs it with a harder truth he heard from a mentor, Merle Freytag: lack of candor can kill. On a boat, a crew member who won’t say “I think we’re off course” is a safety problem. In a company, the same silence is harder to spot and the wreck comes slower, but the mechanism is identical. People who don’t feel known don’t tell you what you need to hear.

“The crew that can’t talk to each other on the water is the same crew that can’t talk to each other in the building.”
Tim DittloffLeaders Rising Podcast

From a Broken Crew to a Leadership Business

Full Sail started with a bad boat. Tim spent a season on a racing crew where the talent was real and the trust was gone. People stopped communicating, then stopped covering for each other, then stopped winning. He walked off that boat with a question: if a crew’s problems are really leadership problems, could the boat teach the fix?

Now he takes executive teams onto the water because the water doesn’t let anyone hide. He anchors it in USCG Rule 5, the rule every mariner learns: keep a proper look-out at all times, by sight and by hearing. He watched an architectural art firm put Rule 5 on its own org chart, asking who on this team is actually keeping watch, and who assumed someone else was.

On a sailboat, every seat has a job. Even the crew whose only task is to sit on the high rail for ballast, the position sailors bluntly call “rail meat,” changes whether the boat holds its line. Tim’s newest teacher on this is a karate dojo he joined, where the black belts still drill the same basic block as the beginners. The basics are the whole game.

One Framework, Three Languages

The clearest story comes from Mongolia. Tim ran a leadership session with a team split across three spoken languages, using the 5 Voices framework as the common one. The breakthrough was a man who tested as a Nurturer, a Voice that leads with people and harmony, who had spent years thinking his instinct to protect the team was a weakness to manage. Given the language for it, he saw it as his contribution instead.

That is what the framework does. It gives a team a shared way to name how each person is built, so the quiet one’s caution and the loud one’s drive stop reading as personality clashes and start reading as roles. It happens when people finally have words for what they already are. Another all-hands never gets you there.

Resources Mentioned

  • 5 Voices Assessment: discover your leadership voice and how your team is wired to communicate.
  • Zach Mercurio, “The Power of Mattering at Work”: Harvard Business Review (May-June 2025), on why people who feel they matter do their best work.

One Step for Leaders

Pick one person you lead. Not the one in crisis, the one who is fine. Steady, reliable, easy to overlook.

Before your next conversation with them, write down what you actually know below the waterline. Not their role. What they are working toward, what is hard right now, what they would tell you if they trusted you enough to say it.

If the page is thin, that is the finding. Go have the conversation that fills it in.

Key Takeaway

You’re only really leading the people you actually know.

About the Guest

Tim Dittloff is a USCG-licensed merchant mariner and leadership coach. Through Full Sail Leadership Experiences, he takes executive teams onto the water to build the trust and communication their work depends on, and he partners with Leaders Rising Network on 5 Voices-based development. Find him on LinkedIn.

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Aaron Lee
About the author

Aaron Lee

Aaron Lee is CEO of Leaders Rising Network and is passionate about unlocking the true potential of leaders and teams. With experience in nonprofits and emergency management, Aaron has guided government, healthcare, nonprofit, and higher education organizations to navigate change and develop leaders who fight for each other. He is the author of The New Generation Leader and host of the podcast of the same name. Aaron holds a degree from the University of Richmond and a Master of Divinity. He lives in Richmond with his wife and two daughters.

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