Below the Waterline: What Leaders Don't Know About Their People with Tim Dittloff

Below the Waterline: What Leaders Don't Know About Their People with Tim Dittloff

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 on LinkedIn [https://www.linkedin.com/in/timdittloff/] * Full Sail Leadership Experiences [https://LeadersRisingNetwork.com/fullsail] 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 * 5 Voices Assessment [https://leadersrisingnetwork.com/5-voices] * Zach Mercurio, "The Power of Mattering at Work" — Harvard Business Review [https://hbr.org/2025/05/the-power-of-mattering-at-work] 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.

Training in 2026: Everyone Wants Growth, No One Has Time

You keep telling your team that development is the priority. You mean it. Then Monday hits. The meetings run long. The email pile grows. The project list shows up with the same work and fewer weeks. By Friday, development is still on the board. It just never got touched. In this episode, Aaron sits down with Becky Rivest to work through Training Magazine's take on what 2026 looks like for people focused leaders. AI is moving faster than policy. Return to office is still a fight. A Gen Z quarter life crisis is pulling good people out early in their careers. And through all of it, leadership development keeps landing at number one on the priority list and last on the actual calendar. Becky names the real issue. It is not that leaders do not care. Every change requires a slow down, and almost nobody has permission to take one. The fix is not another workshop. It is not a new platform. It is one honest conversation with one employee on your team. Ask them if they can see the line from their role to where the company is going. Start there. Everything else follows. Show Outline * 03:53 What overwhelm actually looks like in a leader's day * 06:58 Return to office in 2026 * 09:06 HR, IT, and the AI conversation nobody is ready for * 11:21 Upskilling and the Gen Z quarter life crisis * 14:41 Where change fatigue really comes from * 17:30 Why development stays stuck at number one * 20:57 Rhythms over events and the five moments of need * 25:13 One move leaders can make this week Resources mentioned: * Training Magazine: What's in the Mix for 2026. https://trainingmag.com/whats-in-the-mix-for-2026/ [https://trainingmag.com/whats-in-the-mix-for-2026/] * WSJ: Sharpie brings US production back through upskilling. https://www.wsj.com/business/sharpie-us-production-cost-cutting-d9ba2abd [https://www.wsj.com/business/sharpie-us-production-cost-cutting-d9ba2abd] * Bob Mosher: The Five Moments of Need framework Visit the LRN Learning Center for full show notes at LeadersRisingNetwork.com [https://leadersrisingnetwork.com/training-in-2026-everyone-wants-growth-no-one-has-time/]

Building the System When You Don't Have a Roadmap

Year one was slow. There were empty seats at the leadership table, a culture that needed rebuilding, and no clear map for how to get from where things were to where they needed to go. What came out of those years was not a perfect plan. It was a system, built gradually, through clarity about people, through honest assessment of gaps, and through a commitment to developing leaders on purpose rather than by accident. In this episode, recorded live during the Rising book launch event, Aaron Lee shares the story of stepping into a leadership role with more problems than answers, and what it actually took to build something that worked. Tom Nebel follows with a look at the tensions that don't disappear even when your systems are healthy: leaders who never asked for the role they're now carrying, the balance between support and challenge, and what genuine accountability looks like when it comes from the top. This episode closes out our three-part series from the Rising launch event, and it may be the most personal conversation of the three. What you'll hear in this episode: * What it looks like to build a people system from scratch, without a roadmap * The growth pathway every leader travels, and how to develop people through it intentionally * Why organizations don't rise because of heroic leaders, they rise because of intentional systems * The tension between being supportive and being demanding, and why both matter * What honest humility looks like from the front of the room, and why it changes everything Rising is a book for organizations that are growing but quietly losing clarity along the way. Written by Jeff Lovell and Aaron Lee of Leaders Rising Network, it makes the case that most growth problems are clarity problems, and that the path forward is building an intentional people system, not pushing harder. Get a free copy of Rising. [https://go.leadersrisingnetwork.com/rising-event/] Show Outline * 6:24 - Building a System of Clarity and Infrastructure * 8:50 - Developing Leaders and Overcoming Overwhelm * 12:56 - World-Class Leadership and Organizational Success * 14:28 - Tensions in Leadership and Organizational Health * 19:07 - Balancing Support and Challenge in Leadership * 24:27 - The Role of Intentional Systems in Leadership * 25:02 - The Impact of Leadership on Organizational Success

Why New Technology Makes a Struggling Culture Worse

When something isn't working inside an organization, the instinct is to find a better tool. A new platform, a new system, a new application that promises better collaboration and faster execution. It's a reasonable instinct. And it almost always backfires. Technology is an amplifier. It makes healthy organizations more efficient and struggling organizations more broken. The problem is never really the tool. The problem is the operating system you're installing it on. In this episode, recorded live during the Rising book launch event, Steve walks through why technology implementations so often fail to solve the problems they were meant to fix, and what leaders need to examine before they implement anything new. He then introduces the organizational operating system that sits underneath every initiative, every tool, and every culture conversation: identity, goals, people, rhythms, and systems, all working together or quietly working against each other. This episode is for leaders who have watched a promising implementation fall flat, or who suspect that the real issue in their organization runs deeper than any tool can reach. What you'll hear in this episode: * Why technology amplifies organizational health, and organizational dysfunction, in equal measure * The difference between solving a people problem and masking it with a process solution * What an organizational operating system actually looks like and what happens when it's misaligned * Why clarity doesn't begin at the organizational level, it begins with the individual leader * How identity, goals, people, rhythms, and systems either reinforce each other or undermine each other Rising is a book for organizations that are growing but quietly losing clarity along the way. Written by Jeff Lovell and Aaron Lee of Leaders Rising Network, it makes the case that most growth problems are clarity problems, and that the path forward is building an intentional people system, not pushing harder. Get a free copy of Rising. [https://go.leadersrisingnetwork.com/rising-event/]

Why Culture Drifts (And What Leaders Can't See When It Does)

Most leaders don't think their culture is broken. They're too close to it. What they notice instead is that meetings feel heavier, decisions take longer, and the same energy they keep pouring in isn't producing the same results. That's not a culture collapse. That's a culture drift. And it almost always starts in the gap between what leaders intend and what their teams actually experience. In this episode, recorded live during the Rising book launch event, Jeff Lovell opens with a diagnostic that most leaders will recognize immediately: pressure doesn't create culture, it reveals it. Becky Rivest follows with a look at how clarity shapes communication, especially in the moments that matter most. And Mike closes with one of the more honest leadership stories you will hear, about a season when good intentions, hard work, and urgency combined to make everything worse. This conversation is for leaders who carry real weight for their organizations and are starting to sense that something is drifting, even if they can't quite name it yet. What you'll hear in this episode: * Why culture drifts under pressure and what it's actually revealing when it does * The gap between what leaders intend and what their teams experience, and why it widens with authority * How blind spots compound the higher you rise * Why communication is the outward expression of leadership clarity * What happens when a leader confuses urgency with wisdom Rising is a book for organizations that are growing but quietly losing clarity along the way. Written by Jeff Lovell and Aaron Lee of Leaders Rising Network, it makes the case that most growth problems are clarity problems, and that the path forward is building an intentional people system, not pushing harder. Get a free copy of Rising. [https://go.leadersrisingnetwork.com/rising-event] Show Outline * 0:52 - Why We Wrote Rising * 2:32 - The Weight Leaders Carry * 4:10 - Culture Doesn't Break, It Drifts * 5:00 - What Pressure Actually Reveals * 7:30 - The Gap Between Intent and Experience * 10:00 - Leaders Judge Culture by Intentions, Teams Judge by Experience * 12:45 - What You Permit, You Promote * 15:00 - The One Question That Stabilizes Leadership * 17:45 - Communication as the Outward Expression of Leadership * 18:21 - The Cost of Drama at Work * 19:02 - Finally, Someone Who Will Tell the Truth * 22:12 - Mike's Story: When Hard Work Made Things Worse * 26:09 - The Cost of Urgency Without Clarity * 27:23 - Effort Is a Tool, Not a Solution