What does your culture actually feel like to the people doing the work?

In this follow-up conversation with John Dickerson of Quillo, we dig into the uncomfortable truth most leaders don’t see: DSPs often move through their day wondering whether a supervisor message or a quick “call me” means they’re in trouble.

And that fear—small as it may seem—is one of the clearest signals that your culture isn’t creating psychological safety.

In this episode, John shares real stories from the field that reveal how leaders unintentionally send the wrong messages… and how tiny, daily actions can completely change how supported (or exposed) DSPs feel at work.

We get into:

• Why you cannot train your way out of a culture problem
• What DSPs hear beneath your words (“Am I in trouble?”)
• Why memos don’t fix relationships
• A simple leadership practice that re-humanizes supervision
• What meaningful recognition actually sounds like
• The difference between “talking about people” and “talking to people”
• Why trust is built in the smallest, quickest, easiest moments

If you care about staff retention, employee experience, or building a culture where people feel safe and valued—this conversation will hit home.

00:00 — John opens with the “culture is everywhere” idea
02:18 — The deeper problem behind modern compliance-heavy leadership
05:08 — How DSPs interpret supervisor messages (“Am I in trouble?”)
06:50 — Why you can’t fix relationships through policies or emails
08:41 — The small habits that instantly build trust
10:39 — What leaders misunderstand about “open-door culture”
12:57 — Real talk: how staff actually feel when leaders only call for problems
15:53 — Why culture shifts don’t happen through annual plans
17:12 — The unreachable-staff myth (and what’s actually going on)
34:12 — John’s reminder: culture changes one human moment at a time
36:38 — A simple leadership practice that transforms how DSPs feel at work

Explore Quillo and their work on connection-driven culture: https://myquillo.com/

Join Nate for a free, live session on staff retention (Leadership Lens Series): https://iddleader.com

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