Insights
Being Liked Won't Carry Your Team Through Change. Trust Will.
Dennis Richter is the Chief Business and People Officer at Fullscript, a billion-dollar healthcare platform, with prior leadership roles at Meta, Google, Deloitte, and 12 years in the Army. In this episode of Herding Squirrels, Dennis explains why people aren’t actually tired of change. They’re tired of change that feels disconnected, unfinished, or poorly explained. He shares why information travels down an organization far faster than it travels up, what a live town hall teaches that a scripted one can’t, and why the people holding your company together rarely show up as critical on the org chart. If you’re leading a team through change and wondering what isn’t reaching you, this conversation gives you practical ways to get the real story sooner.
The Honeymoon Tax
Around 90 days into any big change, the energy goes quiet. The dashboard stays green. The strategy holds. But the thing that was moving is suddenly not. Here is the math behind why
Your Team Is Doing Math In Every Meeting
Your team runs a quiet formula before speaking up in any high-stakes meeting. The math is rational, the silence is not weakness, and somewhere in that formula is a variable for you. Here is what they are calculating, and how to change the answer.
Stop Building an AI Strategy
You've read 47 AI posts this week. There's a reason. Festinger named it in 1954, and it's quietly running every AI rollout happening right now. When people are uncertain, they look at each other before they look at the tool. The leaders who get adoption right aren't the ones with the best strategy. They're the ones building the room where honest reactions can surface. Here's what that looks like.
Your Teams Don't Have a Personality Problem
Every organization has the same fight. Sales thinks engineering is inflexible. Engineering thinks sales is reckless. Product thinks everyone is slow. But the personality labels are a symptom, not the cause. The real problem is that no one ever named the shared goal that makes all their individual goals matter.
Your Team Isn’t Disengaged
Your team looks aligned in the meeting. But the real conversation is happening somewhere else. Here are the three layers of silence and how to bring teams back.
Why 'We Need To' Never Works
Everyone on my basketball team has great ideas. YouTube plays, motion offenses, elaborate strategies. None of it stuck—until we changed one word.
Silence is Communication
When leaders stay silent during organizational change, teams fill the information vacuum with worst-case assumptions. This triggers the brain's threat response, particularly around certainty - one of five domains in David Rock's SCARF model. Effective leaders communicate about uncertainty itself: acknowledge what's unknown, share what they do know, explain how decisions are being made, set update cadence, and give teams actionable steps.
Why Your Team Won't Say No
Stop thinking psychological safety is some touchy-feely HR initiative. It's your organizational immune system. When your team's immune system is strong, problems surface early. Course corrections happen naturally. Disasters get prevented, not managed. When it's weak? People retreat into survival mode. Your team is constantly calibrating: "What happens when I speak up here?" The answer to that question, accumulated over dozens of small interactions, determines whether they'll save your next big initiative or watch it burn.
The Million-Dollar Miscommunication
The best teams don't assume less—they confirm more. They've built a culture where asking "What do you mean by that?" isn't seen as incompetence but as professionalism. Next time you catch yourself making assumptions, try this: "Let me confirm what I'm hearing..." It's the simplest way to turn workplace fiction into workplace facts.
Communication & Team Connection: Building Trust Through Better Relationships
Every team is a collection of unique perspectives, communication styles, and working preferences. What looks like a simple conversation to one person might feel overwhelming to another. The challenge isn't having different viewpoints—it's creating the shared language and understanding that allows these diverse minds to collaborate effectively
The Icebreaker Police
"It's an icebreaker!" the engineer announced. For the third time.
Instead of asking "What do you do?" I asked "What do you love about what you do?"
That's when our self-appointed icebreaker detective felt compelled to blow my cover. Multiple times.