Being Liked Won't Carry Your Team Through Change. Trust Will.
Fullscript's Dennis Richter on why your team isn't tired of change, it's tired of ambiguity, and how leaders get the real story before it's too late.
The questions nobody asks at the all-hands don't disappear. They move to lunch, to DMs, to the hallway, until a leader gives them somewhere better to go.
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.
Guest Bio
Dennis is an architect of high-growth organizations with 25 years of experience building and scaling global teams at the intersection of operations, technology, and people.
He currently serves as Chief Business Officer at Fullscript, an intelligent healthcare platform pioneering whole-person care, where he owns the internal operating system of an enterprise that has recently surpassed $1 billion in annual revenue. Prior to this role, Dennis served as Chief People Officer, leading the company through significant growth and organizational evolution.
Dennis’s career spans industry-defining companies and high-growth startups, including senior leadership roles at Google and Deloitte, as well as five years at Meta. At Meta, he served as Head of Global People Operations and as a Special Consultant to the Office of the CEO, partnering closely with senior leadership to scale complex global operations and drive enterprise-wide transformation. He has also served as Chief People Officer for the venture-backed startup Ad Hoc.
His leadership philosophy was forged through 12 years of distinguished service in the U.S. Army, including work within Special Forces and multiple international commands. There, he developed a deep foundation in operational rigor, leadership development, and strategy under conditions of complexity and consequence.
Today, Dennis brings this experience forward by mentoring veterans and military spouses, helping them translate their service into meaningful civilian careers and ensuring those who served have a clear and empowered path to success.
Episode Highlights
[00:01:02] Why every role is a people business, and the balance of giving more than you take
[00:03:23] What makes a culture enduring: one that can scale without losing who you are
[00:05:40] People aren’t tired of change. They’re tired of endless ambiguity.
[00:08:11] The game of professional telephone, and why leaders need to circle back
[00:13:29] Live Q&A versus pre-baked answers, and the power of “I’m not sure”
[00:15:14] Individual contributors as the real influence without authority
[00:22:02] Managers as the translation layer between tactical and strategic
[00:25:10] Protect trust over optics
Key Insights
Ambiguity Is the Real Fatigue: Your team can carry hard news. What wears them down is change that never gets explained, finished, or connected to what came before. Name what’s stopping, what’s different this time, and why it matters. (00:06:01)
Information Flows One Way: What you say travels down fast. What your team knows travels up slowly, if at all. If you aren’t actively pulling feedback back up, assume you’re missing most of it. (00:07:00)
Close the Loop in Cycles: Don’t trust that a message landed because your VPs delivered it. Check back in a week or two, ask where clarity fell short, adjust, and do it again. Two or three cycles builds muscle memory and trust. (00:08:30)
Defensiveness Ends the Conversation: The first time someone tells you your communication missed and you push back, you’ve taught them not to tell you again. Thank them, fix it, and follow up. (00:09:37)
Go Live, Not Scripted: A town hall with pre-screened questions and polished answers teaches your team that leaders never say “I don’t know.” Taking real-time questions, and admitting when you need to find out, makes it safe for everyone else to be honest too. (00:14:00)
Your Team Is Watching: Employees notice far more than leaders give them credit for. How you handle a hard question in front of the room shapes what people say about you at lunch. (00:18:53)
Map Relationships, Not Reporting Lines: Most companies run on human glue and spreadsheets. The people who carry institutional knowledge and quietly resolve conflict rarely look critical on the org chart. Find them before you need them. (00:23:17)
Key Quotes
“People carry hard things. What they cannot continue to carry is endless ambiguity.”
Dennis“That information you thought traveled well rarely travels upward as fast as it travels down.”
Dennis“They’re held together by human glue and spreadsheets.”
Dennis“Protect trust over optics. Tell people the truth earlier than it feels comfortable.”
Dennis
Resources Mentioned
Fullscript: fullscript.com
Dennis Richter on LinkedIn
After action reviews (the Army practice Dennis applies to leading teams through change)
About Herding Squirrels
Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. Subscribe wherever you listen, and leave a review if this conversation was useful.
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