January 2026, Issue 2: Read the Room, Not the Brief. It's how I found the real culture culprits
Hey there! Welcome to our second issue.
We've been busy this month kicking off new client work, experimenting with our content process, and setting ourselves up to thrive this year while we work with people who are tackling the tough and rewarding work of strengthening their team culture.
We're also experimenting with our newsletter format to bring you content that challenges you to think differently about work and the world. We'll share art, musings, music, and ask questions - not to collect data - but to learn deeply about what you're facing so we can help you embrace your inner Rebel.
Thanks for reading!
Craft Corner
Testament is an origin story. A memory. And an epic poem written by a member of our Rebel community. Grab a signed copy now!
Read the Room, Not the Brief
Every new assignment begins with a story someone is eager to tell you. A tidy list of challenges. A retrospective wrapped as a warning. Or, occasionally, a glowing biography of the person who came before you—meant to reassure you that the role is important, the team is special, and the problems are manageable.
I’ve learned not to believe any of it.
The brief—spoken or written—always skims the surface. It tells you the problem the leaders wish they had. It paints a picture clean enough to hand to an outsider without embarrassment. It reveals almost nothing about how the place actually functions.
You don’t find the truth in the handoff.
You find it in the room.
The tone. The gaps. The silences. The people who reach out privately. The people who won’t look each other in the eye.
That’s where the real story lives.
This is exactly what I walked into at a travel technology company in the early days of COVID—when travel was collapsing and the entire industry was running on anxiety, duct tape, and whatever small pockets of operational hope they could find.
I was hired by the VP of Product to steady a struggling team responsible for building a conversational agent—one that suddenly needed to scale overnight. He talked a lot about the heroic work done by my predecessor, the chaos of the early pandemic, the volume of customer feedback, the absence of a project management system, and the kinds of alignment issues you expect when everything is on fire.
But he didn’t name anything as a problem.
He simply described the wreckage in a bright, neutral tone, as if it were all a natural disaster no one could be blamed for.
And even as he talked, you could almost hear what was missing. The things he wouldn’t say. The fractures he avoided. The parts of the truth that shimmered for a moment but then dissolved.
So, I left that meeting with a new task: to discover what was really happening.
What the Room Actually Said
In my first week, I started a listening tour. Nothing formal—just quiet conversations with whoever was doing the real work. Product managers. Engineers. Designers. Release folks. Anyone with hands in or near the machine.
On day two, a technical program manager reached out privately and said, almost urgently, We need to talk. There’s a lot here you don’t know yet.
We didn’t manage to connect for six weeks because the team was so underwater, but the message hung in the air as a warning: things are bad and you’re not getting the whole story.
And it was. Bad. Spectacularly so.
The deeper I listened, the more obvious it became that the core problem had nothing to do with conversational AI or customer feedback or project management tooling. Those were symptoms—loud ones, visible ones—but not the cause.
The real problem was leadership.
Specifically, the three VPs who were supposed to be jointly responsible for the org: my VP of Product, and two VPs of Engineering.
I never once saw them together.
Not in a meeting. Not in a review. Not in a planning session. Not in a moment of shared accountability.
They delivered contradictory messages. They operated from competing visions. They protected their domains like territory in a land war. And they silently instructed their teams—through posture, not policy—to do the same.
You could see the fracture immediately in the work:
Product managers operated in total isolation, writing thoughtful requirements documents that no engineer ever read.
Engineers were told bluntly not to engage product managers because “they’ll create more work that isn’t relevant.”
Release engineering shipped updates daily with no visibility to other teams. No QA. No validation. No shared sense of risk or readiness.
And beneath it all, simmering like a low-grade infection, was fear:
Fear of losing control. Fear of being blamed. Fear of visibility. Fear of other teams.
Culture always flows downhill, and here it was carving deep channels. When leaders don’t share accountability, teams stop sharing truth. When leaders don’t share vision, teams stop sharing work. When leaders won’t speak to one another, teams eventually forget how to do the same.
But nothing illustrated the dysfunction more clearly than the tooling.
There were seven Jira instances inside the engineering org.
Seven.
Each with its own metadata, workflows, language, and definition of “done.”
Each reflecting the worldview of a sub-team that had long ago stopped coordinating with the others.
None of them included Product.
The TPM who’d reached out to me managed one of those seven and had unusually strong relationships across engineering. Through sheer persistence and social intelligence, she had a kind of informal line of sight into the others—not control, not authority, but awareness.
She could see the chaos but couldn’t fix it.
Consolidation wasn’t just a technical challenge; it was a political impossibility.
That’s the moment you understand the scale of the problem.
Seven systems means seven realities.
Seven realities means no shared strategy.
And no shared strategy means the conversational agent was never the real blocker. The blocker was the fracture in leadership radiating across every inch of the work.
Stitching the Work Back Together
Once you understand the real problem, you stop trying to fix the symptoms and instead start stitching along the fracture lines.
I began consolidating where I could—not the systems themselves, which required VP-level alignment that simply didn’t exist, but the information. I built workflows that crossed boundaries. Documentation that connected inputs to outputs. Requirements that actually matched engineering priorities. Communication loops that forced cross-functional visibility instead of relying on accident or goodwill.
And then I turned toward culture.
This wasn’t a consultant’s hit-and-run assignment. I was inside the org, part of the team, accountable to outcomes. So I had both the opportunity and the responsibility to start rebuilding trust—however slowly.
We set up virtual coffee breaks and monthly social hours, not because they fix everything, but because it’s easier to collaborate with someone you’ve spoken to like a human being. Mid-pandemic, when everyone was exhausted and isolated and holding the weight of a collapsing industry, even small moments of connection mattered.
People were wary, but some leaned in.
People were afraid, but some started talking.
People were skeptical, but some stayed curious.
And as they did, the work began to steady.
But culture change has limits when leadership won’t meet you halfway. You can stitch the fabric. You can reinforce the seams. You can build the conditions for trust. But you cannot substitute for a cohesive leadership layer.
And here, the leaders struggled.
They struggled to be honest.
They struggled to share accountability.
They struggled with ego, identity, territory—all the invisible forces that quietly dictate how an organization behaves.
Without their alignment, the needle could move, but it couldn’t lock into place. You can stabilize. You can improve. You can make progress. But you cannot transform.
Not without leadership stepping into the work.
What This Teaches Us
Everything I saw there is painfully common in broken cultures.
The symptoms are always dramatic—missed deadlines, duplicated work, confused roadmaps, seven parallel systems that refuse to talk to each other—but the cause is frequently the same: a leadership crisis.
When leaders don’t share a vision, the organization splits.
When leaders don’t share accountability, the organization hides.
When leaders don’t trust each other, the organization fragments into tribes.
And once the tribes form, truth stops flowing.
This is why cleaners read the room, not the brief. Because the brief will always describe the problem in technical terms—delivery challenges, resource shortages, tooling issues, roadmap risk. It’s tidy. It’s linear. It’s controllable.
But the room will show you the real story:
Who’s afraid.
Who’s angry.
Who’s silent.
Who’s working around the system because the system doesn’t work.
Who’s building bridges quietly while leadership plays a territorial game above them.
That’s where the truth lives.
And if you want to fix culture, the brief won’t save you. You start with the room—its tensions, its silences, the people trying their best inside it. That’s where culture lives and dies.
