The [un]common stuff that lives between strategy and execution, that teams don’t talk about.
Your first read every Wednesday morning, meant to be applied and forwarded.
Every headline sounds the same right now.
Automation. Disruption. Replacement... timelines measured in months, not years.
It's enough to make anyone start asking what the next 6, 12, or 24 months will actually look like inside their organization.
Here's some food for thought for you... the CEO of Anthropic, the $380 billion AI company behind Claude, recently said something that should give every senior leader pause.
Dario Amodei spends roughly 40% of his time on company culture. (Fortune 2026)
As Anthropic has scaled to 2,500 employees, it's become nearly impossible for him to weigh in on every technical and product decision, so he focuses on the bigger picture: making sure employees like working there, that the mission and values are clear, and that people are working toward the same thing instead of against one another. (Yahoo Finance)
Anthropic describes their operating culture in language that most leadership teams would recognize as aspirational. They call themselves a "high-trust, low-ego organization" where people communicate directly, assume good intentions even in disagreement, and take responsibility regardless of role.
That last piece is the one most organizations miss. Regardless of role means ownership is not determined by title. It's determined by proximity to the problem. If you see it, it is yours to name.
That's a fundamentally different standard than "escalate through the appropriate channel," and most leadership teams are running the second model while saying they want the first one.
Where culture actually lives (and why individual development alone doesn't move it)
Leadership development tends to focus on the vertical: how leaders communicate direction, model values, give feedback, and make decisions visible. All of that matters, but there's more behind where culture actually lives.
Culture also lives in the horizontal between peers. In whether:
- A director tells someone in another function the truth when things are not working
- A senior leader flags a risk to a colleague before it becomes a crisis, or waits to see if someone else names it first
- Your leadership team takes shared ownership of a problem or quietly passes it to whoever owns it on paper
That's the trust web. It gets built or eroded in moments that have nothing to do with your all-hands, your values statement, or your last offsite.
The structural problem with the standard approach to leadership development is that it's individual. One leader goes through a program, comes back with a new framework, tries to apply it in an environment where nothing else has changed. The trust web stays exactly as it was. The lateral relationships do not move because the learning happened in a silo.
Culture shifts when people go through something together. Working through the same challenges, in the same room, applying new thinking to the same real problems. Building a shared language for what good looks like. That's cohort-based learning, and the reason it works is not mysterious. You're not developing an individual and sending them back into an unchanged system. You are changing the system by developing the people inside it, simultaneously.
So how do you actually move your team toward this kind of culture?
- Stop protecting your leaders from each other. Most organizations route difficult conversations through the person at the top, which means peers never develop the muscle to work through tension directly. The next time 2 leaders on your team have a misalignment, resist the instinct to mediate. Name it, put them in a room together, and let them work it out with a structure. Your job is to make that the norm, not to be the go-between every time something gets uncomfortable.
- Make the invisible stuff visible. The lateral trust gaps in your organization are not going to announce themselves. You need a mechanism for surfacing how your team actually communicates, where information gets held, and where assumptions are replacing real conversation. If you don't know where trust is thin, you're guessing at solutions.
- Invest in your people together, not just individually. The next time you are evaluating a leadership development investment, ask whether it puts your people in the same room working on the same real problems, or whether it sends individuals off to learn in isolation and hopes they bring something useful back. Cohort-based training builds the peer-to-peer trust that most organizations are starving for, because the shared experience of learning together creates exactly the kind of lateral connection that no amount of individual coaching can replicate.
Culture isn't a value you install it's an intricate web you design, and the design happens in who learns together, who talks directly, and who takes ownership of things that are not technically theirs.
If you want to understand where your team's trust web has gaps before making any of those moves, our S.P.A.R.K. Assessment helps to surface those conversations. Reply to this email to learn more about how we can bring your team closer to your culture goals.
See you next week,
Kendra
Ps. If you want to stay sharp on what's actually happening with AI beyond the noise, here are a few creators I'd recommend following:
- Allie K. Miller, who breaks down AI for business leaders better than almost anyone out there.
- Ethan Mollick, a Wharton professor whose newsletter One Useful Thing is one of the most grounded, practical reads on AI and work you'll find.
In the space between the strategy of these tools and the execution of them, we're seeing a whole mix. Our research with Flywheel Strategic, E3 Omni, and Inflectiv through the Digital Momentum Project is digging into this space within organizations. We'll be sharing some of what we're finding at the Digital Momentum Summit on June 2 in Toronto. Would love to see you there, get your tickets here: dxmomentum.com
Unsubscribe · Preferences
