BLUF/Summary Every growing organization pays a hidden tax that never shows up on a financial statement: the ambiguity tax. It's the cumulative cost of people not knowing who owns what, who can approve what, who to escalate to, and where their job ends and someone else'
BLUF/Summary After two decades of building, advising, and investing in organizations, I've found that every scaling success or failure I've witnessed comes down to the relationship between four things: people, operating system, strategic clarity, and execution discipline. I call this the Keel Framework, and I
BLUF/Summary Government contracting (GovCon) companies face a unique scaling challenge: they must build organizational maturity under some of the most demanding compliance frameworks in any industry — FAR, CMMC, FedRAMP, agency-specific compliance standards, HIPAA, etc. — while simultaneously growing fast enough to compete for larger contracts. Many organizations handle this by
BLUF/Summary Most leaders want a culture of high agency — people who take ownership, solve problems without being asked, and push the organization forward. But they treat agency as a hiring trait rather than a design choice. You don't get a high-agency culture by finding high-agency people. You
BLUF/Summary AI agents offer enormous promise for organizations for collaboration and automation — but they can only act on knowledge that's been captured, structured, and made accessible. If your culture, processes, decision approach, and institutional expertise live in people's heads, your AI investment isn't
Bottom Line Up Front (BLUF): I recently had the opportunity my framework on growing an organization's stability and value, to avoid grow leading to "house of cards" fragility and then moderated a great panel with three CEOs sharing their battle scars on scaling beyond the "
BLUF/Summary Create a culture where goals are challenging enough that meeting 70–90% is considered a massive win. If your team is hitting 100% of their targets every quarter, you aren't setting goals; you’re just documenting current capacity. The Tension of Ambition Finding the right tension
The Trap: Communication Friction In small or rapidly scaling organizations, "tribal knowledge" often includes unwritten, and often destructive, communication habits. When pressure rises, leaders often default to "You" statements—"You missed the deadline" or "Why are you being defensive?" These are verbal
The Efficiency Trap In a recent piece, Scott Young revisited Stephen Covey’s classic concept of the Compass vs. the Clock. In our current "speed-at-all-costs" AI environment, this distinction has never been more vital. Most leaders are obsessed with the Clock: How fast can we ship? How many
The Chaos of Tribal Knowledge and Ambiguous Authority Small organizations often run off of "tribal knowledge." Everyone just knows how things are done because they sit in the same room (or Slack channel) and figure it out on the fly. There's a classic approach of "
The Trap Business leaders are currently navigating a storm of AI headlines. The pressure to transform, to automate before being left behind, is immense. I see this in the companies I support as a board member and advisor. They feel the FOMO, but they struggle to make wise bets in
I recently listed to a great podcast interview about Alpha School, on the Invest Like the Best with Patrick O'Shaughnessy podcast, which is a new education model focused on using AI to personalize education to each student. It was recommended by a friend of mine, and was a