BLUF/Summary I spent thirteen years helping build a government technology company from a small services firm to over 500 employees, serving in roles from COO to CTO to CIO/CISO, before the company was acquired by SAIC in 2021. The company was valuable for many reasons — strong client relationships,
BLUF/Summary For years, we ran a weekly system where every person in a 500-person organization published top five priorities for the coming week, reported progress against last week's five, and shared client feedback and good news, all in a single email sent every Friday by 3pm. No
BLUF/Summary The most expensive technology failures I've seen weren't caused by bad technology. They were caused by organizations deploying capable tools on top of undefined processes, without investing in the change management needed to get people to actually use them. The pattern is consistent: a
BLUF/Summary Most strategies don't fail because they're wrong. They fail because the organization has no recurring rhythm to keep them alive between the January offsite and the December review. Your operating cadence — the cascading system of annual, quarterly, monthly, and weekly meetings that connect strategic
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