The Architecture of Trust: Strategy, Transparency, and the Unseen Signals of Culture
What does it mean to actually run a strategy—not just define one?
This week on Momentum Mode, Corey and I sat down with Dan Dal Degan, a leader whose resume reads like a blueprint for high-growth enterprise success. Known to many as “Triple D,” Dan is an operator, investor, advisor, and boardroom regular. He helped scale Salesforce in its early days—an impact so significant he was thanked by Marc Benioff in Trailblazer.
Dan's experience spans IPOs, acquisitions, and growth-stage transformation. But where our conversation goes deeper is in unpacking something deceptively simple: strategy isn't just a document. It's a living operating system.
If Culture Eats Strategy for Lunch, Then Strategy Better Show Up Hungry
The famous Drucker line—culture eats strategy for lunch—has reached meme status in executive circles. Dan agrees with the spirit but sees a dangerous flip side. Strategy has become the forgotten sibling. It’s often vague, under-communicated, and unintentionally elitist.
“If you walk through your office and ask ten people what the company’s strategy is, and eight can’t answer coherently—that’s not on them. That’s on you as a leader.”
Dan’s view? Strategy should live where the work lives. It should be clear, useful, and specific enough that anyone—whether they’re in product, sales, or support—can make daily decisions through its lens.
If your strategy doesn’t help someone prioritize their time, then it’s just theater.
Measuring What Matters (Without Gaming the System)
We dug into frameworks—OKRs, KPIs, scoreboards—and what it means to actually know if you’re on track. Dan’s analogy? Think of business like the NFL.
Everyone sees the score, but real insight comes from the metrics that predict the win: time of possession, turnovers, third-down conversions. In software, that might mean tracking meaningful customer engagement instead of vanity logins, or measuring time-to-resolution instead of open tickets.
But this raises a deeper challenge: choosing the right metrics requires trust. People need to believe you’re not sandbagging goals or setting them impossibly high to game performance.
That trust comes from what Dan calls “reputational authority”—the peer-respected voices in your org who set the tone for how strategy is received. Not the org chart leaders, but the cultural signal-boosters. Smart leaders enlist these individuals early, because alignment doesn’t happen on Slack. It happens in the micro-moments where someone nods—or doesn’t.
Transparency, Over-Assignment, and the Art of the Walkaway
One of the most surprising parts of our conversation was around over-assignment—the often-taboo practice of setting collective quotas higher than the actual company target to account for variability.
“I talk about over-assignment openly. When people understand it, you can see the tension leave the room. They get it. You build trust.”
Dan goes further: he celebrates walkaways. On weekly forecast calls, his teams don’t just share wins. They proudly present disqualified deals—opportunities they chose to walk away from because the signs weren’t right.
The signal this sends is powerful: time is your most finite resource. Qualify ruthlessly. Say no with pride. Strategy isn’t just about doing more. It’s about doing less of the wrong stuff.
The Salesforce Years: Humor, Cadence, and Marc Benioff’s Secret Weapon
Dan was employee #85 at Salesforce. He saw it evolve from startup chaos to global juggernaut, and credits much of the internal alignment to cadence and storytelling.
“Marc is without peer when it comes to inspiring internal teams. He never took himself too seriously—but always took the mission seriously.”
That’s a balance many leaders miss. We try to lead with perfectly polished strategy decks, but forget the emotional undercurrent: people want to feel informed, yes—but they also want to feel enrolled.
The best leaders? They don’t try to solo it. They orchestrate buy-in from their inner circle first—the lieutenants and cultural influencers—so that the message lands across the company, not just at the podium.
Final Thought: Don’t Mistake Nods for Buy-In
Too many executives mistake silence for alignment. Dan warns against it. If your team is nodding, but not engaged, you haven’t communicated—you’ve broadcasted. And there’s a difference.
To move fast as a company, you need clarity. To sustain that speed, you need trust.
That’s the core of Momentum Mode. Strategy isn’t separate from culture. When done well, it is culture—in action.
From this episode with Dan Dal Degan:
— Why most employees don’t understand strategy—and why that’s the CEO’s fault
— How over-assignment, when handled transparently, actually builds trust
— What Salesforce got right early—and how humor helped drive culture through scale
— Why “walkaway” deals deserve airtime alongside your wins
— How to identify the real influencers inside your company (hint: not the title-holders)
— What makes a metric meaningful—and how to pick the right ones when everything feels important