August 28, 2026
Hi Everyone,
Most leadership teams run some form of quarterly business review. It asks whether you're hitting the numbers, which projects are behind, and who needs help. Useful, but it assumes the plan itself is still right.
The plan only gets questioned once a year, during planning season. For the other ten months, its assumptions can fail without anyone being asked about them.
Today we're sharing a 90-minute quarterly meeting that tests the plan itself, plus a one-page template to run it.
The plan is only as good as its assumptions
Every annual plan depends on a handful of beliefs about customers, pricing, competitors, and hiring. When one of those beliefs turns out to be wrong, better execution won't save you. That's why the review matters more than the goals.
HashiCorp reviewed every one of its company goals every quarter while growing past 1,000 employees. Kevin Fishner, who ran that system as chief of staff, says the point was never to stick rigidly to goals set at the start of the year. "It's a ritual of reflection and introspection. Are we on track to hit goals? Are these the right goals?"
McKinsey's strategy team gives the same advice. Keep a live list of your biggest strategic questions, and check your assumptions in regular leadership sessions instead of saving everything for one annual meeting.
What the 90 minutes look like
Once a quarter, put 90 minutes on the leadership team's calendar and run this agenda:
1. Before the first meeting, write down the plan's top five assumptions. These are the beliefs the plan depends on. "Mid-market customers will keep renewing at current prices," or "We can hire six engineers by Q3." Do this once, when the plan is set, and reuse the list every quarter.
2. Test each one against the last 90 days (60 min): For every assumption, ask what you learned this quarter that supports or contradicts it. Use real evidence, like churn numbers, lost deals, hiring results, or a competitor's launch. Opinions don't count here.
3. Apply the two-of-five rule (10 min): If two or more assumptions have clearly changed, the plan needs a proper review. Schedule it within two weeks. If the assumptions hold, say so out loud and go back to executing.
4. End with a money question (20 min): Ask whether anything you learned should move budget or people this quarter. If nothing moves and nothing gets scheduled, the meeting confirmed the plan, and that's a good outcome.
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βWe built a one-page template for this. Book the first session before Q4 starts.
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Checking the plan is how you protect it
A meeting that questions the plan every quarter sounds like it would lead to more pivots. It leads to fewer. Without it, the plan changes whenever someone feels strongly enough, after a bad month or a pointed board comment. With it, the plan only changes when the evidence shows two of your five assumptions no longer hold.
Harvard Business Review reports that 85% of senior leaders have seen "an explosive increase" in change initiatives in the past five years, and that teams on the receiving end burn out and leave. Most quarters, this meeting confirms the plan, and that's the outcome your team is hoping for.
Go deeper
π First Round Review: Focus on Your First 10 Systems, Not Just Your First 10 Hires β read this for the full HashiCorp system, including how they review twelve company scorecards every quarter.
π McKinsey: Treat strategy as a journey, not an annual management junket β use this to build the live list of strategic questions your quarterly check draws from.
π HBR: How to Prevent Strategy Fatigue β read this before your next pivot; four filters that stop a new idea from becoming a whole new strategy.
π HashiCorp: Operating Cadence β HashiCorp's own write-up of its annual, quarterly, and weekly reviews, with the templates they use internally.
Coming up on Monday
On Monday, we will break down why 40 to 60% of qualified deals end in no decision, and the three habits that change it.
P.S. Can your leadership team name the five assumptions behind your current plan? If they canβt, that's your first finding, and it's worth 90 minutes on its own.