Pilots have checklists. Surgeons have checklists. These exist because high-stakes decisions deserve consistent discipline — a way to catch what you might otherwise miss under pressure.
Managers make consequential decisions constantly. Yet most work without any equivalent discipline. Instinct, experience, pattern-matching — all valuable, but unsystematic.
Four questions matter for any significant decision. Not as a rigid formula, but as a checklist for thinking clearly when the stakes are real.
The Questions
1. What should we do?
This is strategy. Not vision statements or aspirations, but the actual choice: what are we going to do, and what are we choosing not to do?
Good answers are specific enough to guide action. “Grow revenue” isn’t a strategy. “Win the mid-market segment by being the easiest to implement” is closer — it tells you what to prioritise and what to deprioritise.
2. Can we prove it?
This is where numbers come in — not as an afterthought, but as a test of the strategic choice.
The question isn’t “what metrics do we have?” It’s “do we have evidence that gives us confidence we’ve made the right call?” Sometimes that means building new instrumentation. Sometimes it means acknowledging you’re working on belief, not proof, and being honest about that.
3. How do we get it done?
This is action — not urgency or busyness, but the system design for follow-through.
A strategy without an action plan is just an idea. Who owns what? What’s the sequence? What mechanisms keep things moving? And critically: is there the capability and capacity to actually do this?
4. Will it work?
This is prediction — and the question that gets skipped most often.
Before executing, articulate what you expect to happen. Not as a forecast to be held to, but as a testable hypothesis. If this works, what should we see? In what timeframe? What would tell us we’re on track — or off it?
How to use this
For major decisions: Run through all four explicitly. Write down the answers. The discipline of articulating forces clarity — and creates a record you can check later.
For smaller decisions: The same questions, lighter weight. “What are we trying to do, how confident are we, how will we execute, what do we expect?” can run in five minutes if the decision is simple.
In meetings: When discussion is circling, ask which question you’re actually stuck on. Often the debate is mixing strategy (Q1) with execution (Q3), or the real disagreement is about evidence (Q2) not approach.
For learning: After the fact, compare outcomes to Q4 predictions. The gap is where learning lives. Without explicit expectations upfront, you can’t tell whether you succeeded, failed, or got lucky.
The questions scale
A small operational decision benefits from a quick pass through all four. A major strategic bet — an acquisition, a market entry, a transformation — needs the same four questions with more underneath each one. Deeper analysis, more rigorous testing, more explicit scenarios.
The questions don’t change. The weight behind them does.
Red flags:
- Can’t answer Q1 specifically (strategy is vague)
- Q2 gets skipped because “we don’t have data” (you’re betting blind)
- Q3 assumes perfect execution (no constraints acknowledged)
- Q4 never articulated (no way to learn)
Related: Decision Architecture · Decision Rubrics