Leading Through Ambiguity
Create Alignment, Not Illusion
When travel collapsed in early 2020, Airbnb’s revenue cratered in a matter of weeks. The leadership team didn’t pretend to know exactly when travel would rebound or what shape recovery would take. They rallied around what wouldn’t change: the intent to “help people belong anywhere.” From that anchor they drew clear boundaries – preserve runway, protect the host community, refocus on core hosting, pause side bets, and create decision gates to reassess as evidence emerged. Rather than overpromising timelines or certainty, they paired modest commitments (the next decision and the data they’d gather) with flexible options (domestic stays, medium-term rentals, a leaner Experiences offering). The path stayed murky; the purpose didn’t. That is alignment without illusion.
Here’s the core idea: in uncertainty, leadership is less about accurate prediction and more about durable intent. You won’t make the fog go away, you’ll make it navigable. The quickest way to lose a team in ambiguity is to substitute activity for agreement, or to mistake head-nods for shared understanding. If you pulled the timeline slide out of your deck, would your team still know what you’re trying to accomplish, and why now?
Start by holding shared intent, not fixed plans. Shared intent is a one-page articulation of the problem you’re trying to solve, who you’re solving it for first, the non-negotiables you won’t violate, and how decisions will get made while you learn. It’s the stabilizer you need when the seas are rough, the same spirit behind two past Fish Food for Thought themes. In Hold What You’ve Got, the advice was to secure the essentials so you can steer in the fog. In Ship of Theseus, the lesson was that identity persists even as planks change; strategy can evolve piece by piece while purpose remains intact.
To translate that into day-to-day execution, use a simple frame:
Intent: the north star, the problem, the outcome, and the first customer segment.
Boundaries: the guardrails, budget/time caps, SLOs, ethics/safety, the “won’t do” list.
Checkpoints: the decision gates, what evidence you’ll bring, who decides, and when.
Options: the scenario set, two or three viable paths, each with explicit triggers to switch or stop.
This is the I.B.C.O. frame. It keeps you honest about what you know, what you don’t, and how you’ll learn next. Crucially, it also protects you from the easiest trap in uncertainty: overpromising. Practice promise-hygiene by separating the intent (the outcome you owe) from the hypothesis (the method you’re testing), the plan (the next sprint or milestone), and the commitment (the decision you’ll make by a real date, with specified evidence). Plain language helps: “We’re committed to the outcome; our method is a hypothesis,” or “Here’s what would change our plan: if churn on the pilot cohort exceeds three percent, we pause and revisit.” Put stop conditions beside success metrics to curb sunk-cost drift. We can also borrow some techniques from Annie Duke's book Quit: The Power of Knowing When to Walk Away such as establishing clear quit criteria, benchmarks for decisions, and listening to experienced voices from the past.
Decision speed matters, but pace it to the stakes. Distinguish two-way doors (reversible; move fast) from one-way doors (costly to unwind; add evidence). A simple Consequences × Conviction matrix keeps you honest: experiment when both are low, ship when consequences are low but conviction is high, gather evidence when consequences are high and conviction is low, and commit, then instrument, when both are high. Before each gate, run a ten-minute pre-mortem: “It’s six weeks later; this failed. Why?” You’ll catch illusions before they harden into plans.
An operating rhythm makes the framework a habit instead of a slogan. Hold a short weekly ambiguity stand-up to state the top three unknowns, how you’re learning, and what’s blocking you. Run an evidence review every other week where teams show proof of learning, customer behavior, telemetry, funnel friction, instead of just activity. Ask DRIs to submit a short owner’s narrative at each checkpoint: restate intent and boundaries, summarize the latest evidence, note what changed (and why), list the risks, propose the decision, and state the asks.
Artifacts help alignment travel across time zones and org charts. Keep an intent memo as the canonical “why + guardrails.” Maintain a decision log that records date, door type, alternatives considered, why now, and the evidence you expect before the next gate. Treat a risk register as a to-do list with triggers and owners, not a fear catalog. Pair it all with a living customer facts sheet, the top pains for your first segment, quantified and dated, so everyone sees the same reality.
In the fog, leading indicators beat lagging comfort. Watch activation and retention in the new flow, learning velocity (how quickly you run and retire hypotheses), cycle time, and the behaviors that signal real customer progress. Publish a confidence index at every checkpoint and tie it to options, not ego. When confidence goes down while evidence goes up, you’re not failing; you’re seeing sooner.
If you want a mental model, imagine two quick snapshots. In a platform migration, intent might be to de-risk scale limits without customer pain; boundaries include error budgets and a rollback plan; checkpoints focus on shadow-traffic quality and latency; options progress from parallel run to slice cutover to full switch, with SLO-based triggers. In a new product bet, intent might be to expand ARPU in your current segment; boundaries include a two-quarter runway and a small team; checkpoints call for design partners and paid pilots; options range from feature bundle to standalone SKU to partner integration, each with explicit kill criteria. In both cases, the plan flexes while the purpose holds.
Culture makes this sustainable. Normalize strong opinions, loosely held. Reward “I changed my mind because…” moments in public. Rotate the DRI across gates to blunt founder-effect bias. Keep your decision log visible so reversals feel like learning, not loss. These are small, human moves that prevent illusion from creeping in through social pressure.
Ambiguity isn’t the enemy; pretending it isn’t there is. Your edge as a leader isn’t clairvoyance, it’s coordination. When the map is sketchy, the work is to hold a clear intent, establish boundaries that protect people and customers, create checkpoints where truth can change your mind, and keep multiple options alive so you can pivot without drama. Pair that structure with promise hygiene, commit to outcomes, label methods as hypotheses, and pace decisions to the stakes: move fast through two-way doors, slow down for one-way doors, and keep a running pre-mortem to catch illusions early.
Make it a habit, not a slogan. An operating rhythm that spotlights uncertainty (weekly ambiguity stand-ups, bi-weekly evidence reviews) builds shared reality faster than slideware ever will. Lightweight artifacts, an intent memo, a visible decision log, a risk register with triggers and owners, a current customer fact sheet, let alignment travel across teams and time zones. Track leading indicators and publish a confidence index at each checkpoint so adjustments feel like stewardship, not backpedaling. And build the culture to support it: dissent as a duty, reversals as learning, and “I changed my mind because…” as a celebrated sentence.
Most important moves to make this week
Draft a one-page I.B.C.O. for your gnarliest initiative and share it with the team.
Add stop conditions next to every success metric on your roadmap.
Publish a confidence index and the date of your next decision gate.