In Uncertain Times, Ask These Questions Before You Make a Decision

Amid geopolitical instability, climate shocks, AI disruption, and more, today’s leaders aren’t navigating the occasional crisis—they’re operating in a state of perma-crisis.

When the landscape keeps shifting, decisions that rely on old assumptions can quickly become outdated. What worked last time may no longer fit.

In this moment, asking the right questions is one of the most powerful actions a leader can take. That’s because good questions don’t just help you find answers—they open up your thinking and help you see your choices from new perspectives.

Traditional questions aim to reduce ambiguity: What’s the return on investment? What’s our timeline? How will we determine our key milestones? But when volatility is the norm, these questions can unintentionally narrow the field of vision too soon, leading teams to lock in too early, overlook systemic shifts, or delay critical action. While it’s natural to zoom in on what’s familiar when you’re under pressure, that instinct can create an illusion of control, blinding you to emerging risks, obscuring valuable opportunities, or keeping you locked in yesterday’s logic while the world moves on.

In uncertain conditions, leaders need questions that expand perspective, generate new insight, and spark creativity. The right questions don’t just help you avoid missteps—they open new paths.

These are four questions that I use to help my clients work with and through ambiguity. The answers won’t predict the future—they’re to help you think more clearly right now, cutting through noise, surfacing blind spots, and creating momentum when you feel stuck.

1. What decision today will still make sense a year from now?

It’s easy to make decisions that solve immediate problems but create downstream consequences. Asking this question forces leaders to pause and consider the durability of their choices, injecting long-term thinking into short-term chaos.

Answering this question doesn’t require perfect foresight, but it does require clarity: What direction are we truly committed to? What values do we want this decision to reflect? What kind of risk are we willing to carry forward? The question acts as a filter—helping teams move beyond panic or pressure to make decisions that align with where they want to go rather than simply reinforcing where they are. It prioritizes resilience over quick wins and strategy over noise.

Alana, a senior leader at a global consumer brand, was under pressure to cut costs after a disappointing quarter. Her finance team presented a straightforward solution: Eliminate the company’s sustainability initiatives. The move would produce fast savings with minimal operational disruption—just what the quarterly report seemed to call for. But something about the recommendation gave her pause.

After asking herself “What decision today will still make sense a year from now?”, Alana zoomed out to consider the long-term consequences of this move. Sustainability had become a key part of the brand’s identity—especially with its fastest-growing customer base: younger consumers who cared deeply about environmental and social responsibility. Slashing those programs might help this quarter’s margins, but it would send the wrong signal to the market and risk damaging hard-earned trust.

Instead of cutting the entire program, Alana identified which sustainability efforts were most visible and most valued—for example, the company’s ethical sourcing partnerships. This enabled her to preserve what mattered most, while pausing or restructuring efforts that had less direct consumer impact. She communicated the decision transparently to employees, reinforcing the company’s long-term commitment while acknowledging short-term constraints.

The question helped Alana resist a reactive decision and instead choose one that balanced immediate needs with long-term positioning.

2. If a year from now this decision was used as an example of our leadership, what would it teach?

In uncertain times, when data is incomplete and outcomes feel unpredictable, this question helps leaders shift from reactive problem-solving to intentional meaning-making.

This is more than a reflection question—it’s a reframing device. It asks: What kind of story are we writing with this decision? What would others learn—not just about what we did, but about how we showed up?

Unlike a question that focuses on whether a decision will stand the test of time, this question is about what your decisions say about you—your priorities, courage, and clarity. It’s strategic because it prompts leaders to widen the lens and consider how their choices reflect the culture they’re building and the example they’re setting.

Take Raj, a vice president at a fast-growing tech firm, who was leading a high-stakes product launch. One team member raised ethical concerns about how user data might not remain anonymous. While the legal team had signed off, a gray area remained. Delaying the launch would mean missing a major investor milestone. The team was split.

Asking “If a year from now this decision was used as an example of our leadership, what would it teach?” shifted the conversation. It wasn’t just about timelines or risk anymore—it was about character. What lesson did they want to model? What did they want their team—and their users—to remember? Raj decided to delay the launch by two weeks to build in stronger data protections and publicly explain the change.

The result: The company missed the milestone, but gained internal trust, external respect, and investor confidence. And a year later, that decision was held up as a defining example of leadership with integrity.

3. What if this isn’t the storm—what if it’s the climate?

This question flips the way leaders typically frame disruption. Rather than treating volatility as a temporary storm to wait out, it asks you to consider: What if this is the new normal?

That shift is more than semantic—it’s strategic. It challenges the instinct to delay, defer, or design for an imagined return to stability, and it invites you to stop optimizing for recovery and start preparing for persistence and building for endurance. It encourages investments in systems, culture, and capabilities that can flex under pressure—not snap. By confronting uncertainty head-on, leaders move from reactive to resilient, making choices that don’t just survive the current moment, but thrive across whatever comes next.

Darryl, COO of a consumer goods company, had been struggling with a key packaging vendor. Deliveries were late. Quality was slipping. But switching vendors felt risky—the current one had been with them for years, knew their specs, and offered decent pricing. So, Darryl kept pushing for fixes, hoping the issues were temporary.

Then during a meeting with his team to discuss the supply chain, his procurement lead asked him: “What if this isn’t the storm—what if it’s the climate?”

The question flipped the conversation. Instead of treating the vendor’s issues as short-term turbulence, Darryl began to see a deeper pattern: Although the relationship had worked for several years, it hadn’t worked for the past year—a period in which Darryl’s company had expanded into international markets. Maybe Darryl wasn’t seeing glitches; maybe the team was seeing a vendor that could no longer serve their expanding needs. The risk wasn’t in making a change—it was in staying loyal to a relationship that no longer served the business.

Darryl launched a dual-track plan: Begin onboarding a second vendor while giving the current one a final 90-day improvement window with clear benchmarks. If the issues continued, Darryl was ready to make the switch.

The result: fewer delays, better quality control, and a stronger position with retailers. The procurement lead’s question kept Darryl’s company from waiting for things to “go back to the way they were.” The question didn’t offer a prediction, it forced a new frame. And that reframing led to action.

4. What’s the cost of waiting?

In a crisis, the instinct to pause—to wait for more data, for more certainty, for the fog to clear—can feel responsible and prudent. Leaders are taught to avoid rushing, to reduce risk, and to base decisions on evidence.

But in volatile environments, the pursuit of perfect clarity often conceals a hidden cost: the cost of inaction. That’s what makes this question so strategic. It forces leaders to confront not just the risk of moving too soon, but the equally dangerous risk of moving too late.

This question shifts the decision lens from fear-based delay to opportunity-focused action. It encourages leaders to examine what may be lost by hesitating: market position, momentum, team morale, innovation windows, or the chance to lead rather than follow. It’s not ignoring caution—it’s about weighing it against what’s at stake if the moment passes. In crisis, timing often matters more than precision, and waiting for a more complete picture can mean missing the window for your best move.

Monica, a chief strategy officer at a small financial services company, faced a tough decision about adding a senior marketing officer in the middle of economic uncertainty and volatility in the stock market. Her instinct was to wait—for six more months of data, maybe a more stable market, and investors who would be interested in new financial products.

But in a leadership meeting, she asked out loud: “What’s the cost of waiting?”

As the team talked it through, they uncovered real risks: failing to get their name and product in front of potential investors, not reaching the customers who would benefit from their product, losing out to competitors, and damaging internal momentum after months of work. Just as importantly, they realized that waiting for a more stable market would likely mean tossing out the stack of high-quality resumes on Monica’s desk.

By flipping the bias away from fear of acting and toward awareness of inaction, they made a decision that balanced courage and caution. They moved ahead with the hire and re-imagined the compensation structure to heavily reward bringing in new assets. The question didn’t eliminate uncertainty, but it helped the team move forward anyway, with eyes wide open.

Moving from Hesitation to Meaningful Action

In today’s perma-crisis world, waiting for stability is like waiting for a train that’s never coming. When everything around you feels unsteady, using these four questions as strategic tools can enable you to have better analysis, reframe risk, and strengthen your decision-making muscles.

You don’t need perfect foresight to lead well in times of uncertainty, but having the right questions to ask can shape how you respond. They reveal faulty assumptions, spotlight hidden opportunities, and help you focus on what’s within your control. Strategic decision-making isn’t about having all the answers; it’s about asking the questions that move you toward wiser, more resilient outcomes.

Copyright 2025 Harvard Business School Publishing Corporation. Distributed by The New York Times Syndicate.

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