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When the landscape keeps shifting, decisions that rely on old assumptions can quickly become outdated.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.

[Here are the first two questions to answer.]

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.