Dear Advisor,
Why should I plan anything right now? There’s so much going on and things are changing quickly. What’s the value in doing a plan that could change in a week? Help!
Dear Hesitant to Plan,
It’s tempting to think, Why bother? With so many unknowns—labor shortages, AI disruption, tariffs, supply chain shakeups—planning can feel like trying to draw a straight line in the middle of an earthquake.
Here’s the truth: the more uncertain things get, the more valuable planning becomes. Not the old kind with rigid spreadsheets and forecasts that fall apart in a month. The kind that gives you and your team confidence, clarity, and space to adapt together.
Here are four reasons it matters right now:
1. Check your confidence in today’s plans
Uncertainty shines a light on assumptions. Planning sessions give you the chance to pause and ask, Do our plans still make sense in today’s world? Together, you can test what’s solid, adjust what’s shaky, and agree on “no-regret actions”—the moves worth making no matter how the environment shifts.
2. Realign your team around shared goals
When things feel unpredictable, teams often drift into silos, each group just trying to survive. A planning conversation recenters everyone on the bigger picture. It helps people reconnect their day-to-day work to the organization’s purpose and goals. That shared focus builds momentum even when the outside world feels chaotic.
3. Lower anxiety by making the plan personal again
When uncertainty rises, so does worry. People want to know, What does this mean for me? Strategic planning isn’t just about updating slides—it’s about helping each person see where they fit, why their work matters, and how flexibility is built in. When people re-internalize the plan, they carry less anxiety and more energy.
4. Create space for real concerns to be heard
You’ve probably heard the “Yeah, but…” comments in planning meetings. Rather than brushing them aside, use them. Those concerns often surface the issues that need the most attention. Even if you can’t solve everything in the moment, acknowledging and addressing what’s real strengthens trust. People commit more fully when they feel heard.
What leaders can take away
Planning in today’s environment looks different from the past. It’s not about predicting one future—it’s about preparing for several possibilities.
Focus on outcomes, not just numbers. Numbers matter, yet they’re often shorthand for something deeper. Instead of only chasing a revenue target, explore what that number represents: stability, influence, or impact.
Think in scenarios. Picture the best case, the worst case, and the most likely path. It helps your team respond faster when conditions shift.
Act on “no-regret” moves. Invest in things that make sense no matter what happens—like developing your people, strengthening relationships, or improving processes.
Keep the plan alive. Annual planning alone is too rigid. Shorter check-ins—quarterly or even monthly—help keep goals relevant and aligned.
A quick metaphor
Planning in uncertainty is like flight planning. Pilots never expect the route to go exactly as drawn. Weather shifts, turbulence shows up, traffic reroutes them. Yet without a flight plan, the journey would be stressful and unsafe.
Your strategic plan is the flight plan. It gives you direction, prepares you for turbulence, and helps ensure you and your team still land where you want to go—even if you change course along the way.
Closing thought
The real question isn’t “Should we plan in uncertain times?” It’s “How do we plan in a way that strengthens us, no matter what happens?”
Your role as a leader isn’t to have every answer. It’s to create the space for clarity, courage, and connection.
So ask yourself: What no-regret actions could we take this quarter—steps that would make us stronger whether the future turns out sunny or stormy?
What answers come up? We’d love to have a conversation .
And if you’d like to explore that question with peers, join us for our upcoming Leadership Roundtable: Turning Uncertainty Into Action. Together with guest Loren Feldman of 21 Hats, we’ll share real stories from CEOs, reflect on what’s hard, and highlight practical steps you can put into play right away. Reserve your spot here.
