In uncertain times, we yearn for answers. Even better if they are quick and easy and yield the right answers.
Unfortunately, it doesn’t work that way.
In uncertain times, there are far more questions than answers.
And the questions are challenging. The answers are ambiguous, with honest responses like:
- It depends.
- I’m not sure.
- What if <fill in the blank>?
- I never thought of it that way.
As such, it is a bit counterintuitive that in uncertain times, we ask ourselves the hard, challenging, there is no one answer, dig deep type of questions.
And then wrestle with them a bit. You might journal or write. Or wander outdoors and think. Or open the question to your team and trusted peers to bounce it around.
Then rinse and repeat – sometimes with the same question or with another question the first query unearthed.
Due to our human tendency to escape discomfort as quickly and painlessly as possible, getting comfortable with the discomfort of “no easy answer” is a critical leadership skill. As is wallowing in the questions a bit. Breathing into them. Staying open to new ideas, thoughts, and approaches.
This is NOT the time to be the expert, the smartest person in the room, or the infallible person. This IS the time to be open, curious, inquisitive, innovative, and humble.
Given all that, asking the right question(s) is critical. I share a “question bank” at the end of this blog, yet before that, here are some of the characteristics of great questions for uncertain times. I want you to become masterful at crafting great questions when they are called for.
Characteristics of Compelling Questions in Times of Uncertainty
- Open-Ended: Avoid yes/no answers and invite exploration.
- Thought-Provoking: Almost uncomfortable. Challenge conventional thinking and/or prompt deep reflection.
- Purpose-Oriented: They connect back to core values, mission, or desired impact.
- Future-Focused: They stretch thinking beyond short-term reactions to long-term outcomes.
- Challenge the Status Quo: Make it acceptable to rethink all that you are currently doing.
They prompt re-evaluation of existing strategies, habits, or power structures - Invite Multiple Perspectives: They intentionally seek diverse ideas and input.
They are inclusive and benefit from diverse input. - Rooted in Curiosity, Not Judgment: They come from a place of wonder and inquiry, not blame.
- Balance Risk and Opportunity: They explore both danger and possibility in the unknown.
- Lead to Action, Not Just Discussion: They move people toward experimentation, prototyping, or next steps.
- Reveal Underlying Systems or Patterns: They prompt exploration of root causes or interdependencies.
Question Bank for Uncertain Times
Here is a list of questions to select from. Some will apply, some will not. Feel free to adapt, change, and create your own.
- What decision today will still make sense a year from now?*
- If a year from today, this discussion were used as a case study of our leadership, what would you want it to teach?*
- What if the current environment is climate and not just weather? *
- What is the cost of waiting? *
- What assumptions are we making that might no longer be true?
- What does this challenge invite us to become?
- How do our values guide us in this time?
- What might success look like if our current path is no longer viable?
- How can we use this disruption to build something more resilient?
- Where are opportunities surfacing that we should consider?
- What are we afraid of right now, and what does that tell us?
- What is the most important topic for us to be discussing that we are avoiding?
- If we weren’t already doing it this way, would we start now?
- What would our customers, frontline team, or critics say we’re missing?
- What can we learn from others who have navigated similar uncertainty?
- What risks must we take now to avoid greater risks later?
- What is a logical next step to test our ideas?
- Where is our current system reinforcing the uncertainty we face?
- What enabled us to navigate uncertain times in the past?
- What about us makes us uniquely positioned to thrive at this time?
- If we were starting with a blank sheet of paper, what would we create?
I’ll leave you with a few quotes, as good quotes always prompt reflection and insights for me!
“The ability to ask beautiful questions—ones that can lead to breakthrough insights—is one of the most important skills for the 21st century.” – Warren Berger, author of A More Beautiful Question
“Judge a man by his questions rather than his answers.” – Voltaire, philosopher
“If we don’t ask questions—big, scary questions—we limit the size of our lives.” – Debbie Millman, designer and educator
“A good question is like an open door—it invites us to enter, explore, and change.” – Fran Peavey, social change activist
“The important and difficult job is never to find the right answers, it is to find the right question.”- Peter Drucker, management consultant
And finally – please share some of the best questions you use!
*These great questions came from this article: In Uncertain Times, Ask These Questions Before You Make a Decision by Cheryl Stauss Einhorn
