Questions to Ask in Unpredictable Times

By: Jim Mikula

At last week’s Economic Summit State of the Burg, Dr. Ray Perryman addressed an issue affecting many of the Chamber’s members: tariffs. The questions about tariffs are many, including when final tariffs will be determined, where will the tariff levels land, etc. There are also other issues that our members are dealing with such as declining sales as visitors are spending less and the potential for a recession. It seems we are operating in a constant state of uncertainty. Cheryl Strauss Einhorn authored an article for Harvard Business Review about the strategic questions we can ask ourselves to broaden our perspectives, challenge assumptions, and make more resilient decisions.

A key point in Ms. Einhorn’s article is to understand the difference between traditional vs. strategic questions. Standard questions such as those about ROI or timelines, can cause leaders to focus too narrowly, missing systemic changes or new opportunities. In contrast, strategic questions help leaders see beyond immediate pressures and adapt to ongoing uncertainty.

Four Essential Questions for Uncertain Times:

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

This question encourages long-term thinking and resilience, ensuring decisions align with core values and future goals rather than just solving immediate problems. Example: A business owner maintains staffing despite short-term cost pressures, protecting customer service levels and positions the business for future growth.

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

This reframes decisions in terms of learning and values, prompting business owners to consider the lessons their actions will impart about their character and culture. Example: A small business owner delays a product launch to maintain cash reserves, prioritizing financial stability over expansion, which the employees later learn played a key role in maintaining staffing levels during unpredictable business levels.

• What if this is not the storm-what if it is the climate?
  

This question challenges the assumption that current disruptions are temporary, pushing leaders to prepare for ongoing volatility rather than waiting for a return to normal. Example: A store owner reevaluates a long-standing vendor relationship, recognizing persistent issues as a sign to adapt rather than hope for improvement.

• What is the cost of waiting?
  

Leaders often delay action hoping for more clarity, but this question highlights the risks of inaction such as missed opportunities, lost momentum, and competitive disadvantage. Example: A business invests in a marketing initiative despite market uncertainty, recognizing that waiting could mean losing out on acquiring new customers.

In times of instability, these questions help business owners move from potential inaction to meaningful progress. They reveal hidden risks, clarify priorities, and focus attention on what can be controlled leading to more adaptive outcomes. Effective leadership in uncertain times is less about having all the answers and more about asking the right questions. These four questions can serve as tools to surface blind spots, challenge outdated assumptions, and guide teams toward resilient, forward-looking decisions.