If the past five years have taught us anything, it’s that long-standing norms and systems can change quickly, creating uncertainty about a path forward. As management consultant Peter Drucker famously noted, “In times of turbulence, the first task of management is to make sure of the institution’s capacity for survival.” Hiring leaders with well-developed strategic competence is essential to achieving continued impact regardless of what the future holds. But how can you accurately identify strategic thinking when interviewing candidates?

You Might Not Know It When You See It

There have been decades of research and countless articles about what strategic thinking is, why it matters, and how to improve these skills. Drawing from thought leaders like Michael Watkins and Michael Porter, here’s a simplified definition:

Strategic thinking is the ability to gather information, make sense of it in the context of your organization’s goals and competitive position, and translate insights into action that drives impact. Communicating effectively and influencing others is equally critical. The best strategic thinkers don’t just see the path forward; they bring others along to make it happen.

As you move up the ladder toward C-suite or CEO positions, strategic thinking becomes an increasingly valuable job competency. Yet, too often, hiring decisions are made on gut feelings—the “I’ll know it when I see it” approach. Unless you have firsthand experience interviewing hundreds of senior executives, the fact is, you might not.

Even for the Staffing Advisors team (with experience interviewing thousands of top executives), “we’ll know it when we see it” doesn’t fly. Our hiring process accurately predicts success on the job because we collect objective, measurable data about candidates’ competencies. Here’s how we do that for strategic thinking skills.

Before You Interview: Define Strategic Thinking For This Role

Strategic competency is highly context-specific. Before assessing a candidate’s ability, you need to clarify the type of strategic thinking needed to drive impact in this role. Explore questions like:

  • What are the most pressing strategic challenges your organization faces? How complex are they? What larger business problems are you hoping to solve with this new hire?
  • What external pressures (policy shifts, market changes, competition) could impact your organization over the next 3-5 years? How does that relate to this role?
  • What internal dynamics (resources, culture, structure) could influence decision-making and affect strategy implementation?

During the First Interview: Assess Strategic Thinking In Their Past Experience

The first interview is where you assess each candidate’s strategic thinking ability in their former work. Ask about their experience with strategic challenges and opportunities of similar complexity, size, and scale to what you identified in step one. Strategic-minded candidates will offer relevant examples and be able to clearly and succinctly explain 1) what they did and 2) the measurable impact they made. Listen for this type of thinking in their responses:

  • Challenging the status quo. Did they demonstrate a unique perspective or default to conventional thinking?
  • Evaluating the external landscape. Did they consider market trends, competitor actions, or policy shifts when making decisions?
  • Considering multiple scenarios. Did they plan for “what if” situations and build contingencies?
  • Engaging others in the process. Did they know when and how to gather input, get buy-in, and leverage team expertise?
  • Communicating with key stakeholders. How did they sell their vision to the board or other stakeholders? How did they align staff to execute?

It’s also helpful to consider markers that this person hasn’t yet developed their strategic thinking capabilities. These include:

  • Sharing examples that are irrelevant to the job or your business needs.
  • Not accounting for the listener’s perspective (for example, talking in overly technical terms to a non-technical hiring manager).
  • Focusing only on what they did rather than connecting it to broader impact and business objectives.

🡆 Read this for a deeper dive into how to conduct interviews that uncover a candidate’s ability to drive impact.

During the Work Sample Interview: Assess How They Think Strategically Now

The work sample is how you test each candidate’s ability to think strategically in your specific business context and probe for deeper insights. In preparation for the second (or even third and final) interview, give candidates a real-world challenge to wrestle with. The best assignments involve working through a current business issue and reflect the complexity and demands of the role. Provide context about your organization’s resources and constraints to create a close approximation to your working environment.

During the interview, discuss the work sample with the candidate. Propose a roadblock and ask how they might tweak their approach. Ask what they would change if different stakeholders were involved. Prompt them to explain judgment calls.

Listen for the same elements of strategic thinking listed above with a few additions that are more likely to surface during the work sample:

  • Assessing internal strengths and weaknesses. Do they recognize your organization’s unique capabilities and limitations and incorporate that into their approach?
  • Understanding the time horizon. Are they thinking about immediate needs, mid-term strategies, and long-term impact?
  • Building in flexibility. Can they adapt their approach based on new information or changing conditions?

Once you’ve evaluated candidates in both contexts—talking about past work and demonstrating their skills in action during the work sample—you’ll have a rich set of data to compare against your organization’s needs.

🡆 Read this for a step-by-step guide to creating an effective work sample test with examples from past clients.

Example: A Tactical vs. Strategic Response to Membership Growth

In associations, membership growth is often a top priority for revenue generation. If you ask a candidate how they would approach membership growth, a tactical thinker might say, “I’d invest in marketing campaigns and outreach strategies to attract new members.”

A strategic thinker will ask: “What actually drives membership growth?” They’ll ask questions about the broader picture, analyze retention trends, assess why members leave, and identify what differentiates the association in the market. They may propose a solution like:

“The data you shared with me shows that members who attend the annual meeting renew at twice the rate of non-attendees. If we shift our strategy to increase event participation, increased membership will be an outgrowth, and we’ll see more sustained engagement.”

This kind of response is based on a framework in which the candidate challenges the status quo, weighs multiple factors, and connects the approach to long-term impact.

An exceptional candidate will take it a step further and consider collaboration and execution. They’ll ask questions about cross-functional teamwork, potential roadblocks, and how to leverage internal skills to bring the strategy to life.

“To make this shift, I’d communicate this data with leadership and key teams, ensuring alignment on why event engagement matters. Then, I’d get everyone together to test different engagement strategies. That could be refining event programming or incentives for first-time attendees. I’d want to make sure the right people are brought in from the beginning.”

It’s More About Asking the Right Questions Than Having the Right Answers

Strategic thinkers initially come to the table with more questions than answers, then follow a considered process to find possible solutions. You’ve seen this in action before. The organizations that thrived during the pandemic and other market disruptions didn’t have perfect foresight. They were led by strategic thinkers who could adapt, anticipate, and align teams toward a clear path forward.

When evaluating candidates, look at how they think and communicate ideas to varying stakeholders. A skilled strategist may not have every answer or predict every step, but they will have a framework to navigate complexity and be able to bring others along. That’s who can lead your organization through whatever changes come next.

Keep Reading