4 Strategic Questions

Croft in Section 1.4.2, states “By engaging with deep uncertainty, planners take on the challenge of building multiple worldviews as possible explanations of system behavior and change during conflict” (2018). In order to provide possible explanations, planners and analysts will need to develop the right questions. For this chapter we will focus on what Hill and Gerras defined as strategic questions (2020).

4.1 Motivating Problem

How to develop strategic questions that will drive data collection requirements.

4.2 What We Will Learn

What strategic questions are an why they are important.
Types of strategic questions.
Elements of good and bad strategic questions.

4.3 What are Strategic Question and Why are They Important?

Strategic questions are high-level inquiries that help decision-makers understand complex problems, anticipate change, and choose among competing options in uncertain environments. Hill and Gerras argue that strategic questions are essential for guiding national security strategy, particularly when facing ambiguity, long time horizons, and limited information (2020).

Unlike tactical or operational questions, strategic questions are deliberately open-ended. They focus on context, causality, options, and risks. Asking them enables planners to clarify assumptions, uncover blind spots, and develop better-informed courses of action. These questions support both critical and creative thinking and help national security professionals move beyond reactive thinking.

Hill and Gerras emphasize that the ability to ask good strategic questions is not innate—it requires practice and reflection. They cite the Cuban Missile Crisis as a case study where President Kennedy and his advisors asked hundreds of strategic questions over 13 tense days—such as “What happens if we do nothing?” and “What are the Soviets trying to achieve?”—which ultimately helped prevent nuclear war.

In short, strategic questions help planners navigate competitive uncertainty. They encourage multidimensional thinking, challenge groupthink, and promote adaptability in the face of strategic complexity.

4.4 Types of Strategic Questions

Hill and Gerras provide three general types of strategic questions: definition, causations, and intervention questions (2020).

4.4.1 Definition Questions

These clarify the nature of a problem. Definition questions establish a shared understanding of the environment and help scope the issue. There are three types of definition questions:

Define Nature: What is the thing we are analyzing and how is it interacting with the world around it?

“What is the adversary trying to achieve?”
“How serious is this challenge?”
“What is Niger’s current policy towards the US?”

Define Extent: How big is the problem? What is the cost of inaction?

“What is the operational reach of al Shabaab?”

Define Urgency: How is the problem unfolding in time?

“How has the operational readiness levels of the East Africa Response Force changed in the past three years?”

4.4.2 Causation Questions

These explore why something is happening and what the likely consequences will be.They help identify drivers, mechanisms, and emerging patterns. There are two types:

Explanation: Why is it happening? What are the causes?

“Why did the previous Nigerian government lack popular support?”

Prediction: What is likely to happen because of this situation or event?

“What kind of senior leaders is the current Somalian military personnel system likely to produce?”

4.4.3 Intervention Questions

Also called “option” questions, these assess potential courses of action and their implications. These questions guide decision-making by linking means, ways, and ends under uncertainty. There are three types:

Effectiveness: Does it work?

“What is the likely effect of new sanctions on Sudan?”

Efficiency: What is the relationship of benefits to costs?

“What are the readiness improvements resulting from the change in design to African Lion? How do these improvements compare to the costs of this new design?”

Robustness: Is the proposed intervention still sufficiently efficient or effective if we relax key assumptions?

“How effective is our campaign plan if we lose access to bases in Country X?”

4.5 Elements of good and bad strategic questions

Good Strategic Questions	Bad Strategic Questions	Comments
Grounded in the competitive context.	Displays little grounding in the context of the problem or issue.	Strategic questions must relate to real-world competition—between states, actors, or systems. They should reflect the dynamics, interests, and intentions of adversaries or partners, rather than abstract or academic curiosity.
Has two or more variables.	Vague regarding key variables.	Effective strategic questions examine relationships between multiple factors (e.g., adversary intentions and regional stability). This encourages analysis of cause and effect, interdependencies, or trade-offs rather than isolated issues.
Stated clearly and unambiguously in question form.	Presupposes the answer, includes the answer, or signals that only certain answers are acceptable.	A good strategic question is direct, specific, and phrased as a question—not a vague statement or assumption. This ensures it can guide focused inquiry, analysis, and discussion.
Implies the possibility of an observable answer.	Includes causal claims or solutions.	Strategic questions should be answerable through available or collectible data. While they may not have immediate answers, they should point to evidence-based investigation or indicators.
Acknowledges the uncertainty inherent in competition.	Includes moral or ethical claims or value statements that complicate quantification.	Rather than seeking certainty, good strategic questions embrace ambiguity and multiple plausible outcomes. They are designed to probe uncertainty, assess risk, and help navigate through complexity.

4.6 Practical Exercise

Draft three strategic questions—one from each category—based on a current or historical conflict. Evaluate them for clarity, strategic relevance, and utility in informing decisions.

4.6.1 Examples

Good Questions	Bad Questions
How can we improve the protection of our forces against IED attacks?	How do we solve the IED problem?
How does incarceration affect the probability of a first-time offender’s future imprisonment?	Given that prisons are the higher education system of crime, how does incarceration affect the probability of a first-time offender’s future imprisonment?
How does the type of patrol (foot patrols vs. car patrols) affect the prevalence of violence in similar neighborhoods with otherwise similar military presences?	How does a U.S. military presence in Afghanistan affect violence in the country?