Use this question bank to assess how candidates frame problems, choose where to play, and sequence bets under real constraints. Each section includes prompts and cues for what strong answers demonstrate.

Strategy Orientation & Mental Models

• What does “strategy” mean to you in our context?
  Good answers: A coherent set of choices about where to play/how to win, tied to capabilities and constraints; not a list of goals.
• Which mental models do you rely on most?
  Good answers: Examples like JTBD, Porter’s forces, cost‑to‑serve curves, value chain, diffusion of innovation; when each applies.
• Tell me about a strategy you sunsetted. Why?
  Good answers: Evidence thresholds, leading/lagging indicators, kill criteria, and reallocation of capital and people.
• How do you distinguish strategy from planning?
  Good answers: Strategy = choices under uncertainty; plan = sequencing/resources after choices; shows interplay.

Problem Framing & Hypothesis

• If the CEO says “grow faster,” how do you frame that ask?
  Good answers: Define the problem, clarify constraints, generate hypotheses (pricing, channel, product), and define tests.
• Walk me through your last zero‑to‑one analysis.
  Good answers: TAM/SAM/SOM, demand signals, willingness to pay, moat hypotheses, and disconfirming evidence.
• How do you set assumptions explicitly?
  Good answers: Assumption log with owners, confidence levels, validation plan, and review cadence.
• What would make your hypothesis wrong?
  Good answers: Clear falsification criteria and early kill switches.

Prioritization & Trade‑offs

• You have 5 worthy initiatives but budget for 2. Choose.
  Good answers: Clear scoring model (impact, confidence, effort, strategic fit), dependencies, and opportunity cost.
• Describe a time you said “no” to a big request.
  Good answers: Strategic rationale, alternatives, stakeholder handling, and outcome.
• How do you handle cannibalization risk?
  Good answers: Net contribution view, guardrails, cohort analysis, and migration plans.
• Speed vs. quality vs. scope—what breaks first?
  Good answers: Context‑dependent policy with explicit thresholds and escalation path.

Market, Customer & Competition

• How do you choose where to play?
  Good answers: ICP clarity, pain intensity, switching costs, economic buyers, and wedge strategies.
• Tell me about a competitor move you anticipated.
  Good answers: Signals tracked, scenario table, pre‑emptive counter‑moves, and measurement.
• What’s your approach to pricing strategy?
  Good answers: Value‑based, segmentation, elasticity tests, packaging; guardrails for discounts.
• How do you build defensibility?
  Good answers: Data/network effects, ecosystem, switching costs, brand, and cost structure advantages.

Metrics, Goals & Assumptions

• What is your KPI stack for a new bet?
  Good answers: North Star, input metrics, proxy metrics, and review rhythm; risks of Goodhart’s law.
• Forecasting under uncertainty—how?
  Good answers: Ranges, scenarios (down/base/up), decision trees, sensitivity analysis, and explicit assumptions.
• When do you change the North Star?
  Good answers: Business model shifts, customer value redefinition, or stage change with clear migration plan.
• How do you detect leading indicators early?
  Good answers: Lag/lead mapping, cohort views, instrumentation before launch.

Decision Making Under Uncertainty

• Give an example where you chose a riskier path.
  Good answers: Calculated risk, expected value framing, downside containment, and learning value.
• How do you prevent analysis paralysis?
  Good answers: Decision deadlines, minimally sufficient data, DACI/RACI roles, and pre‑commit rules.
• What’s your escalation philosophy?
  Good answers: Clear thresholds, single‑threaded owner, and rapid decision rituals.
• Tell me about a bet that failed but was still right.
  Good answers: Process quality over outcome, learning captured, pivot.

Long‑Term Planning & Sequencing

• How do you build a multi‑year roadmap?
  Good answers: Vision → themes → bets → milestones; dependencies and capacity constraints explicit.
• What would you defer now to win later?
  Good answers: Clear reasoning for compounding advantages, enablement debt, and timing windows.
• Explain a sequencing decision you’re proud of.
  Good answers: Chosen order, why, de‑risking logic, and results.
• How do you handle tech/ops debt strategically?
  Good answers: Capacity allocation policy, risk register, and measurable paydown outcomes.

Cross‑Functional Alignment & Influence

• How do you align execs with conflicting priorities?
  Good answers: Decision narrative, explicit trade‑offs, single truth metrics, and pre‑reads.
• Describe a time you changed minds without authority.
  Good answers: Stakeholder mapping, incentives, pilots, and social proof.
• What artifacts do you use to communicate strategy?
  Good answers: One‑pagers, strategy docs, roadmaps with principles, FAQs, and review cadences.
• How do you keep teams focused when emergencies pop up?
  Good answers: Guardrail metrics, escalation lanes, buffers, and “stop doing” lists.

Systems Thinking & Second‑Order Effects

• Share a time a “fix” created a new problem.
  Good answers: Feedback loops identified, unintended effects, and redesigned policy.
• How do you model interactions across functions?
  Good answers: Causal maps, swimlanes, service levels, and alignment points.
• What risks do you track continuously?
  Good answers: Strategic, operational, financial, and compliance risks with owners and triggers.
• When is doing nothing the best strategy?
  Good answers: Option value, information arrival, and cost of irreversible moves.

Postmortems & Learning Loops

• Tell me about a strategy review you led.
  Good answers: Pre‑registered hypotheses, results vs. expectations, next experiments, and resource shifts.
• How do you institutionalize learning?
  Good answers: Decision logs, playbooks, rituals (QBRs), and open metrics.
• What have you changed your mind about recently?
  Good answers: Evidence, impact, and how you communicated the change.

Case Study Prompts

• Market entry: Pick one of three countries; outline thesis, risks, and 2‑quarter plan.
• Portfolio allocation: You have $3M and 20 engineers; allocate across 5 bets and defend.
• Pricing & packaging: Propose a good‑better‑best model and define success metrics.
• Competitive response: A rival launches a free tier; provide scenarios and counter‑moves.
• North Star redesign: Recommend a new North Star metric and supporting inputs.

Tip: Look for explicit assumptions, scenario thinking, and clear kill/sustain/double‑down logic. Strong candidates connect choices to capabilities and measurable outcomes.