Use this guide to probe for strategic clarity, operating excellence, sound judgment, and values. Each question includes suggested follow‑ups and what strong answers often include.

Strategy & Vision

Walk me through a strategy you set that materially changed the company’s trajectory.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Starts with an explicit diagnosis (market/competitor/financial reality)
• Clear guiding policy and coherent set of actions
• Quantified outcomes (growth, margins, cash, TSR, market share)
• Explains trade‑offs, pacing, and what they chose not to do

How do you translate strategy into a plan the org can actually execute?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• North‑star metrics and 3–5 priorities
• Cascaded OKRs/scorecards with owners and cadences
• Resourcing decisions and sequencing of bets
• Reviews leading/lagging indicators and adjusts

Leadership & Culture

Describe the culture you intentionally built. How did you measure it?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Articulated values with behaviors and anti‑behaviors
• Mechanisms: hiring, promotions, rituals, consequences
• Pulse/engagement data tied to outcomes (retention, performance)
• Stories that reinforce desired norms

Tell me about a time you had to replace a high‑performing but culture‑eroding leader.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Frames risk to the org and values
• Principled, timely decision; clean comms and transition
• Backfills with clear bar and support for the team

Operating Model & Execution

How do you run the business week‑to‑week and quarter‑to‑quarter?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Operating cadence with clear forums (WBR, QBR) and inputs
• Single source of truth dashboards; focus on exceptions
• Debottlenecking cross‑functional dependencies
• Postmortems and learning mechanisms

Share an example where you materially improved efficiency while protecting growth.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Defined unit economics and constraints
• Redesigned org/process/portfolio to raise throughput
• Measured impact: cycle time, COGS/Opex, quality, NPS

Financial Stewardship & Capital Allocation

Walk through a major capital allocation decision you led (e.g., M&A, divestiture, big program).

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Clear investment thesis tied to strategy
• Scenario modeling and hurdle rates; risks & mitigations
• Integration/realization plan and scorecard
• Transparent governance and retrospectives

How do you balance growth, profitability, and cash under uncertainty?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Portfolio view of bets; reversible vs. irreversible decisions
• Leading indicators and trigger‑based plans
• Communication with Board/investors on trade‑offs

Board, Governance & External Stakeholders

How do you get the most from your Board?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• No‑surprises ethos; pre‑reads, 1:1s, and clear asks
• Focus on decisions and learning vs. reporting theater
• Uses independent directors’ strengths; committee work

Describe a time you navigated activist or investor pressure.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Grounds responses in long‑term value creation
• Engages constructively; shows alternatives and rationale
• Aligns comms with actions and milestones

Talent, Team & Succession

What’s your bar for an executive team, and how do you raise it?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Defines competencies and outcomes by seat
• Upgrades with respect; builds bench and succession plans
• Mechanisms: calibration, feedback, performance contracts

Tell me about a succession you executed—planned or unplanned.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Crisis vs. planned scenarios
• Interim structures and risk management
• Communication to employees, customers, investors

Customer, Product & GTM

How do you keep the company customer‑obsessed at scale?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Direct customer time; voice‑of‑customer loops to roadmaps
• Leading indicators of value (time‑to‑value, adoption)
• Mechanisms to close the loop across Product, Sales, CS

Share a bet you killed and why.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Disconfirms with data and user/financial signals
• Frees capacity and communicates the why
• Salvages learnings/assets

Technology & Innovation (if applicable)

How do you de‑risk innovation while sustaining the core?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Ambidextrous approach: core vs. new bets
• Stage‑gates, prototypes, and fast feedback
• Talent/architecture to lower cost of change

Tell me about a platform or architecture decision with 3–5 year implications.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Explains trade‑offs (speed, cost, reliability, autonomy)
• Aligns org design with architecture (team topology)
• Migration plan and guardrails

Change & Transformation

Describe a transformation you led (pricing, reorg, cloud move, go‑to‑market). What changed?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Case for change; stakeholders and risks
• Phased plan with milestones; owner for each stream
• Outcome metrics; course‑corrects with evidence

How do you sustain change after the ‘launch moment’?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Removes old incentives/process debt
• Installs new mechanisms and accountability
• Narrative, repetition, and visible wins

Risk, Compliance & Ethics

What’s your philosophy on risk and controls?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Risk appetite linked to strategy
• Top risks with owners, limits, and early‑warning indicators
• Incident response and learning

Describe an ethical dilemma you faced as a leader.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Articulates principles and stakeholders
• Seeks counsel; documents rationale
• Accepts short‑term pain for long‑term trust

Communications & Executive Presence

Give an example of a high‑stakes communication you led (layoffs, outage, product issue).

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Timely, transparent, audience‑appropriate
• Owns mistakes and outlines next steps
• Follow‑through and measurement of trust

How do you tailor your style for different audiences (board, employees, customers, media)?

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Crisp narrative and visuals
• Checks for understanding; leaves with clear asks
• Consistent message across channels

Crisis Management

Tell me about a crisis you managed end‑to‑end.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Establishes command structure and facts
• Prioritizes safety, customers, and legal exposure
• Rapid comms; after‑action review and systemic fixes

Scenario Exercises (Take‑Home or Live)

In 48 hours, prepare a 6‑slide strategy for entering a new segment. Include goals, bets, resourcing, and risks.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Clear thesis and market sizing
• Phased plan with milestones and KPIs
• Risks, trigger points, and alternatives

Given a 15% budget cut, propose a plan that preserves long‑term value.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Prioritizes by strategic importance and ROI
• Stops/starts/continues with rationale
• People impacts and comms plan

Draft a one‑page memo for a Board decision between two acquisitions.

Follow‑ups: What was the context? Who were the stakeholders? What options did you consider? How did you measure impact? What would you do differently?

What good looks like:

• Decision criteria and valuation considerations
• Integration risks and synergies
• Recommendation with sensitivities and milestones

Red Flags

• Vague strategy with no trade‑offs or measurable results
• Activity over outcomes; no operating cadence or mechanisms
• Over‑index on narrative without data or customer proof
• Blames market/others; no ownership or learning
• Tolerates toxic high performers; weak succession thinking

Evaluation Rubric (Anchor Examples)

• 4 – Excellent: Sets clear strategy, installs mechanisms, delivers measurable outcomes, develops leaders, and role‑models values.
• 3 – Strong: Solid strategy and operations with minor gaps in foresight, measurement, or people leadership.
• 2 – Mixed: Some wins but inconsistent mechanisms, unclear trade‑offs, or weak metrics.
• 1 – Weak: Generic answers, little ownership, poor outcomes, or values misalignment.