20 leadership and strategy questions for senior hires

Strategic Vision & Alignment

1. What is the biggest strategic priority for our organization this year, and how do you plan to achieve it?​

2. How do you ensure strategic goals are aligned with overall company objectives?​

3. How do market trends influence your strategic decisions and planning?​

Decision-Making

4. What criteria do you use to allocate resources among competing initiatives?​

5. Can you describe a strategic risk you took and its outcome?​

6. How do you balance short-term operational goals with long-term strategy?​

Performance & Success

7. What key performance metrics do you use to measure success? Why are these important?​

8. How do you evaluate company or team performance and identify areas of improvement?​

9. How do you address under performance at a strategic or team level?​

Innovation & Change Management

10. What role does innovation play in your strategic planning? Can you provide examples?​

11. How do you lead your team through organizational change or major transitions?​

Leadership Style & Culture

12. How do you describe your leadership philosophy and style?​

13. What practices do you use to foster a healthy team or organizational culture?​

14. How do you motivate your teams during periods of uncertainty and challenge?​

Stakeholder Management

15. How do you communicate your strategy and engage stakeholders across all levels of the organization?​

16. Who should be involved in the strategic planning process, and why?​

Problem-Solving & Adaptability

17. Describe a strategic initiative that did not work as expected. How did you respond?wellhub​

18. What are the biggest challenges and opportunities facing our organization now, and how do you plan to address them?coffeepals​

Long-Term Vision

19. Looking ahead 3-5 years, what major milestones would you aim to achieve for our organization?

20. How do you ensure continuous learning and keep yourself and your teams up to date with industry changes?

These questions help uncover senior leaders’ thinking, strategic planning, and leadership skills vital for successful organizational impact and growth.