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Interview questions Lee is ready to dig into. Copy them, tweak them, or bring your own.

10
Questions

1You’ve scaled multiple companies without outside funding. What key principles of sustainable growth should today’s founders, CMOs, or CROs be prioritising—especially in volatile markets?

2AI is evolving fast, but adoption often stalls after the proof-of-concept phase. From your experience, what’s really stopping organisations from unlocking meaningful ROI with AI?

3Cross-functional silos are still the biggest roadblock to scalable growth. How can leaders unify sales, marketing, and service to deliver a more intelligent, connected customer experience—and where do platforms like Adobe and Salesforce fit in that strategy?

4Mid-market companies are often underestimated—but you argue they’re best positioned to lead in the AI era. Why, and what can enterprise leaders learn from their agility?

5You’ve led or advised on over 20 M&A transactions. What are the most overlooked factors that determine whether a deal delivers value or drains it?

6When it comes to tech stacks, what are the most common mistakes you see companies make—and how can they take a more strategic, composable approach?

7You’ve worked across the UK, US, APAC, and the Middle East. How does geography influence digital strategy, and what universal principles still apply?

8As a former professional footballer, how has that experience shaped your approach to leadership, performance, and building high-output teams under pressure?

9Wellness seems core to how you lead. How do you balance mental clarity and physical performance while managing a fast-scaling business?

10If you were advising a CEO today on staying competitive over the next five years, what would you tell them to focus on—and what should they ignore?

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