2025-08-20: Investing Without Market Signal

When the market doesn’t provide clear signal, where do you place your bets? Do you follow your intuition? Do you focus on process …

2025-07-16: Technical Debt Use and Abuse

How do you balance technical debt with velocity? What is your strategy for managing technical debt? When is technical debt useful and when …

2025-06-18: Technology in Business Context

How do you position technology in the broader business context? What builds trust in technology delivery with other groups? How do you …

2025-05-21: Build Versus Buy

This question arises frequently in the life of a CTO. How do you reckon the trade-offs? What is your decision-making process? How do you …

2025-04-16: Mergers and Acquisitions

They have many components: diligence, alignment, technology integration, team restructuring, client migrations, etc. How do you bring all of …

2025-03-19: Developing Talent

How do your team members improve their skills? What systems do you have in place to help them? How do you encourage continuous learning? Do …

2025-02-19: Adapting to AI

How do you keep up with developments? What tools and tech have you tried? What works and what doesn’t? How do you address security …

2025-01-19: Product-Technology Schisms

Have you encountered this in the past? How do you deal with a separation of product and technology in an organization? How do you prevent it …