Perspectives

Executive perspectives on the questions leadership actually asks.

Considered pieces on technology strategy, AI, governance, cybersecurity, and the leadership work that surrounds them. Written for the executive table — not the server room.

Executive Decision MakingTechnology StrategyAICybersecurityGovernanceModernizationBusiness ContinuityVendor & MSPLong-Term Planning
What I'm thinking about

A short note from Allan.

A recurring executive reflection — updated as the conversations at the table evolve.

The question I keep hearing from executives right now is not "what should we do about AI?" It is quieter than that. It sounds more like: "how do I know whether the advice I'm being given is the advice I actually need?"

That question is not really about AI. It is about trust. Every leader I speak with is standing in front of decisions that are being shaped, faster than ever, by people whose incentives are not fully aligned with theirs. The pace of change has widened the gap between what a leader is being told and what a leader is trying to accomplish.

My advice, most weeks, is the same: slow down for one honest conversation. Not a long one. Just one where the person across the table has nothing to sell you and no reason to hurry the answer. Confidence is almost always downstream of that single conversation.

— Allan Sivils, founder, HaveSight
Executive perspectives, occasionally

Sent only when there is something worth an executive's time.