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The Gap Between Strategy and Reality

Issue #3 19 January 2026

Business & Technology Insight

I've been involved in several conversations this week about the gap between 'digital strategy' and 'digital reality' in organisations. Many businesses have impressive strategy documents but struggle with execution. The pattern I see repeatedly is that strategy is developed at a level of abstraction that doesn't translate easily into actionable delivery plans. The most successful digital transformations I've been part of share a common trait: they start with a small number of concrete, measurable outcomes rather than trying to transform everything at once. Strategy is important, but it needs to be grounded in what's actually achievable with the people, budget, and technology available today.

What I Learnt This Week

This week I was reminded that project recovery is as much about psychology as it is about planning. When you're brought in to recover a failing project, the team is usually demoralised, stakeholders are frustrated, and trust has broken down. Before you can fix the plan, you need to fix the confidence. Quick wins aren't just about demonstrating progress — they're about showing people that things can get better.

Something Personal

I've been experimenting with time-blocking my calendar this month, and the results have been significant. By dedicating specific blocks to deep work, client calls, and admin, I'm finding I'm more productive and less stressed. The key insight: it's not about filling every hour, it's about protecting the hours that matter most.

Tool of the Week

Loom — screen recording made simple. I've started using it to provide asynchronous feedback on documents and deliverables rather than scheduling meetings for everything. A five-minute Loom walking through my comments is often clearer and more efficient than a 30-minute call, and the recipient can watch it when it suits them.

This Week's Challenge

This week's challenge: pick one meeting from your calendar this week and replace it with an asynchronous update. Write a brief summary or record a short video instead. Notice whether anything is lost — and how much time is gained.

Quote of the Week

"Plans are worthless, but planning is everything." — Dwight D. Eisenhower

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