Make Your Strategy Self-Healing
Most strategies do not fail suddenly. They fail through drift.
These short essays reflect how I think about strategy in practice.They are not commentary or updates. They are lenses for seeing where strategy breaks, adapts, or holds. They are written for leaders who value clarity over volume.
If you’re new here, start with:
Your Strategy Has a Shelf Life
What’s so hard about strategy? Everyone claims to have one. There’s no shortage of books, articles, videos, advisors, and strategy-creating courses. But guidance on evaluating a strategy’s effectiveness or its long-term impact on organizational performance? That’s far rarer.
Is Your Corporate Strategy a Turducken?
Executives, academics and consultants regularly design new strategy configurations. Their scope ranges from individuals to processes to culture to markets. They focus on competition, business models, differentiation, pricing, cost, structure, etc. They might apply only to select companies, economies or technologies, or maybe to all.
Smart People Might Be Killing Your Strategy
Corporate restructuring, M&A, competitive intelligence, strategy, new product development, and process reengineering. One thing required for success that they all share is the need for the best and brightest. The smartest person in the room. World-class minds to solve world-class problems. Top grads from the best schools.
Your Strategy Is Not Retro, It's Outdated
Retro is in. Whether art deco architecture, 60's pop music, vintage clothing, dial phones or classic rock, what once was old school is now in vogue again. But not all styles and practices of the past are eligible for resuscitation. Take strategy or, more to the point, strategic planning.
Are You Picking the Right Red-Team Approach?
Red teaming is a structured way to challenge plans, assumptions, or strategies before they fail in practice. It creates a disciplined environment to test ideas from different angles—exposing blind spots, uncovering risks, and strengthening decision-making.
What Topology Can Teach Us About Strategy
Most strategy tools are built on clean lines and rigid boxes (e.g., OKRs, SWOT, five-forces diagrams). But the real world bends, warps, and shifts in unpredictable ways. What if our strategies need to stretch just as flexibly? AI will tell us all pretty quickly.
The Validation Blindspot: Why Companies Rarely Test Their Strategic Assumptions
Time pressure drives companies to fast-track strategy development, viewing assumption testing as an unnecessary delay. Executive teams, eager to show progress to boards and investors, often conflate speed with decisiveness. Many times, executive teams are too busy doing and fail to carve out enough time for thinking. This urgency creates a false choice between thorough validation and timely execution, leading to strategies built on untested hypotheses.