Author Archives: Matthew E May

What Appears to be Strategy Often is Not

I regularly engage in hansei (reflection) after each of my facilitation engagements. It’s a simple learning mechanism, essentially an after-action process of asking: what I expected to happen (my hypothesis if you will), what actually happened, and what explains the gap, if there is one. And there invariably is. The gap is where learning and insight live. It creates new knowledge. It’s ...

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The Art of Strategic Observation

I am nothing if not a consumerist. Meaning, I am constantly impressing upon companies I work with to make sure they have a deep and empathic understanding of their customers…past, present, and future, especially if they are contemplating a strategic shift that entails repositioning or refocusing their efforts to target new and different segments. Generally speaking, most companies are pretty ...

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Snuff out SWOT – Forever

The more strategy development work I do with organizations, the more I’m becoming aware of a prevalent pattern, a pattern which I find counterproductive, even detrimental. It concerns the starting point for their strategy work: in nearly every case, they begin with convergent thinking, the polar opposite of divergent thinking, which I believe is the kind of thinking true strategy ...

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Strategy versus Execution – a Meaningless Distinction

Strategy versus Execution - a Meaningless Distinction

Over at HBR blogs, there is a wonderful debate on the subject of strategy between Roger Martin, who authored the post Stop Distinguishing Between Strategy and Execution, and Don Sull, an MIT scholar who believes there’s a meaningful distinction between strategy and execution. Normally, I don’t bother looking at comments to blogs because in today’s social media-driven world they generally ...

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What is Your Career Strategy?

What is Your Career Strategy?

I’ve taken up a new habit of asking successful people I know: What is your career strategy? I ask it casually, and in person, because I want to see their body language and get a sense of just how front-of-mind their answer might be. My discovery: when it comes to careers, most folks don’t have a true strategy. I’ve gotten ...

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Strategic Transformation at Tennis Canada

My friend Roger Martin (#3 on Thinkers50 list) penned a terrific article in The European Business Review on how the Canadian professional tennis association rose from oblivion to now boasting two young players ranked well inside the top 10 on the professional tennis circuit…in less than ten years. As of this writing, Eugenie Bouchard is ranked #7, and Milos Raonic ...

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Day 1 – Strategy Sprint – A DIY Guide

Day 1 - Strategy Sprint - A DIY Guide

This is the third in a series of five DIY posts on holding a strategy sprint. You now know how to prepare for a strategy sprint, and you’ve gathered the right people. You’re ready for the first full day of sprinting. Take a deep breath, you’ll need it! Day 1 is all about grasping the current situation, understanding strategic choices, ...

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Preparing for a Strategy Sprint – A DIY Guide

Preparing for a Strategy Sprint - A DIY Guide

This is the second in a series of five DIY posts on holding a strategy sprint. The decision to hold a strategy sprint assumes that you’ve come to the conclusion that a new strategy is warranted, that new directions must be explored, and you’ve gotten to this point in a thoughtful and deliberate way. Something has been tugging at you ...

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Strategy Sprints – A DIY Guide

The word sprint means different things to different people. A runner thinks of it as a race, a mad dash of a few seconds. A software developer practicing "agile" thinks of it as a short, iterative cycle of work, often weeks or months, rather than seconds. An entrepreneur practicing "lean startup" methods thinks of it as minimally viable product development effort of a week or less.

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The Magic Question of Strategy

The Magic Question of Strategy

Your grand strategy seems airtight on paper. You’ve arrived at a winning aspiration. You’ve honed in on an open and attractive segment in which to play. You’ve identified the competitive advantages that will enable you to win in your chosen spaces. You’ve got the capabilities and systems to support your choices. But as the saying goes, no battle plan survives ...

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