Andrew Penny

Market Strategy

Underwear, Buyer’s Remorse, and Keeping the Good Vibes Going

Andrew Penny, August 4 2026

Most of us wear underwear. We don’t think too much about it. Then, every once in a while, you decide to try something new. For several weeks, I had been seeing ads for Manmade underwear. Think of it as something like a bra for men—but, you know, ‘down there’.

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Leadership & Management

Tuk R Bust

Andrew Penny, July 21 2026

For me, Tuktoyaktuk  was one of those strange place names that sounds sort of familiar but I couldn’t place on a map. That changed recently. Let me back up a bit. Every year I try to do something that I really don’t know if I can do. One year I took singing lessons and performed in a recital (OK, it was me and three judgmental 10 year olds – but...

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Leadership & Management

Canada at 159

Andrew Penny, July 7 2026

Canada’s progress has been imperfect, uneven, and often slow — but slow steady progress compounded over 159 years becomes something wonderful. Canada’s quiet brilliance is not that it is perfect. It is that it has built a durable brand around trust, stability, resilience, humility, and usefulness. For a small country of just 41 million, and...

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Market Strategy

What sets Off Your 'Squirrel-Alarm'?

Andrew Penny, June 23 2026

I stopped into a local bagel shop recently for a coffee and breakfast bagel after my morning swim. I’d been there a few months earlier and hadn’t had a great experience, but I gave them the benefit of the doubt. Everyone has an off day. Surely they’d have sorted things out by

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Leadership & Management

What Are You Paying For?

Andrew Penny, June 9 2026

As a boy in Montréal, I delivered newspapers door-to-door (neither rain, nor snow, nor gloom of night, etc…)  It was seen as an essential service to keep the population informed and actively participating in our democracy. Getting real ’news’ is a bit harder now but no less essential – particularly for business leaders. To be effective, we need...

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Communication

Teach Your Children Well

Andrew Penny, May 26 2026

Apparently, human intelligence has already been eclipsed by AI. And not just by a little. One comparison I heard recently was this: we are to hamsters what AI will soon be to us. Now, I tend to think I’m at least a few notches above a hamster. Most days anyway. But it does raise an interesting question. What will AI make of

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Market Strategy

Nobody Needs a €4 Fridge Magnet

Andrew Penny, May 12 2026

Recently my wife and I spent almost a week in Barcelona. Great city. Great weather. Lots to see and do. And of course… shopping. The place is absolutely overrun with souvenir shops. T-shirts, magnets, mugs, little Sagrada Família models — the same stuff over and over again. Walking around, I kept thinking: “How on earth do all these places...

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Market Strategy

Strategic Neutral Is Not a Strategy

Andrew Penny, April 28 2026

Not long ago, leadership conversations had a familiar cadence. There was an inherently outward posture — a bias toward expansion. Even risk was framed in the context of opportunity. That orientation has shifted. Now the questions are more circumspect:

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Leadership & Management

Why Smart Teams Get Stuck on Simple Problems

Andrew Penny, April 14 2026

I was in a strategy session recently with a management team trying to build a forecast. Good business. Smart people. Plenty of data. And completely stuck - not “this is tricky” stuck, but “we’ve been talking in circles for an hour” stuck. They were trying to answer a simple question: What does next year’s revenue look

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Leadership & Management

The Greatest Question of All Time

Andrew Penny, March 31 2026

We spend a lot of time looking for better answers. But every once in a while, you come across something more useful than a better answer. A better question. And in my experience, there’s one that stands above the rest - and we use this question in almost every client engagement: “What would need to be

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