Edition 43 | 21 July 2026

Welcome to The Perspective. Each week, a few reflections on work, leadership, and clarity. Not to add to the noise, but to slow things down just enough to think properly. Some practical, some more reflective, all chosen with the same intent: to navigate complexity with a steadier hand.

This week's note starts with something I posted on LinkedIn last week, and follows it into the parts that didn't fit.

Where Strategies Actually Fail

Strategies fail more often at their assumptions than at their arguments.

A well-written strategy usually has all the visible pieces in place. A clear ambition. A defined market or opportunity. A plausible mechanism for how the ambition becomes reality. A set of metrics that will tell everyone whether it's working. Boards approve it. Executive teams execute against it. When it works, credit gets distributed. When it doesn't, the review usually focuses on execution.

What most strategies don't have, because nobody quite wants to make the doubt explicit, is a list of the specific things that would have to hold in the world for the strategy to work. The customer segment behaving the way the plan assumes. The regulatory environment staying broadly stable. A key competitor not moving first. The economy landing somewhere in the range the model was built on. The team retaining a few specific people who make the plan run.

None of that is on the page. And the reason it isn't on the page is that naming those things feels like it undermines the strategy. Which is exactly why it doesn't get done.

But the pattern of failure is remarkably consistent. When strategies underperform, it's rarely because the stated argument was wrong. It's because one of the unstated assumptions turned out not to hold, and no one had ever made the assumption explicit enough to notice when it stopped being true.

The most useful question in a strategy review isn't "Is this the right strategy?" It's "What would have to be true, in the world, for this strategy to work?" And then, if the room is willing to keep going: "Which of those things do we control? Which do we only influence? Which are we, honestly, just hoping for?"

Those are quiet questions. They don't kill strategies; they sharpen them. A strategy whose fragile assumptions have been named is more durable than one whose fragilities are hidden, because the moment the world starts to move against the assumption, someone in the organisation will notice.

Most strategies would be sharper if that conversation happened before approval rather than after underperformance. Boards ask about strategy at the top of the cycle and about execution at the bottom. Almost no one asks about the assumptions in between, even though the assumptions are usually where the answer to both questions actually lives.

The same discipline applies to individual decisions too. What would have to be true for the next role, the next investment, the next five years to work as planned? Naming those things, quietly and honestly, is worth more than any number of scenario slides.

The strategy paper says what the plan is. The stronger question is what the paper doesn't say.

👉 I shared the shorter version of this on LinkedIn last week:

View the full post and comments on LinkedIn

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On My Desk

Recording the first episodes of the podcast this week. Tomorrow is the first day at the mic.

I've mentioned this quietly in an article and haven't said more about it since, so it's worth naming here properly. The podcast is called Playing the Long Game. It's solo: no guests, no interviews, built around the ideas in The Bottom Line, extended into conversations the book didn't have room for. First episode isn't out yet; the season is planned, the trailer is done, and the channels are set up for when episodes start landing.

A few things have struck me in the process. Solo is the harder format, but the right one for what I'm trying to do. The book carries an argument; the podcast has to carry the same one, in my voice, without the scaffolding of a conversation.

The other observation is smaller and more practical. Talking is the easier part. Setting up is the hard part. My content advisor's line early on has stuck with me: "don't compromise on quality". The temptation, especially solo, is to accept the lighting that's good enough, the audio that's fine, the camera angle that mostly works. That's where the drift starts. So the last few weeks have been spent making sure the room can produce work I'll want people to see and hear a year from now, not just for a short while.

A different kind of writing altogether. More on that as it takes shape.

Closing Perspective

Most of what determines outcomes was decided before anyone asked the outcome question.

The strategy meeting, the career choice, the investment, the plan — each rests on assumptions that were never quite spoken aloud. When things go well, the assumptions get called insight. When they don't, they get called luck.

The work is naming them either way, while there's still time to do something about it.

Keep thinking. Move forward.
— Yusuf

Visit my website

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Edition 44 is fully done. No Mastermind section (Series Four wrapped in Ed 43).

One thing worth flagging on the podcast handling:

By naming Playing the Long Game in this desk note, you've moved the podcast from "quietly-being-built" to "publicly-named-and-building." That changes the shape of future editions:

• Ed 45 (Sun City week) — probably no podcast mention. Let this one breathe.
• Ed 46-48 window — depending on when Episode 1 drops, this is where the "Season 1, Episode 1 launches today" section lands.
• In between — any specific moment worth a small mention (first recording done, cover art landing, etc.) is fair game as an incidental in future desk notes.

Full slate status:

• Ed 44 (Tue 21 July) — locked, ready
• Ed 45 (Tue 28 July) — open (Sun City conference, no reference)
• Ed 46 (Tue 4 August) — Sun City reflection anchor
• Ed 47 (Tue 11 August) — open (George conference)
• Ed 48 (Tue 18 August) — George reflection anchor
• Ed 49 (Tue 25 August) — open
• Ed 50 (Tue 1 September) — anniversary note in On My Desk
• Podcast launch — Ed 46-48 window when Episode 1 drops

Anything else?

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Closing Perspective Most of what determines outcomes was decided before anyone asked the outcome question. The strategy meeting, the career choice, the investment, the plan: each rests on assumptions that were never quite spoken aloud. When things go well, the assumptions get called insight. When they don't, they get called luck. The work is naming them either way, while there's still time to do something about it. Keep thinking. Move forward. — Yusuf Visit my website

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