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2 October 2026

Why understanding the 'why' matters when the plan fails

I'm a bit obsessed.

I'm watching SAS Rogue Heroes, perhaps later than most, but it's really caught my imagination. Now, acknowledging some artistic licence, it is supposed to be based on true events. Even if only some of it is, it's still astonishing what a dreamer, a madman and the sensible one were able to achieve with no resources.

One moment has really stuck with me.

A captain was training recruits and told them to question every order. Not whether they should follow it, but WHY they were doing it.

One recruit pushed back: they weren't supposed to question orders. They were supposed to carry them out.

The captain's response was brilliant:

If you don't understand why you're doing something, how are you going to find another way to achieve the objective when the plan inevitably fails?

That got me thinking about organisations.

We spend an enormous amount of time creating plans, processes and instructions, but how often do we make sure the people executing them actually understand the objective behind them?

When the plan works, it doesn't matter quite as much. It's when everything goes sideways that understanding the "why" becomes really valuable.

Maybe that's what good operating discipline looks like. Not everyone blindly following the plan. Everyone understanding the objective well enough to adapt when the plan stops working.

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