"Why smart plans still go sideways"

Have you ever looked back on a project that went off the rails and thought:

I have. And it took me a long time to realise why that keeps happening.

It’s because we treat complex work like it’s complicated.

In a complicated problem, like building a car or writing a tax calculator, you can plan it, estimate it, and (mostly) predict how long it will take.
It might be hard, but if you follow the steps, you’ll get there.

But complex work doesn’t behave like that.

In complex work, like building products in teams of humans, what happens next is shaped by what’s happening now.
The future is unfolding in real time.
No matter how much you plan, you can’t predict every twist.
And if you try to control it like it’s complicated, you often make it worse.

That doesn’t mean you give up on planning.
But it does mean you have to lead differently.

It means leading without judgement, staying in the work as the future unfolds, knowing that outcomes always emerge in ways no one can fully predict.

Because in knowledge work, it’s the way people respond and adapt in the moment that makes the work complex, and the future impossible to fully predict.

Tomorrow, I’ll share a real example where good intentions and a sensible plan still led us straight into an unpredictable last-minute scramble.

Until next time,
Dermot
​The Messy Middle

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