"The go-live scramble no one could have predicted"

In yesterday’s email, I shared how complex work can feel predictable, right up until it isn’t.

Here’s what that looked like in real life.

We had a fixed deadline, outside of our control. The kind you can't move.
The work was scoped. The team had time.
They did something perfectly sensible: they broke down the final requirements into smaller stories to make the work more manageable.

But somewhere in that breakdown, a few details got lost.

No one noticed at the time.
No alarms went off.
Everyone was working in good faith, moving the work forward.

Fast forward to the day before the deadline, and suddenly, it all surfaced.
Gaps. Missed requirements. A scramble to figure out what could ship, what needed to wait, and whether we could still go live at all.

We made it in the end. But it was chaos. And no one enjoyed it.

Looking back, it’s easy to ask questions like:

But that’s the thing about knowledge work.
It’s shaped by the way people interpret, adapt, and respond in the moment.
There’s no guaranteed way to stop surprises from emerging, because people have agency, they can make decisions. The future unfolds through human action.

That’s why leadership in complex work isn’t about controlling outcomes.
It’s about staying close to the work, noticing when things shift, and helping people make sense of what’s happening as it happens.

Where might you need to step in, not with judgement, but with curiosity, before the next scramble starts?

Until next time,
Dermot
​The Messy Middle

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