Breaking the Planning Cycle of Madness

Complex Work Requires Humble Plans

"The wheels on the bus go round and round
Round and round, round and round
The wheels on the bus go round and round
All through the town."

That song keeps playing in my head when I join yet another company that happily keeps looping through the planning cycle of madness.

And boy, do companies love to keep the planning cycle of madness running! Sitting in meeting rooms and polishing our plans to perfection makes everyone feel all warm and giddy inside. All those paper victories make us feel like champions. WINNING!

That happiness doesn't last long because all those pristine plans crumble upon confrontation with reality.

Here’s what I have seen happen many times over.

At some point, we fail to meet our plans, roadmaps, and timelines. The leadership team is angry and disappointed. We must do better the next time! We have to find a way to make our predictions and plans better.

Our default response is to spend more time planning, analyzing, designing, mapping dependencies, and coordinating the work up-front. Our plans look magnificent and astonish everyone, but upon closer inspection, we signed our own planning death sentence.

In our overzealous effort to blow everyone away with our plans, we injected noise and speculation. Our plans look great, but they are now disconnected from reality and mostly rooted in our imagination.

Then, when reality turns out to be different than what we’ve planned, we become paralyzed. Our plans act as an anchor that stifles the ability to collaborate and adapt. We’re so locked into our plans that they drag us down and prevent the collaboration, learning, and discovery that’s necessary to achieve our objectives.

As a result, we fail to meet our plans once again, and we try to do a better job at planning and predicting the next time - and we fail once again. And so the planning death cycle repeats, often ad infinitum.

Complex Work Requires Humble Plans

The key to breaking the planning cycle of madness is to lose faith in our elaborate plans and flashy predictions.

Make humble plans because:
• You don't know as much as you think you do.
• You can't predict as well as you believe.
• What you don't know will come as a surprise and matter far more than you'd expect.
• You will be wrong in ways you couldn't imagine.

Let's all be more humble (and lazy) with our plans.

Instead, let's exert more effort in collaborating better and swiftly responding to changes as we discover and learn more about the work we're undertaking.

Root your plans in reality instead of trying to anchor them in your fantasy.

I originally called it the Planning Death Cycle as an homage to David Bland's Product Death Cycle, but I changed it to Planning Cycle of Madness as it seems more fitting.