Updating Eisenhower on planning

Previously: a long time ago, Dwight Eisenhower probably said something to the effect of: “Plans are useless, but planning is essential”.

Today, software development (and knowledge work writ large) are largely about speed in the service of more. Iterate faster, ask more questions, get more feedback, deliver more often. Success is less likely about having a good or well-formed idea from the outset, and more about how the idea evolves in the hands of people/customers.1

Let’s update Eisenhower’s insight on planning to harmonize with speed and quantity of iteration:

Static plans are useless, but dynamic plans, developed and iterated as information arrives, are the essence of leadership.

You have to plan. Stopping to think a multi-week project through isn't Waterfall or a slow, bureaucratic process. It's how you get your head into a project.

Lacking a plan isn’t an option2. If you choose not to have a plan, you’ll likely end up part of someone else’s plan. Their plan may not have the same outcomes or parameters in mind as you do. Better to have a plan.

Planning with your team is how you get everyone aligned and pulling in the same direction. The worst cases for a plan, that it’s tragically incomplete or wholly invalid, have a silver lining wherein the team that plans together pulls together. In the best case, you’ve front-loaded a bunch of coordination and collaboration, allowing teammates can work autonomously and efficiently.

The initial plan you or your team come up with is very much a rough draft. Surely risks will make themselves known and areas of unknown complexity/scope will present themselves. Don't worry about rigorously adhering to the plan once you're a few weeks into the project. Iterate and add to the plan until you’ve done all the useful work, and it's time to start planning the next project.

  1. There is something to say about slowing down, seeking quality at every turn, and delivering a great, monolithic thing. Usually that involves some combination of internal iteration, auteur mindset, a strong creative scene, or harnessing lightning in a bottle. Everyone wants to fall in this category but counting on that is an unhedged risk.
  2. With apologies to Rush: “If you choose not to decide, you still have made a choice”.
Adam Keys @therealadam