Sep 29th, 2022

Business Insights

The Plan, the Planning, and You

  Written by: Max Hoaglund, Senior Technology Lead

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The word planning, taken at face value, names an activity undertaken by people. It is industry-agnostic, and indeed sector-of-life agnostic; you’re planning various aspects of your personal life and at the same time collaborating with colleagues to plan your work, almost no matter what you’re doing. This activity, regardless of which discipline you’re engaged in or what exactly you’re trying to get done, typically has a concrete output. That output is a noun, an artifact, the plan. Much could be said of this particular artifact and its significance. A plan is a fascinating, context-specific, frangible document that seeks to organize people’s energies to whatever extent is possible. It is acted on and updated for as long as it’s relevant, and it slips into oblivion as soon as it’s not. (Provided you’re not too attached to it.) In that way, a plan is like the present moment – a momentary site of huge investment, preparation, reflection, and action, sloughed off as soon as the real world has moved a fraction of an inch.

The plan-artifact thus helps people (who plan) escape from the preciousness of their present work and their projections about what is to come. Your present work, chosen with great consideration and foresight, might turn out to be irrelevant. Whatever projections you’ve made might fizzle as they collide with the coming reality of the work and the world – they also might prove you right and make you feel brilliant. You’re probably brilliant anyhow, whether or not your predictions are any good.

This plan-thing has great virtues. I could keep listing them and really bore you. I’d like to dispense with that exercise and think for a moment about what it’s like not to plan. But what does that entail specifically? Indeed, it’s generally true that people use their executive functions to orchestrate their activity across time and provide testimony to that effect by saying things like “I was planning to do w, then x…”, “I wasn’t planning on doing y”, or “I hadn’t planned for z”. We must look closely and be fairly picky when we try to articulate the state of not-planning.

Visualizing a handful of activities and identifying the rough order they need to occur in (and what that all has to do with the outcome you want) is really powerful and really human. This is an ancient, broadly available tool which unlocks aptitude and achievement. I’d like to argue that for complex software projects with nuanced outcomes and oceans of dependencies, we have to expand the usage of the word planning beyond that. Five, ten, fifteen, or five hundred people can visualize, prioritize, and execute individually and will contribute nothing to a collective goal on a complex project unless some other thing happens. Not planning is life and work in a state where your energies don’t align with those of your colleagues and neighbors, and a certain thing is missing. Let’s put the label of “planning” on this other… thing. Trust me.

A plan is not a talisman or a lighthouse. Planning, the process, is what really changes the effectiveness of a group of people by its being present or being missing. You can do the planning and dump the plan and still be better off – draw up a plan without properly planning, and you’re sunk. This is the thing.

So what ingredients are discussed over the course of the process of planning which are not directly present in the outcome or final plan? Listing and acknowledging these is really valuable. Here’s a subset of what we think and talk about at Clientek, posed in the form of questions:

  • Since the last time we planned work for project X, what have we learned? How will our next plan reflect that learning?

  • Outside of the work we’re trying to get done for project X, what changes are coming to us and our working environment? When?

  • After we execute the plan we’re creating, what happens?

  • How is the technological landscape changing? How do those changes line up with what we expect to achieve for project X?

  • How did our axioms and best practices help or hinder us the last time we planned? What were we right about?

It costs nothing but time to answer these questions. You might have mentally composed answers to them yourself while reading that list, referencing a project you’re working on. Writing those answers down for yourself or discussing them with your colleagues during planning will almost certainly benefit you. Trying to place these on a timeline or a user story almost certainly will not. Paradoxically, it’s hard to map these questions to points or qualities that a plan has – but without asking them, you’re not really planning.

Planning is a repeated, ritualistic, collaborative activity. When we do it, we get a lot more out of it than just a sprint or a release. We think and talk about what’s going to happen 8 months from now, after the last expected delivery of features. That makes our plans careful, meaningful, and gives us some power over the unexpected. We don’t plan without banking some wisdom for the next plan and future planners.

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