The following is some notes I’ve collected over my twenty years of career, some in tech, some in nonprofit and academia and government, and some as a strategic planning consultant.

I’ll cover the most common stumbles I’ve seen, and end with a little bit of advice for doing better. This is not intended to be an essay, or some something comprehensive like Good Strategy, Bad Strategy. Just fun stuff I occassionally try to describe to others.

I do recognize that a lot of these things stem from context like “toxic workplaces are bad and warp your sense of normalcy long after you leave them”, so if any of these things I write about seems self-evidently obvious, consider yourself lucky.

Rule of three

A simple heuristic for identifying bad planning, either from yourself or others, is how closely it hews to the Rule of Three. For example, if you’re fitting your planning to OKRs, and you end up with three Objectives, each with three Key Results, maybe someone in that process is a little bit lazy.

People like threes. If you turn in a one item plan, maybe it looks like you didn’t do the assignment; if you submit 5 or more, maybe you don’t look focused enough. I would suggest you play with it to see if that’s actually the case rather than always trying to shape everything down to 3: try defensibly submitting just one priority, or twelve, and see what happens.

When I worked at Code for America, there was a period where they adopted a planning framework called OGSM: Objectives, Goals, Strategies and Measures. Unfortunately, its application led to teams creating massive spreadsheets of 3 goals by 3 objectives by 3 Strategies by 3 Measures each. 3-to-the-4th-power is 81. Yikes. This was eventually reigned in.

So to the extent that planning habitually hovers around 3 items per category, that’s the simplest sign that “planning” is a box-checking and template-filling exercise. Either by you, or by the people reviewing it.

Operational Planning and Strategic Planning

What’s the point of planning?

  • To capture the entirety of people’s work and responsibilities and ensure there is proper direction and resources to achieve it all …or…
  • To apply an unnatural focus upon a critical opportunity or risk that might not otherwise get the attention it needs to be addressed.

I call the former Operational Planning, and the latter Strategic Planning. I do Strategic Planning consultation, and a good 20% of my time is spent ensuring that the thing we’re doing together is Strategic rather than Operational.

Both Operational Planning and Strategic Planning are important and necessary. But you gotta keep them distinct. Especially as planners not-infrequently pad out ostensibly “Strategic” plans with activities that would happen anyways due to momentum and natural care (gotta get to three!).

Most of this post is about my experience trying to do Strategic Planning well.

Who appears in a plan? Not necessarily everyone.

A common problem I see with Strategic Planning is a necessity that everyone’s work show up in the plan. I experienced this a lot working in matrixed, cross-functional teams, when every function (Design, Engineering, Support) wanted—if not needed, to justify themselves to others—their work to show up in the strategy for the cross-functional team as a whole.

In good Strategic Planning, not everyone’s primary focus will show up in the overall strategy all the time. Sometimes that looks like this: we’re going to continue operating effectively on our own goals in order to create space for other parts of the team to have a strategic focus. That should be ok!

Roll up or roll down? Don’t wait.

At nearly every tech job I’ve worked, there was the intent that company strategy would be set at the top, by leadership, and then that strategy would roll down to sub-organizations and departments who would do a planning process to align with the company strategy.

That “roll-down” never happened effectively. Instead, the status quo was that individual teams would kinda take a temperature check, read a few recent company memos, and write their own plans based on their own internal goals, and wash those team goals through the contemporary language of the company. Then the department would take those and kind of generalize them into three-ish themes, and that would continue rolling up and never be heard from again.

The most disfunctional times was when teams would wait to plan in the expectation of some company-wide process that never came. And then would be caught flat-footed and disorganized when they were inevitably asked “What is your focus right now? What would extra resources help you achieve? How might you absorb a resource cut?”

The point being here, I would never recommend waiting for inputs to planning. Just do it, and then align with whatever the official process is.

Planning should be sufficient

Some of the most annoying things in my career is seeing my own leadership, or an adjacent team, be casually asked by someone even higher up some flavor of: “what are you doing to work towards [new company priority]?” and the sub-leader immediately kicks off some new planning process to preempt the old one.

Have some backbone, and simply remind them of current plan. I think a lot of the time no one honestly remembers what was previously planned and they’re just making chit-chat. If you have a quarterly planning process, then any new company priority gets fed as input into the next planning cycle (unless it’s actaully pants-on-fire/company-runs-out-of-money-otherwise situation, which is rare),

Measures and Targets are different

I’ve observed people try to find a nihilism between the statements “You can’t manage what you don’t measure” and “When a measure becomes a target, it ceases to be a good measure” (Goodhart’s Law). Whereas I think you just have to allow both to be true at once and allow “target” and “measure” to mean different things.

The Target is what you aim directly at. A Measure is just something you look at occassionally or from the side of your eye and say “huh, interesting”.

This distinction isn’t particularly important, other than to be able to distinguish one from the other, and also recognize when someone with power over you is “huh, interesting” a little too hard and you should pay attention.

Progress and percentage targets

For anything that you’re asked to track as “percentages to completion” you need to ask whether the intent is that you reach 100% or there’s some neg-style “if you hit 100% that means you weren’t audaciaous enough in setting your target” and thus you need to take your actual target and inflate/deflate it the expectation.

The outcome you want is both that you know what you’re trying to achieve (regardless of what you publicly commit to) and you look good doing it.

My advice for anyone in charge is to simply make 100% the achievable target and avoid all of this triangulative nonsense.

Percentages are also annoying when you’re measuring progress towards some boolean done-or-not-done where there’s no benefit until it’s done. 80% of zero value is still zero value.

In my opinion, the entire reason to report on progress is to have some shared context for if or when you need to ask for more resources to finish it out. Same with stoplights. If the only shared context is “things were green but now they’re yellow” that’s a pain; in the same way as “if some projects aren’t yellow, that means we’re not working hard enough” sucks too. Also when percentages or stoplights get averaged and rolled-up 🙄.

Writing a plan vs doing planning

The most common pattern I see for“planning enablement” is the company provides a template for the final document. e.g. fill out this template and turn it in and that’s your plan.

Template-first planning means that a planning process then becomes:

  1. First, filling in the “what are you going to do?” section
  2. Second, making up something narratively consistent to fill out everything else

I see this happen everywhere. People already have stewing what they want to do, and then everything else is backwards justification.

This backwards-justification is one of the key dynamics that we’re going to try to overcome as I now shift towards how I think you should plan instead.

How I think you should plan, instead

The main idea in how I think you should plan is that you break the planning down into stages where you try to get farther and farther away from “what people want to do” and towards a more complex “what needs to be done to overcome the barriers that make it hard for people to do the things they want to do”. Got all that? Good.

Aside: None of this is my new idea. Creating conceptual distance is core part of Synectics (yes, Steve Krug once mentions it) and a lot of this process comes from taking lots of trainings in Technology of Participation, which has entire books on gestalt theory and such.

So of separate stages, that means that you force yourself to do each piece separately, rather than starting at the end (“what you want to do”) and working backwards or all at once. The stages are:

  1. What’s going on? (the dry name here is “Environmental Scan”) Laundry list any new themes, priorities, developments that have happened inside the company and outside it since the last planning process. Go look at the last plan too. “We said we were gonna do X” is a good thing to list here. The thing to be aware of is that people are dying to shout “what we are going to do” so everything at this stage is still somewhat suspect. But that’s fine, we recognize thatand move forward.
  2. What are we going to do? That’s right, get it out there. Shake it out. List the things you want to do. Yes, you’re going to do them. They are very important. They are! I think it’s really important at this stage to let people linger and make sure they see those things they want to do captured. These are the things that are going to happen.
  3. What makes it hard to do those things? (“Barriers”) Like, really, why are they such big things that you felt the need to articulate them so badly. There’s lots of important work that just happens, so why spotlight those things? What are the problems you’re trying to overcome by spotlighting them? This is usually like resource problems, or distractions, or actual disagreements between leaders, or some other problem that constantly steals focus. Remember, you’re not trying to justify the thing from the previous stage, you’re trying to explain why you would ever need to justify them in the first place. Why can’t the work just happen?
  4. Of those things that make it hard, what do you have control over? It’s possible to work this question into the previous stage, but I like to allow people to let loose with all their grievances before trying to narrow them down slightly. This is a good spot though to fully divorce people from the “what I want to do”-brainspace by engaging them with something else to problem solve around….
  5. Of the barriers, what can you do to overcome or route around them? Here we go, this is what we’ve been working towards: solving problems. What actually would address the problems we identified in the previous stage? Write that down.
  6. Of those solutions, what are you going to do? (“The Strategics”) This is the decisional commitment. Remember, we haven’t replaced the initial stage’s “what are we going to do’s”—those are still happening—but rather worked towards a new list of “everything would sure be a lot better/faster/stronger if we did this first or in-addition-to”.

…and then you write that into the planning template to report it out. And in this case, the “justification” for doing The Strategics is listing all of the stuff that you were going to do anyway.

But you can do this badly too, right?

Sure of course, we can do anything badly. It’s possible to wash the initial “what are are we going to do’s” through this entire process and end up exactly where you started, but with several hundred words of retcon around it. That happens.

…but at least I believe this process affords some potential of not doing that, whereas I think most default planning processes (fill out the template) almost guarantee you end up where you started.