The Leaflet #112

1. Simplifying strategic planning 2. Goals instead of tactics 3. Fight library fatigue with randomness

A useful oversimplification of strategic planning

I have heard so much grief from clients trying to both perfect and enact a strategic plan. There are seemingly endless obstacles to each. And I’ve sort of fallen down on a keep-it-simple-stupid method for this.

Consider the strategy to be that which will get you to the goals you most want to have achieved either three or five or ten years from now. Take your pick of timeline. For some organizations, ten years might be the right window; for some, it’s three. Let’s imagine for your team it’s five.

If the organization has fully maximized its mission five years from now—say, January of 2031—that means we will have achieved what? Write those achievements at the bottom of one page. Then at the top of that same page, write today’s date. Divide the paper between those two points into sections for each of the intervening years. Then work backwards: if we achieve xyz by by 2029, what must we have achieved by 2028, 2027, and so on.

Now you have a one-page draft of a strategic plan that is the one ring to rule them all. You break out each of those years as they come upon you, usually three to nine months in advance of the year’s start. And say, okay, we have these goals for 2026 if we were to hit this place by 2029. What does that mean each of our departments is responsible for? You break out goals for the departments based on what those annual goals are. This is your annual planning process.

I have a client who just did this—philanthropic advisors who work with ultra-high net worth individuals to steer their giving towards a particular type of social value. The most senior leaders straight up did it this way, in an hour, in front of me. They did that as a brain trust together. Then they brought the cabinet together and presented it at a two-day retreat, socializing the cabinet to it. Then they gave the cabinet time to set their departmental goals against it, set their people’s individual scorecards against it, and backwards map the OKRs on a quarterly basis that led up to it. Each group presented to the other, they celebrated and agreed on ways they’d check on it and troubleshoot it, re-evaluate it, and made a calendar. That was it.

-ben

In strategic planning, focus on goals, not tactics

Strategic planning should be far more about the what than the how.

What actually matters is the benchmarks you’re setting for yourselves. The optimal moves that get you to those goals along the way will reveal themselves. Those ground-level tactics do not need to be contained within a strategic plan. In fact, putting them there can overcommit you to measures of success and uses of cash, time, and talent that will prove irrelevant. In other words, you set yourself up for wastefulness instead of learning.

You can add some tactical precision to your plan as you learn what works best, year by year. But usually that tactical precision, when you reach for it ahead of time, is arbitrary or aspirational and not based in ground-level learning. You do yourself a disservice by pretending to certainty at that level in a five-to-ten-year planning process.

-ben

One way to handle library fatigue

Last month, Seth Godin offered a pithy label for a modern problem. When you face abundant options, you feel blind and overwhelmed, rather than spoiled and free. Godin calls this “library fatigue.” (He also calls it “vegetable blindness” – you lose sight of what you might want to cook once you hit the fifth rainbow of produce arrayed before you at the farmer’s market).

Library fatigue can flummox you every time you open your phone. You’ve got the Claude or GPT app there. You can summon and send forth the most powerful computer ever assembled. And with the recent vogue for Claude Code, you may now have the sense that you should be using that most powerful computer not just to answer questions and learn things but to build Literally Whatever You Can Imagine!

Choosing three wishes from a genie is hard. Surprisingly, choosing any one wish when you have infinite wishes may be even harder.

My happy fool’s advice is to let the blindness be your friend for a short, defined period. Let randomness be your friend as well. In the library, beset with fatigue: cover your eyes and pull a book off the shelf. At the farmer’s market, hungry and lost: pick the first three vegetables of different colors that you see. With Claude Code, make a crude single page website or an infographic of a spreadsheet.

When you’re overwhelmed, you can’t optimize. Your blind, random choice serves as a starting point. Maybe you like the track it puts you on, and now you can run down that track, refining and optimizing. Maybe you think what you made is utterly useless — now you can try something that has the ~opposite set of characteristics.

The good news is you’re now making your second attempt with some greater knowledge of the tool and of your preferences. The n-1 set of possibilities seems less like a sublime ocean and more like an old phone book – you’re not going to get swallowed up and there’s a ton of stuff in there you can safely, happily ignore.

-eric

COMPELLING QUOTATIONS

Philosopher Agnes Callard on blind spots:

“Error does not tend to survive introspective awareness of itself: when you catch your mind in going astray, at that very moment your mind cleans up its act. As soon as you realize it’s a mistake to think something, you become unable to make the mistake of thinking that. You can still think about it, as, for example, something you used to think, or something someone else might think. You can look at the erroneous thought, but you can no longer look at the world through it. Our errors are blind spots, which is why real open-mindedness is so difficult.”

Philosopher Socrates on Athenians feeling some type of way about his refutations:

“I realized, to my sorrow and alarm, that I was getting unpopular.”

Therapist Esther Perel on intimacy:

As a psychotherapist focused on relationships, I am interested in intimacy in all of its expansive definitions. It is becoming ever more clear that intimacy is not only romantic; it is civic. It is the willingness to be implicated in another person’s safety and dignity. It is the communication, silent or screaming, that your life touches my life and my life touches yours. It is the village reemerging, not due to nostalgia but due to necessity. Crisis, sometimes, makes us kin.