14 Jul A “Three By Five” for a Strategic Thinking Mindset

By Larry Kleinman

May 5, 2025

“How can I think more strategically and teach strategic thinking to others?” 

It’s a question I’ve been asked countless times but never found a satisfying response.  Until recently.

Some months ago, it crystallized:  three principles that are each expressed in five words.  The “3×5”, I call it.

The first two are commonplace sayings.  The third is more novel.  Here they are:

• Put yourself in their shoes.
• What could possibly go wrong?
• Visualize keeping what we win. 

I contend that if one puts any proposition or plan through the 3×5, the resulting iteration will be better grounded, more resilient and likely to succeed. Or it will make plain(er) that it’s ill-advised, premature or problematically vague.  Applying the 3×5 also serves as an exercise in humility and a detector/inhibitor of hype or other forms of over-confidence.  

To the question “why these three?”, I’d offer these observations.

“Put yourself in their shoes” invites us to “meet folks where they are”, a maxim frequently asserted in community and political organizing.  It also applies to any actor of consequence to the proposition–including our own folks, but especially opponents or competitors (including sometime allies dubbed “frenemies”).  To imagine or guestimate their viewpoint illuminates their condition, interests, inclinations.  It informs if, when and how one might engage them and the likely outcomes.

“What could possibly go wrong?” helps illuminate the tendency to skip over anything that dampens enthusiasm (sometimes termed “confirmation bias”).  But it also invites forward thinking that can identify and avert likely missteps.  “Possibly” is, hopefully, a qualifier that doesn’t draw one into a negative orientation, described in my world as “no se puede” (it can’t be done).

“Visualize keeping what we win” seeks to mobilize hope and invoke the long view.  Predictably, one can focus so fully on fulfilling the proposition–establishing an organization or waging a campaign–that we fail to recognize ways to build in strengths or avoid vulnerabilities.  Success, it turns out, is harder than failure.  Harder still is sustaining what success achieves.  “Visualize” points to considering preparation and pacing but doesn’t contemplate actual planning which, in most cases, would be simply too complicated at the outset.  This third element of the 3×5 draws us into the realm of “así se puede” (roughly, “thus, we can”):  the “how” which will come to matter more than we imagine.  

The 3×5 could, in truth, be more than three elements.  And there’s nothing magical about five words.  Those particular three, though, feel evergreen; three feels like the right-sized mental economy.  Chances are, the first two are already in your language bank.  

For those who came of age before smart-phones colonized our information and idea management, 3×5 conjures a hand-sized piece of cardstock with a dozen horizontal lines.  “Index cards”, as they were called, served as the universal holders of knowledge and data worth retaining: recipes, contact information, speech notes.

The index card largely went the way of the Rolodex, but this 3×5 aspires to fulfill the same essence of conciseness and utility.  No cardstock or metal filing box required.