How to rank and value strategists

Skip the titles, ask for portfolios

We just passed Easter Week, so let’s go straight to the top. The Sermon on the Mount is Jesus at his best, issuing morality tales and helping followers separate the righteous from false prophets. 

To illustrate the principle, he tells an anecdote about fruit-growers. His advice in telling the good ones from the bad? “Ye shall know them by their fruits” (Matthew 7:16). Bad fruit farmers don’t grow good fruit and false prophets don’t do good work. It’s a simple message. Judge the worker by the work that’s produced. 

Every time we remind ourselves not to “judge a book by its cover,” we’re paraphrasing Jesus’s fruitful lesson. 

But that’s not what we really do. We love to judge the quality of a strategist by their cover/rank/title. 

I work as a strategist in the US Army. Our organization elevates strategists based on age and time in service. A 50-year-old colonel always receives position and prestige over a 30-year-old major. The presumption is that with more years comes more experience, and with experience, wisdom.

As another Army strategist put it, we promote strategists based on a blend of “education” and “experience,” as “the development of military strategists, like any other discipline, must occur over time.” So that’s what we do. (And for those of you that don’t wear cammo to work every day, the same applies to you too. While a bit more formal, what happens in military organizations runs in parallel with civilian ones.) That’s how the US Army sorts strategists. 

“Experience” here, of course, is code for rank and time. In other words, quantity of service, not quality of work. But merit should matter. 

There’s other reasons to question this time-based approach to sorting good strategists from bad. Old fools exist in roughly equal measure with young fools. Age isn’t all that helpful as a discriminating feature.

It also assumes that strategist learning is straight-line, like the rise on a set of stairs. Again, this is far from true. Lifelong learning is a non-linear process. 

Above all, age and credential clearly don’t matter nearly as much as the work a strategist has performed, and how that record fits into organizational need. 

When selecting a strategist, demand a portfolio. Not a bullet list of bygone positions and old titles. Having been somewhere else should never be enough.

When looking for a solid strategist, in particular, weed out the aides, execs, and bag-handlers. They’ve focused on extending some else’s brain at the expense of expanding their own. 

Here’s what to look for in a strategist’s portfolio. It should tell you a little about who they are, to provide context. Then make them show you their work. Their successes and failures; why and how their successes might’ve gone wrong, and why and how their fails could’ve been shaped back into successes. They should be able to demonstrate the difference between success and failure because that’s what you expect of them in your organization.

Have them tell you their philosophy of strategy, their basic beliefs. Their biases. Much of this will be in text, but get beyond written work and beyond the blank page to their ideas, interests, hobbies, and other fields of competitive strife to which they’ve applied the strategic art. (For example, what strategic lessons can be learned from the Tooth Fairy? From parenting? From travel abroad?)

Finally, exactly what have they created? How’ve they moved an idea into reality, from nothing to something?

If we got past our preoccupation with prior titles and high rank, we’d focus on What did you produce?—not—How long did you exist?  If a 27-year old captain can document better quality work than a 54-year old brigadier general, so be it. 

If we got off this addiction to age, ambitious people would seek real opportunities to practice strategy. They’d avoid serving in higher-visibility roles where they schedule a lot and think not-so-much. Talent would flow to where it can be exercised, not where the spotlight shines brightest. 

If what matters is strategy produced, then the real strategists will find that work. 

And praise be to Jesus, we’ll know how to tell the difference. Not just shiny on the outside, but good all the way through.

How do you like them apples?

*Afterthought: “Life shrinks or expands in proportion to one’s courage.” (Anaïs Nin)

*Editor’s Note: What do you think? Please let me know with a comment, and, if you enjoyed this, forward it on to anyone you think might benefit or find it of interest. Your word-of-mouth mention to another person means everything to this community’s continued growth. 

All the very best & see you next week, Matt