One of my favorite sentences is in the Introduction to Mark Twain’s Adventures of Huckleberry Finn:

“When Huck opens that window to take off from home, the reader has the same thrill of anticipation one feels after hearing the first few bars of a Miles Davis solo.”

—Peter Watrous, The New York Times

It is a favorite because it set me up for revisiting a known storyline with a new perspective: hopping out the window was the critical, decisive moment of before vs. after. Everything “before” was known; everything “after” was improvised. Miles Davis’ music just snaps it all together viscerally: what is next ? (we don’t know).

I think about this line a lot, since improvisation (read: I have no plan) is such a dirty word in business. How can you have no plan? Businesses certainly cannot wander about trying to “find adventure”, leaving all known and certain things behind. It’s irresponsible.

And yet, today more than ever, businesses undergoing digital transformation probably feel as if they are hopping out that window, or at least they’re looking out the window nervously. The prospect of leaving the current way of doing business is not comfortable, but probably needed, and there are few disciplines to guide a successful landing into a new way forward. In short, nothing is guaranteed—neither the old nor the new way.

And so we come to the U.S. Army. Featured as a case study in Peter Sims’ Little Bets, Colonel Casey Haskins describes the transformation going on inside the Army, which is targeting the need to “adapt to demands for more limber, creative operating methods” to enable success in a new era of constantly evolving warfare. Said plainly, they are trying to successfully incorporate improvisation into army doctrine.

The problem: In the previous era of Cold War battlefield tactics, small margins of error necessitated that the focus was centered on precision and efficiency. Approved solutions for anticipated problems were the doctrine for success: “There would be very few people making decisions and the rest of the people [were] executing them the best they could.”

Over time, the “illusion of rationality” (described as when ideas or assumptions seem logical in a written plan, yet haven’t been validated in the real world) kept these doctrines of approved solutions in play—even when they clearly did not work (see Vietnam).

In the current climate of adaptive guerilla warfare, Haskins speaks about the inability of the Army to ever know all of the challenges of a constantly evolving warfare, much less have an approved solution for soldiers to follow.

Haskins then describes the Army’s turn to design thinking as a way forward—defined as this in the U.S. Army’s field manual:

“Design is a methodology for applying critical and creative thinking to understand, visualize, and describe complex, ill-structured problems and to develop approaches to solve them.”

Here, utilizing design thinking as a rigorous discipline gave soldiers an “approved” way to improvise, make mistakes, learn from them, and ultimately find progress in an environment of constant uncertainty. In Army strategist lingo, design thinking allows soldiers to “develop the situation through action.” It is a constant dance between action, discovery, mistakes, and correction. At the heart of the methodology is learning and improvement—a way to find a successful path forward where there are no guides.

This case study has stuck with me for a long time. It is the one, though much bigger in scale and breadth, that feels closest to the spirit of improvisation (Huck out the window), and yet it makes every client engagement that involves innovation or quick progress in uncertain environments seem feasible. Design thinking gives companies (including yours) a way to adapt and succeed progressively in uncertain environments while navigating through digital business transformation.

Postscript: My son (13) read this post and thought the language was over his head. So we talked about the concepts, and how they relate to what I do for a living, and the teams and situations I encounter on a regular basis. His immediate response was that I was only “hinting” at the solution to many of the challenges I encounter, and that I should say in this post what I really thought. Good point.

Openness to and use of design thinking as a credible and effective methodology to work through digital business transformation challenges will be a deciding factor between success and failure of many companies over the next few years (including yours).