Uncertain Times Are Tailor-Made for Strategy.

Don’t Let the Uncertainty Excuse Stop Your Strategy Making.

Matthew E. May
4 min readSep 3, 2020


Albert Einstein once said, “Life is like riding a bicycle…to keep your balance, you must keep moving.”

When it comes to thinking about our business strategy, though, this advice seems much easier to say than do, mostly because it feels like it runs counter to our natural tendency to do just the opposite given the enormous uncertainty created by the COVID pandemic.

We simply cannot let uncertainty beat us. We cannot let uncertainty about the future stop us from moving forward. If we do, we will surely lose our balance.

Unfortunately, I’ve all too many senior executives doing exactly that over the past several months. Heavily influenced by the head-spinning one-two punch of a global health crisis and socioeconomic strife, they pause their forward-thinking strategy development, choosing instead to retreat and adopt a wait-and-see stance. And in a somewhat surprising reversal, I see this even more prominently in the otherwise aggressive and generally more risk-embracing world of smaller high-tech (and often venture-backed) companies than in larger and more mature enterprises.

The typical response when I ask why goes something like, “there’s too much swirl, everything’s up in the air, and we’re too busy scaling.” Or, “hey, we got blind-sided…no one saw this coming, when the dust settles and things calm down, we’ll huddle up.”

I apologize if this seems too blunt, but I call bullshit. Implicit in those kinds of responses — excuses, really — is all kinds of wrongheadedness, on several levels.

First and foremost, I know for a fact that the leaders in a given space aren’t thinking this way. In other words, the competitors are taking this opportunity to strategize — that is, they’re making bets on where to play and how to win, tacking as aggressively as the winds of change. They’re not waiting for dead calm.

Second, the illogic of waiting for things to settle down — for a world more certain — is rather stunning. There is absolutely NO evidence of such a dynamic at play, ever. The world doesn’t work that way. But even assuming it’s possible, when will that be and how would you know? What magic metric would enable us to sound the “all safe” signal? Despite our sophisticated models and algorithms, we remain amazingly bad at predicting the future with, um, any certainty.

Third, strategy is about making integrated and aligned choices. Just because you’ve hit “pause” on formal strategizing doesn’t mean you’ve stopped making choices…to wit, the very choice to hold off strategy making. Every day, inside every business, countless choices are being made at every level. Without a way to align and integrate those choices, your business runs the very real risk of everyone moving in a different direction, very probably to the detriment of long-term company success. Imagine every member of a crew team rowing as they see fit because the coxswain is silent, waiting for the wind and water currents to calm down.

Fourth, there is no learning in abstaining from doing strategy. All you’ve accomplished is resolving yourself from any responsibility, aka the “it is what it is” rationalization, which is essentially a preemptive surrender in order to declare a victimized, woe-is-me sort of victory, which is as hollow-sounding as an empty can. Making bets, testing them out, experimenting with options and exploring new directions…this is the stuff of a winning mindset.

Fifth, accelerated uncertainty writ as large as it is today represents a real opportunity, because it can force us in directions we perhaps should have taken anyway, but were perceived as too risky or uncomfortable. Embrace that discomfort. In fact, lean into it, because that’s where growth comes from. It’s where leadership is revealed.

Finally, strategy is independent of the level of ambient certainty. Uncertainty is by nature uncontrollable. No strategist worth his or her salt would EVER claim that a strong strategy can alchemically transform uncertainty into certainty. (If you have such a strategist advising you in any endeavor, promptly fire them.) Likewise, a choice or set of choices can never guarantee success. Strategy is simply about increasing the odds of success. It involves making and testing hypotheses. Constantly. All too often, strategy is incorrectly deemed synonymous with planning…they are closely linked, but different. Plans tend to be “set and forget.” Strategy involves relentlessly and systematically monitoring the conditions under which the choices of where to play and how to win will yield success. When those conditions shift, so must the strategy. That’s why true strategy is NEVER tied to a calendar (but plans are).

When you think about, strategy is probably the very best tool in the shed for dealing with ever increasing uncertainty, for two simple reasons: First, it sets up an early warning system, focused on leading indicators that, if left unattended, might become real barriers to success. Second, it enables rapid response, and triggers action in the form of modifying the strategy in real time.

Einstein had it right, as he often did. Keep the bike moving, keep your balance, and keep strategizing.



Matthew E. May

ScaleUp strategist at Insight Partners. Co-author, What a Unicorn Knows: How Leading Entrepreneurs Use Lean Principles to Drive Sustainable Growth (2023).