A Sock to the Jaw: How to Plan for the Unplanned

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Kein Operationsplan reicht mit einiger Sicherheit über das erste Zusammentreffen mit der feindlichen Hauptmacht hinaus.

No plan of operations extends with any certainty beyond the first encounter with the main enemy forces.

Helmuth von Moltke the Elder

The best laid schemes o’ Mice an’ Men Gang aft agley, An’ lea’e us nought but grief an’ pain, For promis’d joy!

Robert Burns

One of my favorite sayings comes from Mike Tyson, the champion boxer. I’m not a fan of boxing, but Tyson’s insight is clarifying:

Everybody has plans until they get hit for the first time.

With repetition, this heavyweight wisdom has evolved, so you might be more familiar with this version:

Everybody has a plan until they get punched in the mouth.

Which frankly just packs more wallop. (Sorry, Iron Mike.)

So, if plans are useless, why plan?

I’d wager that whatever ten-year plan you had for yourself a decade ago featured a path or outcome quite different from what actually unfolded, for better or worse. In fact, I’m hoping that’s the case. Life is too varied, rich, and interesting to be hemmed in by plans. And yet, consciously or unconsciously, we constantly plan. Even our hopes and dreams are rudimentary plans of a sort. You maybe just need to flesh out the details.

Ten years ago, my plans included ascending to a college presidency to cap off my career in higher education. Instead—after that proverbial punch in the mouth—my chronic and profound disappointment with the state of leadership in higher education prompted me to walk away altogether. Back then, I never could have imagined doing what I do now, but now I can’t envision doing anything else.

Notice that when plans change, so too may goals. Nonetheless, even if I reach my intended outcome, how I got there will likely be somewhat unexpected.

For instance, think of a time when you were anticipating a difficult conversation. You probably rehearsed it in your head—what you’d say, how they’d respond.

How closely did reality align with your mental script? How far were you into the confrontation before you had to abandon that script altogether? How useful was your plan?

Despite the apparent futility of planning, the best leaders still plan. In a 1957 speech, Dwight D. Eisenhower cited a well-worn military truism: “Plans are worthless, but planning is everything.” What could this mean?

The simple fact is that leaders—even great leaders—can’t foresee or solve every problem or variable. Too many factors lie beyond the leader’s grasp. But, good leaders prepare their teams for inevitable challenges even if they’re fuzzy on the specifics. That way, when unexpected problems arise, they and their teams are better positioned and equipped to handle them.

There’s an added benefit too. While planning helps with problem-solving, it also may prevent problems from arising at all. Think of it this way: being on the lookout for unanticipated obstacles can help keep plans on track. Moreover, effective leaders are always willing to change course when necessary.

Check out: Wayward Drivers, Woeful Leaders: How to Avoid Being Misdirected

There’s a common misguided way of thinking about plans. You’ve heard the demand that we must “stick to the plan no matter what.” Sure, this approach might work out great in fiction, but it’s less often successful in reality. Bosses who aren’t run-for-the-hills types are usually stick-to-the-plan types, with predictably regrettable results.

Check out: Leaders Lunge Toward a Challenge, Bosses Bolt the Other Way

Check out: Where Bosses Prevail, Employees Fail

Because they don’t build reliable team cultures and are apt to cast blame rather than accept responsibility, bosses tend to be flummoxed when plans go awry. That’s when they dig in their heels. One more shot to the face, and they’re bound to go down.

In contrast, leaders are firm but adaptable. When that punch to the mouth comes, they neither crumble nor stay with their current tactic. Instead they weave and bob; they dance around and change things up. Their team members can adapt as well because change is built into their culture. They’re trained to expect the unexpected.

The Power of Planning for the Unplannable

When I was a young university dean, I led a committee tasked with overhauling our general education curriculum. This reform would impact every student and faculty member and enhance the quality of our educational offerings for years to come. My team analyzed the strengths and weaknesses of our old curriculum, studied best practices, and explored other institutions’ approaches as we designed the new curriculum.

Our plans were innovative and solid, but when we presented them to the faculty, you can guess what happened. A sock right to the jaw.

We had a few options. One was to just force through our proposal as is. Another was to retreat, start again from scratch, and hope for a better reception. The third was to solicit and listen to the faculty’s concerns and incorporate their insights into our revisions.

We, of course, chose option three. The new process was daunting because it required us to eat a lot of humble pie over the long haul. But we also knew that doing so would result in a superior curricular plan that had faculty buy-in. As we moved forward, more and more faculty supported our efforts, and we began to craft our final proposal. This new curriculum had the potential to overhaul our little university from a forgotten educational backwater into a transformational powerhouse.

Instead, my boss intervened. He—being a boss—was a big fan of the status quo and impatient with consensus-building. Although he had never given us a deadline and had personally thrown up many gratuitous obstacles, he grew frustrated with our pace and abruptly pulled the plug even as we were on the verge of success. He then imposed his own new version of the curriculum using his favorite tools: subterfuge and brute force—lying and bullying. The result was a much-ballyhooed transition from one mediocre general education curriculum to his nearly identical replacement.

The only significant improvement in the new curriculum was a remnant from the one my team designed. Once again—punched in the mouth and beaten to the canvas—we stood ourselves back up and adapted our plan to the new limited circumstances. We salvaged what little influence we still had to improve my boss’s middle-of-the-road ideas. In this small but impactful way, we still managed to improve arguably the most important aspect of education at the university: writing skills. Best of all, we got my boss to think it was his idea!

The fact is that well-designed plans, even when completely abandoned, set teams up for success. A team culture that leans into flexibility and malleability will be able to bend and snap back no matter how many punches connect. In this way, collaborative planning itself can be a team-building exercise.

Yes, plans are important—necessary even—but anticipating the need for adaptation and resilience is critical for planning. Leaders and teams that accept the inevitability of the smash to the face may even find they relish the challenge if not the swollen lip.

How do you prepare for plans that go awry? How effectively do you snap back?

Great leaders need to be great planners and great adapters, and I can help.

Unlock the Great Leader Within! Download my free resource, the Transform To GREATness Toolkit, now!

I look forward to hearing from you.

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I’m Dr. Jim Salvucci, an author, keynote speaker, coach, and consultant. I served higher education for 30 years as an English professor, dean, and vice president before founding Guidance for Greatness to guide young bosses to become the next generation of great leaders. I’m a certified Tiny Habits coach as well as a certified Thrive Global coach and life coach and hold leadership certificates from Harvard University and the Council of Independent Colleges. Central to my leadership philosophy is that all great leaders are decent humans as well as great teachers, guiding their people and their organizations through values toward success.