I’ve spent more than my fair share of time in exhausting planning sessions, where a handful of people pondered the future of some crisis scenario. Sometimes the stakes were relatively small, when the outcome would only affect a small, local area. Other times, the stakes were far greater, with countries and even geographic regions potentially impacted. I once joked that I had planned operations that spanned 42 countries across three continents. Except it wasn’t a joke. It was 47, and that was just in one year.

Planning That Doesn’t Take Reality into Consideration

Over time, some of those memories stand out more than others. Maybe it’s the stakes. Maybe it’s the people involved. Or maybe it’s just something unforgettable. One such moment—which involved a major operation launched into a hostile country—often comes to mind when discussing the shortfalls of planning. The planning itself was to be conducted under a veil of secrecy that was new to me, making the effort all the more intriguing. After we’d assembled the group in a secure facility far from the prying eyes and ears of the world, the senior planner in the group stood up and addressed us: “We’re going to push five divisions into theater in 30 days.”

Even as he droned on, two thoughts buzzed through my head. First, I thought to myself, Does this guy think he’s George Patton? My second thought I couldn’t keep to myself: “The math doesn’t work. You have one seaport and one airport; there’s not enough throughput to do that in such a short span of time.” The senior planner didn’t miss a beat: “We’re going to shut both of them down to civilian traffic during deployment.” Not one to let the last word go, I replied, “I think the host nation is going to have something to say about that.”

And they did. Even though we’d assembled one of the most capable teams of strategic thinkers available, the plan itself was so fundamentally flawed that it wasn’t executable. The PowerPoint slides were far more impressive than the actual concept of the operation. Eventually, the plan was adapted to account for the throughput delta, only to immediately shift to a plan that required transit authority through another country that was unlikely to ever grant that authority. By the time his brilliant plan was finally executed, it was only a distant cousin to what had initially been proposed.

The Keys to Planning

As a planner, I’ve long since embraced the wisdom of von Moltke the Elder, who recognized that “No plan of operations extends with certainty beyond the first encounter with the enemy’s main strength.” I also wholly endorse Dwight D. Eisenhower’s timeless observation, “Plans are worthless, but planning is everything.” If there is one guiding tenet to planning as a whole, it’s the necessity to produce flexible plans that are executable. In our case, we did neither.

But that’s hardly a rarity in the realm of planning. As often as not, we gather the illuminati, ponder grandiloquent ideas in isolation, and produce lofty, aspirational goals with no real means to achieve them. And that’s only the where the problems start.

1. A plan has to be more than goals.

Any worthwhile effort will produce a roadmap that weaves together those goals, the actions necessary to achieve them, the resources required, and the potential risks you might encounter along the way. The ends-ways-means calculus is a basic formula for formulating strategy; it’s not perfect, but it’s a start. But if your plan is just a list of goals, you needn’t bother with the high fives because you’ll never achieve them.

2. Planning is not a top-down process.

For a plan to be executable, it has to be developed as a collaborative process, especially if you’re expecting someone else to do the executing, which is typically the case. This becomes all the more important when your central idea is flawed and you’re the only one who doesn’t see it. Involve the people tasked to execute your brilliant plan early and often. It’s kind of a big deal.

3. Planning is a change process.

We develop plans to change something: a situation, a position, a state of affairs. Whether you want to improve your score on a physical fitness exam or take down a foreign dictator, every plan involves some form of change. On a fundamental level, that means mindsets and habits have to change, too. If you want to alter the status quo, that means you have to be serious about what it is you’re trying to accomplish and set change as your new “normal.” Give Kotter a fresh read, too.

4. Communicate your planning logic.

“Narrative” is one of the most common—and misunderstood—terms in the planning lexicon. At its core, the narrative is your planning logic, which is ultimately translated into execution. If you can’t explain your logic, then your plan won’t be executable. If you can explain your logic, but it elicits strange looks in response, then your plan won’t be executable. That’s as simple and blunt as it gets.

5. Allow for flexibility in the plan.

Every plan should produce two things: the what (what you’re trying to accomplish) and the why (why it needs to be accomplished). Once those are established, resist the temptation to dictate the how. The more you insist on driving how the plan should unfold, the less flexibility exists during execution. If you accept von Moltke’s precept, then you build in that flexibility rather than restrict it. Allow others to determine the how.

Planning for Success

No plan is going to be perfect, but these five steps will help you avoid the pitfalls of planning that plague many efforts. Your plan still might not survive first contact with the enemy, but a good planning effort will yield the flexibility that allows those executing your brilliant plan to succeed.


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Steve Leonard is a former senior military strategist and the creative force behind the defense microblog, Doctrine Man!!. A career writer and speaker with a passion for developing and mentoring the next generation of thought leaders, he is a senior fellow at the Modern War Institute; the co-founder of the national security blog, Divergent Options, and the podcast, The Smell of Victory; co-founder and former board member of the Military Writers Guild; and a member of the editorial review board of the Arthur D. Simons Center’s Interagency Journal. He is the author of five books, numerous professional articles, countless blog posts, and is a prolific military cartoonist.