Planning for Paradox
Let’s start with the punch in the face.
I am a very ardent believer in the power and necessity of process management. Creatives who believe that “process” is inherently stifling are simply wrong. But process managers who believe creativity is predictable and reducible to simple mechanical methodologies are…also wrong!
This is the first in what will be an ongoing (though probably non-consecutive) series of essays musing specifically about the vicissitudes of process management on professional creative teams.
What do 19th-century Prussian Field Marshal Helmuth von Moltke (aka “Moltke the Elder”), Winston Churchill, Dwight Eisenhower, and Mike Tyson have in common? None of them has ever been in my kitchen!1
Well, that’s true. But there’s something else, too, maybe a little more relevant: they’re all associated with the apparent leadership paradox that while planning is invaluable, plans are useless.2
Which, of course, is not a paradox at all. Planning is a process and plans, as such, are only one artifact of that process — and far from the most important one.
Obviously this is no insight of mine: everyone knows it! But it nonetheless must be super difficult to implement, because the misuse of plans and planning seems as common as…well, as common as sports and military metaphors in business. Here we go.
Close encounters of the fist kind.
Going into a championship fight in 1987, Mike Tyson was asked whether he was worried about his opponent Tyrell Biggs’ plans for the fight. He answered: “Everybody has plans until they get punched in the face.”
I’m no fan or follower of boxing, but I remember hearing this phrase at the time and finding it brutally delightful. It was almost cartoonishly arrogant and violent, like something Clubber Lang would have said in Rocky III.3 In Tyson’s disarmingly child-like voice it seemed more like schoolyard bravado than professional sports.
But the thing is, he was right:
“By round 3, Biggs had all but abandoned his game plan and was overwhelmed by Tyson's power”
Years later, I remembered this phrase when I learned that Dwight Eisenhower had once remarked, somewhat similarly, that “plans are worthless, but planning is everything.” Though less visceral than Tyson’s, Eisenhower’s phrase from the ‘50s had eventually taken on a life of its own: taught to (and then seemingly ignored by) pretty much every project manager ever since.
But anyway, while Eisenhower really did say it, it’s not necessarily attributable to him (nor did he intend it to be, as we’ll see). However, I expect it has taken on so much weight precisely because it can be correctly (if incompletely) assigned to him.
Eisenhower is something of a revered figure in the US: a “self-made man,” successful wartime general, thoughtful statesman, and president4. Rightly or wrongly, he is the very paragon of credibility.
And look: it doesn’t really do much for your career as a middle-manager to sit in an executive staff meeting and quote late-’80s Mike Tyson. But quoting Dwight Eisenhower? That seems like you’re channeling the wisdom of an American hero. It’s a real go-to.
In any event, Eisenhower himself made no claim of coining this phrase — in fact, he always specifically forswore authorship. Over the years he variously attributed the quote to “the observation of a very successful soldier,” or to a “statement I heard long ago in the Army,” or similar.
We won’t know the path by which it got to old Ike, but he was likely referencing, at least obliquely, an 1871 quote by Helmuth von Moltke5 about battle planning. Von Moltke had said:
“No plan of operations reaches with any certainty beyond the first encounter with the enemy's main force.”
In other words: plan all you want, but expect to throw those plans in the fire as soon as combat starts.
For sure, I would not at all be surprised to pull further on this thread and find that von Moltke himself was simply articulating conventional wisdom when he said this, and that the sentiment can actually be traced back to Alexander the Great or Seneca or some damn thing. But I figure 19th century Prussia is far enough for my purposes!
And so, from von Moltke’s lips to Mike Tyson’s ears: Tyson figured himself as “the enemy’s main force,” and thus his opponent’s “plans” were of no particular concern.
Some plans are like maps. Some are like schedules. Which are also maps! Sort of.
I once participated in a project management training seminar in which we discussed that famous Eisenhower quote. The facilitator expanded on the notion with a little allegory imagining plans as “maps.” It went something like this:
Two hikers are following a map through the wilderness. They crest a hill, and Hiker 1 stops short saying, “Oh! There’s a river here!”
Hiker 2 looks at the map and says, “Nope. There’s no river on the map.”
Brow furrowed, Hiker 1 says, “But look! It’s right there!”
Hiker 2 hands the map over, saying, “You look yourself! There's no river on the map!” and proceeds to walk forward right into the river and is swept away never to be seen again. Hiker 1 looks around, fells some nearby small trees, fashions a simple bridge, and carefully crosses the river.
Hiker 1 is now tired from the unexpected and unplanned work of building the bridge, and has fallen behind schedule on the expedition…but is significantly less dead than Hiker 2.
Obviously in the seminar the “map” was a metaphor for a project plan. The story asks, what do you do when reality simply refuses to agree with your expectations?
Hiker 1 is intended to be the model of a thoughtful, practical, get-things-done project manager: face reality, understand the problem, figure out a fix, keep moving. Hiker 2 is intended to represent the myopic, stubborn, by-the-numbers manager who refuses to acknowledge what is otherwise completely obvious, with disastrous results.
Or looked at another way, Hiker 2 is supposed to be Tyrell Biggs, trying to stick to his plan even as he’s being punched in the face.
Schedules have two phases: first predictive, and then prescriptive.
We might think of a schedule as a map, too — but a map of time, rather than of geography.
And they share many similarities. Being that as it may, though, there is at least one key difference between them. I’ve long believed schedules have two phases: first predictive, and then prescriptive.
That is, let’s say we estimate that a given task will take a week to complete. With that entered into the schedule (predictive) it now becomes the box of time available for that task (prescriptive).6 In other words, the notion of “one week” transforms from “how long we think the task will take,” to “how long we have allocated” for it. If your guesses are good, this can work pretty well. Everybody benefits from some constraints, everybody benefits from transparent expectations, and this sort of timeboxing can create both.
That can’t really be true of a map of geography: the map is awfully unlikely to ever be prescriptive in any meaningful way.7 You won’t ever be able to just force that river to not be there, even while you may in fact be able to force a task to be done on time. (Though it probably won’t be pretty. Ask me how I know.)
Still, though, even a schedule can only be so prescriptive.
Sometimes estimates are just wrong. Sometimes things just take longer than it seems they should.
And sometimes predictions are made a little, ahem, optimistic, to get through that next greenlight review, and thus lack prescriptive realism.
As with any other kind of map — or any kind of plan at all — a schedule is exactly as useful as the ability to ignore it when the time comes.
The best laid plans, etc.
Okay, so plans are useless. Why bother making them in the first place? Like the poor little mouse simply trying to set up for winter in Burns’ poem, are we just bound to get some farmer’s proverbial plough through our allegorical nest anyway?
If we go back to Eisenhower’s 1957 mention of the worthlessness of plans, he addressed precisely this. The New York Times, reporting on a speech in which Eisenhower said it, wrote:
“‘Plans are worthless, but planning is everything,’ he said he had heard in the Army. In an emergency, he went on, the first thing to do is ‘to take all the plans off the top shelf and throw them out the window. But if you haven’t been planning you can’t start to work, intelligently at least,’ he said.” (ABB: emphasis mine.)
“Intelligently” seems like a good way to start to work! Whether you use the plans or not, having done the planning, you now have a baseline from which to start. Having thought through how things might go, you understand the parameters of the situation as they actually go much better than if you try to come in totally cold.
Will things go according to plan? They will not.
Will you have some framework in which to think about how things are going? Yeah! At least, hopefully!
You should have a much better chance of intelligently assessing the actual state of the situation than if you hadn’t done all that planning — the plans themselves be damned.
To illustrate, let’s go back to our allegorical hikers. At the risk of taking this silly little story way too seriously, let’s imagine that Hiker 1, having arrived safely, now thinks through how the map could have been so off. What went wrong?
It’s impossible to truly know just from the outcome, but we can examine some possibilities. For instance, could it have been that:
The hikers were actually lost but didn’t know it? That the reason they didn’t see the river on the map was because they weren’t actually where they thought they were relative to the map?
The landscape was more dynamic than expected? Maybe what looked like a river to our hikers was actually the result of recent heavy rain draining off the mountain, say. Or maybe the map was initially drawn in Autumn, and our hikers were here in Spring when the melting snowpack forms a river?
The map was just fundamentally wrong? Maybe it was wrong intentionally (someone hiding something?), or maybe the wrongness was due to lack of attention, or incompetence?
Any of these could be viable explanations. If Hiker 1 believes that future hikers might want to use the map — or indeed, if refining the map was actually the point of the expedition — it’s worth the time to figure out how to fix it.
Should Hiker 1 modify the map to add the river? Well, those possible scenarios above would actually suggest completely different courses of action.
If the map was wrong because previous cartographers were lazy or lacked skill, then sure, add the river. But if the hikers just weren’t where they thought they were, adding the river would make the map less accurate. And if in fact the river is not a permanent feature of the landscape, updating the map will simply change the way it is inaccurate, not make it more accurate.
It’s a real conundrum for the hiker…but not for us! Because look at all that analysis that’s been done! Look at all the new ways we’ve thought about the map, the river, the expedition itself.
If we are the hikers, and the map is our project plan (and oof, this poor little metaphor…), we now have a bunch of new perspectives and lenses with which to look at our progress, our direction, and our next steps.
We had to think through all these different contexts, puzzle out not just what was wrong (we knew that! A river where we didn’t expect one!) but why it might have been wrong. We had to think through what we were even trying to accomplish with the map in the first place!
This feedback loop is critical. Having modified plans is no more valuable than having the plans in the first place. But going through the effort to refine them is planning. Who knows what artifacts — besides the revised plans — might be created by that exercise?
One last point on this before the metaphor completely collapses under its own weight: maybe it’s not a metaphor at all.
I saw this story online and I almost hesitate to reference it — a person actually died. And I only know these few details about it, many other things may have been at play. But with respect, this sure looks like a pretty literal case of relying on a map to the exclusion of…well, any other information.
A lawsuit was filed against Google because the Maps app showed a viable route across a bridge that was actually washed out, and, following this map, a man drove off the bridge and drowned. Again, with all due respect to the deceased and his grieving family…that’s not how maps work.
The linked story says, reasonably enough (though without citation), “Drivers have grown reliant on GPS-based mapping services for navigation.”
I’m sure that’s true! But at some point the driver is…the driver, right? At some point, no matter how much you rely on the map, you actually have to drive the car.
This is a bit morbid, and we’ve gotten away from process management, I guess. But the resonance is eerie.
In my essay “But What If Earthquake?” I discussed the value of thinking through outlier contingencies. The point was not that you could ever have any chance of gaming out all the possible scenarios — and in fact, even trying to do so would be counterproductive, maybe paralyzing.
The point was that the process of thinking through these unlikely scenarios can be very valuable in understanding the project at hand in deeper, more thorough ways. Is it likely that Google Maps will send you over a washed-out bridge? No. Is having the possibility in mind enough to remind you to keep your eyes on the road? I mean…it seems like it might be.8
The temptation is real.
So nothing here is particularly new or insightful; I’m citing quotes ranging from 30 to over 150 years old. Hell, I was taught these principles in a management class twenty years ago, and they were old-hat then! I’ve heard the sentiment over and over ever since. Most managers I’ve talked to understand and agree with the basic concept.
So why point it out yet again? Because. We. Always. Forget.
The process of planning results in plans. It is so tempting to then think: I’ve spent so much time and energy making these plans, I’d better follow them! But those plans are the least valuable results of the process of planning, and blindly following them results in us swept away in a river or TKO’d in a barrage of fists.
Now, managing and leading creative teams, we don’t really face opponents as such.9 Usually there’s not a force working affirmatively to thwart us. We’re usually fighting against time, resources, creative inspiration — or the insufficient allocations of one or more of those. It’s not a battle, not literally.
Neither are we truly lost on a wooded mountainside, risking life and limb against uncaring nature. We’re much more likely to be blindsided by a team member’s sudden departure, or a competitor’s surprise product release, or our company being bought by private equity than we are to be swept away by a river.
In this way the sports, military, or cartographic analogies are just that: metaphors, which need to be used with care. But they can certainly be useful.
There’s one more of those people who’ve never been in my kitchen that I haven’t talked about yet. All the way back in 1941, pre-dating even Eisenhower’s quote, Winston Churchill wrote a version of this unparadoxical paradox.
He used it, in a military context, as a metaphor for creative endeavor. He wrote:
“Writing a book is not unlike building a house or planning a battle or painting a picture…the best generals are those who arrive at the results of planning without being tied to plans.”
I appreciate the nuance here of evaluating from the perspective of the outcome. Only by not being tied to plans can it seem as if you’d planned it all along. Being flexible, responsive, strategically clear, and tactically supple is the result of planning, not of plans. More like Tyson, less like Biggs.
I feel like over my career I’ve been constantly told — hell, I’ve even thought — “process is too stifling!” on one side, and “this is just chaos” on the other. Both might be true, but neither is right.
Poorly designed, maladroitly implemented, or disingenuous process management can certainly be stifling. And a lack of sufficient process management — or indeed a lack of enforcement of process management — will almost certainly result in chaos.
But good process management can cultivate creativity, support smart risk-taking, and result in a happier team making better stuff. There’s a lot to explore here.
Planning is one critical element of good process management, but the plans it produces are nearly useless. Except for getting through greenlight reviews.
Postlude
Okay, Mr. Smarty, if not plans, then what artifacts are produced by the process of planning that do help capture, record, and communicate those nuanced understandings of the project at hand? Well, that will be the subject of another (the next?) essay on process management. (Actually the next one will probably be on the welcome inevitability of “process,” which I suppose should have been first…but here we are.)
Well, Tyson maybe a little more the latter than the former. But the point stands.
Those contemporary references just keep flowing. Certified fresh!
And arguably the last Republican president who wasn’t a buffoon or a criminal (or both…).
By the way, the von Moltke family is fascinating. Helmuth here was an important military leader. His son — known as “Moltke the Younger,” as well he might be — was the head of the German military at the dawn of WWI. And his great-grandnephew was executed by the Nazis for actively working to thwart them in WWII. Wild stuff.
It’s boxing, but with time. Timeboxing!
A civil engineer might disagree, but at some point we’ve really beaten this metaphor truly to death.
Again, I mean no disrespect here, and I’m truly sorry for the loss of life. But damn.
Though, yeah, sometimes it feels like we do…