The Tyranny of the Perfect Plan
Planning is seductive. It's also necessary. But when we lean so hard into the plan, we seem to forget all the things we didn't think of, or could never possibly control.
How many of us have worked in those environments where the desire to create a perfectly correct plan seems to come at the expense of, at least starting to, (imperfectly) solve the problem?
Planning lures us in with its false promises: certainty, control and the comforting notion that we’ve thought of everything. We love plans because they also allow us to show our working like we were taught when tackling a tricky maths problem at school, also giving us the plausible deniability when things inevitably go wrong. “Ah, but it was a solid plan, we spent months on it” we can say, shrugging off the disaster as if a Gantt chart was ever going to defeat reality.
The truth is most plans fail. They’re kind of meant to make us prepared for as many of the implications of something as possible, not so much be the single correct answer that predicts the messy future of real life.
Plans are a bit like watching a nature documentary and thinking you know how to survive in the jungle. And to be fair, if you’ve watching a lot of Ray Mears or Bear Grylls, then the chances are you stand a better chance of surviving. However, it might go out the window when that snake or crocodile rears up from the undergrowth suddenly. Corporate planning experiences this challenge a lot as the customer suddenly demonstrates a pulse and an opinion the folks at head office didn’t put down on paper.
It’s cliche, and he may be an old man who just got beat up by some YouTuber but Mike Tyson was right when he said; “Everyone has a plan until they get punched in the face.” The market also turns out to be a heavyweight champ when it comes to landing haymakers on planning documents!
The worst bit of planning though, is how it breeds this weird strategic constipation. The owner of the plan all too often wants to be seen as ‘right’, losing sight of what the plan was actually for. By the time the team has dotted the last “i” and crossed the last “t,” the project is late, the window of opportunity is closing, and the world has changed. Even when the thing does get into the real world, the plan wasn’t as comprehensive has imagined, or too much detail was spent on things that didn’t matter so much, or something previously unimagined happened to change the context.
It’s like spending hours drafting the perfect best man speech, begging your mate to delay the wedding because you want to get the speech just right, only to turn up at the venue eighteen months later when the couple is arguing about the financial settlement in the divorce. Your world in the institutional bubble likely doesn’t move fast, but the one other people are living in might, so if you’re stuck perfecting your slide deck, you’re already losing out on life.
Be Brave, Take the Small Step
The solution isn’t to abolish planning entirely, this isn’t anarchy we’re advocating for. Winging it all the time is not an ideal strategy either. But, it’s about recognising that the best plans emerge from thinking a bit, then quickly doing, then thinking about that, and doing something again. Instead of sitting in endless meetings trying to blueprint perfection, ask this: What’s the smallest, cheapest step we can take today to learn something valuable?
Momentum doesn’t really come from giant leaps, but more from a series of connected, often small, deliberate moves that result in a big of a snowball effect. Because we did this little thing, this other thing came about. Release a prototype, test a pilot project, run a trial, tweak the trial, try it in another place, get asked why that trial thing isn’t available elsewhere…
Each small action teaches you something real. Maybe the market doesn’t want what you’re selling. Maybe they want it in a different colour. Maybe your idea is brilliant but your messaging stinks. Maybe the regulator says they like it and would like to help you work around the rulebook written before your idea existed? Maybe a competitor tests something completely different? A politician gets caught in a scandal and their replacement makes a splash with some new policy? Oil prices sky rocket. Some new consumer electronics device enters the market changing how companies access the market. A weird orange real estate guy cum reality TV star becomes president (again) …. These are the things you can’t learn in a spreadsheet.
And here’s the kicker: while change can be scary and resisted, people actually love movement. There’s an energy or a sense of purpose when something is happening that people feel part of. A half-baked idea in motion will attract allies, critics and customers. None of whom show up for the perfect plan collecting dust on a shelf!
Case in point: When Starbucks rolled out mobile ordering, it was a simple experiment to speed up service during peak hours. But they didn’t anticipate that customers would clog up smaller stores, creating bottlenecks and frustration. Instead of ditching the idea, they iterated. Today, mobile ordering generates billions in revenue and has become a cornerstone of their strategy, proof that small steps and learning through failure can drive big wins.
Or IKEA’s “pop-up” urban stores. IKEA has long been associated with sprawling suburban warehouses you drive to on the edge of town, but as more high rise apartment dwelling customers went car free cities, they needed to rethink their model. Instead of committing to massive urban outlets right away, they launched small-format pop-ups in cities like Paris, Toronto and Tokyo. These stores helped them test the demand, refine the inventory, figure out the supply chain implications and better understand city shoppers, all while keeping their core brand intact and still offering a cheap soft serve ice cream, hot dog or bag of frozen meatballs at the exit. Now, IKEA is rolling out urban stores globally, with far more confidence than if they’d tried to plan their way to perfection.
Contrast that with cities that spend a decade debating traffic congestion before doing exactly nothing. Or corporations where every “innovative” idea dies under the weight of a cost-benefit analysis spreadsheet. It’s not that they don’t have ideas—it’s that they’re too afraid to try them.
Don’t Let Zombies Take Over
Here’s the trap, though: once you’ve started doing, you must avoid the pitfall of the “zombie prototype.” Zombies are projects that should be dead, the prototypes or pilots that likely didn’t work, or need some investment to get to the next level, but nobody has the guts to boost them or bury them. These undead experiments shuffle along, consuming time, resources and morale, infecting the entire organisation with inertia.
The best organisations understand this. Amazon famously kills projects with ruthless efficiency. Jeff Bezos has said he encourages teams to experiment, but if an idea flops, they don’t drag it out. They learn what they can, shut it down and redirect the energy into the next experiment.
It’s a mindset that says, “Failure is fine, but stagnation is not”. And that’s the difference between healthy institutions and those slowly ossifying under the weight of their own indecision.
The outcome always trumps the process.
If there’s one bit of advice that I’d hope all teams and leaders tasked with improvement or innovation would take, it’s for them to get out of their own way and focus on the outcomes they want, not so much the process they’ve taken to get to the start line.
The perfect plan is riddled with errors, assumptions, guesses, or just options. It’s really about opening doors, and having a bit of an idea what might be behind them. If you like what’s through the door, you keep going, if the door leads to a dead end or a big scary monster, then it’s almost always an option to turn around and go back.
Creating gigantic plans, or worse, commissioning studies to set oneself up for a plan is a paralysis. Remember, each small step, each experiment, adds to the momentum by unlocking possibilities you never imagined at the start.
Let’s be honest, wouldn’t you rather be in the organisation trying things!? Making waves while there’s a parallel universe has a team locked in yet another planning meeting, talking about what slides and spreadsheets will be required for next month’s meeting?