Why every optimized plan needs an asterisk*

Every year, my wife and I go on a short weekend getaway with some of our university friends. Our friend group has stayed together for over a decade, and in that time, everyone got married (or is still procrastinating on the wedding itself), and most of us became parents. Despite all these life changes, our yearly trip has remained a sacred tradition. And while we genuinely enjoy each other’s company and do most activities together, there’s a funny paradox: none of us would ever say, “This was the perfect weekend.”

Why? Because “perfect” means something different to everyone.

# What even is an Optimized Plan?

In any enterprise, we want to get the most out of our systems, people, and processes. “Optimized” then sounds like we’re squeezing the most juice out of a lemon. But here’s the twist: not everyone likes lemon juice. In the context of our trip, no matter how much we like each other, we all need different things. I might have had a busy conference week, so all I want is a good book and a sofa, while my desk-job friend Peter might dream of a very long walk in the forest.

For companies, this dynamic is very prevalent as well. The manager might want to schedule weekend shifts to boost revenue. Employees value their time off. Meanwhile, the sustainability officer wants to minimize travel, and HR wants everyone to stay sane and productive.

Given this dynamic, we should probably put an * next to the word “optimized”. Because while it might be optimized, the real question remains: *“Optimized for what?” Ask ten stakeholders and you’ll get twelve answers. That’s why I often say the hardest part of optimization isn’t the math: it’s stakeholder management. Or, put differently: figuring out what you’re actually optimizing for in the first place.

So my definition?: “An optimized plan is the best plan to achieve *, whatever * might be”.

# It’s a balancing act

In academia, optimization problems are often boiled down to one clean function: a single objective, well-defined constraints, a clear answer. On the outside, it’s quite a bit more chaotic (going on a holiday with 5 couples and 8+ kids is kind of chaotic).

Nobody is going to fight over the basic necessities for a plan: the hard constraints. In the context of our trip, those include beds to sleep in, ample parking space, some sort of a playground nearby and preferably bedrooms far enough away from the living room so the parents can have some fun after the kids are asleep, but close enough that the baby monitors still work.

In an enterprise, we take into account things like employee availability, contracts, delivery time windows, and many others. Nobody cares about “optimized” if these hard constraints are not met, as that would mean the schedule is infeasible.

Then we get to the other constraints, the softer things different stakeholders will disagree on. On our trip, these include things like “who is going to cook which meal?” and “what activities will we do?”

For enterprises, this is where there will be different views on “optimality”. These differences could be profit-based, focus on employee happiness, support the company's “green” ambitions, or a mixed bag of all those and other priorities.

If it’s such a balancing act between all these different constraints… then how do we keep our balance?

# How to deal with this?

There are no silver bullets to deal with this, but there are a few good habits to adopt.

• Try to improve the status quo for everyone. Optimization is a team sport. If your model improves your bottom line but is much worse for the people executing it, you’ve just automated resentment. Employees might even full-on reject the optimized schedule, as your plan broke a hard constraint you didn’t account for: “acceptance by all stakeholders”. Plans that aren’t accepted are doomed to fail.
• Don’t expect stakeholders to know what they want. Most people only realize what matters after seeing a plan that ignores it. Treat feedback not as a failure, but as calibration. Give detailed information on why the plan is what it is and iterate on the weight given to each constraint. Do this often and recalibrate when the business demands require it.
• Build for adaptability. The “optimized” plan today might be obsolete tomorrow. Markets shift, regulations change, people leave, and new priorities emerge. Being able to adapt quickly isn’t just a nice-to-have, it’s essential.

# “Optimized” isn’t “Perfected”

In both business and friendship, there is no perfect plan. There are too many stakeholders for that with different concerns and priorities. There is no “one right answer”. The best we can really do is to find the trade-offs that lead to a better plan for everyone.

So the next time someone proudly announces they’ve got an “optimized plan,” don’t be distracted by the word. Ask them the only question that really matters: “Optimized for what?”