The Promise You Made When Nobody Was Buying

Picture a meeting in late 2014. The Milwaukee Brewers have just finished a season-ending collapse, and the fans are discouraged. Somebody needs a way to sell tickets. The idea that wins is a $1,000 “Timeless Ticket,” limited to 1,000 buyers, good for any future game, including playoff and World Series games, with the best seats available.

It probably looked like the safest promise in the building. A World Series was the last thing anybody in that room had to plan for. Sales started slow, and the team made the offer better.

This year the Brewers swept the Dodgers and reached their first World Series since 1982. According to Admired Leadership’s write-up of the story, fans who tried to redeem their Timeless Tickets were offered nosebleeds or standing room while better seats were on sale to the public, and they could not choose which World Series game they would see. The people who believed in the team when nobody else did found out what the promise was worth at the exact moment it mattered. The resentment made the news.

That is easy to see now, with the World Series on television. It was foreseeable in 2014 too, because the ticket named the World Series in its own terms, and someone only had to ask what it would cost on the night it was used. Most of us stress-test a decision against failure far more often than against winning, and the promises we make in a bad year come due in a good one.

A Promise Made in a Bad Year

Promises made in hard times feel free. The need is right in front of you, and the cost lives in a future that seems unlikely to arrive. Think of a lifetime deal for your first hundred customers, founding-member pricing, or a line on a sales call like “we will always handle that for you.” Each one buys something real today with money that only gets spent if things go well. By a promise I mean anything you said or wrote that someone else is entitled to plan around.

Failure planning is the default for a simple reason. Failure is what you are afraid of in a bad year, so that is where your imagination goes. You ask what happens if nobody buys or the money runs out. Those are good questions. They also leave out the scenario where every promise you made gets used at once.

In that 2014 room, nobody had to argue for the ticket, because the World Series was nobody’s problem. When the upside of a promise is so far away that no one owns it, nobody owns its cost either.

A bold offer in a bad year can be the right call. It can keep a company alive long enough to have a good year, and the Brewers needed to sell tickets. Where it goes wrong is making the offer without ever asking what it costs if things go right. That question belongs to anyone who makes a promise other people will plan around, whether it is a CEO approving a promotion or a salesperson on a call.

Nobody Rents the Presses in Winter

The Greeks have an old story about forethought aimed at a good year, and Aristotle tells it in the first book of the Politics.

People mocked Thales of Miletus for being poor, as if his poverty proved philosophy was useless. Reading the stars, Thales expected a large olive harvest. While it was still winter, he put small deposits on every olive press in Miletus and Chios. He got them cheap, because nobody bid against him. When the harvest came and everyone needed a press at the same time, he rented them out on his own terms and made a lot of money.

While every press owner in Miletus planned around a normal year, Thales planned around a big one, and when the big year came he was the only person ready for it. Aristotle tells the story to show that a philosopher could get rich if he wanted to. For a leader the lesson is narrower and more useful. The same forethought you spend on a bad harvest can be pointed at a good one, and it rarely is. Thales aimed that forethought at profiting from a good year, and the Brewers needed it for keeping their word in one.

The Greek word for that kind of thinking ahead is pronoia. Later the Stoics used it for divine providence, and today it is mostly known as the opposite of paranoia. In ordinary Greek it meant forethought, the care you take before something happens. I have written before that providence is not passive. Forethought is the active half of it, and it has to include the outcome you are hoping for.

The Brewers’ promise sat quiet for years. A promise made in a bad year holds up fine on the day you make it. Every good season after that makes it more expensive, and nobody reprices it, because nothing has gone wrong yet.

Unintended Consequences Arrive on the Best Day

Hesiod tells the other half in Works and Days. Prometheus, whose name means forethought, warned his brother Epimetheus never to accept a gift from Zeus and to send it back if one came. The gift came in the form of Pandora, and Epimetheus took her. Hesiod says he understood only after the harm was already his. Epimetheus means afterthought.

Plenty of leaders run on Epimetheus’s schedule. They plan in a bad year and think about the good year only once it arrives. By then the decision has already been made, and the only choice left is who absorbs the cost. That cost belongs to whoever made the promise. If honoring it means giving up seats you could have sold to the public, you give them up, because the people who believed you first never agreed to carry your mistake.

When success breaks a promise, the damage lands in a predictable place. The people holding the early promises are the ones who said yes first, and they try to redeem them on your best day, when everyone else is showing up too. Success also draws attention, so the break happens in public. That is how a problem a refund could have fixed in an empty stadium becomes a story people repeat for years.

You do not need a baseball team to see this. It shows up all over software:

An internal agent pilot works so well that every team wants it by Friday, and nobody planned for who supports it or who pays for the usage.

A free tier goes viral, and the costs that were rounding errors at a thousand users eat the margin at a hundred thousand. Somewhere in the sales history is an early customer who was told “unlimited” on a call, and the contract never said otherwise.

In each case the plan worked, and the promise attached to it was never tested against the plan working.

How to Stress-Test a Decision for Success

Admired Leadership’s write-up of the Brewers story argues that a plan is incomplete until it has been tested against success, and it lists three habits that would have caught the problem: assign the dissent, ask the people with the least to gain, and test against success as deliberately as against failure. Here is how I would put them to work, with a few additions.

Run the preparade next to the premortem. Gary Klein’s premortem, which Daniel Kahneman made famous in Thinking, Fast and Slow, asks a group to imagine it is a year later, the plan was carried out, and the result was a disaster, then write the history of that disaster. It works because it makes doubt legitimate. Chip and Dan Heath added the missing half in Decisive and called it the preparade: imagine the plan was a huge success and ask whether you are ready for it. Do both, in the same meeting, with the same seriousness.

Assign the dissent. Inviting objections is weaker than assigning them. Name a person whose job is to break the plan if it works, and make it clear that finding the problem is the job, so nobody reads it as disloyalty. The people who proposed the plan are the worst candidates, because they want it to go well. When the boss has already spoken in favor of the plan, the room will be slow to break it unless someone has been told to.

Ask the people with the least to gain. The people closest to a decision are usually the most invested in it working, or the most afraid to say it will not. Go find the people who will be most inconvenienced if it succeeds: support, finance, the on-call rotation, your earliest customers. Ask each of them one question. If this works three times better than we expect, what lands on you?

Hand the model the win. Give the model your plan and ask it to write the story of the plan working three times better than forecast. Then ask it to list who gets hurt, what breaks first, and which promise fails under the load. It takes a few minutes, and the model has no stake in the plan going well and no fear of the person who proposed it. You still decide what to do with the list, but you will have one before the first customer redeems anything.

Write the promise down with its limits. A promise that lives in a sales call or someone’s memory cannot be tested. Put it where it can be read and changed: the pricing page, the contract, the entitlement code. Say what it covers and what happens under heavy demand. This is the part of the system that has to stay in the harness, because a customer can hold you to it.

Reprice at every stage of success. Each time the plan crosses a growth line, such as ten times the users or a playoff run, reread every promise it made in the bad year. The Brewers had years of good seasons to notice that the Timeless Ticket was getting more expensive to honor.

Final Thoughts

Thinking ahead only about failure is half of forethought. It protects you from the bad year and leaves you exposed in the good one, and the good year is when the exposure costs the most, because more people are watching and more people believed you.

The fans who bought a Timeless Ticket in 2014 were betting on the team when it was hardest to. Those are the people a leader most needs to keep faith with. They found out what the promise was worth on the best night the franchise had seen in more than forty years. What you owe them does not depend on whether a reporter is watching. The news coverage shows what breaking the promise cost, and the reason to keep it is that they trusted you when trusting you cost them something.

Whether the good year comes is outside your control, but what you promise before it and how ready you are when it arrives are yours to decide. Every promise you make when nobody is buying will be kept or broken when everybody is, and the time to settle which is while the promise is still cheap to fix.

If you want to lead with the kind of forethought that holds up when things go right, MasteryLab is where that work happens.

FAQ

How do you stress-test a decision for success?

Imagine it is a year from now and the decision worked far better than you forecast. Write a short history of that year, then list who got hurt, what broke, and which promise failed first. Give one person the job of breaking the plan if it works, and ask the people with the least to gain from it, like support, finance, on-call, and your earliest customers.

What is a preparade?

A preparade is the opposite of a premortem, described by Chip and Dan Heath in Decisive. Instead of imagining the decision failed, you imagine it succeeded beyond expectations and ask whether you are ready for that. It catches the problems that only show up when demand, attention, or usage arrive faster than planned.

What are the unintended consequences of success?

Success raises the cost of every promise made before it. Unlimited plans get used, lifetime deals get redeemed, and pilots that work get demanded by every team at once. The damage usually lands on the people who believed first, at the moment you most want their goodwill, which is why it turns into a story people repeat.

What does pronoia mean?

pronoia is the Greek word for forethought, the care you take before an event. The Stoics later used it for divine providence, and the modern sense is the opposite of paranoia. In everyday Greek it meant thinking ahead about what is coming, which for a leader includes the good outcome as well as the bad one.