“What’s the worst that can happen?” A simple question to make life negotiable

The situation’s more complicated, but I’ll first state it simply:

If I had to pick just one way that people go wrong in negotiations, it’s that they don’t negotiate. Facing a dissatisfactory situation, they just live with it. And if I had to pick just one reason that people live with it, it’s that they don’t ask a simple but immensely powerful question of themselves: “What’s the worst that can happen?” By asking that one simple question routinely, I think you’ll find your life becoming more negotiable.

Now the more complicated version: When we encounter crummy situations, we can’t always negotiate our way out of them. In particular, we’re sometimes stuck with a situation no one else can control—a difficult past, a chronic disease, weeks of icy rain in Maryland. But other times, we’re stuck with a situation another person could resolve: A crummy schedule the boss could resolve with flexible hours, a ridiculous price the dealer could resolve with a discount, a relative’s annoying habit they could resolve by just stopping it (!).

In the former situations, negotiation’s not going to get us far (though this post might help). But in the latter, the question we need to—and often don’t—ask ourselves is this: “What’s the worst that can happen?” For example, will the request of our boss really lead her to fire us, will the ask of the car dealer really cause him to kick us out of the dealer, will the huddle with the relative really drive her to the eggnog, never to utter our name again?

If the answer to such questions is yes, then kudos to us for living with it. The costs of negotiation are just too high.

But here’s the problem: Many of us don’t know the answer since we never ask the question. Instead, we implicitly equate the worst that can happen with the worst outcome in the world. But how accurate is that assumption? Will our boss really fire us for requesting some flexibility? Will the car dealer really forgo our business entirely? Will our family member really slosh away our entire relationship past and present in the eggnog? If we never ask the question, we never know the answer.

In sum, by never asking “What’s the worst that could happen?”, we often vastly overestimate the costs of negotiation, which makes any benefits pale in comparison—which makes us suffer through a wide array of solvable situations. It’s an exceedingly common situation, and thus an exceedingly common mistake. Consider some other common examples:

  • Fees from service providers: What’s the worst that could happen if we ask the bank or the airline or the cable company to waive the fee? They won’t, in which case we’re right back where we began. But they’re not going to send us to a different bank or different airline or different cable company unless they’re exceedingly irrational (no comment). And they might just make a “one-time exception.”
  • Creative ideas in meetings: What’s the worst that could happen if we raise a new and creative and slightly oddball idea in a meeting? Generally, people will ignore it and move on. But unless we’ve developed a thorough reputation for irrelevance or insanity, they won’t immediately put our career on the slow-tack. And they might just consider what we said.
  • Family preferences: What’s the worst that could happen if we suggest a different restaurant or alternative family vacation? They’ll decide against us, and then we’re stuck with the same Applebee’s or Disney getaway we were. But hey—maybe they’ll at least consider our dislike of overcooked burgers or overpriced opportunities to wait in line next time.

These are just a few of the innumerable situations where failing to ask what’s the worst that can happen leaves us with the worst that’s already happened. I’m certainly not saying that you always have the ability to ask, nor that you always should. But I’m certainly saying that when you do have the ability, you should always at least consider the worst-case.

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