Should I ask for more? Three clues you might want to negotiate

One of the toughest negotiation challenges is deciding whether to negotiate at all—whether to settle for a particular portion of our own lot or launch into a negotiation to obtain more. Should I press the car dealer for a bigger discount, my colleague for an alternate meeting time, or my kids to try harder on their math homework?

In my never-ending quest to make life negotiable, though, let me offer three simple clues that, at least in combination, suggest it might be worth negotiating rather than settling.

You might want to consider negotiating if:

  1. The current outcome stinks: Most obviously, a negotiation might be warranted if you’re exasperated with the current situation. You’re peeved at the car dealer’s exorbitant offer. Your colleague’s refusal to do their job sends smoke out your ears. If the current arrangement stinks, you might consider negotiating. Importantly, though, this rule should not prompt you to negotiate everything. If you’re just a little bit inconvenienced by the current situation, you should at least check the remaining criteria before negotiating, lest you turn into one of those people who negotiates everything and thus alienates everyone.
  2. You don’t know the other side’s preferences: Assuming you’re dissatisfied with the current arrangement and have an alternative arrangement in mind, you should consider whether you have any idea how your counterpart would react to the alternative. Sometimes, we know well enough: We all know the car dealer would resist a further discount and our coworker would resist any task requiring even a modicum of effort. But in many of life’s negotiable situations, we actually have no clue: We’d really prefer to meet tomorrow but don’t know the other person’s availability. We’d really prefer our favorite restaurant to another night of meatloaf, but we haven’t assessed our spouse’s thoughts on dining out. If you’re dissatisfied with the status quo and don’t know your counterpart’s feelings about the alternative, you might consider negotiating.
  3. The costs of negotiation are low: Sometimes, the costs of further negotiations are extraordinary. As a totally random and made-up example, another day of pointlessly stonewalling will cost 800,000 employees and legions of contractors another round of paychecks and possibly send the U.S economy to the brink of recession. But in many of our more mundane situations, a bit more negotiating costs us nothing in money and a negligible amount of time. Is it really so costly to give the other contractor one more day to reply to our email, or visit the other Chevy dealer down the road? In comparison to the price of whatever we’re buying, probably not.

Ultimately, deciding whether to negotiate versus sit on our laurels requires a great deal of judgment. But hopefully these three clues help you home in on the situations most rife for a deal.