Stretch Goals are Killing Your Team

Jake Wilder
5 min readFeb 16, 2022

It’s Time to Stop Already


“A real leader can somehow get us to do certain things that deep down we think are good and want to be able to do but usually can’t get ourselves to do on our own,” wrote David Foster Wallace. There are few better definitions of leadership than helping those around you to achieve more. It’s the core responsibility of managers everywhere. So, it shouldn’t be surprising that most managers find a way to screw it up.

Somewhere along the way, management got the idea that we could encourage people to perform better by giving them ridiculous objectives. It makes some intuitive sense. We figure that even if people fall short, they’ll be further along than if they settled for a lower goal. Yet this ignores how human behavior actually works.

I’ve done this myself. I’ve signed people up for stretch goals hoping it would motivate them to deliver major improvements. Then I watched as they became so discouraged that they gave up and consigned themselves to defeat. Or they just assumed that I was an idiot and had no grasp on reality. Either way, nothing much got done.

Most people aren’t motivated by a ridiculous challenge. They only see the futility of trying to play a game they can’t win. No one plays that game for long. And they certainly don’t give it their best effort.

Rule 1: People won’t play a game they can’t win.

When people face a problem they can’t solve, they freeze up. That’s why the first step in tackling any problem is breaking it down into manageable actions. It gives people the confidence they need to start. It gives them a direction even if they can’t see the destination.

The problem with unrealistic goals is that the destination is never within reach. While most people are willing to push themselves for a challenge, they want to know that their efforts are going toward something meaningful. Just as you wouldn’t invest in a stock with no potential for return, people won’t invest their time and energy into a project that has no chance of success.

Rule 2: If people can’t see a way to achieve a goal, they’re unlikely to even start.

We’re motivated by progress and recognition. Its why people write down already-completed items on their…



Jake Wilder

I don’t know where I’m going. But at least I know how to get there.