Stretch assignments are one of the most powerful development tools a manager has. They’re also one of the most misused.
The Line Between Stretch and Stress
We have a hike nearby called the Manitou Incline. “Hike” is a generous word for it. It’s basically going straight up for over a mile, gaining roughly 2,000 feet of elevation. At some point on the trail, you’re not really hiking anymore. You’re pulling yourself up steps. Of course, there’s always some goofball who runs past you because they can actually run up the damn thing.
But it introduced me to the concept of a false peak. A false peak is that part of the Incline when you get to what you think is the top, only to realize you’re about 75% of the way there. You’ve got another quarter left. And at that point, you’re stuck, because you need to finish to get to the actual top and take the easy road back down on Barr Trail. It’s been years since I’ve done the Incline, but that false peak stuck with me.
As an individual contributor, I thought of that as what a stretch assignment was. You get to the top, you think you’re done, and then lo and behold, you’re not quite there. And it annoyed me. I found those types of stretch assignments, where you didn’t know where the end was, not very useful and not structured very well. I don’t like to play guessing games or gotcha games with people on my teams. I like for them to know where they stand, and false peaks don’t support that.
The Better Version: Try Before You Commit
But there are good uses of stretch assignments. Another way to think about them is as a trial before you commit.
You can try someone in a position and see how they do. For example, you can add responsibility that they normally wouldn’t have and see how they handle it before you commit to a permanent change. Team lead is a good example where you can see how somebody does being in charge before you’re committed to them managing a team.
My experience is 95% of the time, the people you’re trying out for team lead are really good choices. They are focused on what they can get done for the team. They take care of their own work. They’re looking to do better than just for themselves.
But in doing this over a long career, there’s that 5% who suddenly think, “I can tell the team to do whatever I want, but I don’t have to do it myself.” It’s rare, thankfully, but not unheard of. In this form of stretch assignment, you get to see how they treat it. And fundamentally, you’re not stuck with a bad manager if you end up in that 5%.
The Training Committee Trick
Another version I’ve used multiple times is putting together a training committee. Most organizations have training funds, but you get a mishmash of training requests over the course of a year. Some people don’t think about it. Some people think about it only a week before the training. Some people don’t think about the funds at all.
You try to find the people who are most likely to excel into management and you see if they want to be on the training committee. A committee is good because you put three people on it, which means no single person has to carry the load, so it spreads the workload.
Then you get to see which of them actually has the forethought to think about plans and a roadmap for training requests over the course of the year. The ones that can do that are your planners and potential future managers.
The other thing a training committee gets you is a limited budget. There’s only so much funding, which means somebody’s going to have to say no. You get to have the training committee say no and justify it instead of it going straight to you. If they pass everything off to you, they’re probably not going to be a good manager, because they don’t know how to say no even though the policy or funding situation is clear.
The trick is you get to try this all out before it’s truly consequential. This isn’t a client delivery, a late project, a hiring decision, or a performance problem. It’s a low-stakes environment to test high-stakes skills.
I like this type of stretch assignment. It’s valuable for the person to see what the work is actually like before being fully committed. And it’s valuable for you to test someone out before you’re fully committed to them stepping into the next level.
What Makes a Stretch Assignment Work
- Right-sized challenge. Stretch is 20% beyond current capability, not 200%.
- Clear guardrails. They know what decisions they can make and where they need to check in.
- Visible support. You’re not just available if they need you. You’re actively checking in.
- Permission to struggle. They know that difficulty is expected, not a sign of failure.
- A way out. If it’s truly not working, there’s a path to adjust without shame.
The goal isn’t to throw people in the deep end. It’s to let them learn to swim in water where they won’t drown.
See you next week!
-Frank
