Cool Boss Moves is a series where we share the tips, tricks, and strategies we stole from other great managers — or in this case, we make up ourselves.
This week: Give an important project to an underperformer
Andy: I’ve got one: give an important project to an underperformer.
Emma: Okay! But also: Yikes, wait, huh? I can get my head wrapped around it conceptually, but I’ve never tried it. I take it you have?
Andy: Yes, and to great effect! The underperformer did an awesome job. So great that they got off, and stayed off, their PIP. Another department sent them a gift basket. I felt like a genius. My boss was stunned.
Emma: I have so many questions! Can you set the scene for us? What was this project?
Andy: It was back when I was a Deputy Managing Editor at Groupon, and my team of 15 writers and editors were blasting out hundreds of deals every day. We had this one frequently recurring business with franchise locations all over the country and incredibly complicated terms. Every time that business had deals going live, we got it wrong. There would be tons of customer service refunds, lots of after-hours edits, a deeply unhappy client. The account managers thought my team was a bunch of clowns, the sales team was on the verge of losing the account. It was a total and extremely expensive mess.
I wanted to try having only one person work on this deal every time it came up, instead of randomly assigning someone from the queue like we did everything else. I thought if we could create an in-house expert who would learn this business inside and out, we might be able to finally nail it.
Emma: And you picked an underperformer to be your expert!
Emma: I’m trying to imagine what I would do in that situation, and I’m 99% sure I’d turn to one of my top performers. I can picture myself not trusting that an underperformer could hack it. I also think I’d have “saved” a “special project” like this for someone who was “ready” to go beyond their normal day-to-day. I think that’s a vestige of being a millennial worker bee. The work is the reward! Underperformers don’t get rewarded!
Andy: I hear you. I cut my teeth in that same system, and my instinct is also often: “Give the Big Project to our Top Performer who’s solved so many problems before!” I think we should of course reward great performance with interesting and career-forwarding projects (and more money and flexibility and and and).
I also think we do our teams a disservice if we load up the same few people with everything noteworthy and don’t let anyone else have a chance. The top performers get tired, and the rest of the team also gets tired — they’re never going to get anything new because we’ve already picked “the best people” to give it to. No one wins.
Emma: I really like that way of thinking about a team, as a living organism that acts and reacts in relation to each other, and not just a bunch of siloed individual contributors. Without that perspective, I think favoritism thrives. But I’m curious how you decided that this underperformer was a good candidate for this particular project. I doubt your advice is simply “put your worst person on the most high-stakes initiative.”
Andy: Lol no, not at all. Like we’ve talked about before, ability and performance aren’t the same thing, and the ability part needs to be there — you have to be able to envision them succeeding. I really thought this writer would be great at being our in-house expert: they were responsive, diligent, and knew how to follow a style guide. They weren’t on a PIP for making quality errors; rather they weren’t hitting their quota. I suspected malaise, and thought this was interesting and important enough offer to re-engage them.
Emma: Sort of like playing project matchmaker. Which means you need to understand the people on your team. If you had misdiagnosed why this person was underperforming — maybe they were overwhelmed instead of bored — I can imagine this test not being as much of a home run. You’d be throwing a complicated problem on someone who was burning out.
Andy: Which, to be fair, I have also done.
Emma: Lol, we’ll save that story a different newsletter.
Andy: The other thing that made this project a great fit for an underperformer was its stakes: important, but not mission critical. That gave both of us a lot of breathing room. If it failed, fine. It was an expensive issue, but compared to other problems, it wasn’t a priority. In fact, if I never fixed this issue, it’d be annoying to everyone, but it wouldn’t be surprising.
If it had been part of my KPIs or OKRs, I probably wouldn’t have put an underperformer on it. The honest truth is I’m not willing to risk my own success on an unlikely bet. At the time, I was operating in the same evaluative culture, so I definitely had my own individualistic concerns: my job, my future opportunities, my raises. It’s also worth saying that I was in good standing in my role. I had trust to spend. If I didn’t, my boss would have vetoed my brilliant idea instantly.
In this case, the payoff-price balance was perfect. Failing was expected. Success would be a Mighty Ducks miracle on ice. And it was. The writer hit all their quality and quantity benchmarks and got off their PIP. The late night edits stopped, the customer service fires were all put out, and the client was astounded. The account management team was throwing confetti. My boss couldn’t believe it. And, I no longer had an underperformer on my roster!
Emma: I have to imagine, too, that your relationship to this writer changed over the course of the project.
Andy: Absolutely. It’s so easy to have just one story we tell ourselves about the people on our teams, both high achievers and underperformers. So-and-so is a power player, this person over here is a liability who can’t handle the pressure, etc. Our brains love to categorize things into simple containers — but that’s not how people work. No one is always or permanently one thing.
Emma: It’s really cool to create the potential and possibility to change the narrative of anyone on your team, ideally for the better.
Andy: It’s also really nice to be able to tell your team honestly that, just because they’re on a PIP right now, they’re not doomed. For me, a PIP is more like a traffic report. It’s a clear statement of the current road conditions. It doesn’t mean they’re going to stay like that. My therapist has an embroidered pillow on her couch that says Change is possible, and I think in her line of work she has to believe that. As a manager, I have to believe that, too.