on window shopping
a couple of my friends and i were reflecting on a tendency we noted a couple of people we’ve worked with had — we realized a lot of this was born from a fairly recent transition to management from IC, and a specific skillset around ownership that got lost in the mix on that path.
when you’re an IC, pointing out problems and things around you that are going wrong can be a pretty valuable skill. you get better at thinking outside of yourself, escalating things that you think your manager should focus on, and highlighting things that you feel like should or could be going better. getting good at this can become a fast track to moving from IC → management.
and that’s because once you step into leadership, this quality becomes more important than ever. you want to be able to have your pulse on a team and anything that is going wrong as quickly as possible. you should have a great pulse on the product, processes, and people in a way that allows you to spot things that feel off and act on them as quickly as possible. you kind of want to hone your intuition that way, where you can “smell” something is off before it festers.
there’s a pretty common way this trait goes wrong, though, that i feel like people fall into more often than we realize. what was a superpower can quickly become something that rots when left out, untamed: it can quickly become “window shopping”.
window shopping (
pointing out a bunch of stuff that is not going well, feeling good about doing that, and then walking away from the problem.
when you’re a leader who starts window shopping, one of the worst side effects that happens is you instantly feel wildly productive. you’re pointing out a bunch of stuff that should be better! here’s 10 things that are going wrong! but this is… not your job (anymore). it might have been your job when you were an IC — just escalating problems — but it is very much not your job anymore. your job is now to also solve, fix, build, and inspire.
and if you’re not a window shopper yourself, i know you’ve seen one before — in the person in a meeting who is telling you 100 reasons why something won’t work. or the one who is raising a serious team problem without a single idea of how things could be better. or someone who jumps in to critique a document or design 100 times before offering a single productive solution.
window shoppers are often born from the ICs who never understood how to turn the superpower of problem hunting into the necessary evolution of solution pairing. problem hunting gets easy, it had a positive feedback loop (“thanks for pointing that out!”), and skepticism is a muscle that needs no exercise to build.
the most obvious tip for dealing with window shoppers is to nip it in the bud, ASAP — to pair them quickly with the task of figuring it out from there. (“thanks for raising this, can you drive it from here?”) the harder task, though, is recognizing it’s happening, and spotting them in the first place. i think it’s a fairly easy tendency to coach out of people, but its critical to do so early. a few loud window shoppers can slow your team down in ways you may not be able to point at because of how well they disguise themselves as productive.
the reason i think its so critical is because my theory is that there’s a collective consciousness to optimism, and a measured discipline to building it in teams. (i always imagine skepticism like a weed that can grow quickly in a garden left alone, that leaders have to cull with constant vigilance)
besides — window shopping is no fun, anyway :)