Why Ignoring the Status Quo Led to a Radical Shift in Project Management at Pinterest

Yeah, um, So, uh, I took a, a, uh, so I have a bunch of people that report to me, um. One of them came to me with some, some pre-existing projects. She owned subsites as a portfolio. Subsites is everything on Pinterest that isn't Pinterest, so jobs.pinterest.com, about.pinterest.com, etc. Um, this was a stupid giant waste of her time because we were undervaluing her. So, uh, when I say it was a stupid giant waste of her time, she came to my team as a contractor who was paid the TPM1 functionally, um, and I don't know how familiar you are with TPM1, Brandon are fairly familiar, But um that's a profession that really shouldn't exist because it's saying simultaneously you're the adult in the room but require lots of supervision. Which doesn't work. So this person came to my team in a somewhat odd position. Uh, and I said, OK, this is a problem. Like there, there's something wrong here, right? You own the sub sites portfolio. What developers do you have on it? Oh, we have, you know, one full-time and two contracts, um. The ask forgiveness versus seek permission is I said to her, I don't want you to produce a 2020 plan for this because this was in 2019. I don't want you to produce a 2020 plan for this area. I want you to produce a plan for why we no longer do this job. Um, OK, because our current system is unsustainable. I want you to produce a plan for not this, right? The only thing that's not an option is what we're currently doing because this is dumb. Here's why it's dumb, um, and she and I dug into that a little bit, and she said, but I'm supposed to produce like a plan and some artifacts and some explanations, and I said, yeah, they'll get over that later. Um, and so a month later when my lead came to me and said, hey, what's our plan for subsets? I said, giving it away, and he went, wait. Um, and so they ask forgiveness versus seek permission portion was to say, Um, we need to light this particular Viking ship on fire and give it to IT because it's a sustained responsibility, uh, not an active area of active development. We shouldn't be spending Erin on it. Incidentally, I've already transitioned her to business growth and she's already doing a bunch of work over there, so I hope you don't mind that choice.

Uh, my lead and additionally the existing, this is where we get into organizational structure a little bit. I had to sell it to my lead. I had to sell it to the person who the developers sat under because I managed TPMs, not devs, um, and then I had to sell it to the head of engineering and the head of IT because I was basically taking a million dollars line item out of the head of engineering's budget and giving it to the head of IT.

Absolutely. Um, uh, here's the problem with subsites. So, subsites are the way that 20% of people experience Pinterest for the first time. So, 80% come in through the product, 20% come in through something else, whether it's about, whether it's investors, whether it's jobs, whatever. Um, you can make that a very powerful brand asset. Um, we as Pinterest have chosen not to. If you're not going to make it a very powerful brand asset, you don't take full-time developers and link them along on a Drupal stack that's going to cost you more money in the future than it does today. So I say Drupal stack. Yes, yes, I really did say Drupal, um, and we were never going to spend the time, meaning we product and we're never going to spend the time to migrate it to WordPress or something better than that. Yes, it's really on Drupal 7 actually, um. So there were two valid paths. My role was to force us off the invalid one. It would have been perfectly valid to say, let's fully staff this and make it a product and give it to PMM and make it a focus of brand and like make it a first class experience. It would have also been perfectly valid, and this is the choice we made, to say let's give it to IT, make it sustained engineering, and migrate it to WordPress or some more mobile platform. What we were doing instead was limp it along on Drupal. Um, and that was the wrong answer. It needed to be at 0 engineers or 5, and it was instead at like 1.5. Got

But specifically the ask forgiveness portion was, I'm reallocating my resources away from this because it doesn't make business sense. Your choice is either to give me 4 more or to take away the one I have.