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Published · transcript-backedMatt MacInnis: preference
28 Dec 2025 Lenny's Podcast 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)
“" What we missed was there was a fucking feature flag, a fucking feature flag. And I'm not allowed to say feature flag without fucking in front of it because feature flags are the bane of my existence and the worst things in the world that constantly cause problems.”
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- Speaker
- Matt MacInnis
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- preference
- Recorded
- 28 Dec 2025
- Publisher
- Lenny's Podcast
Transcript context
…A meme, you might say. Yeah, well, sure, a meme. A meme is actually a good example of this in common culture. In pop culture. I think it's why, when people come to the table with ideas from the outside, I welcome those outside ideas. But the first thing I ask the person to do is to tell me what they mean without using those words. So when someone comes in and says, "Hey, I want to do this thing on strategy." I'm like, "Cool. Tell me what you mean without using the word strategy." And it forces them to break it down into its constituent parts. And if they can articulate it clearly without using that word, I know that they know what they're talking about. And if they just fumble around with the word strategy again, I'm like, "Okay, you actually haven't thought this through." So with the PQL, with the product quality list, it's like I could come up with some generic term for this, but I really want a new joiner at the company to understand that this is an idiosyncratic thing to Rippling. This is unique to us. You want to understand this thing. I also want it to become a component of common parlance in the day-to-day work of the product management and engineering teams. So PQL, as cheeky or silly as it sounds, was deliberately sort of angular or stood out as a vessel I could fill with a particular meaning, and so we have a product quality list. And the product quality list is lightweight in the sense that it just articulates in the simplest ways the standards we want you to meet when you ship a product. It doesn't apply to every product, not every line applies to every product, but it's comprehensive and it provides me with a framework for iterating over time as we learn. So just yesterday, we shipped the product to Parker. This is part of our process. When we ship a new product, it goes to Parker, who is the big admin for Rippling at Rippling. If you're not aware, Parker is the sole payroll administrator for Rippling for all 5,200 employees. He personally runs payroll always, there is no exception, for all 5,200 people. He does complain about it sometimes, but it's a remarkable achievement for the software and perhaps for him. So he also installs any new app that we're going to install for ourselves because we dog food the hell out of everything we build. Yesterday, he goes to install this new application. We're about to ship a new app for feedback, allowing people to give one another feedback on their companies. And he installs it and he goes in and it dumps them onto an empty screen. And he's like, "What the fuck is this? What is this? What's going on? Hey, wow, talk about fail." So I chop another one of my fingers off, I'm down to nine. And I'm like, "Well, what did we miss? " What we missed was there was a fucking feature flag, a fucking feature flag. And I'm not allowed to say feature flag without fucking in front of it because feature flags are the bane of my existence and the worst things in the world that constantly cause problems. eature flag. And I'm not allowed to say feature flag without fucking in front of it because feature flags are the bane of my existence and the worst things in the world that constantly cause problems. Engineers put one in temporarily and forget about it. It's like shims if you're building a house and the general contractor puts little shims in places and then forgets that they put the shims there and then builds a wall over them and eventually the shim fails and all of a sudden your door doesn't fit. Feature flags are super dangerous and need to be managed carefully, so fucking feature flags. Anyway, we had one. Parker installs it, they forgot to disable the feature flag. He gets a blank screen when he installs the application. What did I do? My reaction was, "Ugh." Go back to the team, give them direct feedback, tell them not to make that mistake again. But also ask the question, "How do we miss this in the factory inspection process?" And the answer is we didn't have any line item in the PQL for feature flags. So I added a line to the fucking PQL that said, "You are allowed to have one feature flag that governs your entire product at ship." It's an extreme standard that might not be achievable, but it's the standard we aspire to. This framework, the PQL, given these lightweight checklists, iterated on consistently in response to everything we learn as we go, constitutes a very nice lightweight way to lower the beta of the system with hopefully only a modicum of negative impact on the alpha for how we build product. You asked me a very simple question, I gave you a very long-winded answer, but these frameworks help me design systems that scale across one going to 2,000 technical workers.…
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