Toast VP of Product Maggie Crowley and Lenny Rachitsky discuss engineering failures and the hidden costs of legacy software rewrites.
Insight
Software teams should never attempt a side-by-side product rewrite, warns Maggie Crowley
“Just don't do it. Don't rewrite. If anyone ever tells you to do a rewrite, don't do it. A side-by-side rewrite. Nope.”
Insight
Crowley: Product strategy accounts for only 5% of a PM's job
“And strategy to me, and hopefully we'll talk about strategy in a bit, it's one tiny slice. You do a strategy, but it's five percent of the work that you do. Yes, it's important because you want to get your strategy right and you need to pick the right products…”
Insight
Product managers aren't great until they've shipped a bad product, says Crowley
“A question I ask in every product interview is what's the worst product you've ever shipped? And that's because I don't think you're a good PM if you haven't shipped something that's really shitty. Like, you just haven't had enough reps, you haven't done it en…”
Insight
Crowley: Staying multi-year at one company teaches PMs more than job-hopping
“I got to see two or three cycles of the same product, and that, I learned more from that than I did out of the, you know, year or so I spent doing other things each at a time, because you got to see the consequences of your decisions, and that's rare, and peop…”
Opinion
Crowley: Underrepresented PMs routinely get unhelpful feedback to be more strategic
“Another thing I hear, especially as you get further in your career, and unfortunately, if you're maybe an underrepresented person in tech, is that you need to be more strategic, and so that's feedback that almost always happens, especially if you're a woman in…”
Insight
Crowley: You are not a good PM until you ship something terrible
“I don't think you're a good PM if you haven't shipped something that's really shitty. Like, you just haven't had enough reps, you haven't done it enough time, like, and it, and it's not only that you've done it, but that you can admit it, and you know which on…”