Jason Shah: evaluation

Transcript context

…So, you touched on the skill of pushing back on a founder or CEO, and I know that's something you're really good at. I've seen you do this. I'm curious what you've learned about how to effectively do that as a PM at a company pushing back on a CEO or founder when you disagree. I mean, I think this is one of... I actually think it's one of the most misunderstood terms in a sense because I think language like we were talking about earlier is so important, and yet what you call something ends up defining I think 90% of what people understand about a concept, right? And so, pushback is, I couldn't imagine a word more viscerally that makes you feel like you're sort physically going against what somebody else wants, and it gears people into a mindset of then, well, how should I push back. It starts from a place of I need to disagree, I need to say no. It's a very negative mindset, purely based on the word that has come to label a behavior that alternatively could be about how do I shift the direction on something, or how do I help the business actually succeed when I disagree with somebody about something, and that's a very different mindset. And so, the two things that I've seen be most successful would be, I think number one is actually understanding what a goal is or what somebody's kind of issue is with something, and then actually aligning those things in some way. So, in coming back to Airbnb, I remember Airbnb had bought a company, Luxury Retreats. There was a goal to integrate that business and that product into the full Airbnb suite, and there was a lot of potential with that, but I remember that there was part of the product experience that was oriented around chatting with somebody and the idea that the business had had a very large team of wonderful people who helped you as concierges basically for your trip, and so, this was a team that I was on that, to be honest, had fairly low morale. It's always difficult to integrate an acquisition with a company, especially when we were based in different places, et cetera. I remember hearing from a leader who had been at Airbnb for a while who's very effective at persuading senior leadership, and they understood why this was a problem because this chat product was growing in complexity. You'd have to build all these features into it, and nobody could successfully shift the direction, and as a result, it was just this... It was a mess as a result, and there was very low morale because we were taking on too much scope, people weren't sure it was the right product, it was being built up as one giant launch as opposed to an iterative thing. And what was really interesting was that this leader was very effective at understanding that the goal wasn't about building a bunch of features. It was about, as often discussed at Airbnb, a magical experience. And so, when we took a step back, it was reimagined as trip designers, not concierges, and their goal was to design your trip, and part of that meant a very elegant, simple chat experience so that you could have a efficient, fast, positive experience with that trip designer and move on. and their goal was to design your trip, and part of that meant a very elegant, simple chat experience so that you could have a efficient, fast, positive experience with that trip designer and move on. And it shifted the pushback of like, "We can't build this thing, it's too many features, we don't have enough time, we don't have enough resources" to, "Oh, we all want a really elegant, really smooth, slick experience for our customers. How do we do that? What's a trip design or a new concept that is actually going to elevate things? We're not telling you we want a payback scope. We're not saying we want to settle for less. We're actually just not only going to call it something different, but also envision a simpler experience which is more elegant. It's more on brand with luxury." Boom, all of a sudden, everybody gets what they want. It's a better customer experience, less scope, and it wasn't about saying no. It was about understanding what we're all actually sharing as a goal which was a great simple customer experience and then actually building that. So, I saw that to be really effective and I think that that's something I try to bring into my career. I have a couple other examples if it's useful, but that was a big one that I learned from Airbnb.…

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