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Paige Costello

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70
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2023-07-09
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2023-07-09
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  1. Think it's a real thing for mental health. I do think that having social casual relationships as well as more opportunities to talk strategy with people you're not forced into a meeting room with has been super beneficial. I can say that just today I was having lunch and sat down with my head of data science and we had an impromptu chat about how we review our experiments and how to evaluate whether we had ROI on learning, not just the metrics. And it was one of those things where if we had to schedule it, it might not have happened. And if it did happen, it would have been a couple weeks from now.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. And we're trying to, you know, like the next level of standing up during stand up. But it's kind of, I'm sure it's a shared experience for other people who are working in offices to get used to using the whiteboards again, to get used to standing up during your meetings. It's bizarre that we could lose a muscle that we had that was so innate so quickly. And I think even in the last month, I would say, and it's in June of 2023, there's more vibrancy in the office, more conversation, more casual someone eating alone at the cafeteria and someone sitting down next to them. So it didn't happen overnight.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. Took advantage of what's great about working together as teams. And so it's been the standard. So I would say what's unique about maybe Asana is we knew we would do that from the very beginning instead of hemming and hawing about would we be a remote workplace or not and what would that mean and how would we come together and how would we budget for it? We're like, nope, this is going to be an office-centric hybrid because we wanted to create spaces for people to work together and move quickly. It's been interesting watching people get back into the swing of things. It was not, even though we knew it didn't mean on day one, people were great at being in the office. People, you know, were taking stand ups, sitting down. Whereas before you would walk through our office and you could hear people at stand up because there were stand-up chants and people would be out on the floor. Now people are more likely to do their stand-up in a

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. Well, we were fully remote during the pandemic, and then we came back to the office in an office-centric hybrid format. So we're in the office Monday, Tuesday, Thursday, and then work from home mostly on Wednesdays and Fridays. And that dynamic has been designed from the start. We wanted to make sure that we.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. It depends. So it depends on the complexity of the work and it depends how much we want to talk about it. A lot of our crits happen in person on the design side. A lot of spec reviews are more asynchronous. And then we'll say, depending on the number of questions people have, we call a meeting. Otherwise, we do mostly async. But it's a mix. It really depends on the complexity and ambiguity of the solution and how much people have questions about asynchronously beforehand.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. The inflection points are Kickoff, which is that going broad, and then customer and direction selection. So this is both the target as well as of the 10,000 foot views of how you might pursue solving this problem, which path are you broadly going to take. And then going broad within that path on different concepts. And then there's a design concept review. And the product spec, then the full experience review or design crit of the end to end experience and launch. And so that launch review is often just, hey, here's the thing. Here's what we said. Here are the fast follows. Most of the time, by that time, it's already been dog-fitting internally for some time. And it's more of a formal, do we have the right metrics in place? Are we ready to ship?

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. It is, yeah, it's really important because then you also know what success looks like. Because if you pick your success metrics as using a feature, that's you're teaching to the test. It's not actually driving the outcome. So while our planning process is around effectively defining category and like how we win and making sure that customers receive certain benefits from using work management, the through line to the individual project that a team might be leading is they need to know who they're solving. And so it always starts with enough customer insight such that we can creatively do what they're trying to do, like really inventing on behalf of customers.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. The double diamond process that Asana effectively each of our typical reviews or artifacts sit at different inflection points on the double diamond. So we actually ask people to do a kickoff where they collect different information at different scales depending on the size of the problem and the ambiguity they're solving. Some people have already done enough customer selection and research that they're starting with what are the possible solutions to this problem and then they're bringing the spec and that's the narrowing alongside designs, et cetera. But it's really mapping our artifacts against this notion to make sure that the product thinking has that quality of decision making.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. So, you might be familiar with kind of lean startup concepts and double diamond as it relates to going broad and then going narrow. And so you go broad when you ask, like, what customer should I solve for? And then you pick one. And then that's the narrowing. And then you go abroad and you say, what are the problems this customer has? And you narrow and you say, this is the problem they have. And then you go broad and you say, what solution should we do to this? And then you go narrow and you say, this is the solution that we should start with. That process of going abroad and going narrow and going broad and going narrow forces people to get out of their opinion driven lands because so often we really want we need to be curious quantitatively and qualitatively about what we're doing and why and be more systematic and rigorous about getting there. And it doesn't take long, but it just like breaks the frame.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. The area that came to mind when you asked about one of our areas is something called coordinate. And their job is effectively making sure that the slice of a sauna helps teams work together is working effectively. And so that's projects and tasks and the data that you might put into tasks and all of the back and forth that is required when people use Asana for their core working team. Some of the metrics that they care about are like org paying weekly active users, as well as really thinking about healthy project use. So we make sure that we understand what does good look like and what is a dynamic that we want to be creating in terms of people getting real value from using the product. And we build that into our metrics to have as a guardrail to ensure that we're not driving one metric at the expense of people really.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. Not really. I mean, teams know approximately when are they expecting to do the work? But if you ask too much for a particular quarter or a particular week or date, people make strange choices about scope. And so really we align on what success looks like and the teams do their best job to ship as quickly as possible, as iteratively as possible. And we really encourage prototyping. So we added into our product process a notion that we might pivot or cut from stuff that we put on our roadmap because it felt like once it was on the roadmap, it had to be done. And that's just not smart.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. Yeah, absolutely. I think the more you try to do things in a joined up way where you have a single target customer with sales and marketing and you want to make sure that the impact of your releases hit their mark, the more it's important to reflect on it frequently and to be able to pivot quickly because our strategy, even when we think we have a two-year vision, something will change. And then we say, wow, we made so much faster progress on this than we thought. And we actually believe that there's a new opportunity or new technology that we should be leveraging. Let's go bigger on that. And so it reduces the feeling of churn and thrash. It makes us all more principled and it helps us just make sure we're making the best use of our teams.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. Thinking was more durable and problem focused so that our roadmaps were not about features, but we're instead about what was most meaningful to tackle for our business growth. And so that's a big thing that has changed the altitude of planning and how that nests. Another thing that has changed is the time horizon. So before we planned annually primarily, and now we plan every six months, but for a rolling 12 months. And so we have higher confidence in the immediate half, lower confidence in the following half. But we just plan every 12 months every six months because it gives our business more confidence in what's coming and a better opportunity to align our go-to-market and product planning.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. And the workflow pillar. And then within each of those, there are subgroups, and we call those areas. And each of those areas has a very specific target customer and problem space they're solving for. We've often also dialed up the clarity of the metric at that level. So while we have an R&D set of metrics, we have pillar metrics, we have

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. Yeah, absolutely. So when I said I'm responsible for that core product pillar, that's one pillar. But then there's also the adoption in enterprise scale pillar.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. I would talk a little bit about how we set strategy and our planning process and how that's changed in this time, as well as how we actually ship product has changed in this time on the planning front. We have really changed what altitudes we're planning at, the time horizon we're planning at, some of the inputs have gotten a lot more precise and opinionated. So for example, we have always had pillar plans and team plans, but maybe we didn't have an intermediary layer of like an area perspective. Well, what's an area perspective? Well, you know, as your organization grows, we've had to reorganize to create more agency and accountability close to teams that are focused on specific target customers and problems. So if you think about the way Asana is organized, we've got our R&D, the pillar structure, the areas within them, and then

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. Sounds like, yeah, there's another group that's focused on our process management that a lot of the core work and project management core is in my group. And then we have a growth and enterprise scale team.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. Yeah, absolutely. So I leave the product organization that's responsible for our desktop web and mobile apps at Asana. And the teams are composed of all the people in San Francisco and New York who are focused on creating clarity for individuals, teams, and organizations. And effectively, our goal is to help teams work together more efficiently and drive the outcomes they're going for. So you can think about the feature sets if you're an Asana user like goals, portfolios, projects, tasks, reporting, all of that. But really, we want to help people answer the question at work, who is doing what by when and why. So that notion of clarity of purpose, clarity of plan, progress, and responsibility are often so painful in people's work lives. And when there's certainty there and clarity there, people can be much more efficient in getting the work done. So that's where my

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. Your brain is so accustomed to having a scarcity mindset as opposed to like creating alternative options or seeing a different path. Effectively, there's this notion of how might the opposite be true. And the moment I challenge myself and said, how might the opposite be true? My shoulders dropped. I felt more relaxed. I was like, oh yeah, I can do both. It'll be fine.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. The thing I would say is bring the insight. Know thy customer, know thy market, know thy competitors, know thy numbers, know thy product.

    2023-07-09 · Lenny's Podcast · How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit) · IDENTIFIED FROM THE TRANSCRIPT · source