How to ask the right questions, project confidence, and win over skeptics | Paige Costello (Asana, Intercom, Intuit)

Lenny (00:00:00):
You're often the youngest person in the room. What have you learned about how to garner trust and win over skeptics?

Paige Costello (00:00:07):
The thing I would say is bring the insight. Know thy customer. Know thy market. Know thy competitors. Know thy numbers. Know thy product.

Lenny (00:00:15):
I'm curious, what you find most holds back new PMs?

Paige Costello (00:00:19):
Your brain is so accustomed to having a scarcity mindset as opposed to creating alternative options or seeing a different path. Effectively, there's this notion of, "How might the opposite be true?" The moment I challenged 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 will be fine."

Lenny (00:00:45):
Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today, my guest is Paige Costello. Paige is a product lead at Asana overseeing teams responsible for the core product experience of Asana. Before Asana, she was Director of Product at Intercom, and prior to that, she was a group product manager at Intuit where she spent five and a half years. In our wide-ranging conversation, we dig into strategies for building trust with people who are more experienced than you or older than you, we talk about coaching product managers, including why leading by example is often the most effective strategy, we talk about Asana's product development process and how it's evolved over the years as the company has scaled, plus some of Paige's product and career missteps, and what she's learned from those moments. To prep for this interview, I got input from some of Paige's colleagues and former colleagues, and everyone I talked to loved Paige. You'll soon see why. Enjoy this episode with Paige Costello after a short word from our sponsors.

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(00:04:05):
Paige, welcome to the podcast.

Paige Costello (00:04:07):
Thanks, Lenny. Great to be here.

Lenny (00:04:08):
So you don't know this, and I've been telling you this, but I asked a bunch of people that you worked with and maybe currently work with for questions, suggestions of things to ask you. So this is going to be really fun.

Paige Costello (00:04:19):
Wonderful. Now, I want to know who you talked to, but we'll find out.

Lenny (00:04:23):
I'll tell you right now. Big thank you to Jackie Bavaro, Yasmin who's on your team, and Montgomery and Steve Morin who is currently at Asana.

Paige Costello (00:04:32):
Ooh, fun.

Lenny (00:04:33):
So thank you to all of those folks for giving me a bunch of great questions, suggestions.

Paige Costello (00:04:37):
Looking forward to it.

Lenny (00:04:38):
Maybe just to settle a context, can you just talk about... At Asana, what do you work with? What is your team? What do you work on, and what is your team responsible for broadly?

Paige Costello (00:04:45):
Yeah. Absolutely. So I lead the product organization that's responsible for our desktop, web, and mobile apps at Asana. 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. 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. When there is certainty there and clarity there, people can be much more efficient in getting the work done. So that's where my focus is every day. I'm a product leader for that group.

Lenny (00:05:44):
Cool. So, basically, like the core. When people think of Asana, it's all of that stuff is what it sounds like.

Paige Costello (00:05:49):
Yeah, yeah. There's another group that's focused on our process management, but a lot of the core work in project management, core is in my group, and then we have a growth and enterprise scale team.

Lenny (00:06:01):
You've been at Asana for about four years now, right?

Paige Costello (00:06:03):
Yes, four years this summer.

Lenny (00:06:04):
Cool. So something I'm always curious about companies that are at this scale is just the evolution they've gone through in terms of how they develop product, and so I'm curious, just in the time you've been there, how has the product development process at Asana changed, and maybe even simpler, what are some of the bigger changes that have been made to the way product is built at Asana over the years?

Paige Costello (00:06:26):
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 an area perspective. Well, what's an area perspective? Well, 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 the working teams.

Lenny (00:07:23):
It might actually help if you even describe what is a pillar, what is an area in product development.

Paige Costello (00:07:27):
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 and enterprise scale pillar and the workflow pillar. Within each of those, there are subgroups, and we call those areas. 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 area metrics, and then at the team level, there's often one or two that they're really driving forward. So you can think of it as a nested structure around our product strategy as well as how we measure success.

(00:08:14):
When I joined, we didn't have areas. We were organized around projects and around locations, and then we worked to make sure that the thinking was more durable and problem-focused so that our roadmaps were not about features, but were instead about what was most meaningful to tackle for our business growth. So that's a big thing that has changed is the altitude of planning and how that nests. Another thing that has changed is the time horizon. So, before, we planned annually primarily. Now, we plan every six months, but for a rolling 12 months. 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.

Lenny (00:09:10):
Amazing. So I just actually was talking to one of the heads of product at Shopify, and they went through a similar transition where they used to plan yearly, and now they plan for the next six months. So it's interesting that I'm hearing this more and more, and you're saying that every six months, you revisit the plan for the next year. So it's an interesting hybrid of those two.

Paige Costello (00:09:30):
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 a new technology that we should be leveraging. Let's go bigger on that." 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.

Lenny (00:10:20):
I like that it also admits you're not going to actually have a yearly plan, like everyone plans for year, and then halfway through, they're like, "No. Let's start rethinking everything again."

Paige Costello (00:10:30):
Yeah, yeah.

Lenny (00:10:30):
So I like that you're upfront about that.

Paige Costello (00:10:30):
Yeah.

Lenny (00:10:31):
Okay, and then within the plan, do you have quarterly plans and sprints? Is there anything more fine-grained with a detailed roadmap just while we're on the topic?

Paige Costello (00:10:38):
Yeah, 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, a particular week, or date, you will make strange choices about scope. So, really, we align on what success looks like, and the teams do their best job to ship as quickly as possibly, as iteratively as possibly, 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.

Lenny (00:11:20):
Got it. So, essentially, there's a six-month roughly detailed plan of what each team is going to work on?

Paige Costello (00:11:25):
Yeah, yeah.

Lenny (00:11:25):
Got it. Interesting.

Paige Costello (00:11:26):
Yeah.

Lenny (00:11:26):
Maybe just a couple more things just to make them super concrete for folks that might be listening. What's an example of an area? What's an actual team that would be an area? Then, the other question I have just while I'm saying questions is, are there some metrics you could share of just what some of these teams might be gold on just as examples of how you think about metrics?

Paige Costello (00:11:45):
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 Asana that helps teams work together is working effectively. 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 getting what they need out of Asana.

Lenny (00:12:41):
Just a couple more questions along these lines.

Paige Costello (00:12:44):
Yeah.

Lenny (00:12:44):
I'm nerd-sniped about process.

Paige Costello (00:12:46):
Yeah.

Lenny (00:12:46):
I think you use a process called the Double Diamond Process at Asana. Okay. Cool.

Paige Costello (00:12:49):
We do.

Lenny (00:12:50):
I've seen images of this in various places, but I don't know of any company that's actually using it as the process. Can you just describe what the Double Diamond Process is and how you use it?

Paige Costello (00:13:00):
So you might be familiar with lean startup concepts and Double Diamond as it relates to going broad, and then going narrow. 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. Then, you go broad, and you say, "What are the problems this customer has?" and you narrow, and you say, "This is the problem they have." 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 broad, and going narrow, and going broad, and going narrow forces people to get out of their opinion-driven lens because so often, we need to be curious quantitatively and qualitatively about what we're doing and why, and be more systematic and rigorous about getting there. It doesn't take long, but it just breaks the frame.

(00:13:56):
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 scale 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 design, 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. Yeah.

Lenny (00:14:44):
The way you described it is it was very customer-target-oriented. Is that that the actual framework? Is it around who to build this for, and then what to build, or is it more... It is. Okay. You're not ahead?

Paige Costello (00:14:44):
It is. Yeah.

Lenny (00:14:44):
Okay.

Paige Costello (00:14:56):
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 it. You're teaching to the test. It's not actually driving the outcome. So while our planning process is around effectively defining category and 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 for and what it means to have that problem solved. So it always starts with enough customer insight such that we can creatively do what they're trying to do. I mean, really inventing on behalf of customers.

Lenny (00:15:44):
Can you maybe repeat if there's terms for each of those phases?

Paige Costello (00:15:49):
Yeah. Absolutely.

Lenny (00:15:49):
Then, is there an example of a feature or product that went through this that you could share? If nothing comes to mind, that's okay.

Paige Costello (00:15:55):
The inflection points are the 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? Then, going broad within that path on different concepts, and then there's a design concept review. Then, the products spec. Then, the full experience review or design crit of the end-to-end experience and launch. 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 dogfooding internally for some time, and it's more of a formal, "Do we have the right metrics in place? Are we ready to ship?"

Lenny (00:16:52):
Awesome. Do these reviews happen in person, on Zoom, or asynchronous?

Paige Costello (00:16:56):
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.

Lenny (00:17:27):
I'm going to take a tangent with my questions here and talk about work from home policy at Asana. This is something that I've been wondering more and more about how it's changing because it feels like there's been a shift back to the office. So what is the current policy at Asana, and what's changed maybe over the past couple years?

Paige Costello (00:17:42):
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. That dynamic has been designed from the start. We wanted to make sure that we 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, "No, this is going to be an office-centric hybrid," because we wanted to create spaces for people to work together and move quickly.

(00:18:37):
It's been interesting watching people get back into the swing of things. Even though we knew, it didn't mean that on day one, people were great at being in the office. People were taking standups sitting down. Whereas before, you would walk through our office, and you could hear people at standup because there were standup chants, and people would be out on the floor. Now, people are more likely to do their standup in a room, and we're trying the next level of standing up during a standup, but it's... 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.

Lenny (00:19:45):
I've been seeing a lot of tweets of founders just being like, "Work from home has failed. It's time to go back at the office." I'm curious if that ends up rolling into more and more companies, or if it's just a few founders here and there.

Paige Costello (00:19:56):
I 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. 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.

Lenny (00:20:36):
It feels like just coming into the office once or twice... or sorry, being at home once or twice a week is not that different from how things used to be where there was a day of no meetings and a lot of people stayed from home. So it feels like it's almost reverting back to that.

Paige Costello (00:20:47):
Exactly, and people are better at it than they used to be.

Lenny (00:20:47):
Right.

Paige Costello (00:20:50):
So I would say our remote days are more impactful than the days we're together where we're getting into the swing of things.

Lenny (00:20:56):
Yeah. I feel like as a PM, the only day I was productive and getting real deep work done was the No-Meeting Wednesday. It was at Airbnb.

Paige Costello (00:21:04):
Yes. I would encourage you to know your chronotype and to lock that time where you have the most head space to do that work. So, for me, it's mornings.

Lenny (00:21:12):
Say more on chronotype. What is that?

Paige Costello (00:21:15):
I'm a morning person, and so I try to make sure that I don't have any meetings before 10:00, sometimes before 11:00, and that's when I do my hardest task for the day.

Lenny (00:21:26):
I also just thought about standups while I was at Airbnb and how not only how much energy they brought, but almost too much energy sometimes where there's like another team doing a standup, and they're just laughing and clapping, and we're just like, "Shh, we're trying to work over here." I feel like we need more of that again.

Paige Costello (00:21:42):
Totally. Yep, yep.

Lenny (00:21:45):
Okay. So, moving in a slightly different direction, something I heard about you is that you're often the youngest person in the room, and you often lead people with decades more experience than you. I want to ask, what have you learned about how to garner trust and win over skeptics, especially when they're maybe more experienced or older, and especially in other functions, I don't know, execs or designers, engineers, what have you figured out there?

Paige Costello (00:22:13):
The thing I would say is bring the insight. Know thy customer. Know thy market. Know thy competitors. Know thy numbers. Know thy product. If you can be the person in the room who has watched customers use the product and has a point of view about why one tool is significantly better or worse in a given dimension, and you can do that with confidence and clarity, and you don't need to know the other person's functional domain, and you don't need the expertise in what they're experts at, you can bring insight that makes people curious, and trust you, and just immediately believe that there's an opportunity that you're not advocating for that just is true. But I think that's a really tricky and unique thing is not to pretend like you have more experience than you do, but to be willing to ask great questions, and then be curious enough that you're bringing insight to every meeting that people may or may not have, but you're always willing to share.

Lenny (00:23:21):
That's such a good answer because it's like there's not a trick to it. It's just do the work, spend the time to become the person that has answers that people value and obviously, that will respect you, value your opinion, want to hear from you.

Paige Costello (00:23:34):
Yeah. Yeah. Our former board member, Anne Raimondi, and now our head of business wrote an article on First Round that was really great about the trust equation, and it really resonated with me. I don't know if you've heard about it, but she said that trust is equal to credibility plus reliability, plus authenticity, divided by or over perception of self-interest. I think when you're met by someone who doesn't know you, doesn't know your work, your job is to create credibility, and that's where I said bringing the insight is where you can really tip the scales here. Reliability, this is all about your say-do ratio. Authenticity is just being vulnerable, being yourself, and then making sure that people know that you're not in it for some other outcome or cause that perception of self-interest really can change whether people... how much they trust you.

Lenny (00:24:46):
In terms of knowing the insight and knowing thy customer, putting the time, I imagine, is a big element of that. Is that how you do that, or is there anything else along those lines that's just like, "Here's how I get really good at this?"

Paige Costello (00:24:59):
When you take a new role, become best friends with a researcher, and spend time watching customers use the product firsthand because what they maybe report on or are trying to do a study about might be very different from what you observe, but you really just need that front row seat with customers, and so asking, "How do I actually set up time with customers? How do I compensate them? How do I read the tickets?" Whatever. It's amazing how little you have to do to quickly catch up to understanding who the organization is solving for well and poorly, and how people really use your product versus how your teams use your product, especially in organizations where there are heavy dogfooding cultures. It's really risky to become less sensitive to the needs and behaviors of customers because people think they are their customer, and it also becomes very navel-gazey. So I think the more you get out and break up how people are having conversations about what we should do and why, and what we shouldn't do and why, and it's not about your opinion, it's about asking questions, and then bringing insight can really change the nature of the conversation and build trust.

Lenny (00:26:18):
I love that. In terms of confidence, you talked about the importance of communicating these things confidently. Is there anything you've learned about how to be more confident? The managing part of it is like having the answer, but is there anything there that you maybe coach your PMs around or other folks of just like, "Here's how you communicate confidence?"

Paige Costello (00:26:36):
It's a great question. I think being brave and courageous in little moments is just what you have to do. You have to show up, and say it before you're ready to say it, and ask for forgiveness, and be vulnerable. I think when you're vulnerable, people actually trust you more than if you come with all of this armor and say, "I know this, and this is how we're going to do it." So real confidence is often conveyed by being willing to ask the question or to say, "I don't know what you mean by that. Can you say that again?" It's also just how you communicate, looking people in the eye, your body position, your body language.

(00:27:22):
So much of this, I think people forget about because it's really easy to be in a meeting, and looking at your computer, and going through Slack messages. So one of the best things you can do is if you're in a meeting, be in that meeting. Continually scan the faces of everyone in the room, see if someone has a question, pause at the beginning, and welcome people, and chit-chat while people land, and then close asking questions like, "Did I get all of that? Is there anything you would've expected to cover that we missed?" It's really about being open, and that conveys confidence more than being assertive and advocating 100% of the time.

Lenny (00:28:03):
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(00:29:04):
From my chats with folks that you work with, it's really clear that you put a lot of time and energy into mentoring and coaching PMs, and your team, and I think probably broadly at Asana. One thing specifically that came up is that you're very big on leading and teaching by example, not just, "Here's how you do this thing." So, if that's true, I'm curious where that came from for you and why you think that ends up being a lot more successful than like, "In a meeting, you should do X, Y, Z," versus doing it, and then letting them see.

Paige Costello (00:29:34):
I think the main thing is repetition. We're all students of repetition. If you see something done a few times, you're more likely to remember it and internalize it, and so it's also something that... a way that I learn, and so I think that's probably part of it. I remember hearing about a framework called the three Es: experience, exposure, and education. I think it was helpful for me to hear that as a way of growing your career or being more purposeful about your growth because I think when people are earlier in their careers, they tend to think, "Education, education, education," and then they started to think, "Experience, experience. How do I get the experience of being a manager? I need to read about it, and then be a manager." It's very linear.

(00:30:29):
Exposure was such an important one where I thought like, "Okay. So you're not in the driver's seat, but you're in the car, and you hear what's happening, and you're evaluating how this is... what the impact is." This goes back to being really present and analytical, and being a learner because if you can be a learner, not just in an education or experience context, but in an exposure context, you can really grow so much more quickly and in so many more directions than you will get from just what does your day entail from what work is directly required of you.

Lenny (00:31:12):
Is there an example of that happening either to you or you saw a manager leader do this, and you're like, "Oh, I get it now," or you doing that and it helped?

Paige Costello (00:31:18):
So I'll give two examples. I mean, the way I run my meetings are the kind of meetings I want to be a part of. So I try to make sure that I start with a clear agenda, and I move quickly, but give time for conversation and that it's not fully just sharing information, but debating where appropriate. I think knowing how to manage the conversation and courteously pausing people who are going on too long or taking the group in a different direction than was intended, and just think about the experience of everyone there, and create the experience that you hope that they're creating in the rooms that you're not a part of.

(00:32:08):
An example that I have in terms of experience is sometimes the experience is you doing the thing and getting that experience firsthand. Other times, you need an education, you need a mentor, you need a coach who will tell you what they're saying or give you advice. I was in a really high-stakes product review at Intuit, and at the end of it, everyone else had left, and the leader of the business unit as she was leaving the room said, "Always answer the question that they should have asked." "Always answer the question they should have asked."

(00:32:49):
I was pretty surprised by that advice because it was very profound in the moment because I think when you're a student and you are accustomed... If you're an achiever, you like to get As. You're probably going to hear a question and answer it. You're like, "One-to-one, one-to-one, one-to-one." But what I learned from that was that there's actually another altitude, another point of strategy when you're in a meeting or in a conversation to make sure that you're covering the more important point, the bigger picture, the alternative that the person asking the question maybe didn't see or consider. So I think the mix of experience, exposure, and education really helps you make sure that you're consciously moving forward on each of those fronts or finding people who can help you there.

Lenny (00:33:43):
I love that piece of advice, and it makes me want to ask, are there other pieces of advice that have been really impactful to you, or are there common pieces of advice you give to your team that just is a recurring theme of advice that maybe people even make fun of like, "Oh, Paige is always saying this?"

Paige Costello (00:33:59):
There are a few ways to think about advice, and my advice often meets some mark when it's for a particular person in a particular time in their career. So I would say advice I love giving to people who are early in their career is don't self-select because I think it's really easy to say, "I don't have the experience," or, "I'm not X, Y, Z enough," and not apply. So I really push people not to self-select, and I try to remind myself where that's appropriate to do the same thing. Other advice I often give is just think big, ship small. "Think big, ship small." What's the smallest thing you can do to do that thing? But let's not, because we're trying to ship all the time and in small chunks, start thinking in small ways because it's really easy to get a little too incremental, a little too wrapped around the axle around optimizing a metric and miss the bigger picture, and so think big ship small is another piece of product advice I give.

(00:35:02):
The last piece of advice that I would say that I like is more of a way of thinking. So this is a little abstract, but when employees join Asana, they get a book called The 15 Commitments of a Conscious Leader. It's led by the Conscious Leadership Group. They also get two-day training on some language and tools for how to effectively work with other people, and it's a really... For me at least, it was transformational because I learned some vocabulary and methods that I could share with my peers. One of the things that you learn is to be above or below the line, and something that is this concept of like, "Where are you? Are you above the line? Are you below the line?" If you're above the line, you're committed to learning. You're open and curious. Things are funny here, more playful. If you're below the line, you're committed to winning. You're committed to being right. Things are more black and white.

(00:36:10):
All of us have days where we're having a conversation and we're really in that below line space where it's like, "No, it just is this way. There's no two ways around it." That concept of understanding your personal head space, and then being mindful of how you're operating when you're in that place really was great advice for me and also recognizing where other people were when it related to decisions we were making or context. It also helped me think about rejecting false trade-offs and challenging like... Effectively, there's this notion of how might the opposite be true, and that's a piece of advice that I give myself like this morning.

(00:36:55):
I think it was yesterday, actually. I was like, "How am I going to do tomorrow? Tomorrow, I have to deliver the clarity pillar brief to the area leads and make sure they understand our stack ranked metrics, and they need to know exactly what our strategic priorities are and why, and they need nudges, and they need to be able to translate our voice of business and usability lists into those plans. I need to establish a perspective and make sure this is all written down and they really understand it, and I have a great conversation with them where I get open questions and they feel like they can really challenge my thinking. I also am having a podcast with Lenny in the afternoon. Ugh." Right?

(00:37:37):
At first, it was like, "This is just too much. I should try to move or cancel one of these." Then, I asked myself, "How might the opposite be true?" I was like, "I can do both." It was just enough to pop the balloon because sometimes your brain is so accustomed to having a scarcity mindset as opposed to creating alternative options or seeing a different path. The moment I challenged 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 will be fine. We'll have a great conversation. I'm ready to show up, and be curious, and really engage with you on the topics that you've found interesting, and we'll just do that. So, "How might the opposite be true?" has been a really helpful piece of advice or line of questioning that I use with myself to make sure that I'm not taking myself away.

Lenny (00:38:43):
Wow. What a fruitful question that ended up being. That was amazing. How does clarity pillars strategy go? Are people into it? Is it working?

Paige Costello (00:38:52):
Yeah. I'm pumped. It's a really interesting time to be a product leader, especially with all of the tech transform... Truly, the technological transformation on LLMs is astonishing, the pace of development, the ability of our teams to just ship quickly and ship really intelligent things. We're not in an operational "figure it out" land. We're not in a place where we're trying to decide how to do a better job and get it out to customers. We really have lots of interesting paths forward and are trying to make sure that we're on the cutting edge while really looking at like, "What does it mean to serve the companies and organizations that we want to serve with new ways of serving them?" So it was a really fun conversation, and I also had to be honest with people and say, "This is a 70% cut. 30% of this is missing or incorrect, and that's why I'm coming to you early." So I think it went really well, and it's the start of our 12-month rolling planning conversation.

Lenny (00:40:05):
Let me pull on this AI thread because it's clearly top of mind for a lot of people.

Paige Costello (00:40:08):
Yeah.

Lenny (00:40:09):
How do you think about splitting up investment in AI exploration within the product team? Are you like, "Hey, team. Everyone should be thinking about AI as part of their product," or is it there's a team where they're going to think about AI and LLM integrations and, "Everyone else, keep doing what you're doing?"

Paige Costello (00:40:24):
We've had an ML team for quite some time, making sure that we have test prioritization models and notification prioritization models, and are making our product less work for people to use. But when it came to the massive leap forward in LLMs recently, we staffed a team to really prototype quickly, and discover what was possible, and just apply hypotheses outside of the typical norms of how we work. So they went straight to prototyping instead of going through that Double Diamond I was explaining earlier. What that meant was that we were really quickly able to say, "Wow, this is just so much better than we imagined and would never have prioritized it because we thought it would take so much longer." Then, in other cases, "That sounded good in theory."

(00:41:18):
So skipping a lot of that to just really try it on for a size has been key, and then what we're doing is giving the teams with the most expertise in the customer problems. For example, status and progress reporting, the keys to that car and saying like, "Here's the starter. Here's the hypothesis. Here's how far we got with it. It's dogfooding. What do you want to do?" So we're able to nudge people without wasting time and build the skills locally within the teams that then move those experiences forward.

Lenny (00:41:50):
I want to come back to the coaching topic. I had a few questions there that I moved off of, but I feel like that's a rich area of exploration. You mentioned Intuit. You worked at Intuit. Intuit is famous for having a really good APM program and really good training for product managers. What did you take away from that experience that you bring with you to coaching or even I think there's an APM program at Asana, too?

Paige Costello (00:42:15):
Intuit had excellent training programs, the APM program and their manager training. So, on the PM front, the biggest thing that they taught was around customer centricity, and it really started with the founding of the company. For anyone who works at Intuit or has worked at Intuit, they know that there's this story about Scott Cook watching his wife balancing her checkbook at the kitchen table, and staring at it, and saying, "There's got to be a better way, a software." So it was very typical for the product training at Intuit to be all about like, "How do you actually watch customers using your product or just doing the things they do, collecting the artifacts, knowing the workarounds, and using that experience to build opportunities for surprise and insight that then you can capitalize and create products around?" They also are very specific about how they define durable advantage and think about, overall, the product process from a place of customer insight through to the market landscape. So the PM program there was absolutely super thoughtful, especially for taking someone who has never PMed into being a super skilled PM.

(00:43:37):
They also have a wonderful manager training program, and I think the biggest thing that I took away from their manager training was really on the feedback slide. So delivering feedback is something that I think everyone benefits from, but for managers, it's so much more critical because if you don't do it, and you don't say what you mean, and you don't do it in a way that it can be internalized and acted upon, you really don't set up your teammates, your teams for growth or success in their careers. So their program for helping you think about like, "Okay. I'm going to convey this feedback as situation, behavior, impact. The situation is on Tuesday in that meeting at 3:00. Behavior, you interrupted me while I was saying this thing. Impact, made me feel like you weren't listening to me or made me feel like your voice was more important than mine, or impact, blah, blah, blah."

(00:44:35):
It doesn't matter what the impact is because the way you've set it up is it's a subjective observation. It's not what the camera recorded, it's what you experienced. Therefore, it is true and valuable feedback, and it gets the conversation started such that you can then talk about next steps. That format and framing really helped me understand that delivering feedback isn't about being right or about getting the right information to the other person. It's about sharing the impact of different decisions that they're making. So, especially if you have to give feedback about, God forbid, what someone wears to the office, or how do you feel their work is, or how they're communicating or their body language, having an enough support where you can be really clear about what you're intending and the spirit behind that, but that it's formalized enough that people can really engage with it has been enormously helpful, and I still use it today.

Lenny (00:45:35):
It's interesting how some of the most impactful training is such soft skills.

Paige Costello (00:45:41):
So basic.

Lenny (00:45:43):
Basic. Yeah.

Paige Costello (00:45:43):
Yeah.

Lenny (00:45:44):
It's just how to give someone some feedback, but it's like, "Know how to prioritize, how to do a meeting, how to give a presentation."

Paige Costello (00:45:48):
No. Yeah.

Lenny (00:45:50):
It's like, "Here's how you give feedbacks."

Paige Costello (00:45:52):
Yep.

Lenny (00:45:53):
So you've worked with a lot of early product managers. I'm curious what you find most holds back new PMs and help them being successful in their career, and even on the flip side, what most helps new PMs be successful in terms of skills or behaviors, habits, things like that?

Paige Costello (00:46:11):
I would say this illusion that you have to be all-knowing and super confident sets you up to be in a place of advocacy instead of inquiry. So PMs who are newer in their careers or who are in a different space than they're accustomed to working really want to be pro really fast. What pro means is trying to cut that straight path, and that can reduce information and conversation that makes you smarter. So some of the challenges that some PMs face are feeling like they need to be the expert, they need to be the smartest person in the room, or God forbid, they think they're the smartest person in the room.

(00:46:56):
Then, what happens is they're really doing that customer, or product discovery, or spec in a little dark room. Then, they show up, and they say, "This is it. This is right. I know it's right, and let's do this as quickly as possible." Everyone else says, "Wait. What? I don't know. I have a question," or they don't, and they still have a question, which is even worse. So I would say something that really holds PMs back is not being collaborative from a place of true curiosity like performative collaboration where they're not in a room or want to do a review, but ultimately, they don't really want the questions or the feedback.

(00:47:40):
I think trying to make sure that you can be in a place of curiosity and openness because that will make your experience more successful is really important. Other people aren't always going to be right, but if you're present for it, you can ask clarifying questions. You can ask the question behind the question. You can hear the feedback, and then say, "Was that something that I must do, that I should do, or that I should consider?" You can actually develop a conversation that will move your relationship forward, and so I would say that's something that I think holds PMs back.

(00:48:17):
PMs tend to be so ambitious and career-centric. There are so many good things about that, but I would say don't let the sound of your wheels drive you crazy. If you're present in your job, and you actually have fun with it and solve the problems, people will come out of the woodwork, say, "You're great, and tell your boss you should be promoted." You don't need to ask for a promotion. Your outcomes should speak for themselves. Yes, you should have sponsors and people who advocate for you, but a lot of that just comes from that raw connection to the work and to your team.

Lenny (00:48:55):
Everyone I talked to about you is like, "Oh my god, I love Paige." I could see why, but I want to ask you a question. I imagine you've made some mistakes either with a product or your career. I'd love to hear a story of something that went wrong and what you learned from that experience. This might be the last question, depending where you take it.

Paige Costello (00:49:16):
I would say that all of the advice I've given so far is directly related to things I've learned the hard way. So, especially as an IC moving into a management role, you aren't supposed to have all the answers. You need to ask better questions. You need to be thoughtful about direction and agency. So I would say one of the missteps here is knowing how to give guidance or direction in a way that doesn't feel like micromanagement because what you're trying to do is to teach a repeatable pattern instead of giving a precise instruction that can be used once, and then disposed of.

(00:49:57):
So I think that's a pretty common manager path issue, but I think the faster you learn it, and observe it, and use techniques to manage it, the better. So, for example, I would go to my meetings with a stack of Post-Its, and I would write what I wish I was saying on Post-Its and see if someone else would say it first. Then, if by the end of the meeting, I had decided that I still had a Post-It or two that was worthwhile, I would say them. But you've got to police yourself because no one else will do it because no matter how accessible you think you are, other people know that you're the boss. They're not going to necessarily speak over you or challenge you directly.

(00:50:42):
Another challenge I had is I'm a very optimistic person, and I like to look on the bright side. I'm very positive, and I think depending on the culture you're working with or depending on your team, sometimes they need to hear what's really bad, and they need you to be really real, and they need you to tell them like it is. Something I realized was that I had an experience where I didn't realize that people didn't think I was being authentic because they thought something was bad, and I wasn't talking about it, but it wasn't because I didn't think it was bad or didn't see. It was just because my nature was to say, "Well, I'm not going to talk about bad things because we're doing the things we need to do." As long as the plan is good, I wasn't really highlighting all the problems I saw or really pushing on those head on with my team, and so they felt like they didn't know what I was seeing or if we were saying the same things. That was really an interesting experience. Yeah, there were just so many. Yeah.

Lenny (00:51:49):
With that second lesson, is there something you've changed in the way you lead and operate where you now found a way to communicate, "Here's wrong," in a way that's still maybe optimistic and productive?

Paige Costello (00:52:00):
I try to be more real with myself and others. I try to show up and say like, "Hey, this is incomplete." For example, even the thing I did this morning, the clarity brief. I said, "This is 70% finish. The 30% that I don't believe is there yet are these three things. I don't feel confident in this piece of it, and hopefully, we'll have more clarity by next week." So that's an example of just being as real with the small things as with the big things so that people can balance their perspective of you and your work, and the organization and the environment you're creating.

Lenny (00:52:40):
I'm curious how you think about your career going forward. How far out do you think where you want to be, and how do you plan out the future of Paige's career?

Paige Costello (00:52:50):
I try to be really intentional about staying as much as leaving a role. When I think about my career as a whole, I try to think about skills or experiences I want to have as opposed to roles, or companies, or specific problems. So something that I think about is... Effectively, I evaluate whether I'm in a healthy role and in a good setup by asking myself about my learning curve like, "Is the steepness of my learning curve doing me a favor here?" because sometimes you might love the organization, love the problem, and feel like you're just not learning, or learning fast enough, or being challenged.

(00:53:39):
That's something that I think is really important. So thinking about the learning curve, thinking about whether the environment is positively impacting your ability to grow your career and make an impact. So, environmentally, you might have not enough staffing or tooling, or have someone in the management team who is toxic, or have a peer who is blah, blah, blah, blah, blah. That stuff matters, and I think people don't talk about it or take it seriously enough that your environment should include people who are advocating for you, and it should just be a place where you feel you've got the right ingredients to set you up to do the good work.

(00:54:24):
Then, the third piece is really around just the problem, the problem your product is solving. Is it fun? Is it interesting? I often like to think about passions are made, not found because I think people... We do this with nine-year-olds. We say, "What do you want to be when you grow up?" They look cross-eyed, and they say, "An astronaut. Just getting a vet. I don't know." There's this moment of panic, and I would say that being comfortable, saying like, "Go try different things, and see if the problem is interesting to you and if the problem is fun or interesting to you." It doesn't mean it has to be sexy. It doesn't mean the company needs to have a brand name. It just has to be something that you're curious about so that you do a better job at your job. So I would say learning curve environment and problem are things that I use to assess like, "Am I still on the right path, or should I consider an alternative?" But when I think about my own career, I really think about skills and experiences as opposed to roles. So I would say that that's more my frame of reference because otherwise, I think I am living in the future and not enough trying to make the most out of the career I'm living right now.

Lenny (00:55:44):
Well, with that, we've reached our very exciting lightning round. I've got six questions for you. Are you ready?

Paige Costello (00:55:49):
Yeah. Let's do it.

Lenny (00:55:51):
What are two or three books that you've recommended most to other people?

Paige Costello (00:55:54):
My go-to book recommendation for other PMs is inspired by Marty Cagan. I think it's a classic. The other books that I have enjoyed and recommended lately are The Blind Assassin by Margaret Atwood and The Alchemist by Paulo Coelho.

Lenny (00:56:11):
What is a favorite recent movie or TV show?

Paige Costello (00:56:14):
Ooh, I'm very much enjoying The Diplomat right now, and then TV show or movie. Let's see. I just watched the Fire of Love documentary, which is about a couple who study volcanoes, and that was a great change of pace.

Lenny (00:56:32):
I saw the trailer for that. I think I got to watch that, and I finished The Diplomat. It's awesome. It ends really well.

Paige Costello (00:56:37):
I'm not done. Don't spoil it.

Lenny (00:56:39):
But it's just good. I'm just saying it's good. That's not spoiling.

Paige Costello (00:56:39):
Okay.

Lenny (00:56:45):
Okay. Next question. What's a favorite interview question that you like to ask candidates?

Paige Costello (00:56:49):
The good news is I can tell you this and still keep asking it because the answer has always come up differently. So I like to ask, "Tell me about a time something went wrong. What was it? What did you do about it? Yada, yada." Effectively, the question gets that, "When the product failed," When something about the team didn't work," just things that go wrong because that's what happens when you're doing this work, and evaluating people's mindset, and the way they talk about it, and the way they relate to evaluating the situation. I think it's a great question. Really tells you a lot about how people think and how they perceive themselves when things are not working well.

Lenny (00:57:34):
What is a favorite product that you've recently discovered that you love?

Paige Costello (00:57:37):
I've been playing a lot with Poe.com lately. Yeah, just an opportunity to learn more about LLM capabilities in a firsthand way. It's been fun to create little bots. I'm playing with making a page bot. I can't say that the page bot could have had this conversation yet, but maybe next year at this time, you can have a conversation with the other me.

Lenny (00:58:07):
That's what the page bot would say if this was the page bot talking right now.

Paige Costello (00:58:10):
I would say though that the advice, bits and bobs, I gave you earlier are absolutely things that I've been thinking about feeding, but I think the page bot would probably say, "Ship it."

Lenny (00:58:25):
Poe. It's the Quora founder's LLM chat bot?

Paige Costello (00:58:30):
Yeah, and so you can try the different models. So you can do four, and you play five, and Claude, and a few others. Yeah.

Lenny (00:58:38):
There's also a lennybot.com for folks that haven't seen this. Actually, there's a whole post on my newsletter of how it was built, and you get a lennybot.com. It is trained on all of my newsletter posts, and I think... not yet podcasts, but someday it will have podcasts.

Paige Costello (00:58:55):
Ooh.

Lenny (00:58:55):
By the way, someone listening to this, we're looking for someone to maintain this bot and evolve it. So if you're really into this stuff and have done this sort of thing, please DM me on Twitter. I'm looking for someone to take over lennybot.com, make it more... Moving on. Enough about me. Next question. What is something relatively minor you've changed in your product development process that has had a big impact on your team's ability to execute?

Paige Costello (00:59:18):
One of the biggest ones is just, once again, being real about how many reviews and approvals it takes for something to get done and who's actually responsible for reviewing and approving work. So we got really aggressive about, functionally, who is in charge and at what level for a given review, and pushed to say to actually have limits on the number of people per meeting, on the number of sub-task reviews for a given body of work. What this did is it created a lot more agency and pace within given working teams. So what we did was we said, "We actually don't care. We don't want a daisy chain of approvals. We just want one person with whom the buck can stop with them, and they can be responsible for how the work moves forward such that the knowledge is known and we could have connected the dots more effectively than we do or did." So that's the logic there, and it really changed the pace and quality of our work.

Lenny (01:00:25):
I love that. Is there any more you could share, a number? What is the maximum? Is there anything that other people maybe can take as a-

Paige Costello (01:00:31):
Yeah. So no more than three reviews on a given piece of work where people are blocking one approver. If a meeting has more than 10 people on it, we ask the person hosting the meeting to kick out the other people and write better decision notes.

Lenny (01:00:49):
The three reviews is three meetings looking at the product as it's coming together, basically?

Paige Costello (01:00:54):
The three reviews are three people who are assigned a task to look at something, but only one person is blocking whether it moves to the next stage.

Lenny (01:01:03):
Got it. Informed people? Stakeholders?

Paige Costello (01:01:06):
Yeah.

Lenny (01:01:06):
Decision-makers? Okay. Great. Final question. You work at Asana. What is your favorite Asana pro tip?

Paige Costello (01:01:12):
I use Asana to run all my meetings and assign pre-reads. So I use the multi-assign feature in subtasks all the time where I make a task with a due date that says, "Read this thing by this date," and then I assign it to a team or a set of individuals like that really quickly. Then, when I'm in the meeting, I take notes live in a task, and then highlight parts of those notes, and convert them into subtasks so that none of the action items get lost.

Lenny (01:01:46):
Wow. You need to make a video or blog post about this. Not only is it using Asana to build Asana, it's using Asana to run teams within Asana.

Paige Costello (01:01:46):
Yeah. It definitely does that, but-

Lenny (01:01:57):
Asana all the way down.

Paige Costello (01:01:58):
People know who's responsible for what they want.

Lenny (01:02:01):
Amazing. Paige, you are awesome. Thank you so much for doing this. Two final questions. Where can folks find you online if they want to reach out and learn more, and how can listeners be useful to you?

Paige Costello (01:02:10):
You can find me on LinkedIn and Twitter, Paige Costello, and on Twitter, @paigenow. Listeners, well, I'd love to hear how you think AI is going to shape the future of software for knowledge workers, but in particular, if you and your team use Asana, I'd love to know where you'd like to see AI playing a bigger role to drive efficiency alignment for your team. So, as you know, we offer a ton of goal management, work management pieces that help teams and orgs do their work together, and I'd love to hear from you about where you see the opportunity.

Lenny (01:02:49):
Awesome. Paige, again, thank you so much for being here.

Paige Costello (01:02:53):
My pleasure. Thanks for having me.

Lenny (01:02:55):
Bye, everyone.

(01:02:57):
Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.