you're often the youngest person in the room what have you learned about how to Garner trust and win over Skeptics the thing I would say is bring the Insight know that I customer Know Thy Market know like competitors know like numbers no thy product I'm curious what you find most holds back new PMS 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 feel more relaxed I was like oh yeah I can do both it'll be fine
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 respond 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 into it 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 you talk about asanas product development process and how it's evolved over the years as the company scaled plus some of pages 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 talk to love Paige you'll soon see why enjoy this episode with Paige Costello after a short word from our sponsors
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you worked with and maybe currently work with for questions suggestions of things to ask you so this is going to be really fun wonderful now I want to know who you talk to but we'll find out I'll tell you right now A big thank you to Jackie Bavaro Yasmin who's on your team and Montgomery and Steve morinasana and so thank you to all of those folks for giving me a bunch of great questions suggestions looking forward to it maybe just a subtle
context you just talk about arasana what do you work with what is your team what do you work on and what is your team responsible for broadly yeah absolutely so I lead 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 that but really we want to help people
answer the question at work who is doing what by when and why so that 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 that's where my focus is every day I'm a product leader for that group cool so basically like the court like when people think of Asana it's all of that stuff is what it sounds like yeah there's another group that's focused on our Process Management that a lot of the core work in project management core is in in my group and then we have a growth in Enterprise
scale team and you've been at Asana for about four years now yes four years this summer cool so something I'm always curious about uh 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 like what are the bigger some of the bigger changes that have been made to
the way product is built at Asana over the years 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 it and 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 the the working teams it might
actually help if you even describe like what is a pillar what is an area yeah absolutely so when I said I'm responsible for that like core product pillar that's one pillar but then there's also the adoption and Enterprise
scale pillar and the workflow pillar and then when 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 clear of the metric 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 like one or two that they're really driving forward and so
you can think of it as a nested structure around our product strategy as well as how we measure success and 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 road maps were not about features but were 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 amazing so I just actually was talking to the one of the heads of product at Shopify and they went through a similar transition where they used to plant 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 kind of like an interesting hybrid of those two 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 like just make sure
we're making the best use of our teams I like that also admits you're not going to actually have a yearly plan like everyone plans for a year and then halfway through they're like no let's start rethinking everything again yeah I
like that you're upfront about that yeah okay and then within the plan do you have quarterly plans and Sprints is there anything more fine-grained with like a detailed roadmap just while right on topic 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 particular week or date be able to 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 possibly as iteratively as possibly and we really encourage prototyping so we 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 got it so essentially there's a six month roughly detailed plan of what each is going to work on got it interesting 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 like what's an actual team that would be an area and then the other question I
have just while I'm saying questions is are there some metrics you could share just like what some of these teams might be gold on just examples if I think about metrics the area that came to mind when you asked about one of our areas is
something called coordinate and their their job is effectively making sure that the slice of Asana helps teams work together is working effectively and so that's projects and tests 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 like healthy project use so we make sure that
we understand like what does good look like and what is 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 guard rail to
ensure that we're not driving one metric at the expense of people really getting what they need out of Asana just a couple more questions along these lines some nerd sniped about process yeah I think you use a process called
The Double Diamond process at assignment okay cool I've seen I've seen images of this in various places but I don't know of any company that's actually using it as like the process can you just describe what the Double Diamond process
is and how you use it 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 abroad 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 um opinion driven lands because so often we really want we we need to be curious quantitatively and 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 and so this the 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 this back and that's the narrowing along the side designs Etc but it's really mapping our our artifacts against this notion to make
sure that the product thinking has that quality of decision making yeah and the way you described it is it was very customer Target oriented is that just is that the actual framework is it around like who to build this for and then what
to build or is it more 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 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 like how we win and making sure that customers receive certain benefits from using Work Management the through line to the 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 and so there it always starts with enough customer Insight such that we can creatively do what they're trying to do and really inventing on behalf of customers can you maybe repeat if there's like terms for each of those phases and then absolutely and then is there like an example of a feature product that went
through this that you could share if nothing comes to mind that's okay the inflection points are the kickoff which is that going Broad and then customer and directions selection so this is both the 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
then the products back 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 you really hears the thing here's what we said here are the past follows
most of the time by that time it's already been dog fitting internally for some time and it's it's more of a formal do we have the right metrics in place are we ready to ship awesome these reviews happen in person on Zoom or asynchronous 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 I'm going to take a tangent with my questions here and talk about work from home policy dasana 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 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 took advantage of what's great about working together as teams and so it's it's been the standard so I 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 or remote workplace or
not and what would that mean and how would we come together and how would we budget for it you're like nope this is going to be an office 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 we're 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 room
um and we're trying to you know like the next level of standing up during stand-up but it's kind of um 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 like standing up
during your meetings it's it's bizarre that we could lose a muscle that we had that was so innate uh 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's sitting down next to them so it didn't happen overnight I've been seeing a lot of tweets of Founders just being like work from almost failed it's time to go
back at the office and I'm curious if that ends up rolling into more and more companies or if it's just like you know a few Founders here and there 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 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 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 and people are better at it than they used to be so right I would say our remote days are more impactful and then
the days we're together we're we're getting into the swing of things yeah I feel like as a PM the only day I was productive in like getting real deep work done was the no meeting Wednesday it was yeah it was at Airbnb I would
encourage you to know your chronotype and to walk that time where you have the most head space to do that work so for me it's warnings say morning what is that I'm a morning person and so I try to make sure that I don't have any meetings before uh 10 sometimes before 11 and that's when I do my hardest task for the day I also just thought about stand-ups 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 stand-up and they're just like laughing and clapping and we're just like trying to work over here I feel like we need more of that again 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 and I want to ask what have you learned
about how to Garner trust and win over Skeptics especially when they're maybe more experienced oral older and especially in other functions I don't know execs or designers Engineers what are you what have you figured out there the thing I
would say is bring the Insight Know Thy customer know they Market know like competitors know like 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 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 and 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's you're not advocating for that just is 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 like 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 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 they will respect
you well your opinion want to hear from you yeah yeah the um our former board member and raymondi and now our head of business wrote an article on first round that was really great about kind of the trust equation
and it really resonated with me and I don't know if you've heard about it um but she she said that trust is equal to credibility plus reliability plus authenticity divided by or over perception of self-interest and 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 like bringing the Insight is where you can really tip the scales here reliability this is all about your say do ratio authenticity is
just you know 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 like how much they
trust you in terms of knowing the insight and knowing that customer putting the time I imagine is a big element of that is there anything is that is how you do that or is there anything else along those lines that just like here's how I get really good at this when you take a new role become best friends with a researcher and spend time with watching customers use the product first hand 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 for how how do I actually set up time with customers how do I compensate them how do I like 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 like how people really use your product versus how your teams use your product
especially in organizations where there are heavy dog fooding 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 Naval
gazy so I think the more you get out and break 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 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 uh you know a management part of it is like having the answer but is there anything there that you maybe coach your PM's around or other folks have just like here's how you communicate confidence
it's a great question I think Bing Brave and courageous in little moments is just just kind of 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 and I
think When You're vulnerable people actually trust you more than if you come with all of this um armor and say I know this and this is how we're going to do it and 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 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 and 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 have expected to cover that we missed
and it's really about being open and that conveys confidence more than being assertive and advocating a hundred percent of the time this episode is brought to you by round round is the private Network built by Tech leaders for Tech leaders round
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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 on your team and I think probably broadly at Asana and 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 and 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 XYZ versus like what doing it and then letting them see I think the main thing is repetition uh 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 it's also something that a way that I learn and so I think that's probably part of it but I I remember hearing about a framework called the three E's experience exposure and education and I think
it was helpful for me to hear that as like 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 like how do I get the experience of being a manager I need to like read about it and then be a manager is very linear and exposure was such an important one where I I thought
like okay so you're not in the driver's seat but you're in the car and you're here what's happening and you're evaluating how this is like what the impact is and this goes back to being really present and analytical and being
a learner because if 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 you know
what does your day entail from a what work is directly required of you 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 so I'll give two examples one is like the way I run my meetings are the kind of meetings I want to be a part of so um I try to make sure that I start with a clear agenda and I move quickly but give time for conversation and it's not
fully just sharing information but debating where appropriate I think knowing how to like manage the conversation and courteously pausing people who are going on too long um or like 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 an example that I have in terms of experiences like sometimes
the experience is you doing the thing and getting that experience firsthand other times you 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 into it and at the end of it everyone else had left and our like the the leader of the business unit as she was leaving the room said always ask or always answer the question that they should have asked
and always answer the question they should have asked and 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 A's you're probably going to hear a question and answer it 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 the bigger picture the the alternative that the person asking the question maybe didn't see or consider and 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 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 like is a you know recurring theme of advice that maybe people even make fun of like ah Paige is always saying this there are a few ways to think about advice and my advice often like meets a mark when it's for a particular person at a particular time in their career and 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 XYZ enough and not apply and 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 like what's 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 uh is another piece of product advice I give and the last piece of advice that I would say that I I like is more of a way of thinking so this is a little a little abstract but when cut uh when in plays
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 like language and tools for how to effectively work with other people
and it's a really Tran like for me at least it was transformational because I learned some vocabulary and methods that I could share with my my peers and one of the things that you learn is to be above or below the line and and
something that is is this concept of like where are you are you above the line are you bullet line if you're above the line you're committed to learning you're open and curious things are funny here um 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 and all of us have days where we're having a conversation and we're really like in that below line space where it's like no it just is this
way there's no two ways around it and that concept of understanding your head your personal headspace 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 our context it also helped me think about like rejecting false trade-offs and challenging like effectively there's this notion of how might the opposite be true
and that's that's a piece of advice that I give myself like this morning I I think it was yesterday actually I was like how am I going to do tomorrow like 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 less into those
plans and 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 ah right and at first it was like I can't this is just too much like I should like try to move or cancel one of these and then I asked myself how might the
opposite be true and I was like I can do both like like it was just enough to pop the balloon because sometimes your brain is so accustomed to having a scarcity mindset as opposed to like creating alternative options or seeing a
different path and 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'll be fine we'll have a great conversation I I you know ready to
show up and be curious and like really engage with you on the topics that you've found interesting and we'll just do that and 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 wow what a fruitful question that ended up being that was amazing I had this Clarity pillars strategy go or people into it is it working yeah I'm pumped
um it's a really interesting time to be a product leader um especially with all of the tax transform like 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 like we're not in an operational figure at Outland 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 and 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 and so I think it went really well and it's a it's a it's the start of our our
our 12-month rolling planning conversation let me pull on this AI thread because it's uh clearly top of mind for a lot of people yeah 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 or they're going to think about Ai and llm Integrations and everyone else keep doing what you're doing we've had an ml
team for quite some time making sure that we have like test prioritization models and like in 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 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 kind of 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 so much better than we imagined and would never have prioritized it because we thought it
would take so much longer and then in other cases that sounded good in theory and so skipping a lot of that to just really try it on for size has been key and then what we're doing is giving the teams with the most expertise and 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 dog fooding what do you want to do um and so we're able to like nudge people without wasting time and build the skills locally within the teams that then move those experiences forward I'm going 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 rich area of exploration you mentioned into it you worked it into it Intuit is kind of 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 APN program at Asana too and excellent training programs they and their 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 like if for anyone who works it into it or has worked it into it they know that there's the story about Scott Cook
watching his wife balancing her checkbook at the kitchen table and staring at it saying there's got to be a better way software um so it's very typical for the product training into it to be all about like how do you spend and 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 a durable advantage and think about overall like the the product process from a place of customer Insight through to like the market landscape so the PM
program there was absolutely super thoughtful especially for taking someone who has never pm'd into being the super skill PM 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 your teammates your teams for growth or success in their careers and so their their program for helping you think about like okay I'm gonna convey this feedback as situation Behavior impact like the situation is like on Tuesday in that meeting at three o'clock Behavior uh you interrupted me while I was saying this thing the 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 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 and therefore it is true and valuable feedback and it gets the conversation started such that you can then talk about next steps and 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 you know how do you feel their work is or how they're communicating or their body language having enough support where you can be really clear about what you're intending
in 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 it's interesting how some of the most impactful training is like such soft skills amazing and basically yeah just like how to give someone some feedback but it's like not like how to prioritize how to do a yeah you have a presentation it's like here's how you give feedback to someone yeah
so you've worked with a lot of early product managers I'm curious what you find most holds back new PMS in help 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 I would say this illusion you have to be all-knowing and super confident sets you up to be in a place of advocacy instead of inquiry and so PMS who are newer in their careers or who are like in a different
space than they're accustomed to working really want to be Pro really fast and what Pro means is trying to cut that straight path and that can reduce information and conversation that makes you smarter and 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 and then what happens is they're really
doing that customer or product Discovery or a spec in a little dark room and then they show up and they say this is it this is right and I know it's right and let's do this as quickly as possible and everyone else says wait what like I don't know like 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 PM's back is not being uh collaborative from a place of like true
curiosity like performative collaboration where they like not in a room or want to do a review but ultimately they don't really want the questions or the feedback and 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 you 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 that's something that I think holds Pam's back PMS tend to be so ambitious and career Centric and there are so many good things about that but I would say like 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 and yes you should have sponsors and people who advocate for you but a lot of that just comes from that like raw connection to the work and to your team everyone I talked to about you was like
oh my God I love Paige and I can see why but I want to ask you a question I imagine you've made some mistakes either with their product or your career I'd love to hear a story of something that went wrong and what you learned
from that experience and this might be the last question depending on where you take it I would say that all the advice I've given so far is directly related to things I've learned the hard way so like 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 like Direction and agency and so I would say one of the the missteps here is like 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 so I
think that's a 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 and then if by the end of the meeting I had decided that I still had a postage or two that was worthwhile I would say them
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 but they're not gonna necessarily um speak over you or challenge you
directly 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 and 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 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 like as long as the plan is good I wasn't really highlighting all the problems I saw or or like really pushing on those head on with my teen and so they felt like they didn't know what I was saying or if we were saying the same things that was really an interesting experience um yeah there are just so many yeah 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 what's wrong in a way that's still maybe optimistic and productive I try to be more real with myself and others I try to show up and say like hey this is incomplete like for example even the thing I did this morning the 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
Ezreal 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 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 kind of plan out the future of Paige's career I try to be really intentional about staying as much as leaving a role and when I think about my career as a
whole I try to think about like skills or experiences I want to have as opposed to roles or companies or specific problems so something that I think about is like effectively I evaluate whether I'm in a healthy role and in a good setup by asking myself about my learning curve like is it is it 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 and that's something that I I think is really important so like thinking about the learning curve thinking about whether the environment is positively impacting your ability to
grow your career and make an impact and so environmentally you might have like 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 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 and 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 like passions are made not found because I think people
kind of we do this with nine-year-olds 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 and there's this moment of like panic and I would say that 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'm living in the future and not enough trying to make the most about out of the career I'm living right now well with that we've reached our very exciting lightning round I've got six questions for you are you ready yeah
let's do it what are two or three books they've recommended most to other people my go-to book recommendation for other PMS is inspired by Marty Kagan 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 Paula cuello what is a favorite recent movie or TV show ooh I'm very much enjoying the Diplomat right now and then TV show or a 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 I saw the trailer for that I think I gotta watch that and I finished the Diplomat it's awesome it ends really well I'm not spoiling but it's just good
I'm just saying it's good that's not gonna spell it okay okay next question what's a favorite interview question that you like to ask candidates the good news is I can tell you this and still keep asking it if because the answer they've always come up differently um so I like to ask tell me about a time something went wrong what was it what did he do about it yada and effectively the question gets that when 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 what is a favorite product that you've recently discovered that you love I've
been playing a lot with poe.com lately just an opportunity to learn more about llm capabilities in a first-hand way it's been fun to create little thoughts I'm playing with making a page bot I I can't say that the pagebot could have had this conversation yet but maybe next year at this time you can have a conversation with the other me that's what the page about would say if this was the page bot talking right now I would say though but
um the advice bits and Bobs I gave you earlier are are absolutely things that I've been thinking about feeding but I think I the pagebot would probably say ship it um uh the and po just it's the quora founders llm chatbot yeah and so you can try the different models so you can do four and replay five and um Claude and a few others yeah there's also a lennybot.com for folks that haven't seen this somebody built actually there's a whole post on my
newsletter of how how it was built and you go to lennybot.com and it is trained on all of my newsletter posts and I think not yet podcasts but someday it'll have podcasts by the way someone's listening to this we're looking for
someone to maintain this bot and evolve it so if you're really into the stuff and have done this sort of thing please DM me on Twitter and I'm looking for someone to take over lennybot.com make Immortals 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 one of the biggest ones is just being 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 improving work so we got really aggressive about functionally who is in charge and at what level for a given review and pushed
to say like to actually have limits on the number of people per meeting on the the number of subtask reviews for a given body of work and what this did is it created a lot more agency and and Pace within a given working teams and 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 him the book can stop with them and they can be responsible for how the work moves forward such that like the
knowledge is known and we could have connected dots more effectively than we do or did so that's kind of the logic there and it's really changed the pace and quality of our work I love that is there any more you could share in the
number like what is the maximum is there anything that people maybe can take yeah so no more than three reviews on a given piece of work where people are blocking one approver and um if a meeting has 10 more than 10 people
on it we ask the person hosting the meeting to kick out the other people and write better decision notes and the three reviews is three meetings looking at the product as it's coming together basically the three reviews are
um three people who are assigned a task to look at something but only one person is blocking whether it moves to the next stage got it informed people stakeholders decision makers okay great final question you work at Asana what is
your favorite Asana Pro tip 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 it says read the Same by the state and then I assign
it um to a team or a set of individuals like that really quickly and 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 wow you need to make a video or Blacklist about this not only is it using Asana to build a sauna it's using Asana to run teams within Asana all the way down people know who's 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 you can find me on LinkedIn and Twitter page Costello and on Twitter at page now
listeners well I'd love to hear how you think ai's gonna shape the future of software for knowledge workers but in particular if you 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 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
awesome Paige again thank you so much for being here my pleasure thanks for having me bye everyone thank you so much for listening if you found this valuable you can subscribe to the show on Apple podcast 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