An inside look at how CNN builds product | Upasna Gautam

1. 0:00 – 3:13

   Upasna’s background

   1. UGUpasna Gautam0:00

      It happens all the time, right? That is the nature of breaking news. I mean, you have to be ready to pivot at, you know, the drop of a hat. I had a big working session planned with my users to do research with them or do user testing, and breaking news breaks. And it takes so much time and effort to gather a team of editors across the globe to do a user testing session and when breaking news happens, they have to prioritize that over everything, right? So, like, what do you do in that situation? You can be frustrated. Absolutely, it's frustrating. But you always have to have the ability to, A, pivot, of course, but also have backup and, you know, buffers in those types of scenarios. (upbeat music)

   2. LRLenny Rachitsky0:45

      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 Upasana Gautham. Upasana is a product manager at CNN, where she leads the team responsible for the content management system that journalists use to write and publish their stories. She's also on the front lines of elevating the discipline of product management within newsrooms through her work at the News Product Alliance. She's also a long-time meditation and mindfulness teacher, which, as we discuss, ends up being pretty damn handy working at a place like CNN. We dig into how the product team operates within CNN, how they collaborate with journalists, the breaking news dress rehearsals, and also some simple tricks to build your own mindfulness in your day-to-day work as a PM. Enjoy this episode with Upasana Gautham after a short word from our wonderful sponsors. This episode is brought to you by Amplitude. If you're setting up your analytics stack but not using Amplitude, what are you doing? Anyone can sell you analytics. While Amplitude unlocks the power of your product and guides you every step of the way. Get the right data, ask the right questions, get the right answers, and make growth happen. To get started with Amplitude for free, visit amplitude.com. Amplitude, power to your products. Today's episode is brought to you by OneSchema, the embeddable CSV importer for SaaS. Customers always seem to want to give you their data in the messiest possible CSV file, and building a spreadsheet importer becomes a never-ending sink for your engineering and support resources. You keep adding features to your spreadsheet importer, but customers keep running into issues. Six months later, you're fixing yet another date conversion edge case bug. Most tools aren't built for handling messy data, but OneSchema is. Companies like Scale AI and Pave are using OneSchema to make it fast and easy to launch delightful spreadsheet import experiences, from embeddable CSV import to importing CSVs from an SFTP folder on a recurring basis. Spreadsheet import is such an awful experience in so many products. Customers get frustrated by useless messages like, "Error on line 53," and never end up getting started with your product. OneSchema intelligently corrects messy data so that your customers don't have to spend hours in Excel just to get started with your product. For listeners of this podcast, OneSchema's offering a $1,000 discount. Learn more at oneschema.co/lenny.

2. 3:13 – 8:55

   How Upasna’s meditation background helps her thrive in the chaotic world of product at CNN

   1. LRLenny Rachitsky3:13

      (upbeat music) Upasana, welcome to the podcast.

   2. UGUpasna Gautam3:15

      Thank you, Lenny. I'm so excited to be here.

   3. LRLenny Rachitsky3:18

      As you probably know, I'm on this kind of quest to understand how different companies build product, especially companies that are kind of outside the Silicon Valley just, like, standard tech scene. And I've always wondered what it was like to build product at a company like CNN, which is, like, very different from where most, I don't know, tech PMs work. And so, I'm really excited to have you on and to give us a little glimpse into what it's like to build product at CNN.

   4. UGUpasna Gautam3:42

      Awesome. I'm very excited to share as well.

   5. LRLenny Rachitsky3:44

      So, I was doing a little research on you before this chat and I noticed that you've been teaching and studying meditation and mindfulness for, I don't know, maybe a decade. And I imagine that comes in handy at a company like CNN, which also, I imagine, is, like, quite hectic at times with breaking news all the time. And so here's my question, what have you learned or brought from that practice to your ability to lead and ability to just, like, keep your team calm and focused during, I imagine, many hectic moments?

   6. UGUpasna Gautam4:16

      I love that question. And working in product in news is a very beast. We hear a lot about having the skills to thrive in ambiguity in order to be a successful product manager. But to be a successful product manager in news, you have to be able to thrive in chaos. And equanimity is the most important skill I've developed, I think, across my entire life, and it's due to all of those years of practicing, uh, mindfulness and meditation. And equanimity is one of my favorite words. It means mental calmness, composure, evenness of temper, especially in crazy, stressful situations. It's, you know, the ability to remain unrattled in, like, the highest of highs and the lowest of lows. And if you think about it in the dynamic of a workplace or human interaction, it's really the ability to pause before reacting. And reactivity is the root cause of so many of our workplace woes and product management frustrations. And when you're able to pause before reacting, you can start to undo and break a lot of those negative patterns in your brain. And in news, and especially the world's biggest breaking news organization, you can cut through that chaos with equanimity, because it also really gives you this outsized advantage in everything from stakeholder management and team morale to the way you're able to translate user feedback to product development velocity. And the thing is, is you're always gonna hear things and feedback that you don't like and opinions that you don't like, and you're gonna get frustrated. That's product management. That's life. But real power, to me, comes from equanimity, and that comes from managing your emotional reactions and not trying to control others. So, I think when you're able to cultivate that level of self-awareness for yourself, you're able to chart a clear path forward for your team. And...... like, serve as a compass in the chaos.

   7. LRLenny Rachitsky6:22

      Is there a story or example that comes to mind where things were just like, "Oh, shit," and y- you were able to tap into that skill that you've built to stay calm and focused, or even just, like, help your team stay focused?

   8. UGUpasna Gautam6:34

      I mean, it happens all the time, right? That is the nature of breaking news. I mean, you have to be ready to pivot at, you know, the drop of a hat. And so, I think more than just, like, the big chaotic moment in those daily interactions when there's chaos. I think that's when it really shows its power and helps me navigate those day to day interactions when I had a big working session planned with my users, to do research with them or do user testing and breaking news breaks. And it takes so much time and effort to gather a team of editors across the globe to do a user testing session, and when breaking news happens, they have to prioritize that over everything, right? So like, what do you do in that situation? You can be frustrated. Absolutely, it's frustrating, but you always have to have the ability to, A, pivot of course, but also have backup and buffers in those types of scenarios. So any time we're planning, we build in buffers for all of that chaos that's happening on a daily basis.

   9. LRLenny Rachitsky7:41

      Wow, that's cool. Is that a real thing that happened? You were like in a big meeting with all the researchers and then something went- went off the rails in the world?

   10. UGUpasna Gautam7:47

       Oh, yeah, absolutely. Happens all the time.

   11. LRLenny Rachitsky7:49

       I don't know how much you can go into all this, but what is it that you would do in that case, like as a product team? What are they looking for you to do at that moment?

   12. UGUpasna Gautam7:56

       For us, it's not really anything we have to do. It is more so, okay, well our goal of this session was to get user testing done, or user feedback from that user testing session with our editors. And so, what do we do? Okay, well good thing we had a backup plan, right? We don't actually have to go into that scenario, but since, uh, our editors and our journalists are our customers, we're there to serve their needs but they are not here to serve our needs. They have a whole nother job that they have to do. And so, we have to have the ability to adapt and accommodate to those really chaotic schedules across global timezones. And so, that happens. Again, like it's not a- it's not like once in a while. It's a very regular thing that we have to be- be aware of and also account for.

   13. LRLenny Rachitsky8:46

       Got it. Okay, I get it. It's the, like, these journalists are the ones in the meeting that like, oh, they have to go write about the stuff and cover it.

   14. UGUpasna Gautam8:50

       Totally.

   15. LRLenny Rachitsky8:51

       I see. That makes sense. You said that you built in some buffer time for- to

3. 8:55 – 10:26

   How PMs at CNN build in buffer time and create backup plans when breaking news hits

   1. LRLenny Rachitsky8:55

      kind of account for these things. Is there like a systematic way of doing that, or is it just broadly, "Let's add buffer time?" Is there like a rule of thumb you- you think about there?

   2. UGUpasna Gautam9:02

      It depends on the scope of the work we're doing at that time. So, one of my main responsibilities is to rebuild our content management system, which also involves onboarding our editors and journalists to it off of our Legacy platform and onto our new one. So, when we're thinking about onboarding, especially the teams, our onboarding cycle is very long. It involves training, testing, lots of dialogue and feedback, and then only do we actually test and then we onboard. And so, it is a long cycle, and it's longer than it maybe seems like it needs to be because we have to build in those buffers. Sometimes that buffer is a day or two, and sometimes it's a week or a month. And sometimes when we think we need a buffer, we get it done in a day and we quickly move on to the next phase. And so, I think that quick decision making in those times is super important because you have to be able to assess the situation as it stands. And so I think mindfulness is so important too in practices like this, because being able to objectively see the scenario for what it is, make a quick decision and move on to the next phase is- is something we have to analyze every single day.

   3. LRLenny Rachitsky10:16

      It makes me think a little bit about s- a lot of CEOs are very, uh, busy and pulled into a lot of things, and so you have to kind of account for their schedule and it sounds like

4. 10:26 – 15:22

   How the product team works with editorial staff and journalists at CNN

   1. LRLenny Rachitsky10:26

      you have many, many people, ah, you work with that have crazy schedules.

   2. UGUpasna Gautam10:29

      Yes.

   3. LRLenny Rachitsky10:30

      I wanted to dig a little bit deeper into how you or team worked with the news team. It's a- such a unique way of working. Most product teams don't have a whole set of journalists that they have to work with and, uh, stakeholders. So, I'm curious specifically, say a journalist has like, "Hey, I'd love to build a special immersive experience for this story," or, "I need some special feature to help support this work that I'm doing." How does that work? Do they come to you and are like, "Hey, here's the roadmap? When might I- maybe in the quarter I need the thing"? Imagine it's like, "I need this next week." How do you- how do you work with the journalist team basically on product?

   4. UGUpasna Gautam11:04

      Yep. This is pretty much the foundation of all of my work. We talk to our editorial staff every single day and after a lot of observation and learning, I implemented a system to manage that kind of intake with four different touch points or events. So we have weekly demo days, working sessions, breaking news dress rehearsals and office hours. So with weekly demo days, I facilitate those with my product design lead and my tech lead and we use that as an open form of communication to deep dive into features that exist on our platform, also to preview or give a sneak peek of new features to come and kind of recreate their workflows and do a show and tell. Again, we wanted to open that up as a forum to not just our editorial partners, but also anyone across the business who is interested in learning about the product, uh, which is our platform. And it was also a great way to kind of evangelize the product too. Coming off of a Legacy system after several years onto a brand new one is a big change at a place like CNN. And so, we definitely tried to make sure that, you know, smart repetition in different ways is top priority, so weekly demo days is one. Working sessions are interesting. I-... use the term working session because it's a combination of several things. This is a really critical part of our onboarding process, where we gather breakout groups of our journalists and editors to work with us to recreate their workflows in the new platform. This allows us to, you know, address any friction or issues, of course, that are occurring in their workflows. But also, we're able to gather a lot of awesome feedback from them in those sessions. So we used to call them user testing sessions, but started to move away from that and just called them working sessions, so they're more collaborative. And again, it's a really critical part of our onboarding process. We usually do three to six of them, depending on the size of the group before the team is actually onboarded for two hours per session. So they're like deep dives into their specific workflows. So as you can imagine, the way the politics team programs content is wildly different than the way the entertainment team does, or the way that the, um, the health team does. And they're very different than the way that the CNN homepage even, even interacts. So all of those are separate teams we have to work with when it comes to getting feedback. So in addition to that, we also do, I mentioned breaking news dress rehearsals. And you can imagine this is exactly what it sounds like. We create a script and do a simulation of a breaking news scenario to stress test our platform because all breaking news scenarios are definitely not the same either. So this gives us a lot of great feedback in that short amount of time at the speed of breaking news. And then last but not least, we have office hours, which I just started last year. And that's also probably what you can imagine, open blocks of time where me and my product design partner and my tech lead are this, there to answer questions, help people troubleshoot any friction they might be experiencing in their workflow, get their feedback. We just wanted to open up another line of communication, so we do those right now once a week. Sometimes they go up to two times a week if we're in a really rigorous onboarding phase. After those conversations and, uh, sessions and events happen, you know, it's our job to translate their needs into the functions that we, A, either maybe already have that we can optimize. B, we build anew. Or we tell them it's not viable. And the good thing is, is that because they've been along for the ride with us throughout the product discovery process, we've earned their trust and respect so that when we tell them something like it's not viable, they usually get it.

   5. LRLenny Rachitsky15:07

      Man, I have so many questions about just working with journalists. I feel like pushing back on a journalist is probably extra hard versus, uh, other type of stakeholders. (laughs)

   6. UGUpasna Gautam15:14

      It is.

   7. LRLenny Rachitsky15:15

      Can we zoom out a little bit? And you talked about what you work on at CNN, which is the content management system and things around that.

5. 15:22 – 19:02

   The product org structure at CNN Digital

   1. LRLenny Rachitsky15:22

      Can you just talk about, whatever you can share, just, like, what does the product team look like at CNN? How many PMs are there? How is, like, the product org structured and where, where do you fit in there?

   2. UGUpasna Gautam15:31

      Yes. So s- I mentioned earlier, my team sits on CNN Digital. And I think when most people think of CNN, of course you think of TV and linear programming. I have nothing to do with that. CNN Digital is digital, and it's made up of several teams that are structured around a lot of different product areas. It includes everything from the content management platforms that I work on, to data infrastructure, to personalization, to video experience, which includes, like, the products of video editor and the video player, to podcasts. There's a lot. So each of those are product teams. And so we also split out, you know, the way CNN is split out into CNN Digitals because there's a separate core content platform that powers broadcast and linear TV. And the one that I work on powers CNN Digital. So on my team, the core platform team, our stakeholders and our customers are, like I mentioned, our journalists and our editors, which presents a really unique dynamic, and it's one that I love. We have direct access to our customers at all times of day, for better or for worse. And they're embedded into our product development process. And each of those teams under CNN Digital is kind of like a squad, very similar to how it is at other larger tech companies. We have PMs. We have engineers, designers, and delivery managers embedded in those squads. And since my team is a core platform team, our main responsibility is to, A, build our newer, faster, more flexible content management platform to replace our legacy one. And B, onboard our entire editorial staff to it. And so even more specifically, my role is focused on rebuilding the tooling and the editorial experience of that platform, as well as doing the actual onboarding of our journalists. So we work cross-functionally because our team kind of is the umbrella over a lot of different teams. So we truly work cross-functionally to make sure that, you know, we're serving our journalists with the tools that they need to do their job in the most efficient way possible.

   3. LRLenny Rachitsky17:48

      What would surprise people most about how product is built at CNN?

   4. UGUpasna Gautam17:54

      I think the most surprising thing may actually be that there's just so many different types of products that we build. Like I said, I, I think when most people think of CNN you see TV and you think of Anderson Cooper and all of the things-

   5. LRLenny Rachitsky18:08

      Yeah. Mm-hmm.

   6. UGUpasna Gautam18:08

      ... that are very publicly, you know, visible. There is... Most of our product work and product teams all sit behind the scenes. And so I think just that in itself, like, the sheer size of that is, is surprising to a lot of people. So I mentioned, like-... all of the different teams, right? Product teams that are based off of function, content management platforms, infrastructure, personalization, video, podcasts, linear TV. And I think that in itself, the... Like, the sheer size of it. Like, we're, we're, we're not the size of Google by any means, but at the same time, we have the expertise and the depth and breadth of a lot of those larger tech companies.

   7. LRLenny Rachitsky18:52

      I'm curious about the day-to-day operational work of how you build product at CNN. So our first question here is just, do you use, like, OKRs, you know, OKRs with,

6. 19:02 – 20:10

   OKRs at CNN

   1. LRLenny Rachitsky19:02

      like, key objectives and outcomes and 70% of a goal is success?

   2. UGUpasna Gautam19:06

      Yeah. Absolutely. We do. We've used OKRs for a long time and they've served as an anchor for my team over the last three years. I kind of already... I, I can't go into specifics on, like, what our OKRs are, but I did kind of cover the two main parts of it, which is, you know, rebuilding our content management platform and onboarding our users to it. So again, this... It's a long game at, at CNN when you're working o- on a, on a core platform to replace a legacy one. And so we break those OKRs down, of course, even further into, you know... We look two to three years out and build goals based off of that. Then we break them down by quarter and month. And then out of that, for my team and what I do, I need to, for my own sake and my team's sake, break those down by the week. And when we're in rapid development phases, we're planning on a daily basis.

   3. LRLenny Rachitsky20:01

      How about in terms of just planning broadly? How far out does the product team at CNN plan in detail? Like, have an actual roadmap? And is that standardized

7. 20:10 – 21:37

   How CNN’s product teams do long-term planning

   1. LRLenny Rachitsky20:10

      across teams or can each team kinda do their own approach?

   2. UGUpasna Gautam20:13

      It's a combination of both. So we have one that is an overarching, you know, roadmap that tracks to, like, our company OKRs and our product organization OKRs. And then from there, I mentioned we have our squads of product teams, and we have OKRs on those as well that track up to the larger, broader ones. And so once we get down to that level though, there is flexibility and we have autonomy to tackle those how we want, which is really great because the scope of work across our different product teams is drastically different. Working on core platform like I do versus working on video experience versus podcasts. I mean, y- it's apples and oranges. And so it's really awesome that we have the flexibility to kind of make it work for us while also having these larger goals that we know that, "Okay, this is what we need to work towards." And that makes... You know, we... It's like the saying we always hear in product, right? Of stay firm on the goal but flexible on the process. And, like, we've definitely been able to, to use that and leverage that in the way that we track against our goals.

   3. LRLenny Rachitsky21:27

      Something else that a lot of people are always curious about is product review meetings and design review meetings. You talked about a couple of these meetings that you have, but do you have standard product review meetings where

8. 21:37 – 23:51

   Why Upasna involves the tech lead in all product discovery/product review meetings

   1. LRLenny Rachitsky21:37

      folks get together and just review stuff in progress? And if so, how do they work? Like, who runs them? Who comes to them? How do you make decisions? Things like that.

   2. UGUpasna Gautam21:46

      We have multiple variations of those. Some are standing ceremonies, of course, and some are ad hoc. Again, it's really based on the work we're doing in that... In, in whatever phase we're in. But when it comes to product review and product discovery or design review meetings, in addition to my design lead, I've made it a point to bring in my tech lead and engineers along for this product discovery ride. And that's definitely been a game changer as well. When our engineers are able to understand our journalists' needs at the same level as we are, they're able to define the how to do it with so much greater clarity and precision. And so my tech lead is embedded also in our product discovery process. He joins our user testing sessions and our design jams and our editorial conversations, planning sessions, and it's helped him and the rest of our tech and engineering team become experts on the, "Why are we doing this and what are we working towards to better determine technical feasibility?" And he's done an amazing job of also passing that knowledge down to the rest of our engineers on our team. So it's really like this mentality of getting that important feedback from our journalists, understanding their pain points, and then sharing and teaching it across the team. And I think, you know, the key takeaway on that is, it's so important to think of your engineers as partners and not just resources. And when they are embedded, you know, into the process right up front, it makes the whole process, in general, more efficient.

   3. LRLenny Rachitsky23:21

      So it sounds like that was maybe an evolution of the, of the way the team works as engineering's has been looped into a lot of this early stuff more recently. Is that right?

   4. UGUpasna Gautam23:30

      Totally. Yeah. Recently meaning, I mean, uh, we... Again, long game, right? So, uh, it's been, it's been a couple years. (laughs)

   5. LRLenny Rachitsky23:39

      Got it. Going in a slightly different direction, I'm curious if there's any fun or unique traditions or rituals that the CNN product team has. It's always fun to hear about.

   6. UGUpasna Gautam23:50

      So

9. 23:51 – 27:39

   How to boost morale with remote teams

   1. UGUpasna Gautam23:51

      I'll be very honest. We are not one of the cool teams. The politics team, like, and the breaking news teams have all these cool rituals and fun things that they do.

   2. LRLenny Rachitsky24:02

      What kind of stuff do they do?

   3. UGUpasna Gautam24:03

      It's different also because they're usually in person in the newsroom and I work remotely, and so... And, um, and actually most of my team works remotely and so, you know, they have their rituals. But I will say, one of the things that we started to do is... So onboarding teams has been a big goal of ours and that we've slowly checked off the list over 2022, and anytime we successfully onboard a team or launch a new feature, you know, it's not anything crazy or fun. Like, there's only so much you can do when you work remotely, but we definitely make it a point to celebrate. And it's been hard to figure out ways to keep team morale up when you're all remote. And-It started with, we knew we needed to start doing something when we would have a big launch. And it was so anticlimactic and we'd literally hit-

   4. LRLenny Rachitsky24:52

      Mm-hmm.

   5. UGUpasna Gautam24:53

      ... publish and onboard onto like a h- a politics page. And (inhales deeply) we're like, "Oh, okay. So I guess that's it." So one thing we started doing is sending, like... like these gift boxes of, like random tchotchkes and stuff that would, that mean things to us from the whole year. And it's, like just cheap little, like gag gifts and stuff that we send to each other. I have, like random stuff all over my, over my desk.

   6. LRLenny Rachitsky25:18

      Mm-hmm.

   7. UGUpasna Gautam25:18

      And I don't even know if I can share some of it, uh, but... (laughs) Um, so we try to make it a point to at least like share and celebrate, and then when we're in person, we do too. But again, being remote, there's definitely, there's definitely a challenge there.

   8. LRLenny Rachitsky25:32

      Are you ever able to get like a cameo from an Anderson Cooper or someone else on, on air to, uh, thank the team? Is that... It feels like a cool feature, potentially.

   9. UGUpasna Gautam25:41

      So one of my, uh, c- key stakeholders, she is a, she leads the video team at CNN and she is, uh... Uh, we've, we've had some discussions about doing a Sizzler reel for our content management platform, uh, as since we're onboarding people and, you know, building new features and there have been discussions with her about getting a celebrity to come and promote product for us. So working on it. (laughs)

   10. LRLenny Rachitsky26:07

       Yeah. That feels like a missed opportunity. You got so much talent around.

   11. UGUpasna Gautam26:11

       Totally.

   12. LRLenny Rachitsky26:11

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   13. UGUpasna Gautam27:32

       Mm-hmm.

   14. LRLenny Rachitsky27:32

       I'm curious how you balance, uh, new product work and new features versus maintenance and bugs. Do you have kind of a... Is there like

10. 27:39 – 29:21

    Balancing maintenance with building new stuff

    1. LRLenny Rachitsky27:39

       a philosophy at CNN of how much goes to bugs maintenance versus new stuff or is it per team and just how do you all think about that?

    2. UGUpasna Gautam27:45

       It's certainly team specific because again, the scope of work across teams really varies. But since my team's product is an entire platform, it's my job to ensure we're crystal clear on our goals because like I said, they may change on a week by week basis. One sprint might be high priority feature development. And another sprint, maybe we're focused on medium priority optimizations and bug fixes. But we know that anytime there's a critical incident in production, it also takes critical priority over everything else. So it's a balancing and juggling act that relies heavily on intuitive decision-making. But I will say we're also really fortunate to have a global 24/7 editorial support team that we work really closely with. So they are the ones who handle, troubleshoot, escalate incidences, incidents up to the relevant teams. There are a lot of layers to that protocol when an, when a critical incident occurs. And so our editorial support team is that first layer of support, whereas my team might be the second or third depending on the level of severity and who it gets escalated up to. So there's definitely a lot of processes in place. We're not always that first line of defense, which is actually... It, it alleviates a lot of stress to know that we have an entire team around the clock globally dedicated just to that.

    3. LRLenny Rachitsky29:12

       Are you talking about these like incidents and moments? And it makes me wonder, is there a memory of just like a wild time if something happened in the news of just like, "Oh man,

11. 29:21 – 31:21

    The time CNN.com went down in 2020 and the new platform saved the day

    1. LRLenny Rachitsky29:21

       we gotta get on top of this thing." Like, is there like a memory that you can think of like, "Wow, that was crazy."

    2. UGUpasna Gautam29:26

       It's, uh, funny, but also crazy and amazing is... So our new content management platform, you know, it's... We've been building it for a while and stress testing it for a while and, you know, politics and election season at CNN is, is Super Bowl like times 100. And so-

    3. LRLenny Rachitsky29:44

       Yeah.

    4. UGUpasna Gautam29:44

       ... we have to be, you know, all hands on deck, like all layers of support in, intact. And so we have also a lot of layers of fallback in case something happened, right? Like there's layers and layers of infrastructure fallback if cnn.com goes down or an- another service goes down. And so it actually did happen a couple of years ago in the 2020 election, and one of the fallbacks at that time because we were not... We are, you know, we're still on our current content management platform, but we had our new one as we're building it as one of the levels of fallback.

    5. LRLenny Rachitsky30:22

       Mm-hmm.

    6. UGUpasna Gautam30:23

       And if XYZ fails, then it goes to our current platform, and it did. And so (laughs) that actually happened where our new platform saved the day, even though it wasn't fully ready, but that just goes to show we think about that kind of stuff like in granular detail when we think about everything that could possibly go wrong because it has happened and it will happen and it does go wrong. So that was kind of cool. It was validation to know that the platform we have is really stable and strong and secure, that it was a fallback for the election. (laughs)

    7. LRLenny Rachitsky31:03

       Yeah. Man, that must've felt good. That feels like a promotion material right there-

    8. UGUpasna Gautam31:07

       (laughs)

    9. LRLenny Rachitsky31:07

       ... that your work in progress system saved the day.

    10. UGUpasna Gautam31:10

        Yeah. I agree.

    11. LRLenny Rachitsky31:12

        You talked about how you have these, like, breaking news dress rehearsals. Uh, I just noted that and I thought it'd be cool to just revisit that briefly. Like, h- what does that... How does that work? Do you

12. 31:21 – 34:22

    How the product team rehearses breaking news

    1. LRLenny Rachitsky31:21

       just, like, get the team together and like, "Here's, here's a new story that just broke. What do we do?" Like, how does, how does that work?

    2. UGUpasna Gautam31:27

       It is scripted, right? So you can only get so close to the real thing.

    3. LRLenny Rachitsky31:30

       Yeah.

    4. UGUpasna Gautam31:30

       But one thing we do is, I mean, we script everything, right? Like the teams and the players that we need involved in it, what the incident is. And it usually starts, when breaking news occurs, with an email. The news gathering team sends an email-

    5. LRLenny Rachitsky31:44

       Mm-hmm.

    6. UGUpasna Gautam31:44

       ... it to our writers and our producers. And then from there, it goes out all the places it needs to go. If there's a video that needs to be created, if there's an article that needs to be written, if there are, you know... And again, the TV side I have no insight into. It's like a foreign land to me. But as far as the digital scope goes, there's a lot of work that has to be done. Even things like photo and imagery, right? Like, we have a whole team dedicated just to selecting photos. Like the photo desk is very involved with that process. And so that is all scripted out. And so we say, "Okay, here's the news. Here's how it's gonna break." And then we, we, we run it. And so we use, you know, interpersonal communication tools at work, of course, email, and like we run the whole thing from the minute the email is sent to... And of course since we're testing the platform with this breaking news dress rehearsal, to the minute you hit publish on that page. And there's a lot of stuff that goes on in there and it all happens in the span of minutes. And so while that is happening, while that dress rehearsal is happening, we have our engineers and our editorial support team on hand as well. So they're observing what's happening while it's usually me and one of our editorial stakeholders and leads facilitating the actual rehearsal part and, you know, getting user feedback on, "Okay, what... Did something break? Did everything work as it was supposed to work?" And also allows us to understand like how far we can go with stress testing different features on our system. So each one is different, but it's a crazy amount of stuff and information you can gather in such a short span of time because if it cannot serve the needs of breaking news, then it's useless. So it's, it's a lot of work that goes into it for, you know, this three-minute event. (laughs)

    7. LRLenny Rachitsky33:35

       That is cool. It feels like just a cool tactic you could use anywhere.

    8. UGUpasna Gautam33:39

       Yeah.

    9. LRLenny Rachitsky33:39

       And that's a good segue to the next question I had, is just having built product at CNN and seeing how the product team works, what is it that you think you'll take with you to future product teams and future companies that... if you ever move on to anything else?

    10. UGUpasna Gautam33:53

        So I, of course, can't speak for the entire CNN product team, but I can speak for myself and my specific team. So in order to stay competitive in our modern news landscape, building this content management platform and the technology behind it has taught us how to enable rapid development and integration of new features and workflows. And we've been able to quickly

13. 34:22 – 35:50

    The superpowers Upasna and her team have cultivated

    1. UGUpasna Gautam34:22

       test hypotheses while reducing risk. And again, time is of the essence, right, when it comes to breaking news. And when you layer that with a very complex content management technology, there's a lot of moving parts. And we've been able to do that successfully and that's pretty amazing. And because of that, we've developed, I think, this unique skill of high agency under high pressure. And I really think that that's... that skill or combination of skills is our superpower, and that is something you can take anywhere. That is something that, that is an asset to any, any product development team.

    2. LRLenny Rachitsky35:03

       That circles back to our original topic about mindfulness and meditation. Other than just living through it and either becoming a meditation expert or having worked at a company like CNN that has a lot of this, is there any, uh, I don't know, tactic you could share? Something that someone could take tomorrow and be like, "Okay, I'm gonna get better at dealing with crazy unexpected events," based on the experience you've had?

    3. UGUpasna Gautam35:25

       Two parts to this. So one, I would be remiss, uh, as a meditation educator if I didn't say that there is no substitution for meditation. So just gotta do it. It takes a long time and it's a lifelong work in progress. But the good thing is, is that it also... Like the more you do it and consistently you do it, it compounds over time. And I always

14. 35:50 – 42:01

    Why meditation and honing your communication skills help you excel as a PM

    1. UGUpasna Gautam35:50

       y- Okay, if you think of any job description for a product manager, right-

    2. LRLenny Rachitsky35:53

       Mm-hmm.

    3. UGUpasna Gautam35:53

       ... it's mostly the same core stuff. You need to be able to lead a team without having authority. You need to have great communication skills. You need to be able to thrive in ambiguity. You need to be able to work with a lot of different people on the technical side and business side. All of the stuff that we hear all the time, right? But like how do you actually become better at those things, right? Like, there's only so much you can gain from reading a book. To me it's either A, you gotta go do it, and B, meditation has helped so much because of the clarity of mind and clarity of thinking you're able to cultivate because of it, especially when it comes to communication. And this comes back to another tactic, I think, right? So meditation is one. I, I... You can't get around it. It's, it's a very, very powerful tool. I'll die on that hill. But thinking about workplace tactics. Communication is so essential. When I started at CNN it was a very new chapter for me. It's my first official product management role after working a decade in tech in data and search infrastructure, and it was really scary to make that change so far into my career. But when I asked my boss why he took such a big chance on me, he said, "It's because of your communication skills and relationship building skills," and that, "I've seen you in a room where engineers listen to you and what you have to say and you listen to them." And he was like, "That in itself is...... really, really hard to teach. And I was like, "Okay, yeah, I can do that." So when I think about what communication means, I also attach that to mindfulness. Like, mindful communication is so critical for successful product management, no matter what type of product environment you're in. And it means being, like, deeply aware of the conversation you're having. And when I'm having this conversation with you, I'm only having this conversation with you. When I'm talking to my design lead, I'm only talking to my design lead. When one of my journalists is venting because this feature is not working the way we told them it was going to, I am shutting my mouth and I am listening to them vent, and then I'm extracting what the root cause of the problem is. And I think the takeaway and the tactic is that, goes back to exactly what we talked about in the beginning, is the ability to pause before reacting is the key to mindful communication and being a successful product manager. I think a lot of times, we are taught to, like, have all the answers, or we're expected to have all of the answers, and people assume we have all of the answers, so it's a really frustrating, sometimes, place to be in. But if you listen and you know where to go to get the answers, that in itself is, like, a tremendous place to be. So I think the power of meditation, being able to pause before reacting, lets you do things like conversate in the language of the listener. So when I'm talking to my journalists or t- I'm not using technical terms or, like, content management technology terms. They have a whole different vocabulary that they use. They have shortcuts that they have, you know, lingo for in our content management system. They call things nicknames. And so, you have to speak many different languages as a product manager. And there's one thing that, you know, learning and teaching mindfulness has, like, strengthened. It is that communication, yes, it's very important. How do you become an effective communicator? I think a lot of times, we think of speaking articulately first and foremost, or we think about writing well. Which those two are really, really important things, but those can't be effective for us as product leaders if we're not listening. So, I think listening and being able to converse in the language of the listener is the utmost importance. And how do you, like, do that in your day-to-day? It's like, okay, if you're having a conversation with your customer, are you actually listening to what they say, or are you going in with your own assumptions because maybe you're a user of the product? And it was very interesting because I actually started writing freelance for CNN this past year, and I was like, "Oh, okay, I'm a user now." And no, I'm not. I, I'm not gonna say that it helped me understand their pain points so much more and where they're coming from in a whole different light, but again, I am merely a proxy. I'm not actually the user. What they do is still drastically different. And so, when, like, having those, like, customer interactions and stakeholder interactions, the priority should be to listen. And I think that is one of the most important things I've learned. And it's also helped build trust and respect between a previously fragmented structure where product and editorial didn't talk to each other, and now we're a unified, you know, partnership.

    4. LRLenny Rachitsky41:00

       Wow, I love that. (clears throat) I love the reminder that a lot of communication is incredibly important for product managers, and so much of it is not actually you talking, it's you being really good at listening, and that makes you a better communicator. I imagine some people listening to this are gonna be like, "Yeah, meditation, that sound like I should be doing that." What's, like, one thing someone could do to move forward on the path to starting to meditate? Is there a resource you recommend, a tip of just, like, getting- starting to do something there?

    5. UGUpasna Gautam41:27

       Totally. I think when people think of meditation, you immediately think of sitting on a meditation cushion like a monk for an hour. And that doesn't have to be true, especially if you're just starting. And there's also, of course, social media has commercialized what meditation is a lot as well. But at its core, all it is is being deeply aware of the present moment, right? So, I always tell people who are, for example, like, really busy moms

15. 42:01 – 44:39

    How to get started on the path of meditation

    1. UGUpasna Gautam42:01

       who have no time, right, in the morning for an hour-long meditation is, "Okay, take something in your day that you do every single day." You brush your teeth every morning, right? Okay, take brushing your teeth. Can you brush your teeth and just brush your teeth? And when you're brushing your teeth, you are engaging all of your senses and being fully present and aware of how it feels, how it smells, how it sounds. That's, you know, two, three minutes of your day. That's meditation. And I think it's an amazing way to, and an easy way... Oh, sorry, not easy, simple, not easy way always to think about what meditation actually is, is like instead of, like, having to uproot your whole life and the way you live to, like, bring meditation in, think about what you already do every day and how you can just be more present, like, fully present. And that's one of the core examples I give, is start with brushing your teeth and just brush your teeth. There's a old app I've been using for a long time if you're into that. I stopped using it recently, but it's still amazing. It's called InsightTimer. The free version is amazing. It started as, like, a single frame app about 10 years ago, and it's turned into this, like, they've- they've done amazing things with that product. So, that's what I recommend. But again, you don't... I- I think, again, when people...... have a vision of meditation in their mind. They're like, "Well, I need these tools and I need these resources and I need these things and I need knowledge." You don't need anything. You need five minutes and yourself, and that's it.

    2. LRLenny Rachitsky43:37

       Amazing. I imagine many people listening to this coming into it thinking, "I'm gonna learn about CNN and how they build product and then get a free meditation lesson."

    3. UGUpasna Gautam43:45

       Yeah. (laughs)

    4. LRLenny Rachitsky43:45

       What a bonus.

    5. UGUpasna Gautam43:45

       (laughs)

    6. LRLenny Rachitsky43:46

       That was awesome. I'm gonna be brushing my teeth very mindfully today-

    7. UGUpasna Gautam43:49

       Love it.

    8. LRLenny Rachitsky43:49

       ... is my takeaway.

    9. UGUpasna Gautam43:50

       Love it. (laughs)

    10. LRLenny Rachitsky43:52

        Final question around something that I know is important to you. That is, uh, basically there's this growing shift of product thinking in the news industry at large, and I know that's something that you're passionate about and something you're trying to create, is just to kind of move the media industry and the news industry towards more product thinking. So, I'd love for you to just talk about what you're doing there, what's happening there, and then maybe if there's anything people could do to help in that effort.

    11. UGUpasna Gautam44:16

        Compared to the rest of product management as a discipline and the tech industry, product management in news is still in its, I will say, infancy. And that's just because it hasn't been an integrated role for as long as it has been in big tech. But it is starting to become more and

16. 44:39 – 51:54

    The work News Product Alliance is doing and how to get involved

    1. UGUpasna Gautam44:39

       more, not just prominent now, but people are realizing the value and power of it. Because especially in smaller newsrooms, I mean, see- at like CNN, places like New York Times, Washington Post, we have great embedded, you know, strong product teams. But that is not the case for the majority of newsrooms across the country and the world. Newsrooms are strapped for resources, they are strapped in all, all resources, including financial resources. And so first, bringing in product and tech talent is expensive, and that in itself has forced editorial staff and journalists to take on other jobs that they never signed up for. And so they've had to learn how to do things, product management and engineering and coding hacks, because there was nobody else to do it. And so it's interesting because a lot of times when you talk to editors and journalists, they're, they're doing so many other things other than just their reporting of the news, right? They've had to take on other roles because of those restraints in the newsroom. And so there was a group established, a community established during the pandemic called the News Product Alliance, and there was like a realization occurring all at the same time that, wow, there's a lot of us doing this work. Like, w- what do we call it? Is this product management? And it was. It's product management at so many different levels. And so the News Product Alliance was formed during the pandemic in 2020, I believe, by several media and news executives who had been there and done and have seen people in their newsrooms do that. And the goal of it is to increase the awareness and education of product thinking and product management in newsrooms while also increasing the diversity of thought and the, and the diversity of people in those positions as well, and making the resources more readily available, especially for those smaller newsrooms that don't have the money to hire tech talent. And that in itself has... So that group, the News Product Alliance, has grown dramatically in the past three years since I've been a part of it since the beginning. And we regularly produce, you know, the resources that are catered, product management resources that are catered to working in a newsroom because it is different. It is very unique, but there are of course frameworks and processes that are still relevant, right? Like editors who have been cobbling together how to make this thing that they want, but hey, maybe this PRD framework will help you just to k- keep it, you know, eh, on, on, on track. So like these very simple like rudimentary types of things have helped them so much. And so last year we kicked off a mentorship network in which we had about 400 people apply. There's, we accepted 150 mentees from across the world and matched them with 50 mentors from different newsrooms across the world in leadership positions. And each mentee defined a goal that they wanted to work on and all of course having to do with product management, and some of them were creating a product management role for themselves in the newsroom. Some of it was creating a product manage practice. Maybe they were given the title product manager and said, "Okay, you can hire a couple people," but it was all on them and they had no idea what to do, right? And so some of it, it's, it's across the board and it's amazing to see people doing this from scratch who never in a million years thought they'd like walk into it. You know, they're not coming from big tech. They don't have startup backgrounds. They had journalism degrees from around the world and they're learning how to do product and built... Not just learning how to do it, they're building product practices. They're actually building and developing products and features and they're creating more leaders in the space as well and across their newsrooms to empower each other. So, that's been really amazing to see and it's the most valuable professional organization I've been a part of just because it is so niche that, you know, talking about product management is always fun, but when you talk about it at a level that specific, it becomes even more valuable.

    2. LRLenny Rachitsky49:16

       That is some really impactful product work. Where can people find that if they wanna maybe participate, maybe apply if you're doing another cohort in the future?

    3. UGUpasna Gautam49:24

       Go to newsproduct.org. There is a very active Slack group with a couple thousand people in it, a very active and popular job board as well. And you just have to submit an application on the website, a form, sorry, on that, on the website to join the Slack and then you'll get an invitation to join the Slack and then you'll...... have all of the resources, um, at your fingertips. It's very low barrier to entry. We want everyone and everyone who is interested in, in the intersection of news and product to be a part of it. And the cool thing about it is, like I mentioned, it's, it's a global network. Um, we have people from the biggest newsrooms across the world to all of the regional ones to, you know, even big tech. One of my fellow board members was, you know, doing news at Twitter. One was working on the Google News initiative. So, it's a really, really awesome group of people and everyone is so hungry and passionate about sharing and paying it forward.

    4. LRLenny Rachitsky50:23

       We'll put a link to this in the show notes. One last question. Wh- What kind of people are you looking for? Who should apply, if they're listening?

    5. UGUpasna Gautam50:29

       If you are interested in working in news and have a product background or the, the inverse of that, if you work in news and you're interested in breaking into product. So, either side of the coin or any combination of that, news, media, product, technology. Even aud- we have a lot of audience development and analytics and data science folks in there too. It's just an, an amazing community for knowledge-sharing in tech and news. So, there will be a fit for you somewhere or to learn something, or at the very least, to meet other really amazing people.

    6. LRLenny Rachitsky51:07

       Well, with that, we've reached our very exciting lightning round. I've got five questions for you. And are you ready?

    7. UGUpasna Gautam51:14

       I'm ready.

    8. LRLenny Rachitsky51:15

       All right. What are two or three books that you recommend most to other people, or that you've recommended most?

    9. UGUpasna Gautam51:21

       One, Mindfulness in Plain English. Two, How to Win Friends and Influence People. I have to attribute a lot of, uh, my communication skills to my dad forcing me to read that book when I was, like, 10 years old. And-

    10. LRLenny Rachitsky51:36

        Wow, 10 years old.

    11. UGUpasna Gautam51:37

        Yeah.

    12. LRLenny Rachitsky51:38

        Intense.

    13. UGUpasna Gautam51:39

        (laughs) He was an engineer and they were in their very, uh, beginning phases of introducing... Well, at that time, there was no product, but product-type stuff into his engineering practice, and so he had to read that book and was like,

17. 51:54 – 58:11

    Lightning round

    1. UGUpasna Gautam51:54

       "You need to read this book." So, I never forgot about it. And then the third one is actually n- it's, uh, it's not a book, but it's an article that I think is still very powerful and relevant to this day. It's The New Product Development Game, published by Harvard Business Review in 1986, and it looks at a really different approach. One that I resonate a lot with, because it's a lot along the lines of how we work at CNN around rapid development and, you know, time and flexibility being, like, key anchors of successful product development. So, I threw that in there as well.

    2. LRLenny Rachitsky52:29

       Favorite recent movie or TV show? And it can't be White Lotus.

    3. UGUpasna Gautam52:32

       Okay. I haven't even seen that show. (laughs)

    4. LRLenny Rachitsky52:34

       Okay, great. That's come up so many times.

    5. UGUpasna Gautam52:36

       (laughs)

    6. LRLenny Rachitsky52:36

       We gotta not allow it anymore.

    7. UGUpasna Gautam52:38

       TV show is a toss-up between The Mandalorian and Ted Lasso. I know it's not very new, but I don't watch tons and tons of TV, and I usually find, like, the few that I latch onto and then I get obsessed with, and then I gotta take a break for a while. So, those are my last two obsessions. Movie is Everything Everywhere All at Once. Last amazing one that really, really struck a chord with me.

    8. LRLenny Rachitsky53:02

       If you like Mandalorian, check out Andor. It's incredible.

    9. UGUpasna Gautam53:05

       Oh, yeah. It's good too.

    10. LRLenny Rachitsky53:06

        It's like the best Star Wars thing. Okay, you've seen it. Okay, great. You're on it.

    11. UGUpasna Gautam53:08

        Oh, I, I still love Mandalorian more. I do like that one too.

    12. LRLenny Rachitsky53:12

        Oh, wow.

    13. UGUpasna Gautam53:12

        Uh, my, my husband is obsessed. (laughs)

    14. LRLenny Rachitsky53:15

        Okay, okay. Wow, contrarian. Uh, favorite interview question that you like to ask candidates?

    15. UGUpasna Gautam53:21

        What's something that would not exist without your initiative?

    16. LRLenny Rachitsky53:26

        Mm. And what do you look for in an answer that's a sign that this is someone you may wanna hire?

    17. UGUpasna Gautam53:31

        The whole point of the question is like, do you have and can you exhibit high agency? And especially, again, working in news, it's so important. And so, there's not like a specific answer. I think the ability to actually define something specific and tangible in itself is a really, really, really good sign. I think a lot of, uh, the, you know, people definitely get startled by that, by that question sometimes because it requires you to kind of ask, have to know what it is that you put on the table, right? So, um, yeah. It's, it's different every single time. But the fact... If, if they can define something out of that question, it's, it's a, it's usually a positive sign.

    18. LRLenny Rachitsky54:15

        Cool. Thanks for sharing that additional detail. Next question. What's something relatively minor you've changed in your product development process at CNN, or on your team specifically, that's had a tremendous impact on your ability to execute?

    19. UGUpasna Gautam54:29

        Bridging the gap between product and editorial, that mutual res- trust and respect has had an outsized impact on our success as a high-performing team.

    20. LRLenny Rachitsky54:38

        Sadly, not something other people can use, but that's cool to know. They'll have to hire some journalists now, I think, to take advantage of that lear- learning.

    21. UGUpasna Gautam54:46

        I can add onto that to make it relevant for, for others-

    22. LRLenny Rachitsky54:50

        Sure.

    23. UGUpasna Gautam54:50

        ... which is, it just goes back to, you know, there's, there's no substitute for having those direct conversations with your customers and your users, right? And it's like, when you understand that the assumptions you make are not one-to-one or ever gonna be one-to-one with their actual feedback, and developing that line of communication with your users and your customers is of utmost importance, I think, you know, that in itself is, is the key takeaway, right? It's like, how do you bridge the gap between collecting that feedback, having those conversations? Like, how far are you from your users? How frequently are you having conversations? How consistently are you having conversations? And I always think the more frequently and the more consistently, and earlier on in the process that you're having those conversations, the better.

    24. LRLenny Rachitsky55:44

        Final question. Maybe you already answered this. What's the most crazy or most memorable story from working at CNN?

    25. UGUpasna Gautam55:51

        Every election season is absolutely crazy in the best way possible. It's incredible to see our democracy in action and watch history unfold and while that's happening, using the platform you had a direct hand in building. And it's never lost on me that my work impacts the world every single day. And on the crazy, frustrating, stressful days, like, that is what serves as my anchor.

    26. LRLenny Rachitsky56:19

        Awesome. Pos, this was amazing. I learned, uh, how to brush my teeth more mindfully, about elections, downtime, Trump, all these things. Final two questions. Where can folks find you online if they wanna reach out and learn more, and how can listeners be useful to you?

    27. UGUpasna Gautam56:34

        It's very easy to find me online. I am pretty active on Twitter and Instagram. I recently became an amateur content creator, so I share lots of stuff here and there on, on social. So any social platform... Well, not any. Only on Twitter, LinkedIn, and Instagram. So any, any of those three is, is, is good. And I always love to hear feedback on stuff that resonated and made sense, and the stuff that, you know, there are further questions on, always love having conversations around that. So yeah, DMs are always open.

    28. LRLenny Rachitsky57:08

        I know a link to this in the show notes, but just what's your handle o- on these networks?

    29. UGUpasna Gautam57:12

        It's my first and last name, very creative. I thought about it all by myself.

    30. LRLenny Rachitsky57:16

        (laughs) Awesome. And then, uh, I don't know if you answered the second question. How can listeners be useful to you?

Episode duration: 58:11