Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira)

4 Feb 2024 · 1 h 21 min

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In short

Lenny's Podcast: Product | Growth | Career

Episode Title

Lessons from Atlassian: Launching New Products, Getting Buy-In, and Staying Ahead of the Competition | Megan Cook

Overview In this episode, Lenny Rachitsky interviews Megan Cook, Head of Product for Atlassian’s Jira software. The discussion spans Atlassian's successful product strategies, effective team collaboration, remote work tips, and personal insights from Megan’s extensive career at Atlassian.

Key Discussion Points

Background and Introduction

  • Megan Cook: Head of Product for Jira, with 11 years at Atlassian, previously an analyst, developer, and Agile coach.
  • Jira's Reach: Used by 75% of Fortune 500 companies, over 125,000 customers globally, spanning 15 products.

Creating Space for Innovation

  • Psychological Safety and Play: Essential for team success; fosters an environment where open dialogue and innovation thrive.
  • Peer Feedback Groups: Organized smaller groups for regular feedback, promoting a culture of support and openness.
  • Team Onsite Gatherings: Bi-annual events to build relationships, strategize, and share failure stories to encourage learning.

Remote Work Insights

  • Team Anywhere Approach: Emphasizes flexibility and productivity over location.
  • Connection and Productivity: Enhanced by intentional in-person gatherings several times a year.
  • Deep Work and Meeting Management: Importance of blocking time for focused work and utilizing asynchronous updates to minimize meetings.

Getting Buy-In for Ideas

  • Early Involvement: Engage stakeholders early and throughout the development process to build partnerships and advocacy.
  • Open-Minded Approach: Embrace feedback and remain open to evolving ideas.
  • Meeting Strategy: Clearly define the objective (e.g., decision or feedback) and utilize data effectively to support proposals.

Fighting the Good Fight

  • Investment in CSAT: Focused on customer satisfaction, using data and strategic partnerships to drive improvements.
  • Starting Small: Begin with limited resources to demonstrate potential before scaling.

Atlassian's Approach to New Products

  • Iterative Development: Use of a stage-gated process (Wonder, Explore, Make, Impact, Scale) for validating and developing new products like Jira Product Discovery.
  • Cultural Openness to Innovation: Encourages internal pitches for product ideas; supports exploration of emerging technologies.

Staying Ahead of Competition

  • Customer Feedback: Integral to product improvement and innovation.
  • Cultural Support for Innovation: Regular hackathons and focus on emerging technologies such as AI.
  • Strategic Investment: Balancing core business focus with exploring future opportunities.

Personal Insights and Stories

  • Failure Story: Missed opportunity to expand an automation feature into a broader solution; emphasizes thinking bigger.
  • Fight Club Concept: Regular meetings focused on resolving conflicts early, fostering better team relationships.

Lightning Round

  • Book Recommendations: "Inspired" by Marty Cagan for new PMs, "Scaling People" by Claire Hughes Johnson for managers.
  • Favorite TV Show: "Foundation" on Apple TV+ for its thought-provoking sci-fi narrative.
  • Interview Question: Discussing failures to gauge introspection and growth mindset.

Useful Links and Contact Information

  • Megan Cook on LinkedIn: [LinkedIn](https://www.linkedin.com/in/cookmegan)
  • Lenny's Newsletter: [Lenny's Newsletter](https://www.lennysnewsletter.com)
  • Jira Software: [Jira Software](https://www.atlassian.com/software/jira)

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Megan Cook and Lenny Rachitsky explore key factors contributing to Atlassian's success, including strategic product launches, the importance of psychological safety, and maintaining a competitive edge through innovation and customer feedback.

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Transcript

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0:00Well, we put into place something we called fight club. A pro -wiggin' in trouble for talking about fight club. The first rule was you talk about fight club. But it's 30 minutes every week. And it's just for myself, my engineering, and my design leader. And we get together. And we know that we're going in there to have a conflict. I think often when there's difficult conversations, all these conflicts come up, you can put them off until they become much bigger. Or if somebody is conflicted worse, they can try to avoid having it at all. But by having a specific sort of time in your week for something like that, then you're sort of in that mindset.

0:37You know you're going in there to solve a high problem. You know that there's going to be a disagreement and it makes it much better. And I think the relationship we all have is so much better because we get on top of these things early. Today, my guest is Megan Cook. Megan is head of product for Gura, which is used by 75 % of Fortune 500 companies, 125 ,000 customers globally, and is by far the most popular project management tool in the world. Megan has been at Atlassian for just under 11 years. Prior to Atlassian, Megan was an analyst, a developer, and an agile coach. In our conversation, we discuss what Atlassian has done so right and being able to offer 15 different product lines, which many companies dream of.

1:23How they continue to stay head of the market in spite of the many competitors in the space, why Megan considers play so essential to building great teams and great products, a bunch of tactical advice for getting buy -in for your ideas, tips for being a successful PM in a remote environment, also great story failure, and so much more including surfing tips. With that, I bring you Megan Cook after a short word from our sponsors. This time of year is prime for career reflection and setting goals for professional growth. I always like to spend this time reflecting on what I accomplished the previous year, what I hope to accomplish the next year, and whether this is the year I look for a new opportunity.

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3:53Megan, thank you so much for being here and welcome to the podcast. Oh, thanks so much Lenny. I am a big fan of your podcast, and I am excited to be here. I have a lot of things I want to chat about. I've heard about many things that you're extremely good at as a leader, as a product leader. And so I'm just going to poke around a bunch of different areas. I wanted to start with something that I hear you're just a big advocate of and really good at, which is creating space for play on teams, and also just creating a lot of psychological safety, something that you find really important that helps your teams be as successful as they are.

4:29You can just talk about why this is important to you, why creating play and psychological safety or some important to you, and then just how you do this, maybe an example or two if I actually apply this on your teams. Yeah, absolutely. So I think especially recently in the tick industry, it almost feels like we're going through a bit of a wake -up cold at the moment. We were in this time of plenty, and everyone was hiring crazy, and then COVID hit, and suddenly people's behaviors had to really change. People couldn't travel. They had to work from home. There's a whole bunch of industries that got highly impacted by that.

5:05And it created this time of high ambiguity. Full -out of to the start of that, I was noticing within my team, just some little indicators where people weren't all comfortable to speak up, when we'd had really open discussions with Miss Junior Person, or the Miss Senior Person, were happy to talk about anything. There was more anonymity in feedback. Every time things were coming to leadership to give feedback on, it was just sort of painfully polished. And I think once it gets to that level, that's a really bad time to give feedback. Because it probably means that a whole ton of work has gone into it, and you might waste a whole bunch of work if you have to correct direction or make significant changes.

5:53And so I was looking at my team and thinking, yeah, and something doesn't feel quite right here. And then I went to this leadership upside, and one of the speakers there was Ben Crowe. And he's an expert in having the right mindset. See, he works with Olympic Gold Middle East, and Ash Barney is another one. He's a tennis player, he's the number one tennis player in the entire world. So these athletes, he have to really perform under a lot of pressure, from a lot of people. And he talked about how to be in that state of, why, you know, where everything is going really well, and new ideas are coming and you're making progress, you've got great momentum.

6:37And he talked about how to be in that play state, there needs to be this sense of play. And that's, you know, things are fun. Your mind's open to new ideas, you feel really pressing, you're not stressing out and thinking about a ton of other different things. And it's funny because when I thought about play, where my mind went to the opposite of play is work, right? We often hear work in play as opposites together. But his point was actually that the opposite of play is fear. And I realized, I think that's what I would see in a lot of, in my team, and that's why the ideas were getting more incremental.

7:12So, to better decision on my, okay, we need to look at psychological safety in that team, where we're never going to get to some of these bigger, bolder, more innovative ideas. And so, probably, group product managers together, and we sat around and discussed it, and all together came up with some ideas that we've implemented, seemed then, since then, which was, has had a really good impact. So, I'll give you a couple. Yeah, please. Yeah, one of the first ones was, my team of pms is big enough now, where not everyone necessarily gets to know everyone else. And when you don't have that relationship, it can feel a little scary.

7:52You don't have that trust that you understand, have people going to respond to you, and you're not sure about reaching out. So, we divided the team into these smaller groups, the peer feedback groups, and the idea is that they meet every two weeks. Also, somebody brings something that's in a pretty rough graph that they want to get reviewed, and then everyone's expected to get feedback. And because we've got people in there who are different leadership levels, it's a really good opportunity to model the kind of feedback that's helpful, and the culture there is one of everyone lifting that person up to make their work stronger.

8:28So, people can get in there. They can show that you can show work that's really in the early stages, and feel comfortable with them. They can see that getting feedback can actually be really positive. And they can see how all of these people together, they can rely on them and forge those relationships, so they can rely on more people to help them out. This is so interesting, and it's such a good idea. And it's like such a simple and good idea, and I'm surprised that I haven't heard of people doing this before. Basically, you pair up PMs, ICPMs, and maybe managers to give each other feedback, and is the feedback on like one -pagers and PRDs and strategy docs and things like that?

9:08What sort of documents are they giving feedback on? So, it's really open -ended. It can be anything. It can be a, here's a new experience, grill -a -kio -lunching, here's a new strategy I've taken, my own strategies in there, and gone the excellent feedback, surprising feedback from the team. It can be a new experiment that people think of running, and anything to do with the crop. I think as you kind of implied, one of the powers of this approach is it's a small team, so it's less stressful, and there's no, like, you're not in the room often, to, I guess you are sometimes, as you just said, but usually it's like peers, and they could be a little more open and less worried about looking at that.

9:45Yeah, absolutely. And I think it's just, a lot of it is just building that muscle, you might go through an experience once every quarter, or once every six months, and that can feel really stressful. But if you're doing it again and again, you get used to it, you get used to what to expect, you get a bit more practice, it can feel much more comfortable. That's awesome. So it's just simple and powerful idea. It's kind of like, everyone's always suggesting getting a mentor, getting a coach, as a PM, and those are hard to find. And this is just like a little informal, it's almost like a little peer group, board of directors for your work.

10:18We talk about that on the podcast sometimes. So anyway, that's awesome. Really good idea and something anyone can do. Yeah, thank you. Great. Okay. You have a second idea. Yeah. One of the other things we do is we get everyone together, just like a six months. So all of the product managers get together in the same place. And the idea is to have a bit of an on -site, and we start off with just doing something fun. Because everybody, as you might know, Lassian is a remote organization. So everybody works remote all the time. They can work from anywhere. And so people often, they're not used to necessarily being all together in the same place.

11:00It can take a little while to warm up. And then after that, we talk about strategy. We do workshops on different elements of craft using that craft together. And so it's similar kind of thing. People get to build relationships together. They get to sort of see all these different ideas bouncing around, which can help up with their own ideas and help them be more innovative. And this last one, I actually had some senior leaders from all over the organization, coming so I'll share their stories of failure. So just to get everyone used to that idea that it's okay to fail. And actually, if the learnings are really good, maybe it should even be celebrated.

11:41And it's not something to be scared of when taking the big swings and a bad thing. It can be a really powerful way to lend as well. I love that. We've been talking about failure a lot in this podcast. We're super aligned with the power of that. And so just to be clear, so what you do there is, is it the entire product team of Atlassian or is it just your team in this six, every six month? It's just my team. And then we pull away and other product managers that we work closely with as well. And then you fly them all to Australia, I imagine. Yeah, all to Sydney. Yeah, Sydney. Amazing. Okay. And I think so the key there is it's not just like you go meet each other.

12:22It's training almost on different skill sets, helping people level up in, say, craft or I don't know communication or writing or something like that. And then who teaches these things? Is it like individual team members? Are you bringing someone in? We have a real mix actually. So yeah, we'll bring in outside experts or we'll get there's a lot of knowledge and a lot of skill within the team itself. So you know, you'll have different product managers, you have different strengths, we have totally different teams. So someone on a great team, for example, might want to teach everyone about how to create great hypotheses.

12:58Well, we'll get someone extra from the team but until to Atlassian, he has those skills who can come in. I love that also gives those PMs a chance to one learn the skill better themselves because they're teaching it and also just teach and present and public speaking all that stuff. There's all these other benefits to doing that sort of thing. Yeah, absolutely. And I think, you know, as a product leader, it's really important to model the behavior you want to see from your teams, whether that's getting out there, teaching, presenting, explaining different concepts, explaining the business, or just being vulnerable and talking about when things haven't worked out.

13:34When we started this question, you talked about how there was kind of the shift at Atlassian where things started to feel more formal and people started to feel less open to sharing and being criticized in meetings. Just in case people might feel that might be happening in their company, do you remember roughly when what size that started to happen at or signs of like, I'm noticing people are sharing less or being more worried about talking in big meetings? Probably when we got into really different sort of streams of work that were happening where people didn't have as much of a reason to interact with each other.

14:14So I think that was probably around, even around 15, we started to see a little bit of time. Yeah, yeah. Cool, that's a good step. Yeah, you know what, I'll give one more thing that we do. So we've just started trying something you called the Tendoll game for priorities. And we say that's where I think people had to play the Tendoll game for your parties when it comes to a strategy or something like that. We started trying it out with your individual parties. So you and your manager might come in and you can list down all of your parties and then show you through just dividing up $10 where you're spending all of your time.

14:56And I've done this with people and we've sort of gotten down to like I'm putting 10 cents here this week. Or is that what is that 20 minutes? They're even I think spending, I think that's actually moving, right? And so it's being green to see where people are evaluated and alignment on, you know, do my party stack up, but also am I spending the time all the most important things that could be moving the business forward? Awesome. Okay, so you mentioned that you all are remote. And has it been a remote from the beginning? No, I know from the beginning actually when COVID hit, I think that was the big moment.

15:35Okay, okay, got it. That makes sense. So a lot of companies are moving to remote work, trying to figure out how to work remotely. It seems like it's working really well for it last year and at least for what I can see. Is there any advice or any big lessons or tips or tricks you've learned that you could share for how to be effective work your remotely, especially as a product manager? It feels like as a PM, the job has gone so much harder having to be remote. And so yeah, I'm curious if you just have any advice you could share for people trying to make this work for their company or for themselves.

16:04Yeah, absolutely. It's a really good question because it's not easy. And we definitely went through a whole bunch of pitfalls at the beginning, but we're really from believers that you don't need to be in the office to build world -class products. So we call our approach team anywhere and this means that anywhere that last year and anyone at last can choose where they want to work every day. We think it's a bit more human that flexibility should be a perk that fundamentally can change people's lives depending on what else they have on outside of work. And so we think less about where do you work and we think more about how to be productive and effective in your work.

16:44To your point, we started doing this right when COVID hit. So it's been about three years. And actually we just released a guide on without key learnings from that. It's all about a thousand days of remote work which Fixed King and Goandbine on our Work Like Blog under Research at Alaskan .com if they want to dive in them more. But I can give you a couple of tips from that and what we found in some of our research. Yeah, and we'll link to that doc in the show notes. Okay, great. So the first one is just making time for connections. So that human connection is definitely built in person. But what we found is that it doesn't have to be something that happens every single day.

17:26So we found the connection and productivity. They've got boosted by about 30 % when you bring people together. But then intentionally. And it lasts for months. So we found that you can do it on average like three times a year. And so that's why my PM team are getting together every six months. But in addition to that, we get the entire team together every other six months. So we end up all getting together every four times a year. So every other six months, what we do is we get all of the engineers, designers, everybody who's working together. We book out entire floors in the office. And then for an entire week we're just there.

18:06And for some of the bit, we're just working together as you normally would, but at desk and just having those little what a cool type of conversations. It builds the relationships again. Other times we're doing workshops and important pieces of work. Where it's easier to do when you're all in person and sometimes we're just having fun together. So call that a bit of a festival. You mentioned that you measured some kind of productivity improvement. Do you happen to know how they measure that? Because that is really interesting. It's a good question. I don't, but I can get that for you. That'd be cool to know.

18:41So I think we'll keep this in the podcast episode. And then if there's anything in the show notes that we link to that talks about how measured that, that'd be really interesting. Because that's just like a cool stat to have anyway. For all kinds of other things. I'm curious. Yeah. But they measure that. Yeah, absolutely. Okay, cool. Any other tips? I think the second one is to be really intentional. So I mentioned that we went through a sort of a bit of a few stumbling blocks at the start. One of those was immediately everyone sort of filled up. Everybody's calendar with all of these meetings.

19:12Like straight away. It was almost as if, you know, Lenny, if you and I are working together, I used to be able to just like pick my head around. I wanted to earn Aussie something. And people were afraid that now that I can't do that, how do I get those answers? So I need more time with everybody. And that definitely does not help productivity at all. And so, you know, as pms, we need time for creative work. We need that deep work time. And that doesn't happen when you've got all of these meetings with 30 minutes in between each of them. You need sort of, you know, three to four hours. To get that going, to get into that flow state.

19:49So my leadership team and I, we actually sync up our calendars. So we end up having these long stretches twice a week all at the same time. And so we all get a chance to do this deep work. It means we get less time for meetings. But it also means that if something comes up that's unexpected that we all need to work on together, then we've got that time there. So we can be a bit more relaxed about it. We know we can get to it. What time of the day is that meeting? They both have different times. So the first ones take out one afternoon and the second ones take out all of the time in the morning.

20:22Depending on what kind of person you are, one is going to see better than the others. So we just went for one age. I actually have the same thing just personally where I had these deep worked block times on Monday, Wednesday and Friday. The title of the invite was a few book time during this. I will slap you and it really worked well. But I think you're talking about this other missing piece of remote work for PMs where you can just walk by and ask an engineer, hey, how's it going? Ask an designer. Let me, where yeah, let me just take a peek at where you're working on. Like that stuff I think is really hard to replicate.

20:57And if your suggestion is block out this time for your leadership team to be able to check them to each other, is the idea that it's deep work time and don't bother anyone on the team? Or is it, you can also just ping your end manager and like, hey, how's it going? And the idea is that it's deep work time and it's your time to be protected to do that work. What I found that works really well, I think in the manager and report kind of relationship. So I have these really quick, plunchy and one -of -ones with my reports that every week. And then I make sure that I've got space in my calendar because something will come up where, even if we had a longer one -of -one, that might not cover it, right?

21:37They might just need an hour to run through something. There might be a really difficult strategy problem they've run into and so they all know that they can ping me for more time and I'll have that flex in my calendar for that. Awesome. Any other tips along those lines? What you probably noticed about, you know, block a bunch of deep work time is that you don't have as much time for meetings. So that meeting time becomes really precious. And what we do there is I personally hate having status updates as a meeting. So you make it really clear that if we're having a meeting, this is a problem. And if it's just a status update, that's fine, but I can read that asynchronously at a time that works for me and sick and everybody else.

22:19In the team that they want to do that, we actually, we use our end tool to this, which makes it really easy. So it's called Atlas and it lets you or the team put in status updates for a goal or a project regularly and then it'll bundle it all up into an email so you can quickly get across everything that you're interested in, which is being really helpful. And then that just makes the documentation rigorous as well. So you document things and we use compliance, but all of our decisions, strategies, kickoffs for projects, that's all really well -documented Pini starters. Or even if you're down the line and you're thinking, why did we come to that decision in the first place?

23:03What were our assumptions? What were our hypotheses? It's easy to go back and take a look at that and be able to reflect. And I think the last thing is, I work with people who are in the US, they're in Europe, they're all in the world. It's really hard to find a time that works all for an Aussie and American and a European to get together, you know, someone's waking up at 3am or something. So what's the kind of big part of how we work is actually audio and video recordings. So I actually had someone reporting to me for a while who was in France and what we would do was record videos back and forth.

23:42And they're quick. You can, you know, just use clinical language, they're really casual. You don't have to wonder about someone's tone that comes across. So that's becoming almost like a completely new document type for us. And it's been really important in remote work. You can put up a top of a document and explain the document, which is really nice. There's a big part of why we vote, Lume. I was just going to say that, and all makes sense. Yeah, yeah, because it was just becoming such a big part of our life, right? And yeah, it's just massively helpful. Kind of along the same lines, being fully remote, it is harder to get buy -in on things you're working on, I imagine, and something I hear you're great at is getting buy -in, especially getting buy -in on ideas and projects from executives.

24:32So I think things that make it extra challenging at Atlassian, there's two CEOs, which I didn't know until recently. You're also all very remote. And so maybe those two reasons make it extra hard, plus it's just generally hard to get buy -in on projects that you're working on. What advice do you share with product leaders, PMs that come to you asking for advice and how to get better at getting buy -in for your ideas? Yeah, this is, this can be really hard to get right. I watch a lot of people struggle with this. And you're right, being fully remote can make it a bit more challenging. And then I think also, you know, you've got your cross -functional partners that you're working with as this tight -knit team.

25:12And how do you form that relationship? But I'll still with just general buy -in. Most of the time when people come to me and they want to ask how to get buy -in, they've got a date in mind, they've got a particular meeting and they have this idea where they're going to proc this perfect proposal, they're going to present it, and everyone's going to get them thumbs up and they win. And that's the wrong attitude, I think, even to start with, to getting buy -in. It's here of a journey. So, I'll give you an example where I was looking at how do people start their day in Jira and how do people get started in Jira.

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25:50And we had this idea of we could craft more templates so that we could give people more a better way to start with very different use cases when they came into the product. And this could change everything from even just the front homepage where they started all the way to what's happening in product. It would create this really nice flow. Jira is also a platform as well as just Jira's offer the product. There's actually four different products popped on top of it. So, when you want to go and change something like that, you're actually changing it for all of these different products. It's not just the one.

26:27And so, what was really important that was partnering with a whole bunch of different stakeholders say every product that this could potentially negatively or positively impact, we went to very early with the idea and the proposal and we got their feedback. And then we came to them. Again and again, as we developed it further. So, as we got designs, as we got more data, as we tested things out with users, we kept coming back and we take their feedback on board. And so, I think creating this partnership is really important. And I will say the same country be truly executive level. So, often you go into these meetings where you're giving a proposal and you're trying to get that final yes on the decision.

27:07You've got a lot of people in there with a lot of different angles that they can look at that problem and so much good experience to draw on. So, you know, your CTO is going to have a totally different way of looking at something in different concerns from your cheap marketing officer to your headed design. They're going to look at things differently and be thinking that differently. And so, if you know that you're going to be having a big impact in someone's space and you want to hear from them, it's good to set that meeting up early. You know, when you've got some party but it's not fully fleshed out and so that you can fold in some of their concerns because they'll have this much broad of view.

27:42And that also creates people who will be an advocate for you once you get into that room, that final meeting. So, I think all of those in the lead up there's a lot of lead up work to getting buy -in that makes sure that you have a good time in that meeting. Just to maybe summarize so far, what you've shared, one is just basically it's Lou people in early, especially the person that it's going to impact most. I think in addition to that is having that mindset of being open to not necessarily coming up with the right solution. It's more about solving it for the problem with the opportunity right.

28:20So, you want to be clear about like your hypotheses and what are your facts and what are the principles you're using to make a decision and just be open to not necessarily ending up with the solution you thought would be best. I imagine most people think they are always in that state. I am very open to feedback. I am totally open -minded, but really they're not. Is there anything that you think with either convinced someone you're actually not because open -minded as you seem or any advice for how to come across as more open -minded or is there anything there you see? I see this all the time. People think they're listening, but they're not.

28:55It's that you should change. I think one way to force yourself into that situation is to be clear about the hypotheses you have and the facts. So, I think often people can present as this is absolutely the case. This is what I know and this is obviously the correct response to the situation. Where most of the time you've got a good set of data, you've got a good understanding with your knowledge of the space. What is actually going to happen is a hypothesis. There's always going to be something you don't know. Often times you don't know until you ship it. That is absolutely the best test of whether or not what you thought was going to happen will actually happen.

29:41I think when you come to the meeting going, here's the top back. So, we actually know. And here's the hypotheses and here's my plan to prove or to sproot them. Then you're exposing your idea for people to go, oh, here's more than I know about that. The hypothesis is there is some data that you don't have. Here's another way to think about it. I think people can feel like they're not going to be credible. You have to come in, you have to come in confident, you have to come in knowing exactly what that solution is going to be. But I usually find that if you come in there open and you expose your thinking and where you could use some help on perspectives, that actually that builds more credibility.

30:22Because everyone knows that you are not going to have all the answers and you're not going to be able to see the future. And so that can really help building people's trust in you and that you know what you're dying. Is there an example of that that comes to mind to make it even more real of either someone and your team doing that or you doing that? Because I think it's still going to be hard for people to be like, realize, hey, I'm not actually paying attention to anyone and I just want to convince them this idea is right. This is what we're doing. Just come on, get out of my way. Give me the okay.

30:51An example from my post is there was this potential acquisition that we could have made. And I was really, really keen on it because it wouldn't mean adding a whole bunch of much needed capability really quickly to the product. And I just left that momentum and I didn't see any other way that we could do this. So I've looked at a bunch of other options about building it in -house and it just didn't seem possible. And there are a few people that I needed to convince you and my boss, but also the head of engineering for the area. And when I took it to them, what I learned was the head of engineering was able to pull a bunch of people from other areas within the company to come and bolster this effort.

31:34You had all the knowledge that we needed. So what seemed like the impossible task key actually had this extra knowledge to make possible. And in the end, acquisition or not, that doesn't really matter. It's more about being able to get that value back to our customers. That's what we're solving for. And so it was really about coming back, not pulling in love with that solution and that other company was just taking a step back and going, okay, well, really it's just what are we here to do? What's the real goal at the end of the day? Awesome. Okay. Is there anything else you wanted to share along these lines before I move on to a different time?

32:16The other thing I would say is that setting up the meeting when you finally get there can be really important as well. I often see people going there and they've got a big document or a presentation or something and they just launch into it. They're really excited. But actually, you want to take a step back and you want to be really clear on what are you looking for from that group? You can ask for the decision. You can ask for a feedback. You can ask for, you know, you can expose, we are not quite sure about something and you want to be thinking about that angle in particular and helping to us that hypothesis with what they know.

32:53And so, setting that early, you can put that in people's heads as they read three or document or listen to the rest of the proposal. Then I find it's really useful to have a narrative that just encompasses everything that's that you're going to talk about. So just really brief, what's the current situation, what has changed and what are the implications that you now want to, we mean we have a problem to solve and our opportunity that we can go often. And the last thing is just making sure you've got your data. And the people, there's executives, there's people in the meeting, you know, they're usually across a whole ton of stuff.

33:33Just hearing about maybe they've got 10 proposals a day, right? And they're across all different areas in the business and so they're not going to have the detail that you do. So being really thoughtful about what you bring, what are the key points that are going to help them understand the situation is clearly as possible, but then really knowing your data so that you can dive in in more detail where they need it. And then that also helps build your credibility and builds people's confidence in the plan to go ahead. Would you mind just quickly summarizing these pieces of advice and then I was going to move on to another area of strength of yours that I hear?

34:13Yeah, sure. So the first one is to find people who are affected or are negatively or positively, or might have a really good point of view and partner with them as you develop the solution or the response to the current situation. And the second one is to come in with this mindset of being open and being really key on what is the core problem or the value that you want to deliver and just being open to how you get there and things that you don't know which might adjust still in the way. And the last one is just setting up the meeting levels. So coming in, making sure that it's very clear what you need, do you need a decision or something like that and making sure that you've got very good supporting data to build that credibility with your audience.

35:03Love it. I, uh, this is where the term, uh, or the cliche of product managers asking, but what problem were we trying to solve comes from, but it comes from in a really important place of always focusing on, let's all align on here is the problem we're solving because oftentimes as you chat at about the biggest disagreements come from people just thinking they're solving different problems. And on that note, I have a swag store now, Lenny swag dot com. And we have stickers on there a bunch of cliche PM terms, including, but what problem are we trying to solve? And so I think that's, but it's rooted in that's actually a really important question to ask.

35:36Sometimes you get annoying. Yeah, that's such a good, good to have front and center. Yeah. Just need that. It's a big sign. Maybe the sticker needs to be bigger. Exactly. This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate your growth. Thousands of fast growing companies like gusto, calm, kora and modern treasury trust vanta to help build, scale, manage, and demonstrate their security compliance programs and get ready for audits in weeks, not months. By offering the most in demand security and privacy frameworks such as SOC 2, ISO 27 ,0001, GDPR, HIPAA, and many more, Vanta helps companies obtain the reports they need to accelerate growth, build a fishing compliance processes, mitigate risks to their businesses, and build trust with external stakeholders.

36:24Over 5 ,000 fast growing companies use Vanta to automate up to 90 % of the work involved with SOC 2 and these other frameworks. For a limited time, Lenny's podcast listeners get $1 ,000 off Vanta. GoodofVanta .com slash Lenny. That's v -a -n -t -a .com slash Lenny to learn more and to claim your discounts. Get started today. Okay, so something else that I hear you're incredibly good at and it's actually related to all of these things we've been talking about is the way someone describes you as you're really good at fighting the good fight, which essentially is just doing the things that need to be done that aren't necessarily popular or that people are prioritizing right now.

37:02I hear that you led to a big investment in CSAT at Atlassian because you just felt like this was the right way to doing it and there's a few other projects that came out of just like, I'm just going to do the thing that needs to be done. Can you just talk about why that's important to you, what sort of impact that sort of had, and then just like how you actually successfully do that? Obviously it ties into this skill of getting buy -in on stuff. I think that's a really good example actually. The CSAT example because sometimes you can get caught up in let's add value at value at value to the product, but if the customers aren't satisfied with what you've built or in our things, we found that one of the core reasons with the usability wasn't where it needed to be.

37:46Let me kind of access that value anyway, it doesn't matter and sometimes it can be hard to get investments with things like that because it's not like the shiny, exciting new thing. I want to work on the features we already have and improve those. It was about two years ago, our chief experience officer, he could really deeply about improving our CSAT scores and asked me to look into it. Maybe. And this briefly explains CSAT real quick because some people may not be familiar with that term. Oh yeah, yeah, absolutely of course. CSAT means customer satisfaction. So for us, we actually have a survey so that we can measure CSAT and it just us customers to rate how satisfied they are with the product and then different aspects so we can see for different tasks that they need to perform or different aspects of a like the reliability of the speed or the usability, how I had to customers feel about that.

38:48We actually had a podcast episode recently with Judd where we talk about NPS and how much there's data showing it's not actually a great predictor of anything and he's a big fan of CSAT instead. So you could almost think of it as a little replacement for NPS in all the cases. And then sorry, push the off track. Keep going. Yeah, no worries. Yeah, so he can't really deeply about this. I'll see you look into it. Even though this request was coming from the top, that doesn't mean that it gets any sort of funding. So we went through a couple of different steps to see what was worth investing in here.

39:22So first of all, I mentioned we had that survey and so we had really rich feedback. So it's not just a rating for what we get. We get people talking about why they gave that rating and that can really help us zero in on what are the key aspects that's bringing this down. We also had great conversations with our customers. It was the kinds of conversations that are really rich and really helpful, but so painful to listen to and go through because you're seeing some fiddies really struggle with something that you've got was going to bring them so much value. Then we had a look at well, what is this going to impact and say logically, what we found was that usability was one of the key reasons, like I said.

40:10And logically, if your product is hard to use in places, if some of the core actions are hard for people to do, then a new user to that product or a new customer is going to have a longer ramp up time, right? You've got a harder time showing them that there's value and even for an existing customer that's using your product really well when they bring on a new user, that user might have a really hard time getting up to speed and using it and just completely slice them down. So from a business point of view, it can impact your new customer acquisition as well as your ability to expand. So there was some good revenue connections in there as well.

40:52What I also found was that we have a lot of dependencies, so we've got all of these platform teams and a lot of the improvements that would be really good to make to solve at this problem. Depended on many, many teams around it, I say, and they all had different goals, right, and other products that they had to serve to. I don't know if you've ever tried to do a three or four different road mounts so that the timing is just right to get some improvement through, but it's basically impossible. There was no way that was going to happen. But we did find that they were really passionate about this area and proving usability.

41:29So we worked together to find a low cost way for those teams to help us make the changes that we need to, but they didn't have to bear the burden of all the development costs. So each of those teams looked forward, like we call them a shet -it, so that as Adabellus came in and made changes in the code things, that this shet -it would make sure that they weren't causing any issues and we're doing reviews and reviews of designs and things like that. And so getting that by and finding the data to support the reason why this was important. And then we constructed the road mount so that we found this sort of like a low cost way, very cheap way to have some impactful change early on.

42:13That was really, really important. And so we put together some of the, just some of the designs for what the experiences were going to look like. So our our head of design, Charlie, Sutton at the moment has this great mantra of show don't tell. And in this case it was just at the core of getting people excited because you could show the initial experience, you could show the pain, you could bring in a video of a customer trying to use it and what they thought of it. And that just really brought that emotional aspect to it and helped get people on board. And you show the new experience, which is just far and away, and most better, you know, might cut out like 20 clicks or whatever.

42:59And so that all that worked together to get the investment that we needed. I think the last thing that was useful there actually is that we started pretty small too. So I think if you have a hypothesis and you can start small, you can get that investment more easily, you can show success, you can always build on that in the future to get more and more. But in this case, we got about 40 people to come in, join on to this. And then as we ship things, we just made sure that it was quite kept being quite small. And so we got that momentum really quickly. We kept with regular updates. We kept up the excitement about what the team was doing at one stage.

43:39The team picked off something that was there was pretty impactful throughout the whole thing. So that that was dark mode that took a lot of coordination around the whole company to make that thing happen that it was all over you. We loved it. And then, you know, the feedback that we got as well really helps with that. So I actually just yesterday, I saw some feedback on one of the changes we'd made recently. And this customer said it was the best quality of life improvement they've seen in a long time, which just just the way that's phrased even, you know, that gets you excited about the impact that you're having on that person.

44:19And this was the CSAT work or the dark mode. This is CSAT work. This is improving. Okay, okay. One of the processes. Okay, that's amazing. There's a lot of stuff I love about the story. One is just the power of just empowering yourself to do things that you believe needs to be done. There's a lot of pms and just people in general that just assume they don't have any power and the light, the square peg they're in is just all they're going to be able to do. And nobody's going to allow them to do things that they they believe important. No one else agrees with so I think there's just a lot of power and just understanding that you have more power and leverage and agency than you probably think you do.

45:01But then you also have to do it well. So I took a bunch of notes as you were talking of the things that I think are called to getting stuff like this done just like a scrappy project that you're kind of doing in your own with that a lot of buy -in from the top initially. So when it's a small to is make it visual and visceral. So you can like, oh wow, I could see this being amazing and getting people excited as you go. Making it really easy for people, I think is a really interesting takeaway there. Just like we did all the work for you already for these other teams. Like it's going to be so easy.

45:29It's not going to be a lot of work for you. And then showed the data like here's what we've gotten from C -SAT so far. Here's the impact you probably get from it. Here's how much work it'll take like show actual data. And then keep it scrappy. It feels like a lot of this just like stay small keep it scrappy. Don't ask for a lot of resources initially and just kind of show momentum. I think that's really important when you keep it scrappy and small in the beginning. It doesn't feel like it's as big of a bet that that gives you the opportunity to really pre -reached the direction that you're going in could pay off.

46:03And so it's sort of like this little inner edge to getting more investment. Awesome. Okay. I want to move to a different topic around Atlassian as a company. But is there anything else you wanted to share along those lines before we do that? No, let's do it for it. Okay. So one of the most interesting things about Atlassian to me is it's a great example of a company that's been able to launch new product lines. This is the dream of every software company business in general is you start with one product that gets to a certain point and then you hit a some kind of plateau and then you add an additional business product line and then you add more and more.

46:37And somewhere I read Atlassian's 15 products. Is that an accurate number? Yeah, that's right. Yeah, we are up to 15. Yes, Jesus Christ. Amazing. So this is like very rare and the dream of many companies. And so I'm just curious what it is you think Atlassian has done so right to have so many successful individual products. You know what? It's not like we added the first product and got it just right way off the bat. So yeah, 15, we've had a lot of shots at this. So I might talk about two examples. So I think the first one, you know, if I think about Jira software, it started just as a really humble bug tracker.

47:21That was it. There was there wasn't as much to it. And then it's sort of whether these massive changes and how people build software. So it launched in 2003. And if I remember correctly like just to date this, the mobile phone that was most popular in time was the Nokia 6100. I didn't I don't know if you ever had one of those. I don't remember what that specifically was, but I'm picturing an okey phone. It's like a little brick. It was a small brick. Yeah, it was my mother and was favorite phone. It took us forever to get her off that one to sell it better. But um, been you know, it's there's a lot that's changed since that time, right?

47:56There's been agile, there's been cloud. And what we saw recently was more in the expansion of software teams. So they used to be extremely developed, concentric. And I think most people when they think about Jira software, they think, oh, you know, that must be like 80 % developers that are using it. Then actually it's more like 50 % or maybe just shy of 50 % are developers. And the rest is this huge mix of support and operations and sales and marketing, finance, design, HR, legal, just this massive mix of everybody, all the roles you could think of in a company, basically, that get in there and make work happen.

48:36And so what we saw, you know, years ago was, well, software teams aren't just developed as anymore. We saw this in our own teams as well. But we saw that these other teams, you know, the finance and marketing teams, even design teams was sort of coupling together their installations. Jira software is incredibly flexible, which which is a massive pro of it, that these teams were seeing, software teams get more effective that the way they were getting work done and collaborating better. And they wanted that same benefit. And they started using Jira, but we hadn't set it up well for them at all. So it was quite difficult for them to do that.

49:12But the, you know, the positive was that there was this really good signal from our users that they were looking for more from us. And we knew that your marketing team is going to work differently from your development team. That's how it should be. And so we started Jira work management to be more focused on all of these other use cases outside of the software team that I use as we're asking us to go ahead and solve. So that was a really great way to discover the need for a new product where these really strong signals from within our customers in that same area of business that were really well set up to help them.

49:50What was that process like from noticing, hey, designers are using Jira and they're not having a good time. Pams are using Jira researchers. And here's the issues. They're running so just like that insight of like, oh, interesting. There might be an opportunity here to launching at another first version like where they're, I don't know if you're actually involved in this, but whatever you can share would be awesome. Were there design partners? They all chose and like let's work with Salesforce and Microsoft and like make sure they love it. Is it how long was that process? Because I think that's the part people are so curious about just like how do we validate and discover and then actually launch something that's going to work.

50:28Yeah, I was just a question that I can give you a second example. Oh great. Yeah, for sure. So the second example actually came from our product internal innovation program and that like we let anyone pitch an idea for new product in the company if they want to. So we had this wonderful product manager, Tony Cresin. He's so demand for a solution for product managers to go their road maps a bit better before ideas get committed. So as you know, there's all of this, this is fuzzy area right before you actually stop building something. There's a product manager where you're looking at lots of opportunities and ideas and you're prioritizing them and it's not really confirmed real work yet.

51:14And everybody wanted to put that in Jira because once it was in Jira, then everyone just expected it to happen. And so this is this is where Jira product discovery came from. And in the past, we tried things like this before in new products at Atlassian and they've been successful but it's been really hard because large parts of the company process and those checks were optimizing for the success of the bigger products like Jira software. And so we changed that to create really small groups with stage gates that we call wonder explorer make impact and then getting to scale. And then men to assess those bets at every stage.

51:57And the idea was to iterate really quickly either to it not working out and proving that it couldn't be a business or iterate really quickly. So yes, it could and we should invest more in it. And so with each stage, there would be, you know, a little bit of investments. So say that for a stage of wonder might just be the person with the idea and then explore you might add on a couple more people like three people to go and really have a look at, you know, here's a pretty high. Here are some customers that would be interested in it and could help us think about this some more and put together what the roadmap looks like.

52:33And then when you get to make that's when you get a full team. But you know, a full team is, it's going to be full people also. It's still not huge. And I think that's really important because at each stage, you're getting validation, you're getting more customers who are interested and invested in helping you develop what that solution looks like. So you asked about whether we went and partnered with a partner company like Salesforce for something like this for new product. In this case, it was just really partnering heavily with our customers where we saw that interest coming through in our other products like Jura Software and building something that really works your mind before expanding it to more and more customers and finding that product market fit and then upping the investment.

53:23And so we've we've had a couple of new products recently that have gone through that sort of stage roll out. So Jira Prok Discovery, there's Atlas that I mentioned before and I think Compass is the latest one. So what I'm hearing here is essentially there's this step by step gated process that you put new product ideas through and they make it one step at a time and imagine there's a leader that can decide now this one's not working out. Let's end it at the Explorer phase and invest in other ideas. Imagine. Yeah, that's right. Yeah, it's it might be someone who's looking after that particular market.

54:02Yeah, at each one of those stages, there's that check on whether or not we continue to go ahead. And the stages are one wonder. I like that a lot. That's a great name. Explore, make and then where are the other ones? Impact and scale. God, it's impact is like is it showing any impact? Like we made it, is it working and then scale? God, that makes sense. Just like let's go for it. Yeah, M type to be, you know, I can be self sufficient in the revenue that I'm generating and scale. It's just like really launching into it. Yeah, launch it. Yeah, it goes on the website. Okay, so wonders like a PM and an engineer maybe at Hackathon, we have an idea, explores they maybe get a little bit of resourcing and they start exploring the idea, built a prototype, maybe find a design partner too to think about this.

54:49Is that roughly right? Yeah. Okay. Yeah, make sure you've got a clear roadmap. Yeah. And then, okay, got it and then make is that where they expanded to a few more customers and make it like more fully featured. Yeah, so make us wait you'd actually build it. So the prototype, pretty simple, could be a bit cobbled together, make is actually building the product and see if you can get more and more customers. That's maybe you'd start to make it with those customers. This is really interesting because again, I think it last seen as one of the very few companies that has done this so well. And I don't know, this number is absurd.

55:24I've never heard of another company that's 15 successful products. I don't know how successful they are, but they're out there and people seem to be, they're being promoted. I guess is there any advice to share along the lines of if someone is thinking about launching a second product, anything you would suggest they do or think about that may not be thinking about? Yeah, and I think my advice is sort of skeet towards the last in case, right, which is where you're in a 12 ,000 -strong employee company. And how do you see something that you want to run with more of a startup kind of mindset? So when you go to this size, you've got like little replanning and business reviews and all of these different processes and you don't necessarily want to put your seed startup through that.

56:10It's not quite ready for that kind of thing. So I think the key things here that make it really successful is starting really small with the idea and the solution to be proved and don't add too many people. They feel pressured to add too many people. I think it's easy to be really excited about the potential and just want to throw you know four or five teams at it. But that can, you know, like we're talking about this stuff, that can make things run slower. And so you want to protect them. And the second thing is just give them freedom to move really fast and solve these problems in a different way.

56:46So there are different expectations. They don't necessarily need to be a part of that process that I was talking about before. This team should just be running hard to prove whether or not the idea is going to work and whether it's product market fit. And for different approaches, you know, if I, if I want to add something to your software, but we're talking millions and millions of users that, you know, that thing has to be resilient. It's got a scale. There are all these things that uses inherently expect from something like that. But for something small like this, we are proving product market fit.

57:18You don't need to think about that initially. So you've got to hold this to a different standard. Otherwise, you're just going to slay them down way too much. And actually, we found that by letting them tackle problems a little differently, we found innovative way of looking at things that we can pull back into our other products. So for example, if you look at a GiroPlox discovery, and just the way that it gives more of a spreadsheet, kind of you live a little list of ideas and things like that. You know, some of the, some of the experience there is definitely something that we'll be pulling into Giro software.

58:00You mentioned that over the years, Giro has weathered many storms. From my perspective, it feels like it continues to weather many storms incredibly well. One, because there's just endless startups, always coming at Giro, trying to become the new project management tool that everyone uses. And two, it just feels like people are always dissing on Giro. Like, at Giro sucks, I want to use something else. On the other hand, it continues to dominate. Many people love it. I'm curious what you believe at Lassian, generally as Dan and your team has done to keep Giro ahead of everyone. And I know you're probably going to say, we listen to customers better than anyone.

58:37So if that's a big part of the answer, definitely share that. But I'm curious, is there anything else people may not be recognizing of just like why Giro has been so successful for so long? Yeah. So I think the number of startups that into this space just shows how important the problem is that we solve and that that problem teamwork and collaboration. We've got more than 125 ,000 customers around the world who start their day in Giro, millions of users. And the kinds of companies that use it, I just love hearing about what they do with it. They really blame you away. Like NASA landing the Maz River, right?

59:17Or a camera building this design platform, 20 million people. It's just massive. I don't think you can beat that Mars River story. That's a good one. I think when you follow it up with the canvas story, that one, that one's less interesting now, but it's also amazing. Okay. Sorry. Keep going. And so yeah, they're like he said, they are integral to our success, right? We do excessive over them. We think if we do right by them, then we're going to be going in the right direction. I don't think we've ever had this sense of, you know, arrogance of just no matter how big we are, we've always got this healthy dose of paranoia that we need to keep working on improving things and being better.

1:00:00So we, you know, to your point of our customer feedback, that is a big part of it. We bake in these rituals just to make it super easy for everyone to do that. So the, you know, the whole company gets an email every week and it's just got a random selection of feedback from our customers. It's got, you know, how they rate us and just a quote as well. And so everyone's getting this dose of feedback all the time. We have regular shareouts of all of the research that everyone gets. We get in product feedback. We make it super easy to talk to our customers through social media or, you know, LinkedIn or X now.

1:00:41And then we also have a whole community space where customers can have longer conversations with us about different ideas that were coming up with a little feedback that they have for us. So I think I think that is all massively important for keeping Jura ahead of the pack. I think how we stay ahead in other areas is just that the culture is super, super open to innovation, kind of invites innovation. So we have these hackathons, we call them shipping. Everyone, the whole company, stocks, and everyone can play with new ideas of technologies. It's a competition. So the best ideas get visibility.

1:01:21It can get people working with other people that they wouldn't normally. And also the visibility of the ideas helps generate more ideas or live lip -lapse. Like I said before, innovation can come from anywhere. So anyone can pitch new ideas of products. And when we see new technologies emerging that we think are going to be really foundational and interesting, we'll carve off a team to go and look at that. So I think, you know, we've had an AI team central to our last year for a long time, but with the advent of chat GPT, there's sort of like this huge move forward, right? This is the week that's happening.

1:02:00And so in my team, we just carved off a small team to go and explore that and see what interesting things that we could do there. I think we, we don't shy away from tackling sort of subsets of the market that we're seeing that need a bit more love. So, you know, that like the Jura product discovery story that we were just talking about a second ago. And we also use our products a lot. And that helps us find all of those little problems and and makes it really real. We get really excited about the different things that the whole team is working on. And we send lots of feedback to each other. I think that's also a really important part of it.

1:02:42Another area is when we look at how we're investing, you know, there's always this pressure to invest in the core business, of course. But we also make sure that we invest in seeding future businesses. And like we're talking about, they might not always work out. So we had that the compass in the Alice example of ones that have worked out. But we also see things through a Lansing invention. So if there are interesting ideas or technologies, these might support the products later on. That's something that will go and seed out there in the market. And that's led to a few acquisitions as well, which has been really useful.

1:03:22And the last thing is, I think I'm just really impressed at the way that we say agile to move towards these different shifts that come on. It always surprises me just how agile we can be. So for example, in 2020, we decided to double down on our mission to deliver a world -class cloud experience. And it was like hundreds of people just moved around in Lansing to make that happen, which was in a very short period of time, which is impressive. And we know shy back killing things off of their girls. So I'll give you another example of one of those products that was going through that we ended up killing off.

1:04:04So we had a whiteboard product that we thought would be its own product, sort of like a like a geropryte discovery. And when we came to one of those gates with the team, we realized actually, you know, this is more like a really useful document type. And St. A. L. C. that it's a feature in compulence, that it was it was very quick to make that decision. I have this new segment, not many more, called Failure Corner. I'm curious if you have any interesting story of a big failure in your career. And if you do, what you learn from that experience. I think I'll give you a bit of a different one, because I think this one is harder to spot.

1:04:47And I think that's really interesting. Something that I think about a little time, though. So I missed a really big opportunity to move last year and forward when that can the day. And I, yeah, like I said, I think about it every time I review a new idea or look at an opportunity that we're thinking about. So I was on this team, and I was improving the way that our products helped developers get their work done. And so typically we sell them stoned in Jerusalem where they pick up a piece of work, and then they'd switch tools. They create a brand that start running code. And we noticed that they would forget to come back and update the status of their work.

1:05:24And this could create a lot of confusion in the team, right? Another developer could pick up that work, thinking it was in started. And then there was a lot of wasted time. Or if you're trying to trap metrics like how long does it take for a piece of work to get started to through to done, that'll totally ski things. So this was causing a lot of problems. But we didn't want to make developers come back into the tool. That was obviously something that was getting in the way of their work. So we decided to build automation. So they didn't have to. They didn't have to leave their IE or the command line to do that.

1:05:57They can just keep working. So an example is Gerald would detect that in your commit had been created. And then it could automatically move your piece of work to in progress because this code being written against it. And there were a bunch of these examples that parties integrated into it. And I made the decision to put into Jira as a user was editing their workflow. And we shipped it and it performed just fine. People discovered it. They used it. It seemed to give a lot of value. People liked it, which doesn't really sound like a fail. And I think that where I dropped the ball was more about what I should have realized about that feature.

1:06:39So automation is super useful. It can be used by a whole slew of people who aren't just developers. It could be used in every single product. It's more than just moving things to a new status. And so I should have realized that we could have built this amazing service that every product could have moved themselves forward with. And years later, Alessia actually acquired a company that did exactly that. This advanced automation. And it's in every product now. And so you know, you can imagine how much it cost to acquire a company that was really extensive mistake on my part. So when I see you in your idea, I'm always asking myself, how do we push this further?

1:07:19Is there something there that we can 10X, can we apply it more broadly to more types of uses, more products? Is there some bigger opportunity that we can really take advantage of? That's an awesome story. So the lesson there is just think bigger with the products that you like, you almost need to wait for it to first be successful, right? For you just to be like, Oh, but can we do something more with this? Would you think you should have been thinking about that as you were building it or that have been too early? No, I think I think I should have caught that as we were building it because even when I think about the experience, so it was a really good proving ground for it for sure that even when I think about the experience, just where that experience was designed in product limited, its functionality, which is real shame.

1:08:07I guess the takeaway there is just if you're committing to some idea, ask yourself, what would it look like if this was 10X bigger, if this was a bigger deal, can I supply it to other things we're doing? Is that right? Yeah, where could this go in three years, five years? And should that change the way that you think about it now? Great advice, Megan, is there anything else that you wanted to share, or is there anything you wanted to leave listeners with before we get to our very exciting lightning round? I will leave you with something and it's just this practice that I found really useful for my squad that we have implemented pretty recently.

1:08:50So I think an industry would run my work and all of that. So like I said, we have limited time together, but what we put into place is something we call fight club. I'll probably get in trouble for talking about fight club. The first rule is you talk about fight club, but it's 30 minutes every week and it's just for myself, my engineering and my design leader and we get together and we know that we're going in there to have a conflict. I think often when there's difficult conversations or these conflicts come up, you can put them off until they become much bigger or if somebody is conflicted versus they can try to avoid having it at all, but by having a specific sort of time in your week for something like that, then you're sort of in that mindset, you know you're going in there to solve a high problem, you know that there's going to be a disagreement and it makes it much better.

1:09:47And I think the relationship we all have is so much better because we get on top of these things early. This is super cool. It's like couples therapy or something where you just like what issues do we have? Let's work through them right now. I love that. I love that because it's for yeah and it makes it okay to bring up things that are bothering you and things that you think need to change. And with that we've reached our very exciting lightning round, are you ready? Yes, come away. Let's do it. First question. What are two or three books that you've recommended most to other people? Look, I, you know, when I have a habit of sending books to everyone here reports to me every year, just on a school they're working on.

1:10:28So I've got a huge list that actually send out, but the one I send out the most to new PMs especially is just inspired by Maddie Kagan. It holds up really well. It was recommended to me by my first boss and it's just got a bunch of great tips and there's just great foundational knowledge. More recently what I've been sending out for for my managers is scaling people by Claire Hughes Johnson. I think that just came out within the last year actually, but it's just got an incredible amount of really useful tactical things, templates, all sorts of things that you can put into practice. Great choices.

1:11:12We have both them, the bookshelf behind me, both of them have been on the podcast. I wish I could see the whole list of books that you recommend to people. If you don't have this written out anywhere, you should publish some kind of blogger newsletter post of here's the skill and here's the book you recommend. Oh, that's a great idea. Yeah, I'm going to do that. We have a homework assignment. Okay, next question. What is a favorite recent movie or TV show you've really enjoyed? I am so late to TV, but foundation is the one that I've been binging lightly and I think it's just this this huge world and I'm not usually one that gets super into sci -fi, but the way that it brings forth some of these ideas like like for what me technologies could mean.

1:11:54If you haven't seen it and this isn't really spoiling it, the one of the main characters or three of the main characters are actually clones of this empire who rules the universe and decided to clone himself at three different stages of his life so that those people could continue ruling. And I think even that idea just invites the idea of what if we stretch that human life, what are the impact, how to things advance when you've got that same mindset and same people continue on and it's it's super compelling. Foundation the show got ruined for me by reading the books many many years ago is one of my favorite sci -fi trilogy of all time and then I was so excited for the show and I just is nothing to do with the books.

1:12:38Basically it's like the storyline is completely different like the core idea is the same as the only real. So I just can't I just got tired of it and stop. But if you haven't read the books, I think you would love it. It's beautiful. Other books are there? Yeah, yeah, the books are better. The books are always better. I think is a good rule of thumb. Yeah, that is a good rule. I'll think about them. Yeah, I was like a teenager when I read them so I don't know maybe they're suck but I think people have them highly recommend the books if you like the show especially. Next question. Do you have a favorite interview question that you'd like to ask candidates?

1:13:12I think it's an old one for a great one you know on the subject of failure. I love to ask people about their biggest failure and I think it's a good way to get to know somebody because you can see how introspective they are and how much they they think about what's happened and what they learn from it. It shows whether or not they can be vulnerable with you. You can see what they consider to be a big failure. You know, some people will with something that's not really a failure. And also you can see about whether they've got that growth mindset. So have they learned something from that? Have they applied it moving forward?

1:13:50I've found you know a weird weird rule that I found is that a lot of the best tires that I've had had had big failure stories that they've worked through and went from. And so think I think that's great to see what they consider there with the winnings are but also in the solution you can also see how they tackle something like that. So are they the type of person who wants to go and forge something or buy themselves other type of person who will pull together a community to figure something out. So you get that insight into their values and their approach from that question too, which is hugely useful.

1:14:30Is there a favorite product you recently discovered in that you really love? Yeah, you might have just told me from going on and on about this bit, I recently got a smoker, a Trigger smoker, this making me. And just the unboxing experience was incredible. So you get this huge box, cardboard box, you open it up. If you reverse the cardboard box, it becomes a like a play saloon, then you're a kid can jump into and just mess around in, which it's cool. You know, rather than destroy it, you know, just throwing it out, it becomes something really cool and useful. The set of instructions has a six pack of beer at the top, just helps you understand how far through you should be through your six pack as you're constructing it.

1:15:20You get some tools within and they're really good actually. They're not like the usual kind of throw away tools that you get in something to put together something like this. And then there's you know, in addition to that sort of like playful delightfulness in there, as you build it, you discover things along the way. So I opened up the the hopper where you put in your wood fillets and there was a baseball cap, a Trigger baseball cap in there, which is just was unexpected and really cool. And then the whole experience of actually using it, you know, once you set it up is amazing. So it's all connected to my phone.

1:15:59I can just head to the beach and have some brisk going and come home and it's beautifully done. It just works. It's integrated. It's got integrated recipes. Yeah, I love it. I love this. This is that sounds so delightful. Such a great product experience. I'm going to have to get one I think. I think we're going to sell some Trigger smokers. Next question. Do you have a favorite life motto that you often come back to, share with friends, either in worker and life? It's a ren maximizing joy and one I mean by that is it's about finding what's important and leaning into it or finding what's annoying and turning it into something I enjoy.

1:16:39So to give you like a super small sample is I I'm terrible with keys. I will leave that thing away with the place. You'll find it in my cutlery drawer or whatever and I'll never find it again. And I think, you know, and obvious solution to that could be to put a hook on the wall or something where you can just leave them and you go back to that and it's easy to find. But what could say, joy is not actually having to have keys at all, right? And so now I have a fingerprint reader on my front door and I feel a little bit like James Bond every time I enter my house. And I can let people in, you know, if somebody needs to leave the package or something, that's easy to do.

1:17:20So it was turning, turning something in or into into something more joyful. And I think the other thing there is just I really value keeping great relationships and increasing those relationships. And so I always make time for these amazing friends that I have that live in London. And we have this pact where every time either one of us goes to the other's continent, we'll go meet them there. So every time we create a year of which last year I was in Berlin at one point in Amsterdam and the other way. They came over and we just hung out and had a great time. And so it's making sure that you make time for those important things.

1:18:00Along the same lines, final question related to creating more joy. I noticed a beautiful surfboard behind you for somebody that's trying to surf and maybe not being successful. What's one tip you could share with listeners to improve their success with surfing? That isn't surfing the most tumbling sport that you've ever tried. Yeah, I've tried a few times and yeah, I would say so. I think surfing is really interesting. I've never done a sport like it in that it's something that you have to really feel. So I find every time you learn and you think about surfing, you sort of feel it before you know how to do it.

1:18:41So even just being able to catch away a green piss move, right? You're pounding, you're pounding, you don't quite know where to be, you don't quite know how much to paddle for that wave. And you just have to sort of be successful a couple of times before you get the feel for it. And it's the same with trying to find the right wave. When I looked at the ocean the first time to try and pick the wave and pick where to be, I couldn't even see the shape of it to find that right place. It took me just seeing a hundred waves to be able to do that. So my best tip for surfing is get out there, keep doing it, do it over and over and over again.

1:19:22We'll get better. You'll start to see all of these things that you've never noticed before. And get some friends, get some friends out there, get a, um, and surfing accountability buddy to make sure that you're getting out there. That's the best buddy. Amazing. Megan, we've talked about play and safety and buy -in and fighting the good fight and adding any product lines. Two final questions, also surfing. Two final questions working folks finding a line if they want to reach out and maybe follow up on some stuff. And how can listeners be useful to you? Yes, so the best place to find me is on LinkedIn.

1:19:58Megan Cook on LinkedIn, you can also find me if you're a customer in the O 'Acing community if you want to have a chat. And I'm also on social media, so on XC, you can find me there as well. And for useful three, with any feedback, absolutely any feedback on yourself. We're always hungry for that. Also really keen if you want to just chat about how people's ways of working are evolving and shifting and changing and how do you think that's going to turn out and how you see your goals for your team changing, I would love to talk about that. Please get in touch. Awesome. Megan, thank you so much for being here.

1:20:39Thank you, Lenny. It's been fun. Same. Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or a leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's podcast .com. See you in the next episode.

From the publisher

Megan Cook is the head of product for Atlassian’s Jira software, which is used by 75% of Fortune 500 companies, has over 125,000 customers globally, over 15 different products, and is by far the most popular project management tool in the world. Megan has been at Atlassian for just under 11 years, and before this role, she was an analyst, a developer, and an Agile coach. In our conversation, we discuss:

• How to get buy-in for your ideas

• The value of starting small

• How, and why, creating space for play is so essential

• How Jira stays ahead of endless competition

• Atlassian’s approach to launching new product lines

• Tactical tips for making remote work, work

• A personal failure and the lessons learned from it

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Brought to you by:

• Teal—Your personal career growth platform

• Sprig—Build a product people love

• Vanta—Automate compliance. Simplify security.

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Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching

Today’s transcript will be live by 8 a.m. PT.

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Where to find Megan Cook:

• X: https://twitter.com/meganwcook

• LinkedIn: https://www.linkedin.com/in/cookmegan

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Megan’s background

(03:50) Creating space for play and psychological safety on teams

(07:36) Peer feedback groups

(10:30) Sharing stories of failure

(13:33) The “10 dollar” game for priorities

(15:24) Advice on making remote work, work

(24:16) Getting buy-in for your ideas

(28:33) The importance of staying open-minded

(34:05) A quick summary of how to get buy-in

(36:45) Fighting the good fight

(38:15) Identifying customer pain points

(43:04) Starting small and showing success

(46:08) Launching new product lines

(53:35) Atlassian’s gated process for new product ideas

(58:00) How Jira stays ahead of competitors

(01:04:28) Learning from failure

(01:08:30) Fight club

(01:10:08) Lightning round

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Referenced:

• Jira: https://www.atlassian.com/software/jira

• Atlassian: https://www.atlassian.com/

• Bitbucket: https://bitbucket.org/product

• Ben Crowe on LinkedIn: https://www.linkedin.com/in/ben-crowe-67299714/

• Ash Barty on X: https://twitter.com/ashbarty

• Atlassian’s blog, Work Life: https://www.atlassian.com/blog

• Lessons learned: 1,000 days of distributed at Atlassian: https://www.atlassian.com/blog/distributed-work/distributed-work-report

• New research: How to make time for the work that matters: https://www.atlassian.com/blog/distributed-work/calendar-redesign-experiment

• Atlas: https://www.atlassian.com/software/atlas

• Confluence: https://www.atlassian.com/software/confluence

• Lenny’s swag store: https://lennyswag.com/

• What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat

• The UX research reckoning is here | Judd Antin (Airbnb, Meta): https://www.lennyspodcast.com/the-ux-research-reckoning-is-here-judd-antin-airbnb-meta/

• Charlie Sutton on LinkedIn: https://www.linkedin.com/in/charliesutton/

• Nokia 6100: https://en.wikipedia.org/wiki/Nokia_6100

• Compass: https://www.atlassian.com/software/compass

• Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery

• Canva: https://www.canva.com/

• Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3

• Foundation book series: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573

• Traeger smoker: https://www.traeger.com/shop/wood-pellet-grills

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.



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