LLenny's Podcast
← All episodes
Megan Cook (head of product, Jira)04 February 2024

Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition

8Frameworks
15Insights

Episode overview

Lenny Rachitsky interviews Atlassian product leader Megan Cook about creating psychological safety, working effectively in a distributed company, and earning stakeholder and executive buy-in. Cook explains Atlassian's staged “wonder, explore, make, impact, scale” model for incubating products such as Jira Product Discovery, Atlas, and Compass. She also describes how small experiments, customer evidence, visible prototypes, internal innovation rituals, and a willingness to kill or reposition ideas help Atlassian improve established products and seed new businesses.

Key ideas

  • Scheduled peer-feedback groups, playful onsites, failure stories, and a weekly “fight club” help teams address conflict early and strengthen psychological safety.
  • Effective remote work combines intentional in-person gatherings with synchronized deep-work blocks, asynchronous status updates, rigorous documentation, and short video recordings.
  • Buy-in is a journey: involve affected stakeholders early, separate facts from hypotheses, stay open to alternate solutions, and state clearly what a decision meeting must produce.
  • For underfunded improvements, start with a small hypothesis, use customer evidence and vivid prototypes, lower the cost for partner teams, and build momentum through early results.
  • Atlassian incubates products through the stages wonder, explore, make, impact, and scale, increasing investment only as customer and business validation grows.
  • Startup-like product teams inside a large company need small headcount, freedom from heavyweight processes, and standards appropriate to proving product-market fit.
  • Jira stays competitive through continuous customer-feedback rituals, company-wide ShipIt hackathons, internal product use, investment in emerging technology, and organizational agility.
  • Cook's automation failure taught her to ask how a promising feature could become ten times larger, serve more users and products, and evolve over three to five years.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Influence4 steps

Buy-In as a Journey, Not a Meeting

Win the decision before the decision meeting by looping stakeholders in early and staying open on the solution.

Read →
Leadership3 steps

Fight Club: A Standing Slot for Conflict

Reserve a recurring weekly slot with your key peers specifically to surface and resolve conflict early.

Read →
Productivity5 steps

Intentional Remote Operating Model

Make remote work productive by scheduling connection in bursts, protecting synced deep-work blocks, and banning status meetings.

Read →
Leadership4 steps

Peer Feedback Groups

Small standing peer pods that review each other's rough-draft work to build feedback muscle and trust.

Read →
Innovation5 steps

Stage-Gated Product Incubation

Grow new products through five funded stages — wonder, explore, make, impact, scale — validating at each gate.

Read →
Productivity4 steps

The $10 Game for Personal Priorities

Allocate a notional $10 across your priorities to expose where your time actually goes versus where it should.

Read →
Innovation3 steps

The 10x Lens on New Ideas

For every promising idea, ask where it could go in 3-5 years if it were 10x bigger — and let that reshape it now.

Read →
Strategy5 steps

The Scrappy Wedge for Unglamorous Investment

Win backing for unsexy work by starting small, showing it visually, making it easy for others, and proving momentum.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 3

  • Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter

    “Today my guest is Megan Cook.”

    ▶ Watch at ~0:30approx.
  • Megan CookMentionsMegan is head of product for Jira. Megan has been at Atlassian for just under 11 years.

    “Megan is head of product for Jira, which is used by 75% of Fortune 500 companies”

    ▶ Watch at ~0:30approx.
  • Ben CroweMentionsAnd he's an expert in having the right mindset. So he works with Olympic gold medalists

    “And then I went to this leadership offsite and one of the speakers there was Ben Crowe.”

    ▶ Watch at ~6:00approx.

Resources · 27

  • JiraMentionssoftware · Atlassian

    “Megan is head of product for Jira, which is used by 75% of Fortune 500 companies”

    ▶ Watch at ~0:30approx.
  • AtlassianMentionscompany

    “Megan has been at Atlassian for just under 11 years.”

    ▶ Watch at ~1:00approx.
  • TealRecommendssoftware · Teal

    “Teal provides you with the tools to run an amazing job search.”

    ▶ Watch at ~2:00approx.
  • SprigRecommendssoftware · Sprig

    “Sprig is an AI-powered platform that enables you to collect relevant product experience insights from the right users”

    ▶ Watch at ~2:30approx.
  • SydneyUsesplace

    “Yeah, all all to Sydney.”

    ▶ Watch at ~12:00approx.
  • Atlassian Work LifeRecommendswebsite · Atlassian

    “folks can go and find on our Work Life blog under research.atlassian.com if they want to dive in there more.”

    ▶ Watch at ~16:30approx.
  • AtlasUsessoftware · Atlassian

    “We actually we use our own tool for this which makes it really easy. So, it's called Atlas”

    ▶ Watch at ~22:00approx.
  • ConfluenceUsessoftware · Atlassian

    “And then that just makes the documentation rigorous as well. So, you document things and we we use Confluence”

    ▶ Watch at ~22:30approx.
  • LoomUsessoftware · Loom

    “It's a big part of why we bought Loom.”

    ▶ Watch at ~24:00approx.
  • Lenny's SwagCoinedwebsite · Lenny Rachitsky

    “I have a swag store now, lennyswag.com, and we have stickers on there.”

    ▶ Watch at ~35:00approx.
  • VantaRecommendssoftware · Christina Cacioppo

    “This episode is brought to you by Vanta, helping you streamline your security compliance to accelerate your growth.”

    ▶ Watch at ~35:30approx.
  • Jira SoftwareMentionssoftware · Atlassian

    “if I think about Jira software, it started just as a a really humble bug tracker.”

    ▶ Watch at ~47:00approx.
  • Jira Work ManagementMentionssoftware · Atlassian

    “And so we started Jira work management to be more focused on all of these other use cases outside of the software team”

    ▶ Watch at ~49:00approx.
  • Jira Product DiscoveryMentionssoftware · Atlassian

    “And so, this is this is where Jira product discovery came from.”

    ▶ Watch at ~51:00approx.
  • CompassMentionstool · Amplitude

    “there's Jira product discovery, there's Atlas that I mentioned before, and I think Compass is the latest one.”

    ▶ Watch at ~53:00approx.
  • CanvaUsescompany · Melanie Perkins, Cliff Obrecht, and Cameron Adams

    “Or Canva building this design platform for 40 million people.”

    ▶ Watch at ~59:00approx.link ↗
  • NASAUsescompany

    “Like NASA landing the Mars rover, right?”

    ▶ Watch at ~59:00approx.
  • ShipItMentionsevent · Atlassian

    “So we have these hackathons, we call them ShipIt. Everyone the whole company stops and everyone can play with new ideas and technologies.”

    ▶ Watch at ~1:01:00approx.
  • ChatGPTMentionssoftware · OpenAI

    “but with the advent of ChatGPT, there's sort of like this this huge move forward, right?”

    ▶ Watch at ~1:01:30approx.
  • Atlassian VenturesMentionscompany · Atlassian

    “But we also see things through Atlassian Ventures, so if there are interesting ideas or technologies, these might support the products later on.”

    ▶ Watch at ~1:03:00approx.
  • FoundationRecommendstv show · Isaac Asimov

    “I'm so late to TV, but Foundation is the one that I've been binging lately”

    ▶ Watch at ~1:11:30approx.
  • Foundation trilogyRecommendsbook

    “It was one of my favorite sci-fi trilogy of all time.”

    ▶ Watch at ~1:12:30approx.
  • Traeger smokerRecommendsproduct · Traeger

    “I recently got a smoker, a Traeger smoker for smoking meat. And just the unboxing experience was incredible.”

    ▶ Watch at ~1:14:30approx.
  • Atlassian CommunityUseswebsite · Atlassian

    “You can also find me if you're a customer in the Atlassian community if you want to have a chat.”

    ▶ Watch at ~1:19:30approx.
  • XUseswebsite · X Corp.

    “So on X, you can find me there as well.”

    ▶ Watch at ~1:19:30approx.
  • LinkedInUseswebsite · LinkedIn

    “Yeah, so the best place to find me is on LinkedIn. I'm Megan Cook on LinkedIn.”

    ▶ Watch at ~1:19:30approx.
  • Lenny's PodcastCoinedpodcast · Lenny Rachitsky

    “You can find all past episodes or learn more about the show at lennyspodcast.com.”

    ▶ Watch at ~1:21:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take06:00

The Opposite of Play Isn't Work — It's Fear

After noticing her team's ideas getting more incremental and feedback getting "painfully polished," Megan heard mindset coach Ben Crowe explain that reaching a flow state requires a sense of play. His reframe stuck with her: the opposite of play is not work but fear. She realized fear was exactly what was shrinking her team's ambition, and used it as the trigger to invest in psychological safety.

  • Flow states require a sense of play — feeling present, open to new ideas, unstressed
  • People commonly frame work and play as opposites; the real opposite of play is fear
  • Fear was why the team's ideas were becoming incremental
  • Ben Crowe coaches Olympic gold medalists and world #1 tennis player Ashleigh Barty
  • Recognizing the fear prompted a deliberate push on psychological safety

“But his point was actually that the opposite of play is fear.”

Megan Cook · 07:00
#psychological-safety#play#team-culture#mindset
Hot Take28:30

Presenting Hypotheses (Not Certainty) Builds More Credibility

Counter to the instinct that you must walk in confident with the exact solution, Megan argues you build more credibility by clearly separating your facts from your hypotheses and sharing your plan to prove or disprove them. Everyone knows you can't see the future, and often you don't truly know until you ship. Exposing your thinking invites others to add data and perspectives — and earns trust.

  • Separate what you actually know (facts) from what is still a hypothesis
  • Shipping is the ultimate test of whether your assumptions hold
  • Presenting false certainty feels credible but isn't
  • Exposing your thinking invites better data and new perspectives
  • Openness about where you need help builds more trust than confidence theater

“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,…”

Megan Cook · 30:00
#decision-making#credibility#hypotheses#product-management

Explainer· 1

Explainer16:00

Bringing Remote Teams Together ~3x a Year Boosts Productivity 13%

Atlassian's research on 1,000 days of remote work found that connection and productivity each rise about 13% when you deliberately bring people together — and it doesn't need to happen daily. On average, roughly three intentional in-person gatherings a year is enough. That's why Megan's PM team meets every six months and the whole extended team gathers about four times a year.

  • Connection and productivity both get boosted ~13% by intentional in-person time
  • Gatherings only need to happen ~3 times a year on average, not daily
  • Atlassian published '1,000 days of remote work' learnings on their Work Life blog
  • PM team meets every 6 months; whole team gets together ~4 times a year
  • Belief that flexibility shouldn't be a perk — you don't need an office to build world-class products

“we're really firm believers that you don't need to be in the office to build world-class products.”

Megan Cook · 16:00

“we found that connection and productivity, they both get boosted by about 13% when you bring people together, but be intentional.”

Megan Cook · 17:30
#remote-work#productivity#team-building#atlassian

Story· 4

Story00:00

"Fight Club": A Weekly 30-Minute Slot Just for Conflict

Megan's leadership squad runs a recurring 30-minute weekly meeting they jokingly call "fight club" whose only purpose is to surface and resolve conflict. Because there's a dedicated slot, people go in knowing a disagreement is coming and tackle hard problems early instead of letting them fester. She credits it with strengthening the relationships across her engineering and design leaders.

  • A fixed 30-minute weekly slot exists purely to have difficult conversations
  • Attendees: Megan plus her engineering and design leaders
  • Naming the time for conflict puts everyone in the right mindset going in
  • Getting on top of issues early prevents them from growing bigger
  • Improves the working relationship rather than damaging it

“The first rule is you don't talk about fight club.”

Megan Cook · 00:00

“we get together and we know that we're going in there to have a conflict.”

Megan Cook · 1:09:00
#leadership#conflict#team-rituals#remote-work
Story37:00

How a Scrappy, Small CSAT Bet Won Company-Wide Investment

Asked to improve customer satisfaction, Megan found usability was the core problem — unglamorous work that's hard to fund. Instead of forcing many teams to align roadmaps (near-impossible), she found a low-cost model where each dependent team assigned a 'shepherd' to guard code changes. She sold it by showing, not telling — real customer pain videos and before/after experiences — and kept the project deliberately small and scrappy to build momentum toward bigger investment.

  • Value doesn't matter if usability blocks customers from accessing it
  • Aligning 3-4 team roadmaps for timing is basically impossible
  • Solution: each team assigns a 'shepherd' to review changes at low cost to them
  • 'Show don't tell' — customer pain videos brought emotional buy-in
  • Starting small (~40 people) and staying scrappy made it a low-risk bet that could prove itself
  • Dark mode emerged from this effort as a high-impact, well-overdue win

“has this great mantra of show don't tell.”

Megan Cook · 42:30

“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…”

Megan Cook · 43:00
#csat#usability#buy-in#scrappy-projects#product-management
Story46:30

How Non-Developers Using Jira Revealed a Whole New Product

Contrary to the assumption that Jira is ~80% developers, only just under 50% of its users are developers — the rest are support, operations, sales, marketing, finance, design, HR and legal. These non-dev teams were cobbling together their own setups because Jira wasn't built for them, which was a strong signal. That demand led Atlassian to build Jira Work Management for use cases beyond the software team.

  • Common belief: Jira is ~80% developers; reality is just shy of 50%
  • The other half is a huge mix — support, ops, sales, marketing, finance, design, HR, legal
  • Non-dev teams were cobbling together their own solutions on flexible Jira
  • That struggle was a strong user signal for unmet demand
  • Jira Work Management was created to serve non-software use cases

“But actually it's more like 50% or maybe just shy of 50% are developers.”

Megan Cook · 48:00

“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…”

Megan Cook · 49:30
#product-discovery#jira#new-products#user-signals#atlassian
Story1:04:30

The Expensive Failure: Not Thinking 10x Bigger About Automation

Megan built automation so developers wouldn't have to leave their IDE to update Jira status — e.g. a commit auto-moves work to 'in progress.' It shipped fine and people liked it, so it didn't look like a failure. Her real mistake was not realizing automation could be a service every product and every type of user could use. Years later Atlassian acquired a company that did exactly that — an expensive lesson that now makes her ask of every idea: how do we push this 10x further?

  • Built automation so developers could update work status without leaving their IDE
  • A commit could auto-move a piece of work to 'in progress'
  • It shipped and performed fine — which is why the failure was hard to spot
  • The miss: not seeing automation as a service every product/user could use
  • Atlassian later acquired a company that built exactly that — a costly mistake
  • Lesson: always ask how an idea could be 10x bigger, across more users and products

“That was a really expensive mistake on my part.”

Megan Cook · 1:07:00

“So when I see a new idea, I'm always asking myself, how do we push this further?”

Megan Cook · 1:07:00
#failure#product-strategy#automation#10x-thinking#jira

Q&A· 1

Q&A1:13:00

Her Favorite Interview Question: What's Your Biggest Failure?

Megan's go-to interview question is to ask about a candidate's biggest failure. It reveals how introspective they are, whether they can be vulnerable, what they consider a real failure, and whether they have a growth mindset. She's found a striking pattern: her best hires tend to have big failure stories they worked through and learned from — and the answer also shows whether they solve problems solo or by rallying a community.

  • The question reveals introspection, vulnerability, and growth mindset
  • What someone counts as a 'big failure' is itself telling
  • Pattern: the best hires have big failures they worked through and learned from
  • Their solution shows if they go it alone or pull together a community
  • Gives insight into a candidate's values and approach

“a lot of the best hires that I've had have had big failure stories that they've worked through and learned from.”

Megan Cook · 1:13:00
#hiring#interviews#failure#growth-mindset

Tool· 2

Tool14:30

The $10 Game, Applied to Your Individual Priorities

Megan's team adapted the classic $10 prioritization game — normally used on strategy — to individual priorities. You and your manager list your priorities and divide $10 across them to see where your time actually goes. It surfaces misalignments, like realizing you're only spending '10 cents' (20-30 minutes) on something that can't possibly move.

  • Adapts the strategy-level $10 game down to a person's own priorities
  • Divide $10 across everything you spend time on
  • Exposes when a priority gets too little time to actually move the needle
  • Checks both alignment ('do my priorities stack up?') and time-on-important-things
  • Done collaboratively between a report and their manager

“we we've just started trying something new called the $10 game for priorities.”

Megan Cook · 14:30
#prioritization#productivity#management#tools
Tool1:10:00

Book Picks: Inspired and Scaling People

Megan has a habit of sending books to colleagues each year based on the skill they're working on. The one she sends new PMs most is Inspired by Marty Cagan — recommended by her first boss, and holding up well as foundational knowledge. For managers, she's recently been sending Scaling People by Claire Hughes Johnson for its tactical templates and practices.

  • Inspired by Marty Cagan — her most-sent book for new PMs; great foundational knowledge
  • Scaling People by Claire Hughes Johnson — her recent pick for managers
  • Scaling People is praised for tactical, practical templates
  • Megan gifts books yearly matched to the skill someone is developing

“the one that I send out the most uh to new PMs especially is just Inspired by Marty Cagan.”

Megan Cook · 1:10:30

“what I've been sending out for for my managers is uh Scaling People by Claire Hughes Johnson.”

Megan Cook · 1:11:00
#books#product-management#management#recommendations

Takeaway· 5

Takeaway07:30

Peer Feedback Groups: A DIY Board of Directors for Your Work

To build trust in a PM team too large for everyone to know everyone, Megan splits it into small peer feedback groups that meet roughly every two weeks. Someone brings rough-draft work and everyone gives feedback, with mixed leadership levels present to model helpful critique. The culture is explicitly about lifting people up, so PMs get comfortable sharing early-stage work and forge relationships they can rely on.

  • Team divided into small peer feedback groups meeting every ~2 weeks
  • Members bring rough drafts — strategies, new experiences, experiments, anything craft-related
  • Mixed leadership levels model what good feedback looks like
  • Small groups feel less stressful and more open than big reviews
  • Builds the 'muscle' of receiving feedback through repetition

“And the culture there is is one of everyone lifting that person up to make their work stronger.”

Megan Cook · 08:00
#feedback#product-management#team-culture#psychological-safety
Takeaway19:00

Sync the Whole Leadership Team's Deep-Work Blocks

To protect creative time in a remote world where calendars fill instantly, Megan and her leadership team sync their calendars so they all have long uninterrupted stretches twice a week at the same time. One block takes an afternoon, the other a morning, so people can pick what suits them. Because everyone is heads-down together, an unexpected shared problem can be picked up during that same window.

  • PMs need 3-4 uninterrupted hours to reach a flow state for deep work
  • Leadership team syncs calendars for shared long stretches twice a week
  • Two blocks at different times (one morning, one afternoon) suit different people
  • Shared timing means urgent cross-team work can be handled in the same window
  • Managers still keep flex in their calendar so reports can grab extra time

“So, my leadership team and I, we actually sync up our calendars, so we end up having these long stretches twice a week all at…”

Megan Cook · 19:30

“The title of the invite was "If you book time during this, I will slap you."”

Lenny · 20:30
#deep-work#calendar#remote-work#productivity
Takeaway21:30

Meetings Are for Solving Problems, Not Status Updates

With deep-work blocks eating into meeting time, Megan makes remaining meeting time precious by banning status updates from meetings — status is read asynchronously (via Atlassian's own tool, Atlas) at a time that suits each person. Decisions and strategies get rigorously documented in Confluence. Across time zones, async audio/video recordings have become a whole new casual document type — a big part of why Atlassian bought Loom.

  • Meetings are reserved for solving problems; status updates go async
  • Atlassian uses its own tool, Atlas, to bundle project/goal updates into an email
  • Decisions, strategies and kickoffs documented in Confluence for future reference
  • Async video/audio recordings replace hard-to-schedule cross-timezone calls
  • Loom acquisition driven by how central recorded async video became

“I I personally hate having status updates as a meeting.”

Megan Cook · 22:00

“It's a big part of why we bought Loom.”

Megan Cook · 24:00
#async#meetings#remote-work#documentation
Takeaway24:30

Buy-In Is a Journey, Not One Perfect Meeting

Megan says most people who ask how to get buy-in have the wrong mental model: they picture crafting one perfect proposal, presenting it, and winning thumbs-up. Instead, buy-in is a journey of looping in stakeholders early and repeatedly — every product a change could affect, plus executives — folding in their feedback as designs, data, and user tests evolve. Those early conversations also create advocates who back you in the final room.

  • The 'perfect proposal wins in one meeting' mindset is the wrong attitude
  • Partner early with every product/stakeholder a change could positively or negatively impact
  • Keep returning to them as designs, data and user tests develop
  • Executives (CTO, CMO, head of design) each bring a different lens worth folding in early
  • Early involvement turns stakeholders into advocates for the final decision meeting

“And that's the wrong attitude, I think, even to start with to getting buy-in.”

Megan Cook · 25:30

“It's It's more of a journey.”

Megan Cook · 25:30
#buy-in#stakeholders#product-management#influence
Takeaway55:30

Seeding a Startup Inside a 12,000-Person Company

Megan's advice for launching a second product from within a large company: keep the seed team tiny and resist the urge to throw four or five teams at exciting potential, because more people slows things down. Give the team freedom to move fast and solve problems differently, exempt from the heavy planning processes that serve the flagship products. A product proving product-market fit shouldn't be held to the same resilience/scale bar as Jira software.

  • Start really small with the idea and don't add too many people
  • Excitement tempts you to over-staff, which makes things run slower
  • Give the seed team freedom to move fast and solve problems differently
  • Exempt them from the big-company planning/review processes
  • Don't hold a PMF-stage product to the flagship's scale/resilience standards
  • Their different approaches can yield innovations you pull back into other products

“So, I think the key things here that make it really successful is starting really small with the idea and solution to be proved and…”

Megan Cook · 56:00

“give them freedom to move really fast and solve those problems in a different way.”

Megan Cook · 56:30
#new-products#intrapreneurship#product-strategy#atlassian