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Lessons from Atlassian | Megan Cook (Head of Product, Jira)

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 — Brought to you by: • Teal—Your personal career growth platform: https://tealhq.com/lenny • Sprig—Build a product people love: Sprig — Build a product people love: https://sprig.com/getstarted?utm_source=lenny&utm_medium=podcast • Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching Where to find Megan Cook: • X: https://twitter.com/meganwcook • LinkedIn: https://www.linkedin.com/in/cookmegan Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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 (38:19) Identifying customer pain points (43:08) Starting small and showing success (46:08) Launching new product lines (53:35) Atlassian’s gated process for new product ideas (58:29) How Jira stays ahead of competitors (01:04:56) Learning from failure (01:09:00) Fight club (01:10:37) Lightning round 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 • 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 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.

Megan CookguestLenny Rachitskyhost
Feb 3, 20241h 21mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

How Atlassian Builds Products, Trust, And Teams That Consistently Win

  1. Megan Cook, Head of Product for Jira, breaks down how Atlassian scales products, culture, and processes across 15 product lines while staying customer-obsessed and innovative.
  2. She explains concrete practices for psychological safety and play (peer feedback groups, offsites, ‘Fight Club’), operating as a fully remote org (Team Anywhere, deep work, async updates, Loom-style videos), and getting executive buy‑in.
  3. Megan shares how she championed unsexy but critical work like CSAT and usability, Atlassian’s gated innovation model for new products like Jira Product Discovery, and how the company continually adapts to market shifts.
  4. She closes with personal lessons on thinking bigger about features, learning from failure, and intentionally designing more joy into both work and life.

IDEAS WORTH REMEMBERING

5 ideas

Deliberately design psychological safety through structured peer feedback and shared vulnerability.

Megan uses small peer feedback groups, twice‑yearly PM onsites, and leaders sharing failure stories to normalize rough work, early feedback, and the idea that big swings and mistakes are acceptable and valuable.

Make conflict a ritual to prevent resentment and misalignment.

Her weekly 30‑minute ‘Fight Club’ with design and engineering leads is a dedicated space for hard conversations, ensuring tensions are addressed early, decisions move faster, and relationships stay strong.

Remote teams need intentional rhythms of connection, deep work, and async communication.

Atlassian mixes 3–4 in‑person gatherings per year with synchronized deep work blocks, strict avoidance of status meetings, rich documentation (Confluence, Atlas), and heavy use of async audio/video to handle time zones.

Treat buy‑in as a journey, not a single high‑stakes meeting.

Successful proposals start with early 1:1 conversations, clearly separated facts vs. hypotheses, openness to alternate solutions, and meetings framed around what you need (decision, feedback, specific risks) backed by tight data.

You can win resources for unsexy work by tying it to revenue and making it easy for others to help.

For CSAT and usability, Megan combined rich qualitative feedback with clear business impact (on acquisition and expansion), then designed low‑cost collaboration (dependency teams provide ‘shepherds’ instead of full dev capacity).

WORDS WORTH SAVING

5 quotes

The opposite of play isn’t work; the opposite of play is fear.

Megan Cook

We’re really firm believers that you don’t need to be in the office to build world‑class products.

Megan Cook

Most of the time when people come to me for buy‑in, they’re planning one perfect meeting—and that’s the wrong attitude. It’s more of a journey.

Megan Cook

If the customer isn’t satisfied or the usability isn’t there, they can’t access the value anyway—it doesn’t matter what features you ship.

Megan Cook

I missed a really big opportunity. We built automation into Jira, but I should have realized it could have been a service for every product.

Megan Cook

Creating psychological safety and play on product teamsTactics for effective remote product management (Team Anywhere)Getting organizational and executive buy-in for ideas and projectsChampioning “unsexy” initiatives like CSAT and usabilityAtlassian’s multi-product innovation model (Wonder → Scale)How Jira stays ahead amid intense competitionLearning from failure and intentionally designing joyful work practices

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