Distributed.

In this episode of Distributed, host Jack Hannah sits down with Andrew Stellman, a longtime software engineer, author, and engineering leader who has written multiple widely used software engineering books published by O’Reilly.
Andrew reflects on how being forced into remote work after September 11th shaped his thinking about teamwork, what high-performing teams get right about alignment and mission, and why listening carefully is still central to building useful software. The conversation then turns to AI, where Andrew talks about why these tools work best when engineers slow down, think critically, and stay engaged with the code they are creating.
Andrew also shares five habits that help developers use AI more effectively, why learning to skim and read code matters, and why many of the challenges teams face today are not new, even if the tools are.
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Where to find Andrew Stellman:
• X: https://x.com/AndrewStellman 
• LinkedIn: https://www.linkedin.com/in/andrewstellman 
• Linktree: https://linktr.ee/andrewstellman
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Where to find Jack Hannah:  
• LinkedIn: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠⁠⁠
• Website: ⁠⁠⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠⁠⁠
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Timestamps:
(00:00) Intro
(01:27) Andrew’s first experience working remotely 
(03:57) Why remote work depends on shared understanding
(06:54) Why trust is so hard on teams
(08:50) What high-performing teams have in common 
(12:03) Turning user needs into buildable requirements
(15:34) How to get better at explaining problems
(16:38) Why Andrew believes AI improves software
(19:42) Why prompt engineering is really requirements engineering
(24:20) How LLMs make shared understanding cheaper
(26:49) Why skimming is a critical AI-era skill
(30:05) Five habits for getting more out of AI
(35:40) A real example of the rehash loop
(37:59) Why software’s hardest problems haven’t changed
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Referenced:
• Jennifer Greene on LinkedIn: https://www.linkedin.com/in/jennifergreene
• Applied Software Project Management: https://www.amazon.com/Applied-Software-Project-Management-Stellman/dp/0596009488
• Learning Agile: Understanding Scrum, XP, Lean, and Kanban: https://www.amazon.com/Learning-Agile-Understanding-Scrum-Kanban/dp/1449331920
• Beautiful Teams: Inspiring and Cautionary Tales from Veteran Team Leaders: https://www.amazon.com/Beautiful-Teams-Inspiring-Cautionary-Veteran/dp/0596518021
• Head First C#: A Learner's Guide to Real-World Programming with C# and .NET: https://www.amazon.com/Head-First-Learners-Real-World-Programming/dp/1098141784
• On Writing: A Memoir Of The Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375
• Save The Cat! The Last Book on Screenwriting You'll Ever Need: https://www.amazon.com/Save-Last-Book-Screenwriting-Youll/dp/1932907009
• Why Projects Fail: https://www.stellman-greene.com/Why_Projects_Fail.pdf
• Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann
• Beyond Vibe Coding: From Coder to AI-Era Developer: https://www.amazon.com/Beyond-Vibe-Coding-AI-Era-Developer/dp/B0F6S5425Y
• The Cognitive Shortcut Paradox: https://www.oreilly.com/radar/the-cognitive-shortcut-paradox 
• The Sens-AI Framework: Teaching Developers to Think with AI: https://www.oreilly.com/radar/the-sens-ai-framework/

What does craftsmanship look like in an async-first, remote company?
In this episode of Distributed, host Jack Hannah sits down with Steve Schoeffel, co-founder of Whimsical, to talk about async-first work, craftsmanship, and the tradeoffs of running a fully remote company. Steve shares how Whimsical creates momentum without constant meetings, why quality lives in the details, and how async-first work shapes both the product and the company culture.
Steve also reflects on the harder, more personal side of the work. He talks candidly about co-founder misalignment, the strain of leadership during periods of uncertainty, and what it’s been like to learn to hold work more loosely over time.
They also dig into the return-to-office push and why Steve remains convinced that remote work, done well, is worth fighting for.
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Where to find Steve Schoeffel:
• LinkedIn: https://www.linkedin.com/in/steveschoeffel
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Where to find Jack Hannah:  
• LinkedIn: ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠⁠
• Website: ⁠⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠⁠
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Timestamps:
(00:00) Intro
(01:02) An overview of Whimsical 
(02:02) The size of Whimsical’s team and how it operates across time zones
(03:08) What the Whimsical Way is and how it shows up in practice 
(04:58) Why Whimsical is async-first and what that looks like in practice
(10:49) How Whimsical maintains energy and connection in async work
(13:59) Craftsmanship as a core value at Whimsical
(18:21) How Whimsical pursues “insanely great” work
(24:14) What’s been hardest about running a remote company
(28:24) How Steve realized he and his co-founder were misaligned
(32:08) How Steve is learning to detach from work and care for himself
(36:32) Why Steve remains pro–remote work amid big tech’s return-to-office push
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Referenced:
• Whimsical: https://whimsical.com
• The Whimsical Way: https://whimsical.com/whimsical-way
• Kaspars Dancis on LinkedIn: https://www.linkedin.com/in/kasparsd 
• How async work inspires craftsmanship: https://whimsical.com/blog/how-async-work-inspires-craftsmanship
• Development cycles, process, and tooling: https://tuple.app/distributed/head-of-engineering-at-sublime-security-on-development-cycles-process-and-tooling-with-sumeet-jain
• Craftsmanship, the heart of Whimsical: https://whimsical.com/blog/craftsmanship-the-heart-of-whimsical
• Frank Slootman on LinkedIn: https://www.linkedin.com/in/frankslootman
• Shapeup: https://basecamp.com/shapeup

Why does so much software still feel broken, even after years of new tools and processes?
On this episode of Distributed, host Jack Hannah sits down with Scott Hanselman, Vice President of Developer Community at Microsoft, to explore how fear-driven development, speed-first incentives, and short-term thinking continue to shape modern software.
Scott reflects on why craftsmanship has become rare, how some teams still manage to do quality work, and how today’s engineering systems influence the outcomes we see. The conversation also examines how AI is changing the day-to-day experience of engineers, why junior developers need much more support, and what stronger apprenticeship models could look like in practice. Scott shares ideas for investing in people over the long term and building meaningful communities across distributed teams. This episode offers a clear lens on what it takes to build better software by investing in people and systems together.
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Where to find Scott Hanselman:
• X: https://x.com/shanselman 
• LinkedIn: https://www.linkedin.com/in/shanselman 
• Blog: https://www.hanselman.com/blog
• Newsletter: https://hanselman.substack.com
• The Hanselminutes Podcast:  https://www.hanselminutes.com 
• Scott and Mark Learn To Podcast: https://www.youtube.com/playlist?list=PL0M0zPgJ3HSf4XZvYgZPUXgSrfzBN26pf
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Where to find Jack Hannah:  
• LinkedIn: ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠
• Website: ⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠
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Timestamps:
(00:00) Intro
(01:25) Why so much software feels broken and why it persists
(03:38) The outlier companies focused on quality software
(04:30) What software craftsmanship looks like and why it’s rare
(08:18) How to reduce fear-driven development
(11:50) How AI reflects the flaws in today’s software practices
(12:46) How AI affects senior and junior engineers differently
(17:03) Rethinking the mentorship model for junior engineers
(19:11) Best practices for a structured apprenticeship program 
(21:43) Delegate, verify, and integrate: a model for managing AI and junior engineers
(22:05) Why pair programming isn’t enough on its own
(27:07) The case for long-term investment in people
(29:54) Where big tech has fallen short and created division
(32:52) The indie web and alternatives to platform-driven tech
(34:30) How to build community across distributed teams
(38:20) Rapid fire round
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Referenced:
• Everything’s broken and nobody’s upset: https://www.hanselman.com/blog/everythings-broken-and-nobodys-upset
• Instapaper: https://www.instapaper.com
• Pocket: https://heypocket.com
• 1Password: https://1password.com
• Cabel Sasser’s website: https://cabel.com
• Visual Studio Code: https://code.visualstudio.com 
• Boeing: https://www.boeing.com
• Mark Russinovich on LinkedIn: https://www.linkedin.com/in/markrussinovich
• Tech Promised Everything. Did it deliver? | Scott Hanselman | TEDxPortland: https://www.youtube.com/watch?v=dVG8W-0p6vg
• IntelliSense: https://code.visualstudio.com/docs/editing/intellisense
• Usenet: https://en.wikipedia.org/wiki/Usenet
• POSSE: https://indieweb.org/POSSE
• DuckDuckGo: https://duckduckgo.com
• Amanda Silver on LinkedIn: https://www.linkedin.com/in/amandaksilver
• Brain, Bytes, Back, Buns - The Programmer's Priorities: https://www.hanselman.com/blog/brain-bytes-back-buns-the-programmers-priorities
• WeWork: https://www.wework.com
• Simon Willison’s blog: https://simonwillison.net

On this episode of Distributed, host Jack Hannah sits down with Ivett Ördög, a 35-year software veteran and creator of Lean Developer Experience (aka Lean Poker), to talk about what it really takes for engineers to grow their impact. Ivett argues that communication, continuous delivery, and delivering value early are not soft add-ons but essential engineering skills that determine how far developers can go.
Together, they break down how remote work can create better environments for deep focus and well-being, why strong communication skills often determine the jump from mid-level to staff, and how developers at any stage can begin practicing them. Ivett also shares when rewrites actually make sense, how to communicate them to management, and why continuous delivery gives teams the feedback they need to build the right thing.
The episode offers clear, tactical guidance for any engineer looking to level up, advocate for better ways of working, and deliver value earlier and more often.
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Where to find Ivett Ördög:
• LinkedIn: https://www.linkedin.com/in/ivett-%C3%B6rd%C3%B6g-03aa9035/ 
• Website: https://www.ivettordog.com
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Where to find Jack Hannah:  
• LinkedIn: ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠
• Website: ⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠
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Timestamps:
(00:00) Intro
(01:17) The philosophy behind the Lean Developer Experience 
(02:24) Why Ivett now believes remote work produces better outcomes
(06:45) Why people overlook the benefits of remote work
(08:20) How remote work is customizable for needs and deep focus
(11:48) Why communication is essential for developer career growth
(14:52) Two communication struggles engineers face and how to begin improving
(18:46) Where to find speaking opportunities 
(19:30) Tips for eager speakers with no stage experience
(21:15) When rewrites make sense 
(28:14) How to communicate a rewrite to management
(32:15) Ivett’s definition of continuous delivery 
(34:02) Examples of continuous delivery that show its value
(36:54) How to drive change in a slow-moving organization
(40:15) How Lean Developer Experience helps teams practice continuous delivery
(42:45) The value of hands-on learning
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Referenced:
• Lean Developer Experience: https://www.ivettordog.com/leandeveloperexperience
• Ted Talks: The Official TED Guide to Public Speaking: https://www.amazon.com/TED-Talks-Official-Public-Speaking/dp/1328710289
• How to sell a big refactor or rewrite to the business? - Ivett Ördög - NDC Oslo 2025: https://www.youtube.com/watch?v=wdz90PQ2Ak4
• Emily Bache’s Samman coaching website: https://sammancoaching.org
• Jez Humble on LinkedIn: https://www.linkedin.com/in/jez-humble
• Dave Farley’s Weblog: https://www.davefarley.net

In this episode of Distributed, host Jack Hannah talks with Jesse Wilson, a longtime open-source contributor and Cash App engineer, whose work underpins much of the Java and Android ecosystem. Jesse shares why some of the most rewarding engineering work comes from doing things the right way, even when it’s the hard way.
Their conversation dives into the story behind Okio, the I/O library for Android, Java, and Kotlin that’s been downloaded >50 billion times, and what it revealed about craftsmanship, risk-taking, and building for the long term. They also unpack how remote teams can bring back the spark of in-person collaboration by pairing more often, embracing small interruptions, and using shared artifacts to stay aligned.
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Where to find Jesse Wilson:
• Mastodon: https://cosocial.ca/@jessewilson 
• LinkedIn: https://www.linkedin.com/in/swankjesse 
• Blog: https://publicobject.com
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Where to find Jack Hannah:  
• LinkedIn: ⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠
• Website: ⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠
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Timestamps:
(00:00) Intro
(01:28) Why the quick and bad way is never the right choice
(04:07) A story from Okio that shaped Jesse’s engineering philosophy
(06:39) How company culture empowered Jesse to build Okio
(08:46) The challenges of building Okio
(12:40) Why Okio was worth building
(15:08) The value of spontaneous collaboration and why interruptions can be good
(21:10) Handling friction in distributed teams
(27:32) The value of shared responsibilities and scheduled maintenance 
(31:05) How Jesse balances meetings with time for flow state
(35:42) How a shared whiteboard or Google Doc keeps meetings on track 
(40:52) How shared artifacts guide meetings and make wrap-ups effortless
(43:23) Rapid-fire round
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Referenced:
• Okio: https://square.github.io/okio/ 
• Writing Code That Lasts Forever: https://publicobject.com/2018/08/28/writing-code-that-lasts-forever
• Todoist: https://www.todoist.com
• inessential by Brent Simmons: https://inessential.com