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.

—

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

—

Where to find Jack Hannah:  

• LinkedIn: ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠⁠

• Website: ⁠⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠⁠

—

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

—

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.

—

Where to find Ivett Ördög:

• LinkedIn: https://www.linkedin.com/in/ivett-%C3%B6rd%C3%B6g-03aa9035/ 

• Website: https://www.ivettordog.com

—

Where to find Jack Hannah:  

• LinkedIn: ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠

• Website: ⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠

—

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

—

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.

—

Where to find Jesse Wilson:

• Mastodon: https://cosocial.ca/@jessewilson 

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

• Blog: https://publicobject.com

—

Where to find Jack Hannah:  

• LinkedIn: ⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠

• Website: ⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠

—

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

—

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

As AI reshapes how software is built, what does it actually mean to be a good engineer? 

Chelsea Troy, who leads Machine Learning Operations at Mozilla and teaches computer science at the University of Chicago, argues that the future of engineering isn’t about typing faster but thinking better.

In this episode of Distributed, Chelsea joins host Jack Hannah to unpack the three skillsets that matter most in the age of AI: investigative, evaluative, and innovative thinking. She explains why AI tools still fall short in areas that require human reasoning and judgment, how engineers can uplevel the skills that set them apart, and why collaboration and a solid grounding in computer science remain essential.

—

Where to find Chelsea Troy:

• Website: https://chelseatroy.com

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

—

Where to find Jack Hannah:  

• LinkedIn: ⁠⁠⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠⁠⁠

• Website: ⁠⁠⁠⁠⁠https://tuple.app/⁠⁠⁠⁠⁠

—

Timestamps:

(00:00) Intro

(01:08) The 3 most underrated skillsets engineers rely on every day

(08:45) How an interpreter workshop and a Rust compiler project revealed AI’s limits

(14:59) How to level up investigative, evaluative, and innovative skills

(21:25) Why collaboration still matters but isn’t a new challenge created by AI

(25:38) The value of early career pair programming and why it’s hard but worth it

(29:09) Why pairing with an LLM has value but can’t replace human collaboration

(34:33) Formal CS degrees vs. nontraditional paths and why studying CS still matters

(43:49) Rapid fire round

—

Referenced:

• What can we expect of LLMs as Software Engineers?: https://chelseatroy.com/2025/07/14/what-can-we-expect-of-llms-as-software-engineers

• Bob Nystrom’s blog: https://journal.stuffwithstuff.com/

• Tim Peters: https://github.com/tim-one 

• Crafting Interpreters: https://craftinginterpreters.com

• Using the Python Interpreter: https://docs.python.org/3/tutorial/interpreter.html

• Alan Turing: https://en.wikipedia.org/wiki/Alan_Turing

• Ada Lovelace: https://en.wikipedia.org/wiki/Ada_Lovelace

Charity Majors is a writer, speaker, and the co-founder and CTO of Honeycomb, an observability platform for debugging and optimizing distributed systems.

In this episode of Distributed, Jack Hannah talks with Charity about the realities of leading and scaling a distributed company. From why remote work is not best for every situation to the communication tax of distributed management, Charity shares what she has learned about building effective teams, fostering trust, and staying connected in a remote environment. She also reflects on her own leadership journey, from CEO back to CTO, and how greater self-awareness and empathy have shaped her approach to work and life.

—

Where to find Charity Majors:

• Bluesky: https://bsky.app/profile/charity.wtf

• LinkedIn: https://www.linkedin.com/in/charity-majors/

• Website: https://charity.wtf/

—

Where to find Jack Hannah:  

• LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠

• Website: ⁠⁠⁠https://tuple.app/⁠⁠⁠

—

Timestamps:

(00:00) Intro

(01:15) Why remote work isn’t best for everything

(03:20) What Charity learned from her viral Bluesky post on RTOs

(08:33) Why distributed teams need more and better management

(11:33) How to get the most from a remote work experience as an engineer 

(14:30) Why 10x engineers matter less than 10x teams

(18:06) How trust and psychological safety drive high-performing teams(20:58) Signs of a healthy organization for job seekers

(24:17) Charity’s transition from CEO to CTO and the challenges of down-leveling

(26:31) When stepping back in your career can be the right move

(30:44) How self-awareness transformed Charity’s approach to leadership and life

(34:42) Rapid-fire round

—

Referenced:

• Honeycomb: https://www.honeycomb.io/

• Charity’s post on Bluesky about RTO policies: https://bsky.app/profile/charity.wtf/post/3lq4cgak3vk24

• How 37signals handles communication, meetings, and setting work boundaries: https://tuple.app/distributed/How-37signals-handles-communication-meetings-and-setting-work-boundaries-with-Rosa-Gutierrez

• In Praise of “Normal” Engineers: https://charity.wtf/2025/06/19/in-praise-of-normal-engineers/

• Christine Yen on LinkedIn: https://www.linkedin.com/in/christineyen/

• Simon Willison’s blog: https://simonwillison.net/

• Dr. Cat Hicks' newsletter, Fight for the Human: https://www.fightforthehuman.com/

37signals embraced remote work long before it became mainstream. Its Shape Up framework helped define how remote product teams ship fast, but not every team inside the company follows the same playbook. In this episode of Distributed, host Jack Hannah sits down with Rosa Gutiérrez, Principal Programmer at 37signals and founding board member of the Ruby on Rails Foundation.

Rosa takes us inside SEIP (Security, Infrastructure, and Performance), the team responsible for everything from privacy and legacy app maintenance to large-scale infrastructure moves, such as migrating 37signals off the cloud. She shares how a writing-first culture, asynchronous communication, and a flexible, reactive approach let her team thrive outside of the Shape Up model.

—

Where to find Rosa Gutiérrez:

• Bluesky: https://bsky.app/profile/rosa.codes

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

• Website: https://rosa.codes/

—

Where to find Jack Hannah:  

• LinkedIn: ⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠

• Website: ⁠⁠https://tuple.app/⁠⁠

—

Timestamps:

(00:00) Intro

(01:18) Rosa’s role at 37signals

(04:10) How long-form writing is critical to 37signals’ culture

(07:34) How Rosa adapted to 37signals’ asynchronous communication and unique work style

(10:00) The benefits of asynchronous communication for focus, flexibility, and easy reference

(12:08) Why 37signals suits introverts and how they handle in-person meetups

(14:25) Why Shape Up doesn’t fit the kind of work Rosa’s team does

(17:41) How Rosa’s team prioritizes incoming issues during on-call rotations

(21:22) Why Rosa’s flexible work style makes her a perfect fit for SEIP’s reactive team

(26:03) The challenge remote workers face in setting boundaries

(27:46) A case for getting out of the house to create a better work-life balance

—

Referenced:

• 37signals: https://37signals.com/

• Hey: https://www.hey.com/

• Basecamp: https://basecamp.com/

• Ruby on Rails: https://rubyonrails.org/

• Shape Up: https://basecamp.com/shapeup

• Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp-goods.com/products/shapeup

How do you keep a massive, distributed engineering organization with 80,000 employees aligned and actually understanding one another? In this episode of Distributed, host Jack Hannah sits down with Ian Varley, Principal Architect at Salesforce, to talk about how he helps their thousands of engineers across global teams stay informed and connected.

Their conversation explores why clear communication is the backbone of great engineering, practical ways to disseminate knowledge across distributed teams, and how to use AI to make it all faster and easier. You’ll come away with tips you can use right away to break silos, build trust, and make information flow more smoothly in your own organization.

—

Where to find Ian Varley:

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

• Website: https://ianvarley.com/

—

Where to find Jack Hannah:  

• LinkedIn: ⁠https://www.linkedin.com/in/jack-hannah/⁠

• Website: ⁠https://tuple.app/⁠

—

Timestamps:

(00:00) Intro

(01:11) What “borg up” means and why shared understanding matters

(02:20) Practical techniques for using LLMs to communicate more clearly

(05:25) Why you can’t just ask an LLM to write for you

(06:45) How writing itself sharpens thinking and adds clarity

(08:34) The risk of “enshittification” in communication and how to avoid it

(09:38) Using LLMs as a true thought partner instead of a shortcut

(10:55) Why investing in shared understanding pays off in the long run

(16:55) Ian’s unique role at Salesforce as a knowledge sherpa

(22:02) How Ian’s role evolved to Principal Architect with a focus on mentoring and educating

(25:05) What Ian learned from blending engineering, infrastructure, and coordination on HBase

(30:34) How Ian amplifies impact by enabling others to spread knowledge

(33:30) How AI can make work easier

(35:15) Co-Intelligence and the framing of AI as “alien intelligence”

(36:56) Ian’s process for title generating with Claude

(39:00) Closing thoughts

—

Referenced:

• Salesforce: https://www.salesforce.com/

• Haohan Wang’s post on X: https://x.com/HaohanWang/status/194741703347975783

• How Staff Engineers approach leading remote teams with Cassia Scheffer: https://tuple.app/distributed/how-staff-engineers-approach-leading-remote-teams-with-cassia-scheffer-from-wealthsimple

• Creating High-Performing Remote Engineering Teams with Carlos Rosão: https://tuple.app/distributed/creating-high-performing-remote-engineering-teams-with-carlos-rosao-from-newstore

• 10 Principles for Architecture at Salesforce: https://engineering.salesforce.com/10-principles-for-architecture-at-salesforce-82105d5399a8/

• Brad Arkin on LinkedIn: https://www.linkedin.com/in/brad-arkin/

• Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X

In this episode of Distributed, host Jack Hannah speaks with Jori Lallo, co-founder of Linear, to unpack how he and his co-founders shaped one of the most opinionated products in software. They discuss why the team built a product before a business, the principles behind the Linear Method, and how feedback and work trials define Linear’s culture.

The conversation also explores the realities of running a team split across Europe and the U.S., the role of in-person meetups, and how AI is reshaping both Linear’s workflows and the future of collaboration.

For anyone interested in remote work, intentional culture, and the next chapter of software building, this is a conversation worth hearing.

—

Where to find Jori Lallo:

• X: https://x.com/jorilallo

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

—

Where to find Jack Hannah:  

• LinkedIn: https://www.linkedin.com/in/jack-hannah/

• Website: https://tuple.app/

—

Timestamps:

(00:00) Intro

(01:08) Why Linear’s founders built a product before a business

(03:40) How the co-founders of Linear met

(05:01) Shaping Linear’s opinionated philosophy and building tools for modern teams

(09:40) Why the Linear Method still resonates today and where it needs a refresh

(11:45) The role of feedback in Linear’s product culture

(15:40) How Linear approaches hiring

(18:05) The secret ingredient they look for when hiring

(22:18) How Linear operates as a fully remote company 

(24:51) How Linear balances synchronous and asynchronous work across Europe and the U.S.

(27:12) The importance of in-person meetups and social connection

(29:38) How work trials act as a filter for alignment and fit

(31:08) How AI is changing collaboration and work at Linear

(37:31) Closing thoughts

—

Referenced:

• Linear: https://linear.app/

• Karri Saarinen on X: https://x.com/karrisaarinen/ 

• Tuomas Artman on X: https://x.com/artman 

• Y Combinator: https://www.ycombinator.com/

• The Linear Method: Practices for building: https://linear.app/method

• Why and how we do work trials at Linear: https://linear.app/now/why-and-how-we-do-work-trials-at-linear

• The heirloom tomato org chart (Nan Yu, Head of Product, Linear): https://www.youtube.com/watch?v=I4vvBidQcck  

• Clerk Cofounder & CEO on how to build a company that delivers incredible DX: https://tuple.app/distributed/clerk-cofounder-and-ceo-on-how-to-build-a-company-that-delivers-incredible-dx

In this episode of the Distributed podcast, host Jack Hannah talks with Jeff Langr, a software coach, author, and longtime XP advocate. Jeff has helped teams across dozens of companies navigate Agile, pairing, and collaborative programming practices.

Jack and Jeff dig into the surprising downsides of traditional agile software development and how mob programming offers a more inclusive and sustainable way to work. Jeff also shares what works (and doesn’t) about return-to-office efforts and why many organizations are failing to support effective remote collaboration.

Highlights:

• The two rules for making mob programming effective
• Rotations, engagement, and how to avoid team lead dominance
• How Jeff helped skeptics embrace mobbing

In this episode, we cover:

(00:00) – Kicking things off with Jeff Langr

(01:20) – Why mob programming beats solo and pair workflows

(04:15) – Reducing work in progress to boost team flow

(06:12) – The hidden time costs of traditional agile rituals

(08:53) – What makes mob programming a bad choice

(14:26) – How to keep everyone engaged (in-person vs remote)

(18:35) – The two rules every mob team should follow

(23:48) – Navigating fear and vulnerability in mobbing

(24:26) – Turning a skeptic into a mob programming advocate

(25:41) – Why return-to-office pushes often reflect leadership failure



Where to connect further:

Connect with Jeff Langr on LinkedIn and his website

Follow Tuple

Want to hear more? Check out distributed.fm

Connect with Jack Hannah

In this episode of the Distributed podcast, host Jack Hannah sits down with Woody Zuill, the programmer, coach, and speaker best known for popularizing mob programming.

Rather than rehashing the basics of mob programming, Woody talks about what it means to focus on effectiveness instead of productivity and what management gets all wrong. Woody shares insights from decades of experience coaching teams around the world and explains how to create environments that allow real collaboration to flourish.

Highlights:

• The philosophy behind mob programming and software teaming
• Why effectiveness matters more than productivity
• How AI affects how teams collaborate

In this episode, we cover:

(00:00) – Kicking things off with Woody Zuill

(01:10) – The Robert Henri quote that frames Woody’s philosophy

(03:16) – Letting teams self-organize and experiment with how they work freely

(07:41) – Cutting a 500-bug backlog to 17 by working closely as a team

(10:11) – Why separating teams by specialty fragments doesn’t work

(12:22) – Productivity vs. effectiveness and who software is really for

(14:55) – Figuring out what matters through doing, not managing

(17:26) – Will AI replace teams or change how they collaborate?

(19:12) – The role of AI in software development and teamwork

(22:03) – Woody’s advice to new engineers and how to shape better workplaces

References

Jack’s favorite talk from Woody: Mob Programming: A Whole Team Approach

Lean Software Development by Mary Poppendieck and Tom Poppendieck

The Art of Computer Programming by Donald Knuth

The 4 Stages of Psychological Safety by Timothy Clark

Teaming by Amy Edmondson

Where to connect further:

Connect with Woody Zuill on LinkedIn and on his website

Follow Tuple

Want to hear more? Check out distributed.fm

Connect with Jack Hannah