Big news for 2024!

I’m thrilled for this year because I am publishing my first book! This is the work of three (or twelve, depending on how you count it) years. The book, “It Depends: Writing on Technology Leadership 2012-2022,” includes content from this blog and articles originally published elsewhere. I took all those articles, cleaned up the grammar, edited for clarity, and organized them into themes and logical progression. This is something that I’ve been meaning to do for a while, and it took me longer than I expected to finish it, but I’m proud of the result.

The book "It Depends: Writing on Technology Leadership 2012-2022" sitting on a table

The book will be released by Unit Circle Press in March. More information about pre-ordering will be available soon. I also just finished recording the audiobook version, which should be available around the same time.

I’ve also launched two new projects to support the book’s launch. A newsletter and a podcast. I will be serializing the book in the newsletter and serializing the audiobook in the podcast. Both will feature extra content like answers to your questions and additional context around the chapters. The first newsletter and podcast episode are now available. They are both free! Please subscribe to the newsletter and subscribe to the podcast on Spotify, Apple, Google, Amazon or wherever you get your podcasts!

Please check out the book website for more information.

My Belated 2022 Recap: Podcasts

Previous posts cover the books and blog posts I found valuable this year. This post covers the podcast episodes that I wanted to share.

InfoQ – Phil Abernathy on Employee Happiness and the Bureaucracy Mass Index

https://www.infoq.com/podcasts/employee-happiness-bureaucracy-mass-index/

In this Shane Hastie, Lead Editor for Culture & Methods, spoke to Phil Abernathy about his work helping organizations focus on employee happiness to drive customer happiness and shareholder return and the Bureaucracy Mass Index as a tool to identify where companies are bloated and ineffective. He also spoke about what’s needed for real transformation.

Great practical advice on building happier teams and a tool to measure bureaucracy in an organization.

A Brief History of the Metaverse: DIY Metaverse

Tony and Mark – supported by a global community of technologists, enthusiasts, and dreamers – brought 3D to the brand-new Web with VRML. This episode features Owen Rowley, Neil Redding, Linda Jacobson, Brian Behlendorf, John McCrea, Coco Conn — and Neal Stephenson.

With all the talk (and investment) in the metaverse, it is frustrating sometimes that people forget that the technology industry has been thinking and working on this for decades. Tony and Mark were instrumental in creating VRML, and I appreciate them documenting some of the history, but I was a bit disappointed that they omitted some of the other folks that were involved in the beginning.

CALLING BULLSHIT – Spotify: Starving Artists?

Stated purpose: to unlock the potential of human creativity—by giving a million creative artists the opportunity to live off their art and billions of fans the opportunity to enjoy and be inspired by it.

Spotify is the most popular streaming service in the world, with 188 million people paying for premium subscriptions and hundreds of millions more listening for free on the ad supported tier. Which is why it has been called the world’s best place to get noticed as a musician.  But getting noticed and making a living are two different things. In this episode we decide if Spotify is more about  “Honesty” or “Little Lies?”. Listen in to find out.

One of our board members at Anaconda turned me onto this podcast. It’s about purpose-driven companies that don’t live up to their professed goals. This episode focuses on Spotify but also talks about the broader streaming music economy.

A16z Podcast – Creators, Creativity, and Technology with Bob Iger

https://a16z.simplecast.com/episodes/creators-creativity-and-technology-with-bob-iger-L98rXqw2

A wide-ranging conversation with Bob Iger on the interplay between technology, content, and distribution; as well as Bob’s journey — and that of various creators! — especially as the industry evolved from TV and cable to the advent of the internet/ web 1.0 to 2.0 to briefly touching on web3 and other emerging technologies. As well as topics top of mind for all company and community builders: from build vs. buy and the innovator’s dilemma, to managing creativity, decentralization, remote work, and much more.

I didn’t expect to like this podcast as much as I did. I appreciated it not only for his takes on leading teams of creative people but also for his business acumen and for getting more details about creative people I admire and their work.

20VC – 20 Product: Marty Cagan on The Four Questions of Great Product Management, Product Lessons from Marc Andreessen, Ben Horowitz and eBay’s Pierre Omidyar & The Difference Between Truly Great Product Teams and the Rest

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for some of the most successful companies in the world, including Hewlett-Packard, Netscape Communications, and eBay. He worked directly alongside Marc Andreesen and Ben Horowitz at Netscape and Pierre Omidyar at eBay.

I was not a fan of Cagan’s book Inspired. I called it “Ayn Rand for Product Managers.” I worked with some product managers who were all huge fans of it, and the result was not great for working with engineering.

In the time since, I have appreciated what Cagan said in his blog, which was a lot more focused on Lean-style product development and cross-functional collaborative teams. This podcast was further evidence for me that I need to re-evaluate how I see Cagan. I appreciated his perspective.

Planet Money – Episode 576: When Women Stopped Coding

https://www.npr.org/sections/money/2016/07/22/487069271/episode-576-when-women-stopped-coding

Mark Zuckerberg. Bill Gates. Steve Jobs. Most of the big names in technology are men.

But a lot of computing pioneers, the ones who programmed the first digital computers, were women. And for decades, the number of women in computer science was growing.

But in 1984, something changed. The number of women in computer science flattened, and then plunged.

Today on the show, what was going on in 1984 that made so many women give up on computer science? We unravel a modern mystery in the U.S. labor force.

This podcast was oddly personal for me. It talks about how advertising and culture perpetuated a vision of computers as being for boys, discouraging women from entering the computing field. This was the time that I became fascinated by computers. I remember the ads, tv shows, and movies they discuss, and when I entered college for Computer Science my class was 70 men and 2 women. They also talk about my alma mater Carnegie Mellon and the steps that they have taken to address this imbalance.

It is amazing how quickly culture changed computing from being a female-dominated field to being a male one and then how long it has taken us to try and bring it back into some sort of equilibrium.

My belated 2022 recap: blog posts and articles

In the last post, I shared the books that I found worth recommending that I read in 2022. The next post shares podcasts that I found valuable. In this (longer) post, I will share links to the blog posts from 2022 that I think are recommendation worthy. I’ve broken it into sections based on content.

Company/Team Culture

As a CTO, I spend a lot of my time thinking about building effective technology organizations, and I’m always looking for new approaches or lessons in the space.

The pandemic has caused nearly two years of collective trauma. Many people are near a breaking point.  

https://www.washingtonpost.com/health/2021/12/24/collective-trauma-public-outbursts/

An airplane passenger is accused of attacking a flight attendant and breaking bones in her face. Three New York City tourists assaulted a restaurant host who…

If you are wondering why people are such jerks now…

How Flat Should An Organization Be?

https://www.corporatelearningnetwork.com/leadership-management/columns/musk-restructures-tesla-how-flat-should-an-organization-be

Musk Restructures Tesla… Many books and articles have documented the relationship…

I didn’t necessarily agree with everything here, but I think it is worth reading if you are responsible for organizational structure at any level.

How HashiCorp Works  

https://works.hashicorp.com/articles/writing-practices-and-culture

Learn about the How HashiCorp Works project and why there are links to internal HashiCorp materials in this article. Our…

I like the movement in making how companies work transparent. It is useful to read as a leader and a great recruiting tool for those companies. I always wonder how much reality matches the shared documents. If you know you will share with the public, you are likely to be a bit more aspirational than actual, but it is still useful to read.

Medium sees more employee exits after CEO publishes ‘culture memo’ – TechCrunch

https://techcrunch.com/2021/06/03/medium-exodus-culture-memo/

by Natasha Mascarenhas @nmasc_

By now, every CEO should know better than to publish a “Culture memo” to address employee behavior. Have any of them gone over well?

Netflix to Its Techies: Shut Up

https://www.vulture.com/2022/07/netflix-to-its-techies-shut-up.html

by Zoë Schiffer

The sign that Netflix’s culture had irreversibly started to…

The genius of Netflix as an employer was that it has always been very upfront about who it is and how it works, with the understanding that anyone taking a job there knows what they are getting into. This works great until the culture starts to change, so this isn’t about an individual employee being unhappy. It will be interesting to see how Netflix navigates this (or doesn’t).

Culture as a Product: How HubSpot Built its Famed Startup Culture

Around Boston and beyond, HubSpot is known for its strong entrepreneurial culture . The company has received many awards over the years and was recently named…

Hubspot is an interesting company. Having read Disrupted (https://www.amazon.com/Disrupted-Dan-Lyons/dp/0316306096) I am a bit skeptical of how they talk about themselves, but of course, one always should be. That said, even if the public face of companies’ cultures is more aspirational than real, there is still something to be learned. I didn’t decide that the 37 Signals books were worthless because when under stress, the company didn’t live the values they proclaimed.

Bolt Loaned Employees Thousands to Buy Stock—Then Laid Them Off  

https://www.wired.com/story/bolt-stock-loans/

by Condé Nast

The challenge of startup options is that employees rarely are allowed to sell them. When a startup has been around a long time, and startup options are starting to expire, but employees have had the liquidity event necessary to have ready cash to exercise their options, what are they to do? A company I was in also considered a loan program for employees but decided it was potentially problematic. Bolt learned that lesson the hard way, and their former employees are worse off for it.

A big 32-hour workweek test is underway. Supporters think it could help productivity  

https://www.npr.org/2022/06/07/1103591879/a-big-32-hour-workweek-test-is-underway-supporters-think-it-could-help-productiv

by Wynne Davis

I keep hearing that the 4-day workweek is imminent. Maybe someday, but I doubt it will be soon.

Etsy Engineering | Leading your engineering team through an unexpected…  

https://www.etsy.com/codeascraft/leading-your-engineering-team-through-an-unexpected-product

By Najla Elmachtoub May 26, 2022

This article was originally written for LeadDev . In tech, we talk a lot about failing fast: implementing small, incremental…

I talk a lot about failure, failing fast, etc… This article is an actual case study in how to recover when your team has a big failure. I always like real-life stories instead of vague opinion pieces.

Career Development: What It Really Means to be a Manager, Director, or VP

by Umesh

It’s no secret that I’m not a fan of big-company HR practices. I’m more of the First Break all the Rules type. Despite my general skepticism of many standard…

There are tons of posts and books about being a line manager. There are substantially less about levels beyond that. I’m always looking for informative articles or books about more senior leadership levels. This was a decent one.

Tech’s Talent Wars Have Come Back to Bite It  

https://www.nytimes.com/2022/11/10/technology/big-tech-layoffs.html

by Erin Griffith

What Tech People Should Learn From This Era of Excess  

https://www.theinformation.com/articles/what-tech-people-should-learn-from-this-era-of-excess

by Martin Peers

We’re in the Finding Out part of the FAFO scale-up tech boom/bust cycle. We didn’t learn in 2001 or 2008. We probably won’t learn now, either.

Twitter is suffering from mad bro disease

https://www.theregister.com/2022/11/14/opinion_column_twitter/

by Rupert Goodwins Mon 14 Nov 2022 // 09:30 UTC

There is a euphemism in rocketry often heard at SpaceX – Rapid Unscheduled Disassembly. A catastrophic explosion, in other words. Until now, it was not…

The speed of Elon’s decline from “genius who can see a better future and bring it about” to “asshole snake oil salesman with a narcissistic personality disorder” was sudden by any measure. How do we keep people like this from ruining our favorite apps/sites? By keeping ownership and infrastructure distributed…

Remote Work/Return to the office

For the last couple of years, the push and pull of remote vs hybrid vs back-in-the-office has been a major story in the work press. I’ve already made my decision that I’m going to keep working remote and will choose companies that allow me to do that, but in all of this discussion I’m also looking to understand how other companies are approaching things.

Why workers are calling BS on leaders about returning to the office  

https://www.fastcompany.com/90639348/why-workers-are-calling-bs-on-leaders-about-returning-to-the-office

by Kimberly Merriman and David Greenway and Tamara Montag-Smit

There have been SO MANY TAKES about returning to the office post-pandemic, but I found this one decent.

Remote-working jobs: Disaster looms as managers refuse to listen | ZDNet  

https://www.zdnet.com/article/remote-working-jobs-disaster-looms-as-managers-refuse-to-listen/

by Owen Hughes

This may be losing some of its value as it ages, but speaking as an all-remote company CTO, if you don’t listen to your employees about how they want to work, I’ll be happy to take them off your hands.

The Future of Work Isn’t Fancy Tech. It’s Remote Work and Smarter Management  

https://www.inc.com/jerod-venema/the-future-of-work-isnt-fancy-tech-its-remote-work-smarter-management.html

The remote/office debate is dying down any time soon. There is more pressure on returning to offices now, but there is also more resistance. Given the layoffs, employees may not feel empowered to resist the call to return to the office, so maybe that will gain ground.

The Worst Part of Working From Home Is Now Haunting Reopened Offices

https://slate.com/human-interest/2022/03/hybrid-workplace-office-in-person-work-collaboration-hassle.html

by Alison Green

Few people are as knee-deep in our work-related anxieties and sticky office politics…

If a primary driver for bringing people back to the office is better collaboration, you may want to consider how your hybrid remote/office system is set up.

How to embrace asynchronous communication for remote work

https://about.gitlab.com/company/culture/all-remote/asynchronous/

How to get started with async GitLab believes that…

The secret to successful remote work (especially if the team is spread across time zones) is moving to be asynchronous first. The companies that have been distributed for long periods and have scaled have embraced this, but it is harder than it seems, and many companies struggle. Even those that have always been distributed. This GitLab guide is very helpful.

Web Technologies

I spent much of 2022 learning more about WebAssembly as we launched PyScript at Anaconda. I think that it has some amazing potential and is one of the most important technologies of the last few years.

The rise of WebAssembly  

https://www.infoworld.com/article/3651503/the-rise-of-webassembly.html

by Scott Carey

WebAssembly Concepts – WebAssembly | MDN  

https://developer.mozilla.org/en-US/docs/WebAssembly/Concepts

This article explains the concepts behind how WebAssembly works including its goals, the problems it solves, and how it runs inside the web…

If you are in technology, you need to understand WebAssembly and how it can be used. It can potentially be more transformative than many of the technologies we depend on for software development today.

A short history of Flash & the forgotten Flash Website movement (when websites were “the new emerging artform”)

https://www.nathalielawhead.com/candybox/a-short-history-of-flash-the-forgotten-flash-website-movement-when-websites-were-the-new-emerging-artform

This post is a transcript of a talk I gave at UCSC. Thank you for inviting me! I’m sharing it here because It’s a GOOD summary of the history of a technology…

If you were active on the web in the 90s and early 2000s, you will remember the explosion of massively creative web experiences propelled by the Macromedia/Adobe technology Flash. While you can still create those kinds of experiences using modern web technologies, it now requires a level of coding expertise that puts the programmers in the driver’s seat instead of the artist/designer and requires a team instead of a single creative person.

The genius of Flash was that it made complex interactivity and visuals easy for many artists to create, and the result was beautiful chaos. The web is just a bit more boring for the death of Flash.

Spotify’s grand plan to monetize its open source Backstage project via premium plugins  

https://techcrunch.com/2022/12/15/spotifys-plan-to-monetize-its-open-source-backstage-developer-project/

by Paul Sawers

Backstage was created when I was at Spotify. Even in its earliest days, it solved many problems for us in a massively micro-service architecture. It’s cool to see how it has developed over the years, and it was also cool to see that Spotify had open-sourced it. I think it is interesting that Spotify is doing this experiment, but also disappointed because I know of at least one company formed by ex-Spotifiers that were trying to build companies on top of Backstage.

Google: The Model Your Site Was Built On Is No Longer Feasible  

https://www.seroundtable.com/google-site-no-longer-feasible-33939.html

SEO is tough, and Google can accidentally kill your site, and if it happens, they will tell you it is your fault.

Why Elon Musk Is Blowing Up Twitter’s Business

https://www.theatlantic.com/ideas/archive/2022/11/elon-musk-twitter-advertising/672156/

by James Surowiecki

Hours before Elon Musk closed his deal to buy Twitter, he published an open letter to advertisers. Musk knew that big companies, in particular, were anxious about…

“Free speech” and an advertising-based revenue model are incompatible.

Web3/Decentralized Web/Metaverse

When blockchain emerged, I spent some effort to really understand it. Then I realized that it was a technology searching for a use case fueling a tulip-like baseless speculative market. When Web3 started to emerge, I delayed judgment until I could understand it better. While I believe that there are people who believe that it can fuel a world where creators have more ways to be paid for their work and other such lofty goals, the practicality of it is that very little of those schemes require the blockchain, and most of the people in the space are just trying to make a quick buck before the tulip market collapses.

Web3 is Bullshit

https://www.stephendiehl.com/blog/web3-bullshit.html

by Stephen Diehl

You’ll probably hear the fuzzy term web3 bandied about in the press if you read tech journalism. Sprinkled around, all these articles are all manner of…

The title says it all.

Crypto and Twitter Are Imploding at the Same Time and It Is Glorious

https://thetriad.thebulwark.com/p/crypto-and-twitter-are-imploding

Many good takes: eating popcorn, and watching the crypto bros burn down their empire.

5 key lessons after a week on Mastodon

by Sandra Gutierrez G.

I’ve been on Mastodon since 2017, but my usage really increased since the acquisition of Twitter. There have been a lot of stories talking about how people are abandoning Mastodon, but even if it doesn’t become what Twitter was, it is still a vibrant community.

There’s No Fixing Meta’s Metaverse, Scrap It, Start Over  

https://www.forbes.com/sites/paultassi/2022/11/23/theres-no-fixing-metas-metaverse-scrap-it-start-over/

by Paul Tassi

I spent 6 years working on the metaverse at Microsoft during the 90s. While the technology has drastically improved, the reason we didn’t get the metaverse back then is that no one could figure out something to do in the metaverse except shoot each other or have sex with each other. All the folks working on metaverse now have learned nothing from the multiple generations of attempts that preceded them. There is still a smug belief that “if you build it, they will come.” The problem is that there is still nothing to do once they show up.

The Battle for the Soul of the Web  

https://www.theatlantic.com/technology/archive/2022/10/internet-archive-decentralized-web-web3-brewster-kahle/671647/

by Kaitlyn Tiffany

If these problems are intrinsically linked to consolidated tech giants like Meta, Google, and Amazon, why not embrace technologies that decentralize power? This has become a key issue for Brewster Kahle, the 61-year-old founder of the Internet Archive…

Having participated in various forums and working groups for decentralized web stuff over the last few decades, I’m consistently excited by the possibilities and enthusiasm of the folks who work towards those goals and disappointed by their naivete about what people are willing to put up with and how commercial entities are incentivized to coopt and pollute the technologies that do gain some momentum.

Your organization should run its own Mastodon server

https://martinfowler.com/articles/your-org-run-mastodon.html

by Martin Fowler

Whether you are a large company, a political party, an international news agency, an NGO or a government institution, you should seriously consider running your…

What is the point of having a decentralized web if you don’t own your own part of it?

Twitter Turmoil: We Need an Open Protocol for Public Discourse

https://thenewstack.io/twitter-turmoil-we-need-an-open-protocol-for-public-discourse/

by Richard MacManus

Do we want to stay on a social network that shows such callous disregard for its own people? That is the question many of us have been asking as news hit this…

Protocols > Platforms

Software Engineering

Maybe it’s time we re-think docs

https://kathykorevec.medium.com/building-a-better-place-for-docs-197f92765409

by Kathy Korevec

GitHub Docs are open source, and you can contribute to the project by visiting the GitHub repo . You’ve probably heard…

I liked this approach to documentation.

Agile Projects Have Become Waterfall Projects With Sprints

https://itnext.io/agile-projects-have-become-waterfall-projects-with-sprints-536141801856

by Ben “The Hosk” Hosking

All the agility has been sucked out of agile projects Doing agile is not the same as being agile Agile projects have become bloated, lazy waterfall projects…

One of my biggest pet peeves is people deciding that a bad experience they had with a poorly implemented framework or process must mean that that framework or process is clearly bad and that anyone who had a good experience is lying. So many of the “I was involved in a poorly run agile project and so agile must all be a lie” or “my company tried to do the Spotify model, and it didn’t work; therefore, it must not work at Spotify either” type posts just show the ignorance of their authors and nothing else. While I was worried this article was just another one of those, the author is concerned more about poor agile processes and not agile itself. He even gives some good advice. So worth a read.

Machine Learning

Mozrt, a Deep Learning Recommendation System Empowering Walmart Store Associates with a Personalized Learning Experience  

https://medium.com/walmartglobaltech/mozrt-a-deep-learning-recommendation-system-empowering-walmart-store-associates-with-a-5d42c08d88da

by Qixin Wang Nov 4

We developed Mozrt, a deep learning recommendation system for Walmart Academy App, the training content portal for Walmart store and Supply Chain associates.

Walmart built a massive technology team in its fight with Amazon. It is good to see them sharing their work.

Will Julia surpass Python in popularity?

https://analyticsindiamag.com/will-julia-surpass-python-in-popularity/

by Sreejani Bhattacharyya

Short answer, probably not, but it will be interesting to see Julia evolve.

How to play with the GPT-3 language model

https://simonwillison.net/2022/Jun/5/play-with-gpt3/

by Simon Willison

ChatGPT and the Google and Microsoft chatbots get all the attention now, but before that was GPT3, which also remains the only LLM with the ability to train on your own corpora.

Building Communities

Why Communities Are the New Business Currency | HackerNoon

https://hackernoon.com/is-community-the-new-business-currency

July 6th 2022

We’re no longer content with one-way interactions with businesses. We want to feel like…

If you can’t tell from the previous post, I spent some time updating myself on building virtual communities last year. This is a good starting place for folks looking to understand the value.

Your words are wasted

https://www.hanselman.com/blog/your-words-are-wasted

It needs to be said again, perhaps this time more strongly. Your Blog is The Engine of Community . Dammit. Blog More You are not blogging enough.…

Scott Hanselman thinks developers should be blogging more, and when they do blog, it should be on their own platforms. And he’s right.

Music Industry

I’ve been involved in music as a musician, radio DJ, label owner, and streaming software creator since I was 15. I was delighted to rejoin the music industry in December when I took on the role of CTO at DistroKid.

With 100K tracks uploaded a day, a longtail music cull is coming – Hypebot  

https://www.hypebot.com/hypebot/2022/11/with-100k-tracks-uploaded-a-day-a-longtail-music-cull-is-coming.html
https://www.hypebot.com/hypebot/2022/11/with-100k-tracks-uploaded-a-day-a-longtail-music-cull-is-coming.html

by Music Business

Lucian Grainge doesn’t like that people aren’t listening to Universal Artists as much, so he’s putting pressure on the streaming services to remove content he doesn’t think is good. The problem is deciding what content is good and what content is bad. Streamers already remove fraudulent content. So, who decides if your band shouldn’t be on Spotify because you might take a stream away from Justin Bieber (who himself was discovered because he uploaded his songs to YouTube). Gatekeepers are all about protecting their interests at the cost of innovation and getting others a shot.

Why Amazon VP Steve Boom just made the entire music catalog free with Prime

https://www.theverge.com/23433343/amazon-music-prime-steve-boom-taylor-swift-midnights-spotify-apple-streaming-podcasts-decoder

by Nilay Patel

It’s never been clear how much Amazon cares about music streaming as a business. It’s always been an also-ran in the streaming wars that only has listeners because it is an add-on to Prime and is the default service with Alexa. Amazon hasn’t invested much in the service, but maybe that is changing now…

My Belated 2022 recap: books

I’d like to share some of the things related to technology, leadership, or management that I found particularly instructive. There was plenty of other good stuff, but these were the ones that stood out.

After making a concerted effort to write more in 2021, my blogging in 2022 fell off a cliff. I hope to be better this year, but while I wasn’t writing as much, I was still reading, watching, and listening. I’d like to share some of the things related to technology, leadership, or management that I found particularly instructive. There was plenty of other good stuff, but these were the ones that stood out. These are not affiliate links. I don’t get any kickback for recommending them.

I will split these into multiple posts because the list is rather long. The first post surfaces on the books that I’d like to share. The second will focus on blog posts/articles, and the third will be on podcasts that I found valuable.

Books I read in 2022 that I would like to recommend

These are all amazon links, but they are not affiliate links. I do not get any money for recommending these books.

The Phoenix Project

by Gene KimKevin BehrGeorge Spafford

You probably didn’t need me to recommend this book to you, because it is one of the classics of technology leadership. In fact, this isn’t the first time I’ve read it. I hadn’t read it for many years, and picking it up again, I was surprised at how relevant and valuable it still is. If you haven’t read it, it is a very easy read.

The Art of Community: Seven Principles for Belonging

by Charles H. Vogl

This book isn’t specific to technology; it is about building inclusive communities of any type. It is valuable for people leaders in that it talks about the necessary parts of belonging to any group. It is focused more on communities of choice instead of work communities, but the insights are the same. As someone who has also spent a lot of time building online communities, it is extremely relevant for that as well.

Being Mortal

By Atul Gawande

This isn’t a leadership or management book, but it is a book about living intentionally, and I found it valuable on multiple levels. As it was a New York Times bestseller, you didn’t need me to recommend it to you either, but I will say that I personally appreciate the author and his message.

The Business of Belonging: How to Make Community your Competitive Advantage

by David Spinks

This book is about building online communities for companies. It has overlap with the Art of Community book, but it is much more practical and meant for people who do this for a living. I found it a bit introductory, but it had some good ways of articulating specific points that I will reuse. If you are new to this space, it is a great introduction.

The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter

by Michael D. Watkins

Another classic of management that I had read before but reread as I prepared for my new role at DistroKid. Once again, it had been a long time since I had read it, and I was struck by how practical and true its advice was. I realized that when onboarding to previous roles, the companies where I started off the best were when I followed its advice deliberately or intuitively.

Lead Together: The Bold, Brave, Intentional Path to Scaling Your Business

by Brent LoweSusan BasterfieldTravis Marsh

This is either a book you will read and find yourself nodding along with, or a book that you will read and throw down in disgust after the first couple of chapters. It is a semi-practical guide about how to be more inclusive in your leadership. For those who have read Fredrick Laloux’s Reinventing Organizations and are trying to figure out how to move their company towards Teal, this book will be useful. For those who are tired of being in a top-down organization or are constantly accused of being a micro-manager, this book is worth toughing out even if you don’t agree with all of their suggestions because it will give you choices and ideas that will help you grow as a leader.

Becoming a CTO

A former co-worker reached out to me recently. They are a director of engineering at a midsize startup and just got their first headhunter inquiry for a CTO role. Having never been in the role before, they wanted to know what the position was like and how to prepare for the interviews.

I realized that while there are some books on technology leadership careers, there aren’t many resources explaining the most senior levels. My goal is to provide some insight and advice for those interested in someday becoming a CTO.

I’ve been a CTO for five and a half years

I’ve worked at a hundred-thousand-person company, seed-stage startups, and many of the variants in-between. I started as a developer and followed a traditional path of moving up to more senior levels on the development track and then moving to lead, engineering manager, director, VP, and now chief technology officer. I’ve been the CTO at three different companies in two countries and three parts of the technology industry. I’m part of a few networks where I meet and talk with CTOs of all sizes and stages of companies.

I’ve learned that one reason there isn’t a good reference for the role of the CTO is that the size of the company and the expectations of the CEO define the job. Some of my role expectations and responsibilities are like those of many of my peers at similar-size companies. However, there are also significant differences in our expectations from our executive peers and boards.

Because of the variability of the role, I will broadly share my direct experiences, joined with an understanding of the expectations of other CTOs that I know.

The early-stage company CTO is often the developer-in-chief

At earlier stage companies, the CTO is often the technical co-founder. They are likely the developer who built many of the earlier versions of the software and helped hire the original development team. Their responsibilities are primarily technical: driving architecture, doing advanced development tasks, and creating technical vision.

Frequently, the first CTO of the company is hired for their ability to code and not their ability to grow or manage a team. Depending on the person, they may also lead the development team. Still, often the team’s management will eventually move to another person, an experienced manager, who may report to the CTO or be a peer to them.

The early-stage CTO is the leading technical voice for the company externally, especially if they are a co-founder. They talk to investors and potential partners and meet with potential vendors. If they also manage the development team, they will solely represent engineering in the senior leadership team. As a result, they will have responsibility for the decisions made by the engineering team. Nevertheless, if they do not manage the team directly, they might not be involved in the decisions around the day-to-day operations.

A mistake that inexperienced founding CTOs often make is that they don’t understand their role beyond coder-in-chief. They focus solely on the technology and are not active participants in the company’s leadership. As a result, they do not work cross-functionally. CTOs fixated on the how without the why or what will not be in the role very long once the company grows.

If they have no experience leading an engineering team or organization, the early-stage CTO will be challenged to grow with the company. If they cannot scale, eventually they will end up in a subordinate role reporting to a more experienced CTO hired to replace them.

The midsize company CTO is responsible for leading the organization, corporate strategy, and making technical decisions

Once a company reaches a size at which it needs new processes and structures, the scrappy leaders who helped get the company off the ground are often replaced with more experienced leaders knowledgeable in taking companies through the next growth stage. If the CTO hasn’t grown into the larger role, they will be part of that replaced group.

The midsize company CTO is a full-fledged executive team member working cross-functionally and meeting with partners, investors, and customers. Frequently, the midsize company CTO will also manage the engineering organization. The CTO is responsible for setting technical direction, making sure good architectural decisions are being made, and establishing best practices and working methods. They are still expected to have good technical depth, but don’t often actively contribute to shipping code. A red flag for me personally is seeing a CTO role description where the expectation is to lead a 50-plus-person organization while also actively coding on the product. It means the executive team does not have appropriate expectations for the role.

A midsize company CTO spends significant time establishing culture and practices for the teams they are responsible for; they are also very directly accountable for the organization’s decisions and its track record of delivery. The CTO meets internally with members of the other functions, such as sales, marketing, HR, and finance, to share direction for the organization and get feedback. The CTO is responsible for the administration of the teams, including the budget.

The CTO is also responsible for hiring, performance management, and team structure and may be very active in their teams’ recruitment and interview processes, especially in a scale-up type of company.

A CTO leading a more extensive development organization must be a generalist, understanding different roles and responsibilities. Their remit may include Corporate IT and Technical Support. In some companies, they may also manage the business analytics, security, product, and UX teams. A CTO who is too focused on the areas closest to their background or does not respect non-coding functions will not succeed.

As a midsize company CTO, you will often spend as much time with your peers and their teams as you spend with your own. As a result, you will need to learn about their functions and how your teams can work together. CTOs who “stay in their lane” will not be seen as an equal member of the senior leadership team and may lose their say in decisions that affect the organization.

It is very unusual for someone to move into a midsize company CTO role without having some experience leading a multilevel-development organization and working with other business functions.

Growing (or moving) into the CTO role

If you are a manager or a manager of managers with the goal of being a CTO, there are a few things you can start to focus on that will help you on your path.

Learn about the business your company is in

Offer to sit in on sales calls, on user research interviews. Try to understand the company’s financials when the CFO presents them. If you can’t, make a friend in the finance team and ask them to explain them to you. Understand the KPIs not only for your team, but also for the teams around you.

Learn about the other functions

Get recommendations of reading or conference talks from your peers in the product, UX, and marketing teams. Think about how their work influences yours, and yours influences theirs.

Respect and learn other technology areas aside from your own

If you lead an area you don’t have personal experience in, approach the people in that function with respect and a genuine desire to understand their work. They want to help you know what they do and how they do it.

Hone your craft

Hopefully, you are already working on deepening your skill as an engineering manager or director, but are you trying to understand the bigger picture? Read other companies’ (public) handbooks, engineering blog posts, and conference presentations about their ways of working. What practices are interesting? Which can you try in your team? How do you think they will scale, or what issues do you think they may have?

Ask your CTO if there are tasks they can delegate to you

The best way to learn the job is to do the job. Even better is having someone who is already doing the job explain to you how they perform it so you can help them.

Start thinking in terms of strategy

The main difference between the expectations of line managers and senior managers is the emphasis on strategic thinking. Executives contribute to the company’s strategic planning and use their understanding of the company’s goals and the current situation to make sure that their teams are setting up the conditions for the company’s success. Strategic thinking is a learnable skill, but it takes practice.

The rewards of being a CTO

Being a CTO was not what I imagined it to be when I first decided it was my career goal. It is a lot of work, carries much stress, has fewer perks than you might think, and can be somewhat lonely. However, it is also the most personally rewarding job I have ever had. With the challenges, there is also incredible responsibility, tons to learn, the ability to influence the company’s direction, and the chance to affect the lives of dozens or hundreds of people on your team. I have yet to regret my choice to pursue this role.


Thanks to Laura Blackwell for editing assistance

Living in an Employer’s Market as a Developer

The great thing about being in technology is that it is a growing field. There are tons of jobs, and companies are always complaining about how hard it is to find talent.

That is until it isn’t.

It isn’t clear what will happen during this pandemic, but the layoffs and hiring slowdowns or pauses have started.

Many developers have never known a time when companies were not clamoring for their services and bidding against each other.

Having my startup go bust in the dot-com bubble bursting of 2000-2001 and having seen what employment options were like in 2008-2009, I thought I could give some advice to those of you who may be in brand new territory.

If you find yourself unemployed during a bust, you will need to change your tactics. You may be used to an employee’s market, but you are entering an employer’s market. Companies will suddenly find many options for their roles—very qualified, even overqualified, folks who are willing to take a lower salary for their positions. Jobs you wouldn’t have considered previously are no longer returning your e-mails. They can find people better than you cheaper.

Even if you currently have a good job, the security of that role may not be what you expected. Be prepared.

Save your money

If you live somewhere expensive, the rent and other prices are likely to go down more slowly than salaries. You need to start cutting your expenses and build up a cash reserve.

Hopefully, you already have a few months of money put aside somewhere other than the stock market. In a crash, selling your investments in the dip is the last resort. If you don’t have that cash reserve, start building it now.

Stop unnecessary purchases: buy groceries instead of door-dashing meals, take public transportation instead of Lyft, do your laundry instead of sending it out. This is the way that most people live.

You will be surprised how much money you can save by making a few changes. Once you have your reserve (enough to live on with a reduced, reasonable, lifestyle for a few months), you can go back to your spending patterns, or continue to build your savings (which is smarter). During the previous busts, very good, very senior developers ended up unemployed for many months.

Stay Positive

I left a good job at Microsoft to join a startup in 1999. That startup crashed a few months later. After trying to help the leadership revive it for a few months, I joined a friend in building a new startup. We had some angel money, but I was paying the rent and some of the other bills myself sometimes. We were ready to go out for our first real round of funding in September of 2001.

After 9/11, what was left of the investment and job market completely fell apart. We could not raise money. After a few months of trying to keep things going, I needed to start earning a paycheck again. I was selling my stock to pay the bills, and those shares were now worth half of it they had been before.

I assumed it would be easy to find a job. It always had been.

Jobs were suddenly scarce.

I found myself applying blindly to companies that I would never have considered before. Few replied.

Weeks turned into months. I started to lose faith. Occasionally, I would get an actual interview. But by then, the fire had gone out in my eyes. I was passed over for roles that required way less experience than I had. I had lost my confidence, and it showed in interviews.

Eventually, through a friend, I was able to land a contracting job, back at Microsoft. It was a bit humiliating, but I was happy to be working and earning again.

I later found out that I was one of the last people to get that level of contract. The contracting company realized that it could hire people of my seniority at lower contract rates.

Working again gave me my confidence back. I did well and got converted back into a full-time role. When I did, though, my manager negotiated my salary down. I had to take a serious pay cut. I had no choice, and he knew it. I took the job.

Now, as an employee again, I was on interview loops. I spoke to many good developers who were in the same situation I had just left. They had lost their confidence, just like I had. Their answers to questions were non-committal. They were tentative. They were so used to being rejected that it made it hard to approve them.

If you find yourself in that situation, you need to do your absolute utmost to project a positive aspect and some self-confidence in your discussions with recruiters and employers. Even if you have to fake it. Displaying confidence will make a substantial difference in how you interview.

Some money is better than none

If you get an offer, it may be well for a lot less than you expect. You may need to take it anyway. Some money coming in is better than none. The market will rebound eventually, and salaries will go up again. When that happens, you will be able to find a new role that will pay you appropriately. I left Microsoft for a second time when the market rebounded, and I got an offer for more than my old salary from somewhere else.

If the offer is much, much too low, take it. Keep looking for another role, but now with some security. No one says you have to put every position on your resume.

What you want to do and what you can do

Are you a developer, but a company is open to giving you a job as a tester or program manager? Are you an engineering manager, but a company is interested in talking to you about a product manager role?

If you are finding it hard to find a job doing what you want to do, it may be time for a temporary (or permanent) career change.

I wouldn’t automatically recommend this, though. If you switch into another role, when the market opens up, you may find it hard to go back to your preferred job. The market now sees you as a product manager or tester and may not consider you for a development role (especially if you are in the new position for a while). You may find that you enjoy the new job and want to pursue a new career, which could be a benefit. This situation happened to a few friends of mine during the 2008 crash.

If you decide to take the career-switching role out of necessity, make sure you keep your development chops up: contribute to open source, build apps or sites, whatever keeps your skills up-to-date.

You may be tempted to take a role outside the industry. This should always be the absolute last resort. Even with a strong resume, you may find it hard to get back in if you are in a very different field for a few years.

The sad fact for those who struggle during these periods is that most folks in the field will keep their jobs. When their companies start hiring again, these people will have a strong survivor’s bias. They may not understand the choices you had to make.

Build (and maintain) your network

Keeping up with your friends in the industry is probably going to be your best bet at finding a new role. Your friends can get you past the gatekeepers at the companies and make sure you are seen. They also may have more insight into what roles are open.

At first, it may be difficult to reach out to them. You may be embarrassed about the situation you are in. Get over it.

If you have been in the same company for a long time, or don’t have a big network in your area, start attending meetups or local conferences. Meet developers at other companies. You are likely to meet a lot of other folks in your situation, this is ok. You can form a group to share tips about companies hiring, maybe they may know someone at a company with a role appropriate for you.

Stay in your safe harbor

If you have a good job, with a good salary, keep it. Build your savings because even good companies don’t always survive. If you were considering that it might be time to move on and find a new role, don’t.

Even if you have an offer in hand, when companies hit a rough patch, after freezing hiring, they start rescinding offers. A friend of mine left his steady job during the bust to join another established company. He quit his old job and then the weekend before he started his new one, his offer was rescinded. He was now unemployed. His former company didn’t want him back. They got someone more senior for his role at the same salary.

The Reality

If you have been privileged to not know a time when you were worried about money, this will be scary. Hopefully, you find a new job, and this time will be brief. Many people in the world are not that lucky. They live constantly worrying about how they will pay their rent, or feed their families. When you are on the other side of this, realize how lucky you are and take your new perspective to be a better, more empathetic person. Do your best to help those in need, now that you have an understanding of what their reality is.

It will get better

Economies are cyclical. After the dot-com bust, there was exceptional growth in the tech industry. After the 2008 contraction, the tech sector went back into massive growth mode. If you lose your job and find it hard to get a new one, don’t despair. Things will get better. Until then, just focus on doing what you need to until that happens. Learn from this experience and be ready for the next contraction, because there will be one. Always.

If you don’t lose your job and you are in a position to make hiring decisions, try to be human. If you interview someone who seems to have lost all hope, try to see the person underneath who has had some bad luck. If you were lucky enough not to lose your job, don’t think you are better than those who did. Ask about their choices. Don’t assume that if someone went from being a developer to doing another job that it was a deliberate choice. Understand their story before making a decision.

These are amazingly challenging times for many people. Remember that if you lose your job during this downturn, even if things seem very bleak, you are probably still better off than 95% of the world’s population. If you want to grow your skills while looking for a job, you could build a website for a charity. That will leverage your skills, build your confidence, and do something for others too.

We’ll get through this.

Can’t get a government website to validate you? Here is possibly why.

I’ve had multiple problems with multiple State of Washington or Government websites in the last year. Strange, inscrutable errors when trying to validate my identity, with no clear solutions.

Trying to get my updated social security info? It’s right there on the website. Except that the website won’t let me log in. I get a weird error. So, I have to go to the office to wait in line and talk to a person.

Trying to sign up on the state health care exchange? The dreaded: “Due to No Security Question Answer available. null” error. That error is well documented on the internet. The solution suggested every time? Upload all your documents to the website. That answer is wrong. In both cases, the government was trying to contact a credit bureau to get your personal information to test you on your knowledge about yourself.

I figured this out too late for the social security office, but figured it out for the health care exchange.

I froze my credit. You should too. It is a good (not perfect) guard against identity theft.

However, that frozen credit prevents anyone from trying to use your credit history information to validate your identity. This isn’t a great way to validate identity anyway since a lot of that information is available publicly.

The only solutions are to deal with their support teams (the front line folks never know about this and so you need to explain it to them), go to an office and wait in line to show them a physical ID, or temporarily unfreeze your credit.

Luckily, the credit bureau sites let you easily unfreeze your credit temporarily. However, that is a very poor security solution, since it is a blanket unfreezing. That is bad if you are doing it to apply for a new credit card. It is even worse if you are using it for ID Validation on some random website. In the case of the government sites, I couldn’t tell which credit bureau they were using, so I had to unfreeze all of them. Really bad.

We need better identity validation solutions that work securely over the internet for government to use. Luckily, I’m now in a position to help.

Slides from my talk on Distributed Teams

Compare the Market was nice enough to invite me to speak at their tech managers’ off-site about distributed teams. This talk reflects my own experience leading distributed teams.

I was presenting to them over video. Their meeting included people in two different offices and also folks dialing in from home. Ironically, in the middle of my talk, I got disconnected from the video conference. Because I was sharing my slides full-screen and had my speaker notes on my second monitor, I didn’t notice. So I spoke to myself for about 15 minutes before I realized what happened and dialed back into the meeting. It was a bit mortifying, but the folks in the UK were extremely nice about it. I can’t think of a better example though of the challenges around working with teams who have to communicate over electronic means constantly, so it was a good illustration of the issues I raised. 🙂

Using Deep Learning to Train a World-Class Candyland Player

A child playing Candyland
Photo by Amboo Who? https://www.flickr.com/photos/amboo213/4753020084

I’ve been spending the last year working on machine learning methods to train an algorithm that could be competitive with professional-level Candyland players. I’m happy to report that as of today, I attained my goal.

For the first pass of my automated Candyland player, I built a very simple rules-based engine. The engine ran efficiently on a Mac Book Pro. The rules-based engine did ok in lab tests with strong amateur players. I knew it couldn’t stand up to the rigor of professional Candyland tournament play, however.

For the second pass of my player, I created a more sophisticated look-ahead engine. Before taking its next card on its turn, it would simulate every possible permutation of the rest of the deck. While this was very processor intensive, by moving it into AWS and distributing it across 100 xLarge instances, it ran near real-time, although at some expense. The results of this player weren’t significantly better than the first engine.

In my third pass, I trained a shallow Convolutional Neural Network with 100,000 Candyland games. The results of this were disappointing. Playing against my look-ahead engine, over 500,000 games, it did no better than winning 50.05% of the time. Adding more layers didn’t improve the score significantly.

The fourth permutation of my Candyland player was a fully recurrent neural network running across a few dozen AWS GPU instances. This player played itself for several weeks improving the weights in its network using a genetic algorithm. The results from this were fascinating. It was able to win against itself 100% of the time.

This morning, April 1st, 2018, I played three games against the RNN player. While I am not a professional level Candyland player, I am rated 1200 on the amateur circuit, and it was my favorite game in 1st grade. This last version of my player beat me all three times! I think it is finally ready.

I’m going to be setting up some exhibition games with my Candyland player as soon as I can track down someone on the professional Candyland circuit. Not only will this gain some positive publicity for machine learning, but I’m hoping that it will help me recoup the $350,000 in AWS bills that I racked up building, testing, and training my players.

Talks: 1st half 2017

I’ve been remiss in posting since I’ve been back in Seattle. Readjusting to life in the states, and adjusting to the new role has kept me busy. I hope to rectify that in the future. I have been lucky enough to be invited to speak several times this winter and spring in the US and Europe. If you’ll be there or live nearby and want to meet up, drop me a line on twitter and let me know!