StaffEng

Please note that this episode contains brief mention of suicide.

Today's guest needs no introduction! Of course, they will get one anyway:
Will Larson is the CTO of Calm and has worked at Stripe, Uber, and Digg. He is also an author and has written two books, one of which is on Staff Engineering and serves as the inspiration for this podcast! In our conversation with Will, we discuss one of his earliest blog posts on a catastrophic launch at Digg and why he felt it was important to write about his experiences. We talk with Will about the expanding role of Staff Engineers and how that is affected by the rate of change in the field of startups and technology companies as a whole. Later, we explore the tracks of technical leadership and management within technology companies and the pros and cons of the pendulum model. Will shares what he’s learned about the skills needed for leadership positions and why working with a team of managers versus a team of engineers requires a completely different skillset. After that, we talk about Will’s career in writing and public speaking. We loved having Will on the show, so join us for engaging conversation spanning many topics from the potential for leadership in technology companies to the joy of writing!
Links

• Will Larson on LinkedIn
• Will Larson on Github
• Will Larson on Amazon
• Irrational Exuberance
• Calm
• Staff Engineer: Leadership beyond the management track
• An Elegant Puzzle: Systems of Engineering Management
• Digg's v4 launch: an optimism born of necessity
• High Output Management
• The Engineer/Manager Pendulum

The structures of an organization can often be self-reinforcing, and in a changing environment, this becomes a recipe for future vulnerabilities. That is why senior ICs need to play a slightly discordant role at times by alerting teams to issues conventionally outside of their bubble of concern. Peter Stout is a Technical Director at Netflix where he has a cross-functional role at the juncture of business and technology. He joins us on the show today to share some of the finer details around what inhabiting this position in the above manner looks like. We start by hearing Peter describe himself as a generalist, and share how this played out in the broad focus of his college degree as well as in his career pivot from Chemistry into Software Engineering. We discuss the rapid growth of the engineering team at Netflix, how this has led to less tightly-defined roles for junior and senior engineers, and how this factors into the way Peter approaches his place in the organization. Peter talks about the shift he made from technician to technical director and how much of the skills he learned from the former position he brings into the latter. He talks about his tendency to seek out the blank spots in the organization and how he tries to focus on a long-term vision, using that to guide him as he connects the dots between teams and influences decision making. Here Peter considers his role as a disruptor and how he gauges how much pressure to apply while still staying largely in sync. We also have a great conversation about Peter’s approach to mentorship and his philosophy around how he grew into the leadership position he occupies. Tune in today!
Links

• Peter Stout on LinkedIn
• Netflix
• Range
• The Leadership Pipeline

This episode is a celebration of the journey we have been on as this podcast comes to a close. We have had such a great time bringing you these interviews and we are excited about a new chapter, taking the lessons we have learned forward into different spaces. It's been a lot of work putting this show together, but it has also been such a pleasure doing it. And, as we all know, nothing good lasts forever! So to close the circle in a sense, we decided to host a conversation between the two of us where we interview each other as we have with our guests in the past, talking about mentorship, resources, coding as a leader, and much more! We also get into some of our thoughts on continuous delivery, prioritizing work, our backgrounds in engineering, and how to handle disagreements. As we enter new phases in our lives, we want to thank everyone for tuning in and supporting us and we hope to reconnect with you all in the future!
Links

• David Noël-Romas on Twitter
• Alex Kessinger on Twitter
• Stitch Fix
• Stripe
• JavaScript: The Good Parts
• Douglas Crockford
• Monkeybrains
• Kill It With Fire
• Trillion Dollar Coach
• Martha Acosta
• Etsy Debriefing Facilitation Guide
• High Output Management
• How to Win Friends & Influence People
• Influence

Often the biggest impacts a Staff Engineer can make in their organization are not technical but rather people-related. When teams are value-aligned due to good leadership, they go on to make larger impacts than they would otherwise have. As Senior Principal Engineer at Dropbox for almost a decade, James Cowling learned a lot about how people think and work together, and he joins us today to share some of his insights. Joining this conversation, listeners will hear about James’ experience at the helm of numerous high stakes projects at Dropbox, such as migrating the company off Amazon S3 by building their own distributed storage system. For James, the main job of a tech lead is getting their team to have a firm grasp of the why behind a project, and to become completely values-aligned as a result. James takes us through his approach to diagnosing struggles within teams and how he helps groups to step back and course correct by drilling down on their purpose within the larger organization. We talk about the strong culture that gets built as a result of this approach and the power it has to keep teams robust. In today’s conversation, James also gets into how Staff Engineers themselves can stay in tune with the larger company, the single most important quality to nurture in Software Engineers who hope to grow into leadership positions, and a whole lot more.
Links

• James Cowling on LinkedIn
• James Cowling on Twitter
• Convex
• Dropbox
• 'Stepping Stones not Milestones'

Staff engineers may not get much time to code anymore, but this does not mean problem-solving and system design is not an integral part of their day-to-day. Today’s guest is Bryan Berg, Staff Engineer at Stripe, and he joins us to talk about the nuances of his position and his unique approach to the many challenges it entails. As a Staff Engineer, Bryan acts as Tech Lead of the Traffic team, and we begin our conversation by hearing about how he landed in this role. Bryan describes the ambiguous challenges he faced during earlier days at Stripe, and the knack he had for finding and working on processes and systems that were previously underinvested in. We then jump forward to the present and dig into what Bryan’s current role entails, hearing him describe a wide range of tasks from reviewing documentation, communicating between teams, writing vision documents, and ensuring the work he directs falls into the company and stakeholder requirements. We also explore the interesting concept of when to draw on past experience versus keeping an open mind when facing new challenges. On top of all this, our conversation covers how Bryan judges the success of his work, sustains faith in his ideas, pitches to colleagues, debugs difficult pieces of code, and finds inspiration to be a great technical leader.