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

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

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.

Today we talk to Ben Ilegbodu, Principal Frontend Engineer at Stitch Fix, about how he manages to stay close to the code at a senior level. We hear how he arrived at Stitch Fix and what his first tasks were to identify the pain points in customer teams. From getting the IC's on his side to learning the importance of marketing your ideas to upper management, Ben talks us through his exciting career. He describes how he handles urgent tasks, and why it's crucial to do the important tasks first. We hear how giving an honest answer to where in the priorities list a task falls is key to inter-team efficiency, and why it's so important to keep communicating throughout long-term projects. Tune in to find out Ben's approach to mentorship, and how he plans on motivating high-school students to take the steps to become a developer. Don't miss out on this must-hear episode filled with practical advice on being a Staff+ engineer.

Links

• Ben Ilegbodu on LinkedIn
• StaffPlus Live Conference

Moving from an architect role to a product-oriented one might seem like a big leap, but there are overlaps between the two roles. Today's guest, Ashby Winch, has recently made this transition, and in today's episode, they share what this has been like. Up until recently, Ashby was an architect, with their most senior role at a large logistics operation in the U.K. Now, they have shifted to a product management job, and they are using the skills from the previous role for this new position. We hear about Ashby's diverse experience, how they came to work as an architect, and what inspired a career pivot. Ashby talks about the challenges they have had with having a loosely defined role and how they have made the best of this situation. Our conversation also touches on the relationship between architects and product managers, the importance of communicating context to developers, and advice Ashby wishes they knew earlier in their career. Tune in to hear it all!

Links

• LinkedIn
• Medium

Today’s guest is Josh Kaderlan, Staff Software Engineer at Lob, a direct mail and address verification API company that automates and simplifies direct mail and address verification, giving businesses greater flexibility, visibility, and accuracy of offline communications and data. There are so many different and non-traditional paths to becoming a staff engineer and, in today’s episode, you’ll hear a bit about Josh’s; starting in quality assurance, moving into development, and ultimately ending up where he is today, which he attributes to his wide breadth of knowledge and the valuable lessons he learned along the way. We discuss why Josh considers himself a generalist, the role that incident management plays in his work, and how he influences his peers by cultivating authentic relationships. Most important to Josh is how the work he does improves the experience of his colleagues and provides value to customers, and he shares some of his tips for staff engineers and organizations looking to have a similar impact. Tune in today to learn more and receive some practical advice and resources!

Links

• Josh Kaderlan on LinkedIn
• Lob
• ‘Staff Archetypes’
• Hacker News
• Rands Leadership Slack

During today’s conversation, we speak with Ben Edmunds, Senior Staff Engineer at Wayfair. You’ll hear all about his role at Wayfair, from his day-to-day active projects and how he goes about setting OKRs to the legacy and new deploy tooling he uses, and the method he has adopted to guide engineers. Ben shares ample advice for young engineers and stresses the value of learning more than one coding language. He reveals the finer details of life at Wayfair and the tools he uses to make sure that goals are reached, which include surveys, direct conversation, and partnership. We talk about the role of auxiliary engineering, the templates engineers build for application in partnership with an engineering team, and Ben points listeners in the direction of topics they should research, depending on whether they are looking to improve their software engineering or technical leadership skills. We hope you join us for an action-packed episode today!

Links

• benedmunds.com
• @benedmunds

Today’s guest is a principal software engineer at Microsoft who works at the interface between external and internal elements of the organization. Nell Shamrell-Harrington works on the ClearlyDefined open source project, which tracks open source licenses across open source ecosystems, and is also part of the Rust Foundation's Board of Directors. In today’s episode, you’ll hear about the “field commander” role that Nell plays in both of these organizations, and some of the major learnings they have had along the way (with particular emphasis on the importance of ensuring that technical interventions are responding to the needs of the business and the community). Nell also shares their experience of mentoring veterans through Operation Code, their approach to mentoring in general, and how this impacts their day-to-day job. 

Links

• Nell Shamrell-Harrington on LinkedIn
• ClearlyDefined
• Rust Foundation
• Operation Code
• Tanya Reilly on Twitter
• Sylvia Botros on Twitter

Oscillating between the roles of individual contributor and management has been a recurring theme on this show. Our guest today, Rich Lafferty, has some special insights into this pattern that can help anyone looking to improve their work. Rich works as a Staff Site Reliability Engineer at PagerDuty and has spent many years interfacing with various departments and building projects and proposals. In our conversation with Rich, we discuss how his past roles have informed his work at PagerDuty and how he gets the most out of his teams without exploiting the authority that comes with his more senior role. We delve into Rich’s process for building proposals and learn some of his tips and tricks for ensuring the best possible outcome by investing in the foundation and design phase. We also explore the importance of early feedback, why you need to include a diverse group of individuals, and how to gradually grow your feedback group. Tune in as we discuss everything from risk management to high and low context culture, and much more!

Links

• Rich Lafferty
• Being Glue
• Behind Human Error
• The Manager's Path: A Guide for Tech Leaders Navigating Growth and Change
• John Allspaw