The Engineering Leadership Podcast

John Kim has had an unconventional career, pivoting from professional gamer to software developer, to serial entrepreneur. We discuss how to assess your career, make pivots, and balance your growth long term. John shares principles from complexity science to help you navigate unknowns, risks, & opportunities in your career. Plus other powerful frameworks to make better career decisions."So if you're working at a bigger company, what you're really trying to optimize for is how quickly can you move up in turn terms of 'Abstraction Layer.' It's not about titles. It's about, can you actually understand the next layer of abstraction within the business.So if you're like an IC, what is the engineering manager's priority right now for your team? What is the, let's say a director of engineering's priority right now for the team?And if you actually start caring about those things, you'll be able to make a lot more faster progress." JOHN KIM, CO-FOUNDER & CEO @ SENDBIRDJohn S. Kim is the Co-founder and CEO of SendBird, the world's no.1 chat API. The platform currently serves over 100M monthly chat users across the world's leading companies such as Reddit, Delivery Hero, Yahoo!, Rakuten, Paytm, Accolade, Livongo, and DHL. John is a serial entrepreneur, engineer at heart, and an expert in the API economy and communications tech space. Little known fact about John is that he was Korea's no.1 pro-gamer for Unreal Tournament. SHOWNOTESHow John went from professional gamer to #1 chat API company @ Sendbird (2:47)Creating vs. consuming & why John walked away from professional gaming (6:58)John’s early career pivots: from software engineer to social gaming & Y Combinator (9:08)How to apply the complexity science principles of “Convergence” & “Divergence” to your career decisions (11:17)Navigating “Abstraction Layers” & why you need to invest time to build “social capital” in your career (15:31)The “Human Capital” Framework & balancing the skills you accumulate throughout your career (19:04)Building emotional capital, training for cognitive empathy, & the tradeoffs of agreeableness (20:41)How to manage expectations & communicate with stakeholders when you need to pivot (27:34)How John applied these principles to make career decisions and pivot his company (30:23)How to pick careers aligned with your happiness and motivation (37:10)How to pivot your career using the “2PM” framework (people, product, market, money) (39:59)Future founders: Why you’ll be happier making 10 year career decisions & quick pivots (44:04)Takeaways (46:23) Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!Send in a voice message: https://anchor.fm/engineeringleadership/message

Tia Caldwell, former Director of Engineering @ Slack, shares different frameworks she’s used to motivate teams and unlock their superpowers! We cover methods to identify, maximize, & balance strengths on your team, how to shift your team’s mindset from drama to EMPOWERED so they can better confront adversity & challenges. Plus we share the explicit conversations you should be having in your first 1:1s to create greater psychological safety!“You don't need to have this manager game face. I think there's this perception that when you're a manager, you're supposed to be the person who knows the answers to everything… And while a part of the execution piece is really necessary with being an effective manager, I think the other part is relationship building. You need to invest the time in understanding how people work. Because people will be more open and honest with you, it'll help out with retention for your team and overall happiness. But if you don't… it's not going to go well because you'll be treating people as resources and not humans.”TIA CALDWELL, FORMER DIRECTOR OF ENGINEERING @ SLACKTia led the Monetization Team at Slack, a leading global collaboration hub that makes people’s working lives simpler, more pleasant and more productive. Over the past 15 years, she has led and managed engineering teams at Netflix and Microsoft, covering a breadth of projects such as Xbox, Office 365 and Streaming Content Delivery.She serves as a facilitator in /dev/color and is the co-founder of Color Code (https://www.colorcode.org/), a scholarship fund dedicated to future leaders of color in tech. Tia studied computer science at Xavier University of Louisiana and spent her undergraduate years doing research for the Missile Defense Agency. SHOWNOTESHow do you motivate your team? Find their Superpower! (3:05)Tia’s Superpowers (8:02)Knowing your superpowers maximizes strengths & protects against your weaknesses (10:09)How superpower awareness & common language changes how you operate, make decisions, & structure teams (12:31)Why you should balance your team’s superpowers to increase collaboration and be more effective (17:06)“The Drama Triangle” (20:51)How to recognize what role you’re playing in “The Drama Triangle” (28:30)Shift your team’s mindset with “The Empowerment Triangle” (32:45)How to shift someone from “Victim” to “Creator” or from “Villain” to “Challenger” (34:27)Personal operating manuals & having explicit conversations to get the best from your team (39:06)“What’s your grumpiness level?” & other ways to create psychological safety in your 1:1’s (41:37)How to prompt self-reflection and identify how your team wants recognition & feedback (46:03)Why relationships & removing the “manager game face” are your most effective tool (49:20)Takeaways (50:52) Find all the links & resources shared by Tia HERE: https://sfelc.com/podcasts/superpowers-psychological-safety-and-empowering-your-team-tia-caldwellLooking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

We deconstruct two distinct career paths in engineering & leadership, and a co-founder relationship 15 years in the making. In part 2, Tom & Viraj share why they decided to start a company together, how they assess start-up opportunities, early company building & values-defining conversations, and other strong opinions on how they’re creating the engineering culture and execution at Common Room. VIRAJ MODY, CO-FOUNDER & CTO @ COMMON ROOMViraj led engineering organizations at Convoy and Dropbox, helping both companies scale their teams and products. Viraj was also a founding engineer at Audiogalaxy, where he worked alongside Tom, which was acquired by Dropbox. TOM KLEINPETER, CO-FOUNDER & CHIEF ARCHITECT @ COMMON ROOMTom was a Principal Engineer at Dropbox, and before that the CTO at Audiogalaxy and FolderShare, startups which sold to Dropbox and Microsoft, respectively. He’s also the co-host of The Downtime Project - https://downtimeproject.com/ a podcast that helps engineers learn from the Internet’s most notable outages. SHOWNOTESTom’s career path - from engineering leader to principal engineer (4:07)Viraj’s career path to become an engineering leader (8:54)How to reduce mental overhead by connecting with your team and leveraging candor & authenticity (14:27)How to shape the culture and execution of an engineering org at a new company (17:46)Early company building & values-defining conversations (22:33)How they decided to start a company together & Tom’s framework to assess joining a startup (28:27)Tom & Viraj’s strong opinions on building engineering organizations and culture (34:34)What Tom & Viraj admire most about working with each other (40:33)Takeaways (43:01) Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at https://sfelc.com/

We deconstruct two distinct career paths in engineering & leadership and a co-founder relationship 15 years in the making! Tom & Viraj share formative startup experiences that shaped their careers as a Principal Engineer & Eng Leader. Plus insights shaping their new company on assessing risk, dealing with open-ended problems, being decisive, & removing non-coding time for engineers VIRAJ MODY, CO-FOUNDER & CTO @ COMMON ROOMViraj led engineering organizations at Convoy and Dropbox, helping both companies scale their teams and products. Viraj was also a founding engineer at Audiogalaxy, where he worked alongside Tom, which was acquired by Dropbox. TOM KLEINPETER, CO-FOUNDER & CHIEF ARCHITECT @ COMMON ROOMTom was a Principal Engineer at Dropbox, and before that the CTO at Audiogalaxy and FolderShare, startups which sold to Dropbox and Microsoft, respectively. He’s also the co-host of The Downtime Project - https://downtimeproject.com/ a podcast that helps engineers learn from the Internet’s most notable outages. SHOWNOTESThe Beginning - How Tom & Viraj first met over 15 years ago (3:48)The Early Days - Microsoft, Tom’s start-up jump to Audiogalaxy, and why Viraj followed (8:55)Lessons in hiring and assessing risk at an early stage startup (15:07)”Yo, I don’t even know how to use a Mac…” + other strong opinions & mantras from their early start up experience (24:07)What happens when you remove decision-making delays & non-coding time from an engineer’s schedule (29:03)What principal IC’s & engineering leaders have in common... “Your job is to be decisive!” (34:08)Takeaways (39:17) Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

Harpaul Sambhi, Founder & CEO @ Magical reveals the tools he uses to accelerate his personal and professional growth. You’ll learn how to engineer successful outcomes with your goals through accountability mechanisms, how to build a personal board of directors or leverage friendly competitions like the “master of the universe award” to learn, pivot, & grow faster."When we do our goal setting, especially if you're trying to compete with someone... is to do the personal side just as much as the professional side. And you get that layer of intimacy that is often not necessarily shown in these types of meetings. And as a result, they become an exceptionally vital part of your life.” HARPAUL SAMBHI, FOUNDER & CEO @ MAGICALHarpaul Sambhi is a serial entrepreneur and life optimizer. His current company Magical is reinventing copy and paste, automating mundane, soul-crushing tasks.He previously sold his company, Careerify, to LinkedIn in 2015 and joined the product management team. SHOWNOTESThe origin story of Harpaul’s hunger for personal growth (2:47)Introducing the “Personal Board of Directors” as a tool to accelerate your personal & professional growth (4:25)Accountability as a mechanism to achieve your goals (7:38)How a personal board of directors works and impacts your thought process (10:07)How to identify your gaps and leverage your personal board of directors (14:31)Increase the richness of your discussion and reduce “off the cuff thinking” with “prep notes (20:47)How to curate and build your personal board of directors (25:33)Where to start building your personal board of directors (33:32)How to use “friendly competitions” like the “Master of the Universe Award” to accelerate your growth (37:14)Focus on your goal’s inputs vs. outputs (43:22)How the “Master of the Universe Award” impacts your relationships (45:34Takeaways (48:50)Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

Alexis Rask, Executive Coach & Partner @ Sweat Equity Ventures shares how to ask powerful questions. You’ll hear simple tactical ways to increase the power of your questions, what the most powerful question is, common failure modes of open-ended questions, how to get over your fear of silence, plus stories of the most powerful questions we’ve ever been asked."When I say a powerful question, I'm saying 'What's the really right question, for this right moment, that is going to TRULY unlock someone's thinking, in a way that gets at new information.'" ALEXIS RASK, EXECUTIVE COACH & PARTNER @ SWEAT EQUITY VENTURESNamed 40 under 40 by Silicon Valley Business Journal, Alexis is an experienced business operator turned Executive Coach to Silicon Valley's top founders and VCs. Prior to founding her coaching firm, Future Consulting, Alexis founded the Marketing Solutions team at LinkedIn in 2006. She opened offices, hired out the sales and customer success teams, and developed the go-to-market plans. She has also served as COO/CRO at Shopkick which sold for $250million in 2014. She is also a faculty member of UC Berkeley's Executive Coaching Institute. SHOWNOTESWhat’s the most powerful question you’ve ever been asked? (4:40)Failure-modes of open-ended questions & how to use powerful questions to get to “the heart of the matter” (11:54)The impact of a more powerful question (18:55)Emotional intelligence & how to get the best from people (25:40)Why “WHY” is the perfect follow up question (31:24)How to use powerful questions in your 1 on 1’s (38:49)How to get over the fear of silence… (41:40)Identify opportunities to ask more powerful questions with the “mental review” (48:18)Takeaways (54:19)Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

Wendy Shepperd, GVP Engineering at New Relic, leads large-scale strategic programs with a focus on precision and teamwork. She shares her experiences navigating the challenges of multimillion-dollar cloud migrations, emphasizing the importance of effective communication and stakeholder alignment. Wendy reveals insights into project planning, execution, and the significance of celebrating team successes. Her mantra of making memories during tough times highlights the value of learning and collaboration in achieving project goals.

Will Larson CTO @ Calm shares with us how to focus your time on what actually matters. You’ll hear about many of the common traps engineering leaders fall into and his frameworks to help you better target your time to focus on long-term, high-impact work."A lot of times they'll be like, 'Oh no one's working on this... I can make a huge improvement here!' But then they'll get signals from leadership that 'Actually this isn't valued...' And so I think it's really important to understand what SHOULD be valuable, and then understand what IS actually valued, and then make your own decisions based on that in terms of where you want to put your time." WILL LARSON, CTO @ CALMWill previously working at places like Stripe, Uber, and Digg. He's been writing on his blog, Irrational Exuberance, since 2007 with 600+ different posts covering tons of topics on engineering leadership, management and career.He is also the author of “An Elegant Puzzle” and his *NEW* book “Staff Engineer: Leadership Beyond the Management Track” Follow Will on Twitter @LethainHere is the interview Will referenced with Aaron Suggs (engineering sponsorship & being a ‘frequent first follower’) SHOWNOTESWhen Will confronted the existential question “Am I actually working on what matters?” (3:56)Where most people go wrong when evaluating how they spend their time (8:52)How to focus on long-term impact and avoid short-term “snacks” & “preening” (10:12)How to navigate a company that recognizes high visibility work over high-impact work (13:12)How to mitigate & reduce status-chasing in your teams (16:09)What high-visibility, low impact work looks like with engineering leaders (18:20)“Chasing Ghosts” and the trap of projecting familiarity onto problems (20:59)How to catch yourself “chasing ghosts” (27:31)Focus on what really matters by seeking the “existential issues” & where there’s “Room AND Attention” (32:10)How to identify and anticipate future existential issues with the “Iterative Elimination Tournament” (35:28)Creating “Room and Attention” & identifying your unique capabilities as an eng leader (38:20)Get projects unstuck and prioritized fast by “Lending Privilege” (42:11)Why Will wrote his new book - “Staff Engineering: Leadership Beyond the Management Track” (45:42)Takeaways (48:40) LINKS & RESOURCESWill's blog Irrational Exuberance: https://lethain.com/Here’s the interview Will referenced with Aaron Suggs on engineering sponsorship & being a ‘frequent first follower’: https://staffeng.com/stories/aaron-suggsWill's book An Elegant Puzzle: https://lethain.com/elegant-puzzle/Will's *NEW* book - "Staff Engineer: Leadership Beyond the Management Track": https://staffeng.com/book Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

Edward Kim, co-founder & CTO @ Gusto shares the different forms that “fear of failure” can take in your engineering org. Eddie shares incredible stories to help you spot the different signs of “fear of failure”. And you’ll hear different ways you can change your team culture, process and operations to reduce fear of failure.“But as you continue to scale and you grow... that thing that you optimized for starts to become a disservice to you and the company. Because what happens is this fear of failure, if you take it too far, it starts to change a lot of things about the business.” ABOUT EDWARD KIMPrior to Gusto, Edward was the CEO and co-founder of Picwing, a Y Combinator startup and photo-printing platform. Before Picwing, Edward worked as a senior project engineer at Volkswagen Group of America Electronics Research Lab, where he led research and development for cloud-based navigation and speech recognition systems for Volkswagen and Audi.Edward is also the developer of several award-winning Android apps that have generated more than $1 million in revenue. Edward holds bachelor’s and master’s degrees in electrical engineering from Stanford University. SHOWNOTESWhat it means to “remove fear of failure” as you scale (2:25)Signs that indicate your company is optimized around a fear of failure (6:19)How to know when “healthy management” actually means your company has a fear of failure and is holding you back (10:54)Other forms “fear of failure” can take in your organization (14:20)MTTR over MTBF - Why you should prioritize recovering from failure over avoiding failure (17:40)“Rage-fixing” & Eddie’s breakthrough moment confronting fear of failure at Gusto (23:43)“Kicking the flipchart” & Eddie’s breakthrough moment #2 (27:52)How to maximize unplanned or unintended crucial conversations (33:54)How to decide when you need to abandon the agenda and “kick the flipchart” (37:37)How psychological safety can make your team more resilient to fear of failure (40:17)Takeaways (44:07) Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

Erica Lockheimer shares with us her imperfect path to engineering leadership, why the unconventional path matters, and what you can do as an individual leader & organization to empower engineering leaders with unconventional backgrounds. Plus you’ll also hear how to overcome self-doubt and launch an apprenticeship program!“Whether you're a manager or whether you're an individual contributor, you are a leader in your role. Use the voice that you've earned in the seat that you own. What can you personally do to create a different outcome. And all of us have that power in a role that we have.” - Erica Lockheimer ABOUT ERICA LOCKHEIMERPrior to LinkedIn Learning, Erica served as the VP of Engineering heading the Growth Engineering team, where her focus was on increasing growth in new members and deepening engagement with members across LinkedIn's products. She started the Growth Team from the ground up to now a high-performing 120-person team.She is also responsible for LinkedIn's Women In Tech (WIT) initiative that is focused on empowering women in technical roles within the company. Prior to LinkedIn, she worked at Good Technology as Director of Server Engineering, In 2014 and 2015, Erica was also voted amongst the top 22 women engineers in the world by Business Insider. Erica is a San Francisco Bay Area native, has 2 kids, loves to run and is a graduate from San Jose State University with a B.S. in Computer Engineering. RESOURCESAbout REACH: https://careers.linkedin.com/reach/AboutReachShalini Agarwal, LinkedIn REACH Lead & Eng Leader https://www.linkedin.com/in/shalini-agarwal-5b735b2/ SHOWNOTESErica’s first experience on a hiring committee (2:28)Erica’s imperfect path to engineering leadership (6:51)Erica’s career decision-making criteria (12:01)How to overcome self-doubt (13:32)Jerry’s personal story of the “imperfect path” (16:25)Other "unconventional paths" to engineering leadership (17:27)How Erica evaluates potential in people (25:03)What type of support to provide when you’re pushing people outside their comfort zone (27:44)How to create more opportunities for unconventional candidates in the hiring funnel through LinkedIn REACH (30:20)About apprenticeship programs (35:41)How to start launching your apprenticeship program (39:25)How diverse teams impact product and change outcomes (41:12)How to have a conversation about bias in your algorithm (43:44)Final words of wisdom for those with “unconventional” backgrounds (45:07) Join our community of software engineering leaders @ https://sfelc.com/