The Engineering Leadership Podcast

Darian Shimy, Engineering Lead at Square and sports coach, shares coaching techniques for engineering teams. Topics include scaling leadership through effective delegation, creating trust, ownership, and accountability, using repetition in communication, and adjusting communication style to improve engagement.

Darian Shimy, sports coach turned engineering leader at Square, shares coaching techniques applied in teams, effective delegation, and creating trust. Topics include communication for improvement, leveraging time for productivity, scaling junior team members, and handling failure risk.

David Silverman (@dksilverman) shares how to prioritize effectively, regain productivity, compartmentalize pain, and accelerate your rate of learning to succeed through a crisis. You’ll also hear how to apply his lessons to real case studies shared by engineering leaders from our community.“When you're dealing with uncertainty, the main thing you're trying to drive and change as the leader, is you're trying to increase the rate of learning.” ABOUT DAVID SILVERMANLeadership expert and best-selling author David Silverman has paved the way in transforming groups into high-performing, agile, and adaptive teams that drive success. David continues to bring out the best in people as CEO and Founder of CrossLead. A graduate of the United States Naval Academy, David served in the US Navy as a SEAL Officer for 12 years. Building off of his collective leadership experiences, David created CrossLead as a holistic performance management solution for today’s environment. CrossLead is designed to empower leaders, teams, and organizations to scale the adaptability of elite small teams to the entire enterprise.David previously co-founded the McChrystal Group and led the company as CEO from 2011 through 2015. During his time at McChrystal Group, David laid out the framework for CrossLead as a co-author in the New York Times bestseller Team of Teams: New Rules of Engagement for a Complex World.If you want to learn more about David Silverman and CrossLead, connect with him on LinkedIn or check out CrossLead.SHOWNOTESDavid’s experience with uncertainty from the Navy SEAL’s (1:15)How to compartmentalize and deal with physical and mental pain (5:16)How to restore and improve your productivity (13:11)How to increase your rate of learning to succeed when things are changing fast (16:26)The difference between “wartime” and “peacetime” leaders (26:10)How to prioritize effectively in a crisis applying the framework “Ship, Shipmate, Self” (29:33)How you can build trust in a crisis (34:29)Applying Dave’s lessons in a company trying to find product-market fit (38:11)How to apply the tools to deal with uncertainty to support your family (40:55)How to deal with uncertainty when you’re not the decision-maker (45:23)How you can boost team morale in the short and long term (48:41)How to create trust and camaraderie remotely (51:56)How to deal with cross-team or cross-organization issues and negotiations (54:06) Join our community of software engineering leaders @ sfelc.com  Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

How do you have an effective performance conversation during a pandemic? Jonathan Raymond (@jonathanrefound) will introduce us to a super-easy to use and effective framework to provide critical feedback. You’ll learn how to apply the framework using real community challenges and tease out the actual language you can directly use to initiate those conversations.“That's what feedback is about. It's not to correct the mistake, it's to start a conversation.” JONATHAN RAYMOND - Author of “Good Authority”, Founder & CEO @ RefoundJonathan spent 20 years building careers in business development and personal growth before figuring out a way to bring them together. He advises CEOs and organizational leaders on how to create a people-first culture that drives results. Refound works with organizations going through dynamic change, from Fortune 100 companies like Panasonic and McKesson to tech startups. Jonathan loves being a dad to two girls, surfing, and yoga. He also has a surprisingly good jump shot. SHOWNOTESWhat to do when someone on your team is obviously less productive (1:17)Why people are afraid to give critical feedback and what makes it hard (6:01)What is “The Accountability Dial?” (9:06)How you can open a feedback conversation using “The Mention” (11:04)Understanding the reality of where people are at and how you can move forward using “The Mention” during this pandemic. (17:21)The right time to deliver critical feedback effectively. (23:06)What happens if the first feedback conversation doesn’t work? Reopen it by applying “The Invitation” (30:41)Signs you know your feedback is working. (33:04)How to have a performance conversation during the pandemic by applying “The Mention” & “The Invitation” (36:39)Introducing the other stages of “The Accountability Dial” (42:50)How to increase team morale and give positive feedback using “The Accountability Dial” (53:34)How to create an environment where feedback goes both ways between manager and employee. (55:04) Join our community of software engineering leaders @ sfelc.com   Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Farhan Thawar (@fnthawar) , VP of Engineering @ Shopify shares the hiring framework he’s built where 15-minute interviews result in both faster placements AND better fits. You’ll hear how to find talent in non-traditional ways, what happens when you leverage creativity, and how speed in hiring is a massive competitive advantage.“The problem with interviews in general are they're very biased to either things you've done before or they're biased to some other signal...like school you went to company, you worked for, GPA in some cases, right? Google used to use that... And it excludes a wide swath of people. That's my number one problem with interviews. Not that good candidates can pass an interview. It's that non-traditional candidates will likely fail your interview” ABOUT FARHAN THAWARFarhan is currently VP, Engineering at Shopify via the acquisition of Helpful.com where he was co-founder and CTO. Previously he was the CTO, Mobile at Pivotal and VP, Engineering at Pivotal Labs via the acquisition of Xtreme Labs. He is an avid writer and speaker and was named one of Toronto's 25 most powerful people. Prior to Xtreme, Farhan held senior technical positions at Achievers, Microsoft, Celestica, and Trilogy. Farhan completed his MBA in Financial Engineering at Rotman and Computer Science/EE at Waterloo. Farhan is also an advisor at yCombinator and holds a board seat at Optiva (formerly Redknee). SHOWNOTESFarhan’s origin story being recruited to start Helpful.com by Daniel Debow. (1:28)Impact and examples of going above and beyond in recruiting using unusual ways to reach potential candidates. (8:30)Using speed as a competitive advantage, especially when you’re small. (12:44)How to prevent speed from backfiring by thinking about decisions as “one-way” or “two-way doors.” (14:36)Critical structures to best assess candidate fit. (15:17)How Farhan starts from first principles to leverage creativity in recruiting. (20:38)Farhan’s MOST IMPORTANT indicator of performance, and how to uncover it in an interview. (25:49)Results of speed in the hiring process - 15 min interview (31:36)How the 15 min interview works. (33:47)What’s different in hiring an engineering leader. (35:41)How to increase your pool of potential candidates through “backward promotions,” interim titles, and recruiting people who haven’t “done it” before. (42:41)Examples of what happens when bias is removed in the interview process and people are given a shot. (48:03)Farhan’s most terrible leadership mistake & how to turn underperformers into extremely high performers in 30 days with Performance Improvement Plans (PIP’s). (49:36)Farhan’s most impactful leadership action: the power of personalization. (53:56) Join our community of software engineering leaders @ sfelc.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Max Levchin shares lessons and stories that have been critical to his development as an engineering leader. He shares stories from the early PayPal days and foundational insights for leading Affirm as a mission-driven, values-based company. He also shares essential principles for building and hiring, and how the hardest problems are almost never about code. “I should just solve the thing that matters. I don't need to worry about the hard stuff, it will show up on its own. And there's plenty of hard problems and the more you work with people, the more you'll realize that the truly hard problems are always about humans, they're never about code.” - Max Levchin MAX LEVCHIN - Founder and CEO @ Affirm Max Levchin is the founder and CEO of Affirm, a financial services technology company, co-founder and Chairman of Glow, a data-driven fertility company, and co-founder and general partner at SciFi VC, a private venture capital firm. All three companies were created and launched from his San Francisco based innovation lab, HVF (Hard, Valuable, Fun). Max was one of the original co-founders of PayPal where he served as the CTO until its acquisition by Ebay in 2002. In 2002, he was named to the Technology Review TR100 as one of the top 100 innovators in the world as well as Innovator of the Year. In 2004, he founded Slide, a personal media-sharing service for social networking sites such as MySpace and Facebook, which he sold to Google in August 2010. Also in 2004, he helped start Yelp, where he was the first investor in and Chairman of the Board from 2004 until 2015. He has served on several boards such as Yahoo!, Yelp, and Evernote. Max is a serial entrepreneur, computer scientist, philanthropist and active investor in more than 100 startups. BEN JUN - CEO @ HVF Labs Benjamin Jun is Chief Builder at HVF Labs (hard / valuable / fun), a fintech startup studio. The lab focuses in areas where technically differentiable solutions can unlock world-changing companies. HVF founders have spun out companies such as Affirm, Divvy Homes, and Yelp. Ben was co-founder and CTO of Cryptography Research, which provides security technologies for payment systems, mobile handsets, digital content protection, and the manufacturing supply chain. While there, he developed and architected security technologies that shipped in over 25 billion consumer devices. Cryptography Research was acquired by Rambus for $340M in 2011. SHOWNOTES Max’s unsung passion for cryptography and how it came to be. (4:53) Max’s cryptography side-hustle stories while starting PayPal. (6:01) How Ben tried to convince Max to leave Peter Thiel and PayPal. (9:58) PayPal’s early milestones, and why that’s different than what’s commonly celebrated in the press and Silicon Valley. (11:46) PayPal’s “one metric” that matters. (13:10) How Max is different as a leader now vs. during his time at PayPal. (18:00) What to think about when transitioning from a VP of Engineering to becoming CEO (20:52) How Max builds complimentary teams. (24:25) “Max’s aura test” or “the hallway avoidance test” in hiring. (26:16) How to guide your company and know you’re doing the right thing. (29:00) Join our community of engineering leaders at sfelc.com Send in a voice message: https://anchor.fm/engineeringleadership/message Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What should be the role of engineering leaders in recruiting? What levers do they have at their disposal? In this fireside chat, you'll hear the perspectives of two recruiting heavy-hitters, Aditya Agarwal & Dan Portillo, on how engineering leaders can optimize for successful hiring outcomes. ADITYA AGARWAL - Former CTO Dropbox; Partner-in-Residence @ South Park Commons (@adityaag)Aditya Agarwal is a Partner-in-Residence at South Park Commons - a collective of technologists, tinkerers, and entrepreneurs who have come together to freely learn, explore new ideas, and help each other launch their next venture. Aditya was the CTO and VP of Engineering at Dropbox. He scaled the Engineering team from 25 to 1000 and was responsible for new product development, infrastructure, and technical operations. Aditya came to Dropbox via the acquisition of Cove, a company that he co-founded. Prior to Cove, Aditya was one of Facebook’s first engineers. He helped build the first versions of key products like Search, NewsFeed and Messenger. He was Facebook’s first director of Product Engineering, overseeing engineering for products like NewsFeed, Profile, Groups and Events. Aditya serves as an independent director on the board of Flipkart, India’s leading e-commerce company, the advisory board of Carnegie Mellon’s School of Computer Science and on the board of trustees of the Anita Borg Institute. He is also an active investor and advisor to Silicon Valley startups. DAN PORTILLO - Talent Partner @ Greylock (@dan_portillo)Dan is Talent Partner at Greylock. Previously, he was VP of Success & Engagement at Rypple, and VP of Organizational Development at Mozilla, creators of Firefox. Earlier in his career Dan spent a decade building out successful early-stage, venture-backed consumer and enterprise companies. Dan also served as a Council member for Code2040.org, a non-profit creating opportunities for underrepresented minorities in tech. SHOWNOTESHave you ever not promoted an engineering leader because they couldn’t recruit a good team? (3:18)What is the role of engineering leaders in the recruiting process? (5:21)Sourcing advantages from Aditya’s experiences from Dropbox and Facebook. (7:34)On taking the long view and thinking long term about recruitment. (9:42)How Aditya closes candidates creatively. (11:21)Aditya’s favorite story from Dropbox closing a talented intern. (14:23)How to leverage compensation, even if you’re a small stack at the table. (18:59)What Aditya tells engineering leaders who are building teams for the first time. (21:48)Does comp asymmetry reward good performers or good negotiators? (23:03)Using comp as a tool to value, reward, and recognize performers not on the sexiest problems. (25:32)Recruiting when you don’t have a brand. (27:58)What engineering managers need to know to effectively sell the company and recruit. (29:53) Join our community of engineering leaders at sfelc.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Alyssa and Chanda share stories and mental frameworks about how to strategically think about and accelerate your career journey. You’ll hear examples of how to navigate between large and small companies, how to level the playing field by strategically leveraging emerging tech fields, intentionally harnessing skip-level managers, and establishing a growth mindset. Alyssa Henry - Head of Seller & Developer Business Units & Infrastructure Engineering @ Square Alyssa Henry is the Seller Lead at Square, which creates tools that help sellers start, run, and grow their businesses. She leads product management, design, and engineering for Square’s seller- and developer-facing products. Alyssa has been integral to shifting Square from a single app focused on payment processing into a broad financial services platform and commerce ecosystem that serves the complex needs of verticals from restaurants to retail. Prior to joining Square in 2014, she previously served as VP of Amazon Web Services (AWS) Storage Services and Product Unit Manager for Microsoft SQL Server Data Access. “People want to work on something that matters, something where they’re growing and learning. Autonomy, mastery & purpose resonates with everyone.” Alyssa Henry Chanda Dharap - VP of Engineering @ NodeSource She is currently the VP Engineering at NodeSource, bringing 20+ years experience leading Engineering and Product teams with a strong focus on emerging trends and new technologies. With a solid mix of both global corporate and startup experience, Dharap has a proven track record of excellence, most recently in the the Node.js ecosystem, leading cross-functional efforts around solutions to drive the API economy. Prior to joining NodeSource, she held a product leadership role at Adobe, where she was responsible for the vision and technical direction of a next-generation search platform for Adobe’s cloud ecosystem. Dharap holds a Masters and a Ph.D. in Computer Science from Pennsylvania State University, and has also earned a certificate in Strategic Decision and Risk Management from Stanford University’s Center for Professional Development. SHOWNOTES Alyssa’s work at Square supporting new entrepreneurs start and grow businesses. (5:13) The experience and challenges transitioning from a large to small company. (6:51) How you transition from running an engineering team to broad cross-functional teams. (8:49) How Alyssa grew her teams at Amazon and Square. (11:41) Early adoption of emerging technology, having a growth mindset, and the power of skip level mentoring to drive career development (15:28) Alyssa’s questions she asks to assess her next career opportunities. (18:59) When should product and engineering be in the same organization? (20:45) Lessons from growing at hyperscale. (21:13) How to retain core members of a team, especially in a high-turnover industry. (23:29) Want to get involved with our community of engineering leaders? Check us out at sfelc.com Send in a voice message: https://anchor.fm/engineeringleadership/message Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

While you don't jump out of bed excited about it, you know how powerful it is for morale when you make the choice to tackle technical debt. Learn a framework for how to do the same thing with organizational debt, and unlock untapped energy, creativity and connection on your team in the process.“As organizational leaders, when it comes to organizational debt, we know that we take shortcuts. We make easy decisions. We do things that are expedient in the moment. But it has a cost. But we have to deal with it as a responsible leader.” ABOUT JONATHAN RAYMONDJonathan Raymond (@jonathanrefound) is the CEO at Refound and author of the award-winning book, Good Authority. In 2018, he was named one of Inc. Magazine’s top 100 leadership speakers. Refound trains leaders on how to give effective feedback and create a culture of accountability. The former CEO of EMyth, Jonathan has led business transformation projects in technology, renewable energy, and the coaching industry. He’s a half-decent barista, a bad-but-enthusiastic surfer, and will never give up on the New York Knicks. SHOWNOTESWhat is “organizational debt?” (3:45)Defining technical debt. (5:05)How you know when you have technical or organizational debt. (6:34)The first step to solve technical/organizational debt. (7:26)Second step, what’s next before entering “solution mode.” (10:47)Understanding the problem now that the issue is in the open. (12:03)How you sell someone on doing something new (13:05)Where we often leave the process of solving organizational debt unfinished. (15:10)The active solution after the first three steps. (17:25)What separates good engineering leaders from mediocre ones. (20:00)Become the engineering leader your team is waiting for. (21:39)Additional examples of organizational debt. (23:48)Who owns organizational debt. (24:53)Dealing with over-leveling or title inflation. (25:48) Join our community of software engineering leaders @ sfelc.com Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Jason Warner (@jasoncwarner), CTO @ Github shares management principles fundamental to how he leads remote engineering teams. He shares how to scale leadership by applying the right tools and frameworks for effective communication. Jason also tells us the structures and strategies he applies to build & maintain trust throughout an organization.“Every leader in an organization should make THE SET of decisions that ONLY they can make. And then delegate all the other ones. And the only way that you can do that is if everyone is empowered to make the right decisions with the right context, and you have invested ahead of time and trained the neural net of the organization to make those appropriate decisions well.” - Jason Warner ABOUT JASON WARNERJason oversees the Office of the CTO, whose mission is to explore the unknown and non-existent aspects of technology and software in order to build a map of GitHub’s future. He oversees over 704 engineers, 85% of whom operate remotely. He was previously Senior VP of Technology at GitHub, where he played an integral role in scaling the Engineering, Product, and Security Teams, and built GitHub’s product roadmap.He’s been the leader of fully distributed companies for the last 10 years. Prior to GitHub, Jason was VP of Engineering at Heroku. He oversaw Product Engineering for Ubuntu Desktop and Ubuntu Phone at Canonical.He’s also a member of the Advisory Board of INNOVATE Ohio - reporting to the Lt. Governor advising policy decisions that impact growth in technology and aim to make Ohio the most INNOVATIVE state in the country in the next 5 years. RESOURCESThe Art of Simple Sabotage SHOW NOTESWhy challenges with trust, communication, and engagement are NOT unique to remote teams. (2:34)The differences between building trust in remote and co-located teams. (4:05)Why micromanaging is the easiest way to cause breakdowns, destroy productivity and negatively affect morale. (5:40)Jason’s biggest fear as a leader and the fundamentals he uses to scale leadership. (9:17)Structures for effective communication at different scales. (12:20)Early signs of mistrust and how to easily measure the health of an organization(14:39)How you can use “organizational canaries” to get unfiltered feedback (19:26)How to maintain trust & avoid destroying relationships. (24:14)Effective executive communication using the “V-shaped” pathway. (27:17)Examples of how to measure gaps in your communication feedback loops. (31:46)How to turn concepts of healthy communication into mechanisms in your team. (34:48)Signs of bad communication and you can overcome them. (37:10)How to train your organization to make better decisions when you’re not in the room (41:17)Why you should prioritize tools for asynchronous communication and institutional memory (43:45)How you can increase the fidelity of your communication. (46:56)Frameworks to think about team engagement. (51:53)Why Jason believes the role of in-person communication will diminish over time. (57:54)Two actions you can take IMMEDIATELY to improve hiring for your remote team. (1:03:05)Back pain as a metaphor for addressing the root issues in your organization. (1:07:36)Jason’s greatest joy as an engineering leader. (1:12:35) Want to get involved with our community of engineering leaders? Check us out at sfelc.com  Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.