The Engineering Leadership Podcast

We were overwhelmed by questions from our event with Doug and Emma! This is a bonus follow up conversation that further digs into measuring productivity through “Waterlining” and Kaplan Meier estimating, hashtags in communication, remote 1:1 best practices, and Doug shows us some of the creative ways he applies Zapier integrations for his personal productivity!"What it does is it forces a debate as to A what's most important and B do we really want that thing below the line waterline? Because what happens sometimes is people are super excited about this thing. And then when you see this rank list of stuff, you're like, Oh, but wait a second. There's like running the business stuff below the water line. We actually have to get that up and staff that..." - Doug Gaff DOUG GAFF - VP of Engineering @ ZapierDoug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. Doug currently resides in the Greater Boston Area. EMMA TANG - Engineering Manager @ StripeEmma is an Engineering Manager in Data Infrastructure at Stripe based in San Francisco. Her team focuses on building distributed computation infrastructure to support Stripe's business. At Stripe, we believe in investing in our remote culture, and have built out the remote engineering hub, and tripled the number of remote engineers in the last year. SHOWNOTESHow to Measure Productivity - Waterlining and Kaplan Meier (2:44)Waterlining as a tool to discuss priorities (9:10)Using hashtags to understand intent and to increase the bandwidth of communication (11:02)Best practices for remote 1:1’s when you don’t see the productivity levels you want (17:37)Tips for onboarding new grads (23:03)Doug’s remote work routine and lifestyle (24:47)Doug’s favorite Zapier integrations to increase productivity (29:21)Takeaways (33:45)---Join our community of software engineering leaders @ https://sfelc.com/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Doug Gaff and Emma Tang discuss high-bandwidth communication, innovation accounting, preventing developer burnout, influencing teams, and communicating priorities. They’ll help you move from frustration and survival in remote work, back to optimized productivity!“Personal stuff is totally in bounds and people just listen. And they don't try to solve a problem for you. And I might be like, I'm red today. I didn't get any sleep. I'm stressed about this thing. I'm not sure I'm going to get it done or this thing's happening personally. I'm worried about a friend who's not well... and it requires a certain level of vulnerability and you've got to have a trust, comfort level, but, that's another thing like as leaders, the best thing you can do is demonstrate this kind of behavior so that other people know it's okay to do it.” - Doug Gaff DOUG GAFF - VP of Engineering @ ZapierDoug is the VP of Engineering at Zapier, the software solution that helps your other software work together more effectively. As the leader of an organization with over 100 engineers, he has learned a lot about effective management and leadership. Doug currently resides in the Greater Boston Area. EMMA TANG - Engineering Manager @ StripeEmma is an Engineering Manager in Data Infrastructure at Stripe based in San Francisco. Her team focuses on building distributed computation infrastructure to support Stripe's business. At Stripe, we believe in investing in our remote culture, and have built out the remote engineering hub, and tripled the number of remote engineers in the last year. SHOWNOTESIdeas for Remote “Offsites” (3:27)How to ensure clear, high-bandwidth communication (5:44)How to make engineers feel connected to the mission and company (9:44)Measuring productivity with “Innovation Accounting” and “Waterlining” (15:03)It's time to trust your people and fix your cultural anti-patterns (21:19)How to prevent developer burnout (25:03)How to influence leadership teams remotely (28:26)How to communicate priorities to multiple groups and teams (33:00)Health metrics to track your team - Happiness surveys, pull requests, and “innovation accounting” (35:11)Takeaways (38:34) ---Join our community of software engineering leaders @ https://sfelc.com/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Martin Casado and Sonal Chokshi explore what makes a great VP of Engineering at startups! You’ll hear how successful VPEs are evaluated, the ideal experience and success criteria. You’ll hear rapid-fire responses covering how to scale yourself, KPIs, the ideal VPE hiring time for startups, and what VPEs should definitely NOT do. MARTIN CASADO, GENERAL PARTNER @ ANDREESSEN HOROWITZHe was previously cofounder and CTOr at Nicira (acquired by VMware for $1.26 billion). At VMware, Martin was SVP & GM of the Networking and Security Business Unit (which he scaled to a $600 million run-rate). Martin’s early career was at Lawrence Livermore National Laboratory working on large-scale simulations for the Department of Defense, networking, and cybersecurity.He holds both a PhD and Masters degree in Computer Science from Stanford University, where he created the software-defined networking (SDN) movement and cofounded Illuminics Systems (acquired by Quova). He’s been awarded both the ACM Grace Murray Hopper award and the NEC C&C award, and he’s an inductee of the Lawrence Livermore Lab’s Entrepreneur’s Hall of Fame. Martin serves on the board of: ActionIQ, Astranis, DeepMap, Imply, Kong, Pindrop Security, RapidAPI, SigOpt, and Yubico.“In my experience over a number of engineering leaders is whether or not they're a good engineer is totally orthogonal to the actual role. And in fact, someone that's deeply passionate about a particular architecture technology or approach can be very damaging because you have a power asymmetry in the team.” - Martin Casado SONAL CHOKSHI, EDITOR IN CHIEF @ ANDREESSEN HOROWITZ AKA "a16z"Sonal built and oversees all of Andreessen Horowitz’s editorial operations, including showrunning and hosting the a16z Podcast, leading production of the a16z Crypto Canon; and more. Prior to a16z Sonal was a Senior Editor at Wired. Prior to that, Sonal was responsible for content and community at Xerox PARC. Before moving back to California from NYC, Sonal was doing graduate work in developmental and cognitive psychology at Columbia University's school of education and worked as a researcher "ethnographer" on NSF grants around teacher professional development and early numeracy. She studied English and Psychology at UCLA. SHOWNOTESHiring misconceptions & Why VPs of Engineering are so valuable (4:21)Ideal experience and success criteria for a Startup VPE (8:45)Does a VPE need to be a good engineer? (10:56)Two key areas VPEs are evaluated (13:01)How to balance product and engineering as a VPE (17:34)The hard issue of managing people (19:54)Why engineering analytics and conscious decisions are important to building great engineering orgs (22:24)Good KPIs and how to scale yourself as a VPE (24:19)When is the right time to become a VPE at a startup? (26:25)What a VPE should NOT do (27:44)What is a CTO’s role and how do you work with them as a VPE? (31:00)Takeaways (32:0) LINKSa16z Podcast Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Wade Chambers, CTO & SVP of Engineering at Grand Rounds, shares his extensive leadership experience to redefine success in engineering roles. He dives into how to enhance team potential and the importance of mentorship. Wade discusses methods for overcoming career stagnation, presenting three key areas where growth often gets stuck. He emphasizes the value of self-awareness and principled leadership, urging listeners to apply insights from personal reflections for continuous development and reassessment of their career trajectories.

Wade Chambers, CTO & SVP of Engineering at Grand Rounds, shares his 25+ years of experience in engineering leadership. He discusses 'conscious growth' and the power of neuroplasticity in advancing careers. Wade emphasizes confronting discomfort for self-discovery and effective leadership. He reflects on early managerial failures and the importance of vulnerability in career progression. Listeners will gain insights into aligning personal growth with organizational goals and the role of mentorship and feedback in navigating career challenges.

Andrew Fong shares how to identify, operationalize, and reinforce values in your organization as well as his strategies to scale organizations through values-based decision making and in cultivating values-based environments. You’ll also hear stories about the massive role values had in the outcomes of several large-scale infrastructure projects at Dropbox."If we can operationalize this, the micro decision making on the ground becomes much more powerful and it doesn't force us into a command and control environment." - Andrew Fong ABOUT ANDREW FONGAndrew is the Vice President of Infrastructure at Dropbox. In this role he oversees all infrastructure engineering and operations efforts which are responsible for scaling Dropbox’s infrastructure stack in order to support hundreds of millions of users worldwide. Prior to Dropbox, he was at YouTube, Google, and AOL in various infrastructure capacities SHOWNOTESWhat it means to “operationalize values” and why it matters (2:12)How to operationalize values in OKRs (4:45)How to identify values in your team or organization (8:01)How to reinforce values in your organization in meetings, all-hands, and personally (14:35)How to operationalize values in recruiting (18:52)How operationalized values impact projects: Dropbox’s data center migration story (20:41)Lessons learned from Dropbox’s “Magic Pocket” project (26:09)How to make values endure beyond people in projects with long time horizons: be explicit with your decision making process (29:27)How to operationalize values in small teams and start ups (34:46)How Andrew operationalizes his personal values (40:31)Takeaways (48:11) Join our community of software engineering leaders @ https://sfelc.com/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Organizational change is hard. In part 2, Jean-Denis Greze explores how you can adapt and transform the strengths, capabilities or “spikes” of your organization by intentionally using the strategies of “Isolation”, “Outlets” and “Shocks.” He shares a ton of great real-world examples and case studies to help you apply these strategies in your org."The thing that I think makes over a 10 year period, a really good engineering organization is that at any one moment in time, it has very few spikes, but over a long period of time, it has all the spikes." - Jean-Denis Greze ABOUT JEAN-DENIS GREZEJean-Denis Greze is Head of Engineering at Plaid, the technology company giving developers access to the financial system and the tools to build many of the most influential applications and services of the modern financial era. Companies such as Venmo + Paypal, Coinbase, Robinhood, Acorns, Clarity Money and hundreds more are built on Plaid.Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox, where he led the growth, identity, notifications, Paper and payments teams.Prior to Dropbox, Jean-Denis worked in fintech in New York and has CS degrees from Columbia as well as a JD from Harvard Law School. SHOWNOTESHow to mitigate weaknesses in your organization using the strategies of Isolation & Outlets (2:47)How to use “Isolation” in your business units as an org building strategy: examples from Plaid and Xbox (8:44)How to use “Isolation” in recruiting & product strategy: examples of apprenticeships to hire, roles you've never hired for, and incubator programs (12:17)How to use "Outlets" to create different conversations, adopt different values, and set new priorities (16:38)The “Portfolio Theory of Time Allocation” (19:41)How to introduce "Shocks" proactively to change and adapt your organization (28:32)How to intentionally use Acquisitions to “Shock” your organization (33:35)How to intentionally use Reorgs to “Shock” your organization (36:06)The power of peer groups and re-reading (45:19) Join our community of software engineering leaders @ https://sfelc.com/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Organizational change is hard. Jean-Denis Greze shares how he thinks about building organizations that can adapt in a way that preserves strengths, mitigates weaknesses, and develops new capabilities or “spikes” through periodical “forced changes.” He’ll explore what those forced changes are and what they’ve looked like at Plaid and other companies."You're asking me what makes us different. I think it's that we've been really deliberate about building what I would call a ‘spiky org’ as opposed to a very balanced organization. The reality is when you're in a fast-growing company, it's much easier to do a few things well than to try to do everything.” - Jean-Denis Greze ABOUT JEAN-DENIS GREZEJean-Denis Greze is Head of Engineering at Plaid, the technology company giving developers access to the financial system and the tools to build many of the most influential applications and services of the modern financial era. Companies such as Venmo + Paypal, Coinbase, Robinhood, Acorns, Clarity Money and hundreds more are built on Plaid.Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox, where he led the growth, identity, notifications, Paper and payments teams.Prior to Dropbox, Jean-Denis worked in fintech in New York and has CS degrees from Columbia as well as a JD from Harvard Law School. SHOWNOTESWhat you should focus on when building an organization: Be a "spiky" org (2:31)How to change and adapt your organization that preserves your strengths, mitigates weaknesses, and develops new capabilities: force yourself to adapt your “spikes” (7:01)Recruiting, Growth and Performance Management as “spike” examples in organization building (and why it's NOT useful to be good at all three of them) (8:15)The org design dilemma between "Hiring Well" vs. "Firing Fast" (12:01)The org design dilemma between business impact vs. craft and quality (18:27)How you know when you should change your strengths, values and build a new "spike" (24:48)The dilemma of building an organization with bottom-up vs. top-down decision making (27:47)How to develop new strengths, capabilities, or “spikes” in your engineering organization (32:20)Jean-Denis's process to create space for questions, creativity, and problem-solving (36:33) 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.

Eisar Lipkovitz shares the value of being direct as well as other insights on leadership. You’ll hear how to practice the art of direct communication, how to prepare for difficult conversations, and overcome the fear of being direct. Plus Eisar’s insights on where engineering leaders get stuck in their career and how to help them grow."At the end of the day, the main reason I think direct is effective is you actually sort of get to the core of the issue where a lot of people dance around the details and they're conflict-averse" -Eisar Lipkovitz ABOUT EISAR LIPKOVITZEisar is Executive Vice President of Engineering at Lyft. Prior to Lyft, Eisar spent 15 years at Google in various leadership roles, overseeing the tremendous growth of that business while streamlining operations and reducing product complexity. Since 2014, his team of several thousand engineers built Google’s Display, Video, and Apps Advertising products.Previously, Eisar worked on the infrastructure behind Google Search, driving many innovations during a tremendous increase in scale and a transition from web to structured data. Prior to that, he worked for four years at Akamai during the explosive growth of the Internet. Eisar began his career at Israeli Air Force after graduating from Tel Aviv University with B.Sc and MBA. ShownotesWhy being direct is more effective and how to practice the art of direct communication (2:27)How to overcome conflict aversion and the fear of being direct (9:16)How to prepare yourself for a direct, difficult conversation (13:14)How to balance communicating vision and strategy vs. the details (16:42)How to navigate conversations when people don’t understand you (20:31)How to make your conversation more direct when someone is speaking ambiguously or in code (26:07)How to help junior engineering leaders grow (28:29)Where people typically get stuck in the engineering leadership career track (32:59)How inclusion creates environments for more direct conversations about real world challenges (36:26)What has brought you the greatest amount of joy as an engineering leader? (38:00) 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.

Vidhya Srinivasan shares her framework for how she’s navigated her career and operated under high pressure. You’ll learn the practices she uses to deal with and diffuse pressure plus how to coach and create opportunities for engineering leaders to be more comfortable with failure and risk."one question that I often ask myself is... 'Given how I feel right now if I, were to fast forward five years and I look back, would I feel the same level of pressure or anxiety about the situation?' And I've yet to come across a situation where it would still be that relevant five years out" -Vidhya Srinivasan ABOUT VIDHYA SRINIVASANVidhya is the VP/GM at Google Ads responsible for engineering and product for Measurement & Analytics @ Google Ads. Previously, she led engineering, operations & product management for Amazon Redshift and other analytics services at AWS. Before that, she was an engineering leader for 10 years at IBM. SHOWNOTESHow Vidhya has approached and navigated her career (2:04)Vidhya’s framework she uses to deal with high pressure (7:20)How to diffuse pressure (12:55)How Vidhya’s dealt with and diffused pressure personally and professionally (15:44)How Vidhya learned to operate out of hunger vs. fear (19:35)How to coach engineering leaders to be more comfortable with failure and risk (28:28)How to create opportunities for your team to fail and take on more risk (33:38)When you should step in and help your team (36:23)Who is someone who’s most inspired you to be a better leader? (38:39)What’s brought you the greatest joy as an engineering leader? (40:01) 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.