The Engineering Leadership Podcast

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How to Lead Large Scale Projects with Wendy Shepperd GVP Engineering @ New Relic #31 Mar 09, 2021

Show notes

Wendy Shepperd, GVP Engineering @ New Relic covers how she leads massive-scale strategic programs with precision execution. You’ll hear how to lead great project kickoffs, successfully execute across multi-year time horizons, navigate complex dependencies, launch, & of course celebrate success with your team.

"One of the things I tell my teams all the time, especially when things get hard... is I say " Hey, y'all we are making memories! One day we're going to look back on this time and talk about what we learned and laugh about it and share stories about it."

ABOUT WENDY SHEPPERD

Wendy Shepperd, GVP Engineering, leads product development for the New Relic Telemetry Data Platform, the leading SaaS multi-tenant observability platform used by tens of thousands of engineers to build and operate more perfect software for their customers. She also oversees global infrastructure, architecture, managed services, and engineering operations for New Relic.

Having worked with a variety of organizations from start-ups to billion-dollar companies, Wendy brings a unique perspective on what works well for different types of situations and at different stages of growth. She loves growing leaders and building winning teams that execute with precision. Currently leading her fourth multi-million dollar cloud migration, Wendy has developed deep expertise and a fair amount of scar tissue around the many aspects of complex platform migrations in large-scale environments.

SHOWNOTES

Wendy's lessons learned after leading 4 multi-million dollar cloud migrations (2:29)
How to decide when to fix-forward or roll-back your complex strategic project (6:36)
What great project execution looks like in a complex cloud migration (9:37)
Wendy’s keys to a smooth cloud migration & the major steps of strategic planning (13:57)
How to lead a successful planning phase for your project (16:28)
How to resolve conflict when your teams and projects have different priorities (18:46)
How to move your project forward despite unknown dependencies (22:22)
How to hold a great project kickoff and what to avoid (26:59)
How to sustain momentum and successfully execute large, complex projects with precision (31:33)
Wendy’s team, leadership, and communication cadence during Project Cumulus (37:19)
How to handle real-time coordination and execution during pre and post-project launch phases (39:27)
Wendy’s favorite project milestone celebration (42:33)
How Wendy’s past work as a technical writer impacts her leadership now (44:54)
Wendy’s less obvious, but essential advice to lead large, complex projects (46:43)
Takeaways (48:56)

Looking for other ways to get involved with ELC? Check out all of our upcoming events, peer groups, and other programs at sfelc.com!

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Spend Time On What Matters with Will Larson CTO @ Calm #30 Mar 02, 2021

Show notes

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 @ CALM

Will 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 @Lethain

Here is the interview Will referenced with Aaron Suggs (engineering sponsorship & being a ‘frequent first follower’)

SHOWNOTES

When 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 & RESOURCES

Will'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-suggs
Will'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!

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Remove Fear of Failure From Your Org with Edward Kim Co-Founder & CTO @ Gusto #29 Feb 23, 2021

Show notes

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 KIM

Prior 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.

SHOWNOTES

What 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!

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"The Imperfect Path" with Erica Lockheimer VPE, LinkedIn Learning @ LinkedIn #28 Sep 28, 2020

Show notes

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 LOCKHEIMER

Prior 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.

RESOURCES

About REACH: https://careers.linkedin.com/reach/AboutReach

Shalini Agarwal, LinkedIn REACH Lead & Eng Leader https://www.linkedin.com/in/shalini-agarwal-5b735b2/

SHOWNOTES

Erica’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)

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Leading AI/ML Teams with Craig Martell Head of LyftML @ Lyft #27 Sep 20, 2020

Show notes

Craig Martell shares the biggest mistakes leaders of ML teams make, what to do if you have no experience leading an ML team, key skills your ML team needs, plus different models/approaches to building an ML team. You’ll hear the most expensive and time-consuming parts of ML, how to estimate timelines, unique tech debt, and how to manage expectations.

“If I had to give one piece of advice about starting AI in your company, one of the first people I would hire is a really great data scientist, even if they can't code. Just so they're the one who's going to start training you and helping you think about, how to gather data, how the modeling is going to work, what you're going to need, whether that feature that you want to build is even modelable in the first place..." - Craig Martell

ABOUT CRAIG MARTELL

Craig is Head of Lyft Machine Learning. He’s also an adjunct professor of Machine Learning for Northeastern University’s Align program.

Prior to joining Lyft, he was Head of Machine Intelligence @ Dropbox, and led a number of AI teams and initiatives at LinkedIn, including the development of the LinkedIn AI Academy. Before LinkedIn, Craig was a tenured computer science professor at the Naval Postgraduate School specializing in natural language processing (NLP). He has a Ph.D. in Computer Science from the University of Pennsylvania and is the co-author of the MIT Press book Great Principles of Computing.

RESOURCES

(ML training) Galvanize: https://bit.ly/3ckF6Gz
(website) Andrew Ng: https://bit.ly/3cgerdU
(courses) ML: https://bit.ly/3iNB9gf | AI for Everyone: https://bit.ly/2HeZKwl
(course) Fast.AI: https://bit.ly/35SPwMD
(book) "Hands-On ML with Scikit" : https://amzn.to/35SbGyh

SHOW NOTES

An overview of the machine learning lifecycle (2:49)
The most expensive and time-consuming aspect of the machine learning lifecycle (6:07)
The key skills of a machine learning team (7:21)
How do you build an AI/ML Team and what are the different models? (8:41)
What to do If you’re an engineering manager with no AI/ML skills or experience (15:19)
How deep does your understanding of AI/ML have to be in order to lead effectively? (18:48)
How do you estimate project timelines for AI/ML teams? (19:15)
What are the biggest mistakes engineering leaders make managing AI/ML teams? (20:52)
How do you manage expectations in an organization that’s in the early days of AI/ML development? (21:33)
What are sources of technical debt unique to AI/ML systems? (22:13)
How do machine learning teams interface with product teams? (23:55)
AI/ML resources for executive engineering leaders (25:44)
When’s the right time to invest in AI/ML? (26:10)
Can you apply the Pareto Principle (80/20 rule) to AI/ML development? (26:40)
Takeaways (28:12)

Join our community of software engineering leaders @ https://sfelc.com/

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Give Up Control and Expand Your Impact with Maria Latushkin CTO @ Omada Health #26 Sep 13, 2020

Show notes

“Giving up control” is about empowering other people to scale yourself, and scale your effectiveness. Maria Latushkin shares with us why you need to give up control as an engineering leader and what holds people back. Plus you’ll learn tons of different ways to influence and manage your performance when it’s dependent on other people’s effectiveness.

“You are responsible for the delivery of the team. At the end of the day, nobody really cares like how much YOU work. You can be working around the clock. And it's not how great you are or what you produce. It stops being about you and it starts being about the function that you lead.” - Maria Latushkin

ABOUT MARIA LATUSHKIN

Maria is responsible for leading Omada Health’s technology vision and team. Prior to joining Omada Health and moving to the healthcare space, Maria has spent over 15 years in eCommerce, retail, and enterprise SaaS companies ranging from series B startups to large companies, such as Walmart.

SHOW NOTES

Why you need to give up control as a senior engineering leader (2:07)
What holds people back from giving up control? (9:27)
The impact and trade-offs you make when you avoid or resist giving up control (15:31)
How to influence and manage your performance now that it’s dependent on your team’s effectiveness (23:49)
How to make sure people heard you, so that you know you’re on the same page (29:04)
Does the discomfort of “giving up control” happen at every transition to a new leadership level, or is it a one-time thing? (32:44)
How to regain “control” and empower your team (39:40)
The Impact - how you feel when you give up control (41:25)
Takeaways (43:36)

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Join our community of software engineering leaders @ https://sfelc.com/

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Growing Into a VPE - Patterns & Anti-Patterns ft. Cathy Polinsky, Jerry Krikheli, Richard Wong, Erica Lockheimer & Claire Lew #25 Sep 06, 2020

Show notes

A dynamic conversation between 4 current and past VPs of Engineering who cover tons of patterns and anti-patterns about being a VPE! You'll hear how leadership is different in large vs. small companies, mental models to determine your greatest leverage, why you DON’T need to act like an owner, how to put trust into practice when you’re transitioning into a new role, and about the imperfect path to become a VPE.

SPEAKERS:

CATHY POLINKSY CTO @ Stitch Fix

JERRY KRIKHELI VP of Engineering @ Houzz

RICHARD WONG SVP of Engineering @ Coursera

ERICA LOCKHEIMER VP of Engineering @ Linkedin Learning

And CLAIRE LEW CEO @ Know Your Team

SHOWNOTES

What Cathy means by “the best leaders spot patterns, understand problems, then build systems to solve them” (3:55)
Jerry’s view on how the practice of leadership is different at large companies vs. small companies (7:30)
Erica’s perspective on how the transition to VPE is different than other eng leadership roles and how to put trust into practice (12:27)
Why Richard resonates with “act like an owner” and what it actually looks like in practice as VPE (16:40)
Cathy’s top 3 priorities as VPE that determine how she spends her time and how to refocus your team (23:50)
Richard's mental model to determine where he has the most leverage for impact and why being technical isn't always about writing code (26:16)
Jerry's 3 key hiring traits and how to create an environment where you're the first to know when something's wrong (30:10)
The imperfect path to become a VPE and Erica’s advice for engineering leaders with an “unconventional” background (34:01)
The common struggle to balance being a problem solver and being the bottleneck as a VPE (39:11)
How they cope with and manage stress (42:55)
Takeaways (45:00)

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Join our community of software engineering leaders @ https://sfelc.com/

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*Bonus* Optimizing Productivity for Remote Engineering Teams with Doug Gaff, VPE @ Zapier & Emma Tang, EM @ Stripe #24 Aug 30, 2020

Show notes

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 @ Zapier

Doug 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 @ Stripe

Emma 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.

SHOWNOTES

How 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)

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Join our community of software engineering leaders @ https://sfelc.com/

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Optimizing Productivity for Remote Engineering Teams with Doug Gaff, VPE @ Zapier & Emma Tang, EM @ Stripe #23 Aug 30, 2020

Show notes

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 @ Zapier

EMMA TANG - Engineering Manager @ Stripe

SHOWNOTES

Ideas 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)

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Join our community of software engineering leaders @ https://sfelc.com/

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How to Become a Startup VPE with Martin Casado, General Partner @ Andreessen Horowitz & Sonal Chokshi, Editor in Chief @ Andreessen Horowitz #22 Aug 27, 2020

Show notes

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 HOROWITZ

He 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.

SHOWNOTES

Hiring 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)

LINKS

a16z Podcast

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