Episode 43 | The Midwit Trap, & Why Tech Companies Are Falling For It

Eiso and Jason discuss how engineering leaders can fall into the trap of midwit thinking (the infamous bell curve meme) where they have a surface level understanding of complex topics and use buzzwords to sound knowledgeable.

Former Atlassian CTO Sri Viswanath shares his lessons on engineering leadership, such as aligning goals, handling difficult situations, and optimizing team metrics. Jason, Eiso and Sri talk about their experiences with system failures and the importance of technical mentors and CTOs in promoting better leadership.

Jason and Eiso share their love-hate relationship with OKRs and discuss the pedantic nature of setting objectives and how they ultimately help to align and empower organizations. They talk about setting and tracking goals, the often performative nature of OKRs, and the dangers of abstracting oneself away from the product you’re building.

Jason and Eiso explore the intersection between finance and engineering leadership and discuss the importance of position sizing in engineering orgs. From promotions to product initiatives and technology choices, leaders are constantly making bets. So the guys delve into decision making, risk management, trust, and the dangers of placing the wrong bets.

Jason and Eiso get real about censorship culture in the tech industry. From free speech to the rights of employees and the role of companies in society. They chat about privilege in tech, whether we need democracy within tech companies, the role of culture stewards, and more.

Jason and Eiso deep dive into corporate politics, hierarchies, and the sociopaths that often sit at the top as they analyze the behaviors of famous C-Level leaders, such as Microsoft’s Steve Ballmer, and pick apart what Engineering Leaders can learn from them.

Phil Calçado is the Global CTO at PicPay, one the largest engineering orgs in Latin America. He joins the podcast to re-tell his war stories as an engineering leader at SoundCloud, Digital Ocean, SeatGeek, MeetUp, and more celebrity-tier tech companies.

Happy 2023! or is it?… Jason and Eiso talk about the economic recession and share their predictions for the year ahead. They chat about what happened in 2022 that set the stage for 2023, what the hiring halt means for software engineers, what will happen to those that didn't prepare, and more!

Allison McMillan, VP of Engineering at Quota Path, joins us to talk about the transformation engineering leaders go through when they become parents and the lessons we can take parenting to our day-to-day as managers. From communication to rewards vs. consequences to dealing with other humans and their unique challenges.

Alexandra is a Senior Engineering Manager at Fellow.app and the author of Remote Engineering Management: Managing an Engineering Team in a Remote-First World. She joins us to discuss creating an excellent remote work foundation and the challenges of jumping back into in-person interactions when needed. We also chatted about how remote emotions translate to in-person ones, segmenting emotional reactions, wearing different masks, and more.

Bethany Foote is the Head of Infrastructure Engineering at Outschool and has had a hell of a journey as a software engineer. She joins us to talk about how diversity makes companies better, share the stories she's heard from women in tech over the years, and how they taught her how to be a better leader, mentor, and coach.

Shannon Vettes is a Transversal Product & Engineering Leader and self-proclaimed "process nerd" with a knack for reorgs (as long as you reaally need them!) and for making engineering leaders' lives easier. She joins the podcast for a deep dive into the PMOs and Program Manager's roles and when's the right time to introduce these roles and processes in your organization.

Adrienne Lowe shares her journey as an empathetic leader and how her goal to give people energy (rather than take it away) paved her way through a success engineering leadership career.

Jason & Eiso talk about Velocity in Software Engineering, what it means, how to measure it, why data and metrics won’t magically solve all your problems, and what engineering leaders can do for their teams to go faster.

Kohsuke Kawaguchi, the creator of Jenkins, pulls back the curtain on building tech companies in Japan. He shares his lessons from Cloudbees and how building two very different engineering organizations from the ground up showed him the importance of diversity in engineering teams.

Join Chad Fowler, Jason Warner, and Eiso Kant in a heartfelt existential episode on what it means to be an engineering leader that will have you question if the manager path is the right one for you. An essential listen for anyone trying to find meaning in their role.

Cesar Lugo, Software Engineer and founding member of the Engineering Intelligence team at Typeform, joins us to talk about the power of engineering metrics and how data can help influence how organizations behave.

Jason and Eiso ad lib on a variety of topics. From consensus-driver cultures, the trouble with software engineering endorsements and capacity planning best practices.

Craig Kerstiens joins us for a chat on decalcifying engineering teams, why you need to get your teams to ship more, and finding A-Players. Craig runs product and engineering at Crunchy Data and has been incredibly influential in the Postgres community.

Meri Williams, one of the most inspiring engineering leaders in the world, joins us for a discussion on managers vs. leaders, coaching vs. mentoring, how leaders can advise team members from different backgrounds, and the power of sponsorship.

Jason and Eiso explore what motivates engineering leaders. They chat about how engineering value creation differs from other functions, what role ego plays as a motivating factor, engineering leadership role models, and more.

Charity Majors, co-founder, and CTO of honeycomb.io, joins us to talk about everything that's wrong with engineering cycles, how throwing money at the problem by hiring more people is making it worse, and what we can do about it.

Dana Lawson, SVP of Engineering at Netlify and the human incarnation of sunshine, joins us on the podcast to share her lessons on hiring engineers and the interview process. We also spoke about the tech industry's changes in the last decade and how you can build inclusive software engineering teams.

Andrew Conner, Co-Founder and Engineering Leader at Levels, joins us to share his journey of leading an engineering team at a company with a strong hardware component. We spoke about building remote asynchronous companies, the importance of feedback loops, deep work, and transparency as you collectively build software and hardware.

Katie Wilde, the VP of Engineering at Ambassador Labs, joins us to spill the tea on Holacracy and decentralized management systems. Find out why these organizational structures don’t work for companies building software and how they can drive your best people away. Katie also shared how her previous company, Buffer, transitioned from a Holacracy into a strong engineering leadership culture, through goal-oriented 1:1s, effective feedback, and creating a strong sense of responsibility among its leaders.

Co-Founder and CEO of Moov Financial, Wade Arnold, has had a hell of a journey as a software engineering leader. He joins us on the podcast to chat about building companies, attracting great software engineering talent, and increasing velocity as you scale.

We welcome Jonathan Nolen, Senior VP of Engineering and Product at LaunchDarkly, to talk about his 100+ people Product Delivery team - a term coined by the company, where Engineering, Product, and Design come together. We spoke about what this three-function team means for engineering organizations, how you can build a culture of shared responsibility, and much more!

Eiso and Jason step up to the mic and make their wild guess on how the state of software engineering will evolve, given what we know now. The tech industry will look a lot different in 20 and 30 years. From autonomous coding to self-driving cars to automatically powered engineering leadership. We might not be ready for that yet, but our kids are gonna love it.

In an episode dedicated to what we think the next generation of engineering leaders should avoid, Jason and Eiso talk about the books every engineering leader reads, the over-glorification of 80’s maniacal leaders, OKRs, and other tech industry things we love to hate.

Senior Director of Engineering at Datadog, Nuno Antunes, joins us to talk about a highly requested topic: Transitioning from Software Engineer to Engineering Leader. From striking the right balance between being a people vs. process-oriented leader to the challenges of building teams in fast-growing companies, this episode is jam-packed with teachable moments, workshop approaches, and the organizational shifts we've witnessed through the years.

Dagger Co-Founder and Docker’s former VP of Engineering, Sam Alba, joins us for a retrospective on company culture and how early-stage teams should develop it as their companies evolve. As Dagger grows from a founding team of three to ten and so forth, Sam, Jason, and Eiso, share their views on building companies, leading by example, and the importance of embracing culture in a genuine way.

Erik Bernhardsson joins us on the podcast to chat about building engineering teams and the delicate balance between innovation and productivity as organizations grow. We also shared our views on team mentalities, skunkworks projects, and more as we tried to answer the question: "what is success in engineering?"

Community creator and engineering leader at Apple, Michael Lopp (aka rands), joins Jason and Eiso to chat about the power of storytelling for engineering and the state of content for engineering leaders. The author of "Small Things Done Well" shares his opinions on video conferencing, distributed work, and how managers can create more authentic connections with remote teams.

On our 10th episode, Eiso and Jason present a conversation dedicated to CEOs and everything they need to know about their engineering organization and leadership. From tech debt to dependency management and communication styles, understand engineering team's infrastructures, the timings and expectations of building product, and much more.

Sam Lambert, CEO of PlanetScale and previously VP of Engineering at GitHub, joins us to talk about building high-performance teams. We chatted about leading with influence, advocating for your team, creating delightful hiring experiences, knowing when to fire people and how to keep your software engineers close to your end-users to build great products.

Jason and Eiso wrap up their three-part series on Engineering Leadership roles by taking a deep dive into Engineering Managers and Tech Leads. Learn how to hire your first engineering manager, whether to hire your engineering leaders from inside the company, and how the roles of tech leads change as your company grows. We also covered communication techniques and how to design your teams as the company scales and communication lines increase.

Jason and Eiso continue their deep dive on different engineering leadership roles, sharing their thoughts on CTOs, VPs, and Managers, how to hire for these roles, and adopting organizational structures that promote transparency and trust in the decision-making processes that shape your business.

In this episode of Developing Leadership, we kick off our deep-dive series on different Engineering Leadership roles. Jason and Eiso discuss how CTOs, VPs of Engineering, and Engineering Managers should navigate through the various stages of their company. From prioritizing at different seed rounds to developing a go-to-market strategy, building their company’s architecture, and the day-to-day of each of these roles.

Former GM of Snyk, Anton Drukh, recently became a mentor for VPs of Engineering and joined us on this week's episode to discuss his experiences leading a team split between two very different cultures. His journey as a leader working with teams in Israel and the UK is a lens into how diversity of mentalities can be an essential asset for tech companies and how it played a role in Snyk's success.

Neo4j just raised the biggest round in database history and their CEO, Emil Eifrem, joins us on the podcast to tell us about his experience transitioning from a day one CEO to running a company with more than 500 employees.

Jason and Eiso share the frameworks that have helped them navigate big and small decisions through the years and look back at how key decision-making moments shaped how they operate as leaders today.

How do we make sure that we are deliberate about the culture of our organization and not find ourselves pushing for outcomes without care of how we achieve them? Jason and Eiso go through the building blocks of positive company culture and explore how companies and leaders can adapt as their teams grow from two people in a garage to thousands of employees.

In the first episode of Developing Leadership, Jason and Eiso talk about how the roles and perceptions of engineers and engineering leaders have changed over the decades. From the catastrophic offshoring trend of the early 2000s to the golden age of development, the tools, the processes and the culture shifts.