Aug 17, 2023 · 1h 12m · in-depth
How to supercharge your engineering org | Kellan Elliott-McCrea (Adobe, Dropbox)
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In this in-depth conversation, engineering leader Kellan Elliott-McCrea shares tactical frameworks for scaling engineering organizations, navigating the disruptive impact of AI on team sizing, and overcoming velocity bottlenecks through goal clarity and systems-level management.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Brett holds 18.9% of the talking time here. How this is scored →
Brett as informed peer 4.5 Guest teaching 4.9 Guest disagreement 1.2 Brett pushing back 1.4
speaking balance: gold is Brett, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 53:20 Rejection of Servant Leadership and Shit Umbrellas
Kellan directly attacks popular modern management dogma, arguing that servant leadership and managers acting as 'shit umbrellas' ultimately infantilize teams and breed destructive organizational drift.
Hardest push from Brett ▶ 59:28 Brett Questions Omission of Firing UnderperformersBrett catches Kellan leaving out personnel replacement from his list of capacity levers and immediately calls him out, forcing Kellan to defend his systemic philosophy on talent.
Biggest teaching moment ▶ 23:10 Predictability versus High-Upside Company BuildingKellan educates listeners on how Jira and modern engineering management practices inherited from consulting prioritize linear predictability over venture-scale breakthroughs.
Brett holds their own ▶ 40:08 Brett Synthesizes Ecosystem Damage from Google CopycatsBrett contributes deep venture experience by articulating how startups imitating Google's elaborate perks and structures without their cash engine caused immense ecosystem damage.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Brett as informed peer | Guest teaching | Guest disagreement | Brett pushing back | Why |
|---|---|---|---|---|---|---|
| Future Trajectory of Engineering Teams and AI Impact | 4 | 2 | 1 | 0 | Brett introduces the podcast and frame of reference, welcoming Kellan and outlining his leadership history at Etsy, Flickr, Dropbox, and Adobe. Kellan shares initial insights on how industry growth and AI will reshape engineering sizes. | |
| Enduring Engineering Principles Versus Evolving Management Realities | 4 | 5 | 1 | 1 | Brett asks what core tenets of engineering leadership have evolved or endured over 10-15 years. Kellan explains why small teams and trust remain enduring fundamentals while modern teams increasingly require focus on management quality and concurrency. | |
| Tooling Abstractions, Operational Complexity, and Concurrency Dynamics | 5 | 6 | 2 | 2 | Brett probes the paradox of increased abstraction layers versus growing team sizes. Kellan clarifies how complex abstractions and misleading tooling create geometric rather than linear coordination costs. | |
| Long-Term Outlook on AI and Engineering Team Size | 5 | 5 | 1 | 2 | Brett pushes Kellan on input/output mapping in engineering compared to sales or brand marketing. Kellan reframes modern software as collaborative rather than individual heroics, stressing team-level health metrics. | |
| Measuring Team Autonomy, Goal Clarity, and Compensation Models | 4 | 4 | 1 | 1 | Brett explores sub-team compensation and societal equity norms. Kellan explains the friction of team-based comp against individualistic cultural and HR norms in America. | |
| Equity History, Management Spans, and Organizational Doubling Points | 4 | 5 | 2 | 2 | Brett questions Kellan's specific rule of thumb regarding the 12-person threshold. Kellan details the natural breaking points of context management and organizational doubling. | |
| Diagnosing Execution Velocity and Overcoming Communication Pitfalls | 5 | 6 | 3 | 2 | Brett asks why executive clarity consistently fails across growing orgs. Kellan candidly dismisses Jira-driven predictability as counterproductive to venture-scale ambition. | |
| Pragmatic Goal Setting and Alignment in Practice at Frame.io | 4 | 5 | 1 | 1 | Brett asks for concrete examples of alignment in practice. Kellan explains how Frame.io establishes quarterly constraints centered on specific customer outcomes rather than abstract 18-month roadmaps. | |
| Cross-Team Coordination, Shared Values, and Internal Platform Risks | 5 | 6 | 2 | 1 | Brett asks whether leaders should optimize for cross-team coordination or decouple dependencies. Kellan cautions against technical architectures like microservices built merely to avoid human communication. | |
| Cultural Values and the Challenge of Multi-Product Expansion | 5 | 5 | 1 | 2 | Brett detours into the multi-product company challenge across tech giants. Kellan compares Dropbox's single-product scale culture with Adobe's diversified acquisition approach. | |
| Systems Thinking and the Pitfalls of Emulating Tech Giants | 6 | 5 | 1 | 2 | Brett and Kellan align on systems thinking, critiquing startups that cargo-cult Google perks and organizational setups without having Google's cash engine or structural context. | |
| Strategies for Entering New Engineering Orgs and Expanding Capacity | 5 | 5 | 1 | 2 | Brett inquires how Kellan navigates onboarding into new systems. Kellan explains why he does not bring an entourage of former colleagues to new organizations because talent fit depends on the system. | |
| Coaching Through Curiosity, Synthesis, and High-Bandwidth Communication | 5 | 5 | 0 | 1 | Brett drills into Kellan's definition and implementation of coaching. Kellan explains his focus on genuine curiosity, horizontal synthesis, and publicly reflecting feedback. | |
| Navigating Disagreements, Emotional Detachment, and Servant Leadership Traps | 4 | 6 | 3 | 2 | Brett asks about detachment versus caring in leadership. Kellan forcefully pushes back against the 'servant leadership' and 'shit umbrella' tropes that isolate teams from hard corporate realities. | |
| Defining Management Quality Through Repeatable Outcomes and Team Health | 4 | 5 | 1 | 2 | Brett asks for specific criteria that define high quality engineering management. Kellan emphasizes repeatable business outcomes, psychological safety, and preventing toxic team-versus-team hostility. | |
| Levers for Building Capacity and Managing Organizational Talent Fit | 5 | 5 | 1 | 2 | Brett challenges Kellan on why replacing underperformers was not initially listed under capacity growth levers. Kellan breaks down how talent success is fundamentally system-dependent rather than a moral failure. | |
| Cultivating Business Literacy and Removing Delivery Bottlenecks | 4 | 5 | 0 | 1 | Brett asks how leaders systematically build business literacy within engineering orgs. Kellan provides tactical rituals such as 'bring a graph' meetings, transparent unit economics, and lowering deployment cycle times. | |
| Influential Mentors, Leadership Models, and Concluding Thoughts | 3 | 4 | 0 | 0 | Brett concludes by asking Kellan about personal inspirations and mentors. Kellan credits his nonprofit executive parents, complex systems thinking, and colleagues like John Allspaw and Camille Fournier. |
Statements from this episode (34)
Elliott-McCrea: Capping Flickr's engineering team at 20 made it fragile
“Flickr was very famously a team of 20 people, and we never wanted to get larger than 20, which meant that once people started leaving, we didn't have a lot of resilience, and very quickly that organization got unhealthy.”
Elliott-McCrea: Management quality matters more for scaling than code reviews or architecture
“You know, I really have come to believe that high quality management is one of the keys if you're going to scale your organizations. And so the degree to which I invest in that versus invest in architectural principles or code reviews or other things has grown…”
Elliott-McCrea: Data tools often validate employee existence rather than drive software
“I actually feel like a lot of the data products that are available today are really like targeting people's need to prove that their work is actually working or validate their existence within a team rather than actually driving the software to Development for…”
Elliott-McCrea: Team complexity scales geometrically with parallel work streams
“Fundamentally, the rule of thumb I use here is your team is your unit of concurrency. And so the number of work streams you want to be solving at the same time is how many teams you need. And so the more things you're trying to do at the same time, the more te…”
Elliott-McCrea: Half of all software engineers joined the industry in the past decade
“You know, if you look at the last 10 years, half of everybody working as a software engineer joined the industry in the last 10 years.”
Elliott-McCrea: Engineering teams could shrink within five years
“I think that over the next 18 months to three years, I actually don't think we'll see substantially different changes, but over the next five years, I could see teams actually getting smaller again.”
Elliott-McCrea: Modern software tools are higher level, not simpler
“We say the abstraction layer has gotten better, but in many ways we are using more sophisticated tools. They have not gotten simpler. They have merely gotten higher level and more productive, but they're not simpler to use.”
Elliott-McCrea: Engineering health should be measured at team level, not individual
“So your unit of measurement for health is at the team level versus the individual level, especially as you scale.”
Elliott-McCrea: Tech employee tenure averaged 18 months over the past decade
“For the last decade, you know, average tenure has been about 18 months in these kind of companies that we're talking about, which means it's very hard to actually build an experiment with culture in the way that we were for a while.”
Elliott-McCrea: 12 reports is the maximum span for effective management
“12 people is sort of the upward limit of where most people can manage effectively. You know, six to 12 with eight kind of being the sweet spot is just kind of how much most people can sort of juggle the amount of context you need for each individual in order t…”
Elliott-McCrea: Software problem timelines range from days to years based on clarity
“One of the things that's really different about software engineering than other types of engineering is the fungibility. Problems can take two days or they can take two years. And the fundamental difference is the excitement and clarity you have around the sol…”
Elliott-McCrea: Slow engineering execution always stems from leadership's lack of clarity
“When I'm going and having these conversations with leaders, and this is, I think the standard conversation most people have is it starts with leadership. If we're moving too slow, it always does. We've always believed that we've been more clear. We've created …”
Elliott-McCrea: Jira is built for control and predictability, not greatness
“Jira is not built for building greatness. You can use it that way. But fundamentally it's about someone who's trying to create a sense of control and a sense of predictability over it while at the same time actually asking to be surprised.”
Elliott-McCrea: OKRs have an undeserved bad reputation and work well
“I hate to say this, but at the most fundamental level, it looks a lot like OKRs, which have a bad rep, but are kind of great.”
Elliott-McCrea: Microservices are often proposed to avoid talking to coworkers
“I think that we see over and over again, technical solutions proposed around the idea of, I don't want to talk to my coworkers. I think microservices is like the canonical example of this, but we see it in all different ways.”
Elliott-McCrea: The tech industry faces a wave of disappointing internal platforms
“And one of the places where we see this really becoming a problem right now, and I think this is downstream of us all having so much success using Amazon, is that we really see the rise again of internal platforms and teams taking dependencies on, on these int…”
Elliott-McCrea: Dropbox's runaway early success created a flawed product development mindset
“Dropbox hit a home run basically out of the gate. And there was kind of an expectation that that's how you built products. And like people came from different places and very different experiences, but pretty deep in the culture was this idea that you build it…”
Elliott-McCrea: Dropbox maintained unified engineering whereas Adobe runs multi-product via acquisitions
“Dropbox was a very unified engineering culture, unified practices, unified technology stack, unified hiring, all of those things. And Adobe is not like, it's just a little bit of a wild west in a way that's kind of crazy. And that's just the history of its of …”
Elliott-McCrea: Company success does not always require high-quality engineering
“I think that one of the things we've realized is that there are actually multiple paths to success and multiple high quality ways to run a team. And that also that some companies
Path to success doesn't actually run through a high quality engineering.”
Elliott-McCrea: Google hires often struggle elsewhere because its internal systems don't replicate
“I think the canonical example of this is Google, by the way. I mean, I think that
Sort of in industry. Now we've kind of learned you hire people out of Google and they show up and they don't know how to operate because they've been such a determined high funct…”
Berson: Modeling startup cultures after Google caused net damage to the ecosystem
“I'd also argue that a lot of people trying to model their orgs and culture after Google has probably created
More damage to our ecosystem than sort of positive outcomes.”
Elliott-McCrea: Senior leaders get roughly six months before inherited problems become their fault
“There's sort of this interesting window where you get about six months and then it's your fault. I mean, that's my standard deal with anyone senior is you get about six months and then it's your fault. And that's just as true when you're Coming in and it is ea…”
Elliott-McCrea: Leaders should not automatically bring former colleagues into new organizations
“One of the things that people ask me is you look like you've worked with a bunch of great people. Like, do you just like bring them with you to every organization? And the answer is, of course not. Like every organization is different and partially I need the …”
Elliott-McCrea: Leaders build trust by publicly adopting employee language and ideas
“And so in your public communications, people are looking to see if you adopted their language, their ideas, that sort of stuff, because that's how you build trust. You know, you actually were listening, you trusted, you updated your ideas, you incorporated the…”
Elliott-McCrea: Detachment is critical for senior leaders to avoid burnout
“And I actually do think that a certain amount of detachment is actually pretty critical as you become a senior leader and the people who don't learn that Detachment are the ones who either fry or end up trying to micromanage a system that's too complex for the…”
Elliott-McCrea: Shielding engineering teams from company chaos causes them to misalign
“Actually, one of the early stereotypes about engineering managers in our industry is as the shit umbrella, you know, just gonna keep people from being distracted by all the crazy. And what that is, is those teams end up just drifting off. You know, you talk ab…”
Elliott-McCrea: Pitting a team against others easily manufactures strong identity
“One of the easiest hacks for creating strong identity as a team is to put the team in a combative situation.”
Elliott-McCrea: Building businesses has gotten harder while software has gotten easier
“Building new businesses has gotten harder, even while software has gotten easier.”
Elliott-McCrea: Stack ranking and firing the bottom 10% damages company culture
“I'm not doing a sort of a stack rank and cutting the bottom 10% ever, because I think it has other problems with the culture that it creates.”
Elliott-McCrea: Companies must adapt for juniors; senior hires must adapt themselves
“The more junior somebody is, the more it is your responsibility to make it work for them. And the more senior they are, the more it is their responsibility to figure out how to adapt and to identify that they are in the wrong place.”
Elliott-McCrea: Most common leadership failure is not teaching engineers business context
“I think the most common failure I see is people failing to teach Their engineering teams or their product and engineering teams, how to think about the business they are in.”
Elliott-McCrea: Etsy ran many bad experiments because internal statistical understanding was poor
“At Etsy, it was about understanding experimentation beyond just AB. Like, we were a very experimental heavy company, but we did a lot of bad experiments because our statistical understanding was poor.”
Elliott-McCrea: Dropbox historically avoided internal financial discussions
“At Dropbox, Dropbox didn't ever care to talk about money. And so understanding, like, let's go with the basic unit economics. How much does a gigabyte of storage cost? I'm not going to answer that question because that's, you know, a secret for Dropbox and it'…”