Here’s the cruel irony of technical leadership: the best technical leaders are promoted precisely because they were exceptional engineers, but the act of promotion itself guarantees they will soon become unfit to make hands-on technical decisions. The very skills that earned them the corner office are the ones that will decay fastest once they’re no longer writing code every day.
Software technology operates on a different timescale than most industries. In software, 12 months is an eternity. What was cutting-edge architecture last year is today’s technical debt. The framework that solved everything in 2023 is the legacy system holding teams back in 2025. This velocity creates a unique trap for engineering leaders: a technical background is a starting point, not a permanent credential for decision-making. The core requirement for technical leadership isn’t maintaining expertise — it’s knowing when to stop imposing technical opinions.
The Velocity Problem: Software’s Time Compression
The pace of change in software development is relentless. We swung from monolithic applications to microservices (hey, that’s how Google does it!), and now the industry is moving back toward (modular) monoliths. Frontend frameworks have cycled through jQuery to Angular to React to Vue to Svelte, each promising to solve the problems the previous one created. Infrastructure has shifted from on-prem to cloud to serverless, with new paradigms emerging faster than anyone can fully adopt the last one.
This creates a brutal reality for technical leaders: if a leader hasn’t written production code in the last 18-24 months, their knowledge is likely at least two generations behind. The patterns they mastered are now considered technical debt. The tools they championed have been replaced. The architecture they designed is the legacy system the team wants to refactor.
The problem isn’t laziness or lack of interest — it’s simple math. As managers, most of their time must be dedicated to people, finance, strategy, and hiring. They simply cannot maintain the 40+ hours per week of deep technical immersion required to stay sharp. They’re making a trade-off, and that trade-off means their hands-on technical expertise has an expiration date.
The Failure Mode: Overconfidence and Imposition
Technical leaders often feel they must validate their promotion by participating in tactical decisions. They want to prove they’re still “technical” by weighing in on database design, framework selections, or architecture patterns. Their past success blinds them to their current knowledge gap, and they impose solutions based on expertise that expired years ago.
The Executive as DBA
An executive with an database background from their developer days decades ago insists on a particular table structure using a relational database, completely unaware of the other options (Event sourcing, document stores, graph DBs, etc.) because that’s how it was done 20 years ago. Even if the design is “correct”, the decision removes technical autonomy from the people who will actually build and maintain the system.
The Microservices Obsession
Executive fascination with trends often lags the engineering community by years. I’ve often wondered about the particular attraction of microservices to both non-technical and technical business people. They’ve evidently missed the recent backlash: the complexity, latency, operational overhead, “undebug-ability”, and maintenance cost of poorly designed microservices that have burned so many projects to the ground is not on their radar yet. There’s a misapprehension of the difficulty of reversing of this kind of change, and the nightmare scenario that occurs when you get the boundaries wrong. They’ve never heard the first rule of distributed systems, “don’t distribute your systems,” which is only slightly misquoted but is correct 9 times out of 10. They also seem to get the (potential) benefits wrong (it’s a lot more about forcing independence of teams than “scalability”).
The same pattern repeats with blockchain, AI tooling, and every other hyped technology. Executives read an article about some trend, and suddenly it becomes a strategic initiative. The team, who have been living with the real-world trade-offs, are forced to implement solutions they know are wrong for the current context.
Here’s the rule: if the decision is purely technical — database choice, architecture pattern, specific framework — the leader’s role is to ask questions about trade-offs, not provide answers. The job is to understand the business implications, not to dictate the technical implementation.
What’s Needed: Humility, Deference, and Delegation
The shift from technical expert to technical leader requires a fundamental identity change. A great technical leader transitions from being the person who knows the answer to being the person who facilitates finding the right answer.
Deference is strength. True leadership is having the humility to say: “I don’t know the current best way to do this. I trust the team we hired to make that call.” This isn’t weakness or abdication of responsibility. It’s recognition that a leader’s value now comes from scaling the team’s expertise, not from being the smartest person in the room.
A technical background is valuable because it allows leaders to understand risk and scope, to ask intelligent questions, and to recognize when something sounds wrong. But it becomes lethal when it translates into tactical imposition. Expired expertise, confidently applied, will create the very problems leaders are trying to solve.
The best technical leaders I’ve worked with weren’t the ones who stayed current on every framework — they were the ones who stayed curious, stayed humble, and trusted the experts they hired. At the end of the day, building software is a people problem anyways.
A technical background gets leaders to this position. Humility and deference determine whether they succeed.