The Real Cost of Moving into Engineering Leadership

Every engineer who steps onto the leadership track eventually hits the same wall: the calendar fills with one-on-ones, performance reviews, staff meetings, and cross-organizational coordination. Blog posts, emails, and career ladder development consume the hours that used to go into system design and debugging. The truth is simple—you end up being less technical if you choose the leadership track. There's no way around that reality.

That's why the decision to leave the Individual Contributor (IC) track has to be intentional. The two tracks mirror each other all the way up, from engineer to distinguished engineer on one side, and from manager to CTO on the other, and both carry similar prestige and influence. In fact, ICs at many companies often hold more power than their leaders do. If you're moving into leadership expecting to gain technical depth, you'll be disappointed. You have to genuinely love managing people—waking up and hoping to be more technical in a leadership role than you were as an IC isn't realistic.

There are also personnel dynamics to confront. Former peers become reports. As much as you try, those relationships change, and you may need to alter someone's career trajectory, shift their role, or even manage them out. Doing that professionally while respecting their technical ability and their humanity is part of the job.

But once you're leading, a harder question emerges: how do you earn credibility with teams whose technical depth now exceeds your own? It's a challenge for any CTO leading engineers who are far more detailed and technically sophisticated. Without that credibility, gaining buy-in for strategy and vision becomes significantly harder.

Read Everything You Can Get Your Hands On

A CTO job is a tough road if you don't like to read. But if you genuinely don't have time, there's a workaround: podcasts at 1.5–2x speed. Either way, you need to consume data outside of meetings and absorb it quickly.

When you have a question about how something works in your organization, go read the code and documentation yourself. Spend time on GitHub reading commits, examining test results, and checking whether releases are happening properly and on schedule. This isn't just about learning—you'll also see the coding and documentation patterns across teams and can share thoughts on best practices. Ask peers for one or two things to read each month; there's always a new source of information to discover.

Keep Coding, But As a Hobby

A large company does not want its CTO consistently pushing new code to production. That's not a good sign for the organization. But as a leader, you still need to know how to code and stay current on dev tools.

Shopify's move to cloud-based development environments with the internal tool Spin makes this feasible. Running spin up shopify provisions a cloud instance, checks out the largest repos, and sets up runtime permissions in about 30 seconds. The next command, spin code, opens VS Code (or your preferred editor) directly in the repo. It's a straightforward way for a CTO to get hands-on with the same toolchain engineers use daily.

Approach coding as a hobby rather than a production responsibility. Work on side projects that won't necessarily ship to production repos. This builds awareness of the continuous integration (CI) tests, continuous deployment (CD) pipelines, and the broader development environment your engineers see every day. That insight is invaluable for staying technical and understanding your team's daily work.

Join Hackathons, Internally and Externally

Hackathons offer another avenue to stay engaged. Shopify runs multi-day internal events called Hack Days where projects are built, reviewed, judged, and given feedback across the organization. Being involved keeps you informed about upcoming innovations and the products being built for merchants.

External events work too. Shopify sponsors Technovation, a program for girls and young women (ages eight to 18) who build apps to solve real-world problems. Reviewing code and scoring projects as a judge puts you directly in the technical details while supporting STEM education.

Hire Well, and Reap the Technical Benefits

Running a team takes an enormous amount of time, and the wrong people in the wrong roles makes it worse. When leadership gaps appear, the temptation is to fill them quickly and take shortcuts because hiring is slow. Resist that.

Hiring with intention pays off technically. Good technical people can teach you things faster than you can read about them. Shopify has made a significant commitment to WebAssembly, so the company hired engineers who are versatile with that technology. It also employs several Rails Core Team members and committers.

When you need details on these or hundreds of other technologies, a well-built team means you can read a Slack channel, join a technical review, or spend a few minutes with someone more technical than you and absorb the essentials quickly. Great engineers enjoy discussing their projects. Wrong hires, by contrast, pull you into performance reviews and HR meetings—time that can't be spent reading, coding, or learning.

Build a Personal Tech Advisory Board

A wider perspective on where technology is heading is invaluable, even with a strong internal team. One approach is creating a private Slack channel with roughly 20 senior engineering leaders, both internal and external to your company.

This is a space to ask questions, be vulnerable about what you don't know, and request industry-specific guidance. Whether it's a new technology your teams have mentioned, a hot upcoming trend, or very specific questions about using a given technology at scale, the rules of engagement stay simple: ask, be helpful, and share.

Backlog Discipline Keeps You Technical

Operational issues are the silent killers of a CTO's technical edge. Outages, downtime, and an ever-growing backlog will pull you out of architecture and product strategy and into the tactical weeds of incident management. Every remediation action item and post-mortem follow-up chases you further from the codebase.

The fix is routine maintenance. Teams should be grooming their backlogs weekly at minimum. As CTO, you need to know the remediation items from the latest incidents and push aggressively for resolution. The goal is to drive teams so they can innovate without being buried under tech debt.

There is no launch without operational fallout. A product, feature, or service goes live, and issues surface. At that point the balance between fixing what broke and building what's next becomes the central question. Ignore the operational side and it compounds, consuming more time each cycle. Before long, you're a tactical firefighter, not a technical leader.

Getting ahead of bugs and remediation items, then explicitly allocating time for both innovation and tech debt, is what preserves your capacity for the work that matters. It is the difference between leading engineering and being led by your incident queue.

The Habits That Keep You Hands-On

Sustaining a technical edge as a CTO is a deliberate practice, not a side effect of the role. The reliable path includes continuous reading, regular time spent coding and reviewing source code, and using hackathons to keep the work enjoyable. Hiring well compounds those efforts. A trusted team of senior advisors who can challenge your thinking and share the load lets you stay engaged with the technology rather than drowning in process.

None of this is easy, and it's always evolving. If you have techniques that work for you, the author is open to hearing them on Twitter at @leinwand.