Engineering Leadership (CTO Checklist)
Definition
A working inventory of what an engineering leader is accountable for, organized as People / Processes / Technology.
The premise that makes it useful: “Head Of” roles differ mainly in scope, not in kind. If CTO is the broadest of them, then any aspiring engineering leader can read the CTO list and identify the subset that applies to their current role — and start small, delegating the rest.
Core Ideas
People
Your team
- Develop your leaders — the best leaders develop the team to the point that their own position can be handed to one of them (Level 5 leadership).
- Delegate to your leaders.
- Stay in touch with the whole org: meet individual teams and listen; run skip-level 1-1s across a broad range.
- Lead with trust and transparency.
Personal development — the infrastructure, not the intent:
- A documented career ladder, with good definitions per level including examples of meeting and exceeding expectations.
- A technical training matrix with expectations per role.
- A management training program.
- Every single person has a career path and a development plan to get there.
- A robust, transparent performance review process.
- Feedback given promptly and constructively throughout the year — no surprises at annual review time.
Exec team
- Invest in relationships with key execs.
- Understand the company’s key opportunities and challenges.
- Contribute to company strategy — and ensure a tech strategy exists that supports it.
Delegation
- Be explicit about what you own vs what you delegate.
- Set clear expectations when delegating.
- Use delegation as a growth opportunity, not just load-shedding.
Culture
- Develop psychological safety by leading by example.
- Enable innovation by setting guard rails and pushing decision-making down.
- Move at the right speed — not too fast, not too slow.
Networking — the structural problem of the role: you have no CTO peer inside the company.
- Find CTOs at other companies and speak to them regularly.
- Present at public events (paying it forward, raising the company profile).
- Write occasionally, e.g. on the company tech blog.
Processes
Hiring
- Move fast — you cannot hire the best candidates slowly.
- Build a team whose priority is hiring.
- Consistent interviews (different questions, clear shared goals) and consistent expectations per role.
- Plan ahead for open roles; market the company.
Scaling
- Know the roles needed to support company growth, and the team structure that supports it.
- Know how many member changes a team can tolerate in a year.
- Be prepared for the culture transition: from a small company where everyone knows each other and the rules live in people’s heads, to a large one where teams work independently and the rules are written down.
Getting shit done
- Identify the people who can actually get things done (e.g. in Product) and build relationships with them.
- Have a clear vision and a strategy for realizing it.
- Build momentum with a constant stream of delivery — and make sure those small frequent deliveries add up to the larger goals.
Budget
- Know it, know where it’s going, and share it with your teams.
- Give teams a budget where possible — push decisions down.
Change
- Have a robust company-wide change process (e.g. the DACI framework).
Technology
Architecture — documented: high-level principles (what and why), guard rails (goal: autonomy with alignment), golden paths for common needs (e.g. distributed tracing), coding standards.
Data — guidelines for source data / data lake / warehouse, the process for moving data between them, and a top-level warehouse schema.
Security — application (OWASP Top 10), network (principle of least privilege), ongoing testing (pen testing, white-hat programs like Bugcrowd, vulnerability scanning, static analysis), and compliance.
Software delivery — developer tooling and IDEs, source control, build processes, release pipeline, observability, pre-prod environments.
Infrastructure — infrastructure-as-code; dev / sandbox / prod environments.
Delivery monitoring — DORA metrics; a developer-productivity tool.
Testing and quality — documented expectations: static analysis, merge-request expectations, QA processes, and testing expectations covering coverage levels, test execution time, test plans in dev and prod, and defect density.
Developer productivity — DORA metrics to understand it, explicit attention to feedback loops, and dedicated people or a team for it.
SRE — an ops/SRE function, monitoring and alerting, SLAs/SLOs/SLIs, incident response procedure.
Documentation — best practices, guard rails, projects, APIs and UI applications.
Industry trends — have an actual process for staying current, not an intention.
The two tools against the size of the list
The full surface is daunting by design. The author’s counter: start small and delegate — and surround yourself with people smarter than you.
Relationships
- Developer Productivity Measurement — the “developer productivity” line item done properly: Goals-Signals-Metrics, not DORA alone
- Measurement Dysfunction — the risk attached to DORA/defect-density targets once they become goals
- RACI Model — the responsibility-assignment counterpart to the delegation section
- Widget Factory vs Film Crew — which culture the guard-rails-and-push-decisions-down stance implies
- Observability · Cloud Security — two technology line items with their own pages
- Legacy Systems — what the architecture and documentation items are defending against
- Problem Finding — how the roadmap items on this checklist get discovered in the first place
- Talent Retention — the salary-compression cycle, and the five levers that break it
- Work Culture & Management · Coaching and Manager Development
References
- CTO Checklist
- Level 5 Leadership — HBR · DACI framework · DORA metrics