The difference between good and great engineering organizations isn't technology — it's people. As CTO, you're responsible for creating an environment where talented engineers can do their best work.
Hiring Engineers at Scale
Hiring is the highest-leverage activity a CTO does. One great hire can transform a team; one bad hire can poison it. Yet most companies approach hiring haphazardly.
Building a Hiring Process
1. Define What You're Looking For
Before posting a job, get specific about what you need. Not just skills and experience — what problems will this person solve? What does success look like in 6 months? What traits predict success in your environment?
Generic job descriptions attract generic candidates. Be specific about your company's unique context.
2. Design Your Interview Process
Your interview process should:
- Evaluate candidates consistently (structured interviews beat unstructured)
- Test for actual job skills (not puzzle-solving ability)
- Give candidates a realistic preview of the work
- Respect candidates' time (marathon interviews lose good candidates)
- Reduce bias (diverse interview panels, blind resume reviews)
3. Evaluate Holistically
Technical skills are necessary but not sufficient. Also evaluate:
- Problem-solving approach: How do they think through unfamiliar problems?
- Communication: Can they explain complex concepts clearly?
- Collaboration: How do they work with others? Take feedback?
- Growth mindset: Are they curious? Do they learn from mistakes?
- Values alignment: Will they thrive in your culture?
The Technical Interview
Technical interviews are notoriously bad at predicting job performance. Here's how to make them better:
✅ Do
- Use problems similar to real work
- Allow candidates to use their preferred tools
- Focus on problem-solving process, not just output
- Ask follow-up questions to understand thinking
- Give candidates time to ask questions
- Provide feedback to candidates who ask
❌ Don't
- Use puzzle questions or brainteasers
- Require memorized algorithms
- Trick or stress candidates deliberately
- Let interviewers go unprepared
- Evaluate on whiteboard handwriting
- Ghost candidates after interviews
💡 Consider Work Samples
The best predictor of job performance is a sample of actual work. Consider paid trial projects (1-2 days), take-home assignments (with time limits), or pair programming on real problems. These are more predictive than whiteboard interviews and often more pleasant for candidates.
Closing Candidates
Getting candidates to accept offers is a skill. Great candidates have options.
- Move fast: Slow processes lose candidates to faster companies
- Sell the opportunity: What will they learn? What impact will they have?
- Be transparent: Don't oversell. Honest assessment builds trust
- Personalize: Different candidates care about different things
- Involve the team: Candidates want to meet future colleagues
Building Engineering Culture
Culture is what happens when you're not in the room. It's the unwritten rules that guide behavior. As CTO, you're the primary culture carrier for engineering.
Elements of Engineering Culture
Psychological Safety
Team members must feel safe to take risks, ask questions, and admit mistakes. Without psychological safety, people hide problems until they become crises, and innovation stalls.
How to build it: Admit your own mistakes publicly. React calmly to bad news. Thank people for raising concerns. Never punish the messenger.
Ownership & Autonomy
Engineers do their best work when they own outcomes, not just tasks. Give teams clear goals and let them figure out how to achieve them.
How to build it: Define success clearly, then step back. Resist the urge to dictate solutions. Celebrate initiative even when it fails.
Technical Excellence
High standards for code quality, testing, and documentation pay dividends over time. But excellence doesn't mean perfectionism — it means consistently good work that improves over time.
How to build it: Code reviews, clear standards, investment in testing infrastructure, and celebrating good engineering practices.
Continuous Learning
Technology evolves constantly. Engineers who stop learning become obsolete. Create an environment that encourages growth.
How to build it: Learning budgets, conference attendance, internal tech talks, time for exploration, book clubs, mentorship programs.
⚠️ Culture Is Set by Behavior, Not Posters
Values on the wall mean nothing if leadership doesn't model them. If you say "work-life balance" but reward people who work 80-hour weeks, your real culture is overwork. If you say "learning is valued" but never give people time to learn, your real culture is pure execution. Watch what you actually reward and punish — that's your real culture.
Performance & Growth
Your job is to help every engineer reach their potential. That requires clear expectations, regular feedback, and growth opportunities.
Engineering Ladders
A career ladder defines expectations at each level and provides a path for growth. Good ladders include:
- Clear levels: Junior, Mid, Senior, Staff, Principal, etc.
- Defined expectations: What does someone at each level do?
- Multiple dimensions: Technical skill, scope, leadership, communication
- IC and management tracks: Not everyone should become a manager
- Examples: Concrete examples of what each level looks like
One-on-Ones
Regular 1:1s are your most important management tool. They're for the employee, not for you.
Effective 1:1 Structure
- Frequency: Weekly for direct reports, bi-weekly for skip levels
- Duration: 30-60 minutes
- Agenda: Let the employee drive it
- Topics: Their concerns, growth, blockers, feedback — not just status updates
- Notes: Keep notes to track patterns and follow up
Giving Feedback
Most managers give too little feedback, and what they give is too vague. Feedback should be:
- Timely: As close to the event as possible
- Specific: "In yesterday's meeting, when you interrupted Sarah twice..." not "You need to communicate better"
- Behavioral: Focus on actions, not personality
- Balanced: Include positive feedback, not just corrections
- Actionable: What should they do differently?
Retention Strategies
Losing good engineers is expensive — both the direct cost of hiring and the productivity loss. Prevention is better than cure.
Why Engineers Leave
The most common reasons:
- Management: "People leave managers, not companies"
- Growth: Feeling stuck with no path forward
- Compensation: Below market, especially at growing companies
- Impact: Work that doesn't seem to matter
- Culture: Toxic environments, lack of psychological safety
- Work-life balance: Burnout and unsustainable pace
Retention Practices
Stay Interviews
Don't wait for exit interviews. Regularly ask employees: "What keeps you here? What might cause you to leave? What could we do better?" Address issues before they become resignation letters.
Career Development
Help people see a future at your company. What's their next role? What skills do they need? What opportunities can you provide? Engineers who see growth stay longer.
Compensation Reviews
Review compensation proactively, not just when someone has an offer in hand. Market rates change. Recognize growth. Waiting for counteroffers is too late — and signals you'll only pay market rate under duress.
Recognition
Public recognition for good work costs nothing and means a lot. Celebrate wins, acknowledge effort, and say thank you. Simple but often neglected.
Difficult Conversations
Leadership includes having hard conversations: performance problems, interpersonal conflicts, organizational changes, and sometimes terminations.
Performance Conversations
When someone isn't meeting expectations:
- Be direct early: Don't wait for formal reviews. Address issues promptly.
- Be specific: Clear examples, not vague concerns.
- Agree on expectations: What does good look like? By when?
- Provide support: What help do they need to improve?
- Document: Keep records of conversations and agreements.
- Follow through: Check in regularly. Recognize improvement or escalate.
When It's Not Working
Sometimes, despite effort, it doesn't work out. Letting someone go is never pleasant, but keeping a poor fit hurts everyone — the team, the company, and the individual.
💡 The Two-Year Regret Test
Ask yourself: "If this person is still here in two years, unchanged, will I regret not acting today?" If yes, it's time to act. Waiting rarely makes these situations better.
Key Takeaways
- Hiring is your highest-leverage activity — invest in a great process
- Culture is defined by behavior, not statements. Model what you expect.
- Regular 1:1s and specific feedback are essential management tools
- Retention starts before someone considers leaving
- Have difficult conversations early — waiting makes them worse