What I Learned in My First Year as CTO: 14 Hard‑Earned Lessons

My Software Engineer Career

2005‑2008: Software Engineer

2008‑2012: Senior Software Engineer

2013‑2014: Chief Technical Expert

2014‑2019: Chief Engineer/Architect (also Director)

2020‑present: Chief Technology Officer (first leadership role)

Transitioning from individual contributor to CTO brought both pressure and responsibility, prompting a search for guidance that ultimately proved nonexistent.

What Is a CTO?

Matt Tucker’s framework describes a CTO with five characteristics; most CTOs combine two or more of these traits. My role differs because I work for an IT‑service company, which adds fragmentation and extra challenges.

Key challenges in an IT‑service organization:

People are the most valuable asset; growth ties directly to headcount, yet attracting top engineers is hard.

Clients demand cutting‑edge technologies (React, Golang, Flutter, Cloud, Kubernetes) but often underestimate the cost of adoption.

Experienced engineers are scarce and expensive, especially for service firms.

I adapted Tucker’s model to fit my context and estimated the time I spent on each area during the past year.

First‑Year Lessons Learned

1. Believe in Yourself and Pursue the Role

Many engineers aspire to be CTO, but promotion requires proactive effort; I spent 2‑3 years preparing while fearing the Peter Principle.

“Most people miss opportunities because they are shy to ask.” – Steve Jobs

2. Plan Your Time Wisely

After drowning in meetings, I carved out dedicated hours for deep work, switching between maker and manager schedules and declining unnecessary meetings.

3. Delegate, Don’t Do Everything Yourself

Effective delegation follows Jenny Blake’s “6T” taxonomy (Tiny, Tedious, Time‑consuming, Teachable, Terrible‑At, Time‑Sensitive) and a seven‑level delegation ladder (Tell, Sell, Consult, Agree, Advise, Inquire, Delegate).

4. Reduce Chaos

Leaders must clarify problems and produce actionable plans, using questions, concise todo lists, performance monitoring, and thorough documentation.

5. Show Discontent When Needed

Expressing justified dissatisfaction signals expectations and drives accountability without becoming emotional.

6. Learn from Others’ Mistakes

Observing peers’ failures helps avoid repeating them and accelerates personal growth.

7. Accept That You Don’t Have All Answers

Provide a structured template for problem reporting so teams take ownership of solutions.

8. Recognize That Your Mentees May Leave

Training engineers often leads them to product‑focused companies, which is natural but highlights the talent pipeline challenge.

9. Code, but Don’t Over‑Commit

Balance coding with higher‑level responsibilities; pair‑program when needed and focus on code reviews and design.

10. Quality Is Rarely the Top Priority for Clients

Clients often prioritize speed and cost over quality, making it essential to manage expectations and protect product standards.

11. Maintain Professional Distance

Higher positions bring isolation; leaders must balance personal relationships with objective decision‑making.

12. Choose Battles Wisely

Use Camille Fournier’s decision‑making flowchart to focus on high‑impact problems.

13. Keep Momentum Without Becoming a Bottleneck

Make incremental improvements and recognize when to defer or reverse decisions, distinguishing reversible from irreversible choices.

14. Own the Impact of Your Words

Take responsibility for decisions and communicate transparently to avoid being forced into unwanted actions.

Original source: https://shekhargulati.com/2021/01/03/being-chief-technology-officer-lessons-learned-in-my-first-year/