From tools developer to CTO: Lessons learned scaling a dev team

The transition from being an individual contributor writing code daily to leading teams and products is a gradual journey filled with lessons. As a former software engineer turned CTO at a high-growth startup, I've experienced first-hand the challenges and mindset shifts required in scaling up from code monkey to tech leader. Here are some of the key lessons I've learned along the way that may help other programmers stepping into leadership roles navigate this path.

From Coder to Leader: The Journey of Growth

Going from working solo on projects to managing a team and overseeing a broader product vision required fundamental changes in my day-to-day work. I had to move away from the comfort of heads-down coding to focusing on the bigger picture strategy. This involved letting go of perfectionist tendencies and learning to delegate tasks rather than doing everything myself.

Some of the main adjustments I had to make:

• Shifting my mindset from the tactical details to thinking long-term and strategically about product and team direction. Considering the downstream impacts of decisions was an important skill to develop.
• Switching from solely individual contributor work to providing oversight across projects, guiding the team vision, and coaching teammates. Learning to motivate others and resolve conflicts was critical.
• Moving away from micromanaging and perfectionism. I couldn't attend to every minor detail anymore. I had to allow autonomy and avoid bottlenecks.
• Leveling up communication, collaboration, and people management abilities. Technical skills were no longer sufficient. I needed to inspire, influence, and connect on an interpersonal level.
• Taking a growth mindset focused on continuous improvement over chasing perfection. As long as progress was being made, it was more beneficial to ship and iterate.

Laying the Groundwork: Preparing for Leadership

Before taking the reins in an official leadership capacity, I took small steps over time to develop the necessary skills.

• Seeking out mentors within the organization who could provide guidance on growing my management abilities. Their insights were invaluable.
• Taking on minor leadership opportunities like running meetings or guiding an intern to get exposure to overseeing others.
• Improving communication by presenting at company meetings and taking writing courses. Being able to articulate ideas persuasively was essential.
• Practicing delegation by handing off appropriate tasks to teammates to empower them, even though it was faster to do them myself. Building trust in others was key.
• Enrolling in leadership training programs to learn core management concepts around team building, goal setting, project planning, and group dynamics.

Laying this groundwork of basic skills gave me confidence that I could handle greater responsibilities when the time came.

Stepping Up: Handling New Responsibilities

Once I moved into an official management role, I had to step up and apply those foundational skills I had developed. Key areas of focus included:

• Providing direction by setting a clear product vision and strategy tied to company goals like increasing customer retention. Giving context around the why and where we were headed.
• Managing resources across projects and guiding prioritization and scheduling to meet deadlines and dependencies.
• Coaching teammates 1-on-1 and giving constructive feedback on how they could grow. Celebrating wins and improvements.
• Resolving any conflicts through compromise rather than top-down decrees. Listening first, then deciding as a team.
• Representing my team in cross-functional meetings with heads of design, marketing, and sales. Advocating for their needs.

There were certainly bumps along the way, but by proactively seeking insights from mentors and peers I was able to work through the hard times.

Adapting Your Mindset: Thinking Like a Leader

Evolving my mindset from individual contributor to leader was critical but challenging. It required developing new mental muscles.

• Moving away from a focus on individual tasks to a broader strategic perspective on goals, timelines, and resource allocation.
• Balancing perfectionism tendencies with the need to ship and iterate. The perfect is the enemy of the good.
• Exercising emotional intelligence, empathy, vulnerability, and intuition in working with people. Technical skills weren't enough.
• Cultivating a growth mindset and focus on progress. Judge myself and the team based on improvement, not perfection.
• Letting go of control while still providing guidance and oversight. Trusting in my team’s abilities.
• Fostering psychological safety where team members feel comfortable sharing opinions without fear of retaliation.

This mental shift was the most difficult but also most crucial part of evolving as a leader. It’s an ongoing process.

Leveling Up Your Soft Skills: The Human Element

As my management responsibilities grew, I quickly realized that soft skills were paramount to success as a leader.

• Communication: Listening first, then clearly conveying plans and explaining the rationale behind decisions. Combining empathy and logic.
• Motivation: Recognizing great work and wins. Explaining how each person's contributions ladder up to company goals.
• Delegation: Handing off appropriate tasks and empowering others to develop. Providing guidance but avoiding micromanagement.
• Feedback: Offering regular coaching and constructive suggestions focused on growth, not criticism.
• Trust: Admitting mistakes, being vulnerable and keeping confidences to build credibility and reliability.

Developing these soft skills enabled me to connect with teammates on an interpersonal level and lead much more effectively. Technical expertise alone was no longer sufficient.

Continuous Growth: What Comes Next

As a leader, complacency is dangerous. I must model the growth mindset I aim to cultivate in my team.

• Continuing to learn and improve by reading industry blogs/newsletters, taking online courses, attending conferences, and participating in local meetups.
• Expanding my network of peers and mentors across the industry to gather diverse perspectives.
• Reflecting on mistakes and feedback to grow my self-awareness and humility.
• Relentlessly advocating for my team externally while constructively challenging them internally.
• Paying my experience forward by mentoring new leaders and emerging talent.

Leadership is a never-ending journey. To be effective, I must keep evolving. The day I stop learning is the day I start falling behind.

Key Takeaways: Essential Lessons for New Leaders

For software developers transitioning into leadership, here are some of the key lessons I've learned:

• Take on leadership responsibilities progressively over time. Build skills incrementally.
• Soft skills like communication and empathy are just as crucial as technical expertise. Develop emotional intelligence.
• Guide with vision and strategy, not top-down control. Enable autonomy balanced with accountability.
• Invest time into mentoring and developing your team members. Delegate to empower others.
• Stay humble and hungry to keep learning. Surround yourself with diverse mentors and peers.

The road from coder to leader will have its challenges, but by keeping these principles in mind, you can navigate the obstacles and guide your team to the next level. With a growth mindset focused on progress and a commitment to developing both your hard and soft skills, you’ll be prepared to lead effectively. Keep learning, keep reflecting, and keep evolving. Platforms like DevHunt can help you discover new tools and technologies to aid in your learning and development as a leader.