From Engineer to CTO: Navigating the Rocky Road

· 5 min read
From Engineer to CTO: Navigating the Rocky Road

Sam Carow’s path to becoming a CTO was anything but straightforward, according to her post on Reddit I stumbled upon. In fact, her story is marked by plenty of twists, turns, and tribulations. But it’s also full of grit, growth, and girl power.

Sam started fresh out of college, chasing the prestige and paycheck of a corporate sales job. But she quickly realized she was downright miserable as a salesperson. So when she quit after 9 months, she had a backup plan.

With nowhere to go but up, Sam started applying to every restaurant in her New York City neighborhood until she finally landed a waitressing gig. It wasn’t glamorous, but it paid the bills.

While waiting tables, she taught herself to code, applying on a whim to a 3-month coding boot camp. The program was an enormous struggle for Sam. She cried almost daily, barely passed, and emerged without a clear path forward.

But Sam didn’t let self-doubt stop her. She started emailing startups with tiny bug fixes, earning a junior engineering role through sheer persistence and hustle. She even couch-surfed at the office for weeks until her first paycheck hit.

Over the next decade, Sam leveled up her skills, going from total coding newbie to senior engineer at Reddit. She founded an internal development program for women and minorities, spoke at major conferences, and led multiple teams.

Sam never pictured herself as founder material until a text from an old friend offering her the CTO role at his startup. This made her realize she had what it takes all along.

After months of vetting the business idea, Sam took the leap. Today, she’s living the dream as CTO and co-founder of her own company.

Sam’s story offers hope that anyone willing to hustle hard and believe in themselves can make it in tech. Her journey may have taken some unexpected detours, but Sam proved her skills and heart can take her anywhere.

Challenges of Transitioning to a CTO Role

I can only imagine how challenging Sam’s path was. For many engineers, it’s a much smoother sail. Yet, transitioning into the CTO role from an engineering role is quite challenging, even for the best of us. One of the main difficulties is the shift in focus from hands-on technical work to a more strategic and managerial approach. As engineers, we find it difficult to let go and gain the required soft skills. Here are a few areas to focus on if you transition to a CTO role.

Communication and requirements management

Misunderstandings due to poor communication can and will quickly derail a project. It’s quite common for the product manager to request a new feature without providing enough specifics. The engineering team then builds something that misses the intent. This results in wasted effort and delays.

Clear and ongoing communication is vital. Requirements should be documented in detail and go hand in hand with design mockups. The team must also regularly sync up to stay aligned. Cultivate a collaborative culture where everyone feels comfortable asking questions to minimize misalignments.

Estimating project timelines and costs

It’s easy to underestimate how long feature implementation will take. We are often overly optimistic or bow to pressure to deliver quickly, resulting in overwork and degraded quality. I once promised a major release in 6 months when I started as a CTO while the team was still inexperienced with Node.js. After several months, we were badly behind schedule and the team was burning out from the pace. I never repeated that mistake.

As managers, we must challenge optimistic assumptions and build room for the unknown. Taking a data-driven approach based on past metrics and adding multiples helps a lot. If the timeline is compressed, the only solution is to get more people to offset the increased workload (which comes with other challenges).

Team composition and skill development

Building a cohesive team with balanced skills is an art and science. For instance, a group of only senior engineers may lack creativity and refuse to adopt new approaches, while too many juniors make slow progress. When hiring, look for complementary strengths. Mix proactive self-starters with team players.

Make sure to spot underperformers and help them grow through training and mentoring. Build connection through offsites and team-building activities. Become aware of interpersonal dynamics. And, of course, create consistent code standards and processes before it’s too late to get everyone on the same page on the tech side.

Adapting to new technologies and maintaining legacy systems

The tech landscape changes quickly. There’s a lot of pressure to adopt the latest and coolest tools. But, you’ll soon learn that legacy systems are tough to replace or update. The codebase is often too large and complex to the point where risks and costs outweigh the benefits. We once considered migrating a large codebase from JSON-API resources to GraphQL, which could introduce major revenue issues, so we decided to keep the legacy system intact.

Analyze tradeoffs carefully when evaluating new tech. Come up with a roadmap for gradual modernization. Look for ways to split monolithic legacy code into independent modules. Most importantly, build expertise in both old and new systems when scaling the team.

Software quality and bug management

Bugs are a fact of life, but they often degrade the user experience. Chaotic bug tracking leads to fix delays, so ensure you have a streamlined process and prioritize them right. Without supervision, a single engineer may try to juggle dozens of open tasks in a single sprint, causing delayed feature delivery and bugs slipping through the cracks.

Perform frequent code reviews, and make sure you test well and monitor each release. Set SLAs for resolving priority bugs for the user’s peace of mind. Build a dedicated QA team instead of relying on engineers to test their own work. Conducting post-mortems on major issues to prevent recurrences and learn from bugs.

Organizational culture and management styles

Developers thrive in environments with psychological safety and autonomy, yet both are hard to achieve because of the nature of our work. Micromanagement stifles productivity, but it’s widespread across the industry.

An authoritarian manager demanding status reports and second-guessing every decision will seriously undermine morale. On the other hand, being entirely hands-off can lead to chaos. The ideal is an empowering culture with guidance when needed.

Great managers should set goals and let engineers choose how to achieve them. Provide mentoring and feedback rather than directives. Coach self-organization and problem-solving instead of imposing solutions.

Work-life balance and stress

Software engineering can quickly become all-consuming. Passion leads to overwork, which leads to burnout. Long nights and weekends are seen as the norm at some companies. This has physical and mental health consequences over time. Poor work-life balance also leads to high turnover.

Set the tone from the top that long-term sustainability is valued over short-term heroics. Don’t schedule meetings on Friday afternoons and set cutoff times for the workday. Encourage vacation time and staying away from work on weekends. Build in slack time for people to recharge. Productivity stems from rested, engaged minds.

Sam’s inspirational journey from waitress to CTO demonstrates that anyone can break into the tech industry and climb to the top with enough determination and grit. Her story encourages those from non-traditional backgrounds who face barriers and self-doubt trying to get that first foot in the door.

The path to a CTO role is hard, but the ambition to keep learning, hustling, and reaching for bigger goals pays off in the long run. Sam exemplifies how to turn struggles into strengths. She never saw setbacks as dealbreakers but as opportunities to pivot and push forward smarter.

For engineers looking to level up into leadership, Sam’s story also underscores the importance of developing soft skills like communication, strategic thinking, and managing, not just hard technical expertise. Mastering these ‘people skills’ opens up possibilities many individual contributors overlook on their way up the ladder.

Originally published on Medium.com