The Stressful Leap from Engineer to CTO

· 5 min read
The Stressful Leap from Engineer to CTO
You know who the best managers are? They’re the great individual contributors who never, ever want to be a manager, but decide they want to be a manager, because no one else is going to be able to do as good a job as them.— Steve Jobs

I fully agree with Steve Jobs on that. Most good engineers prefer to stay in senior engineer positions instead of transitioning to leadership roles as tech leads, engineering managers, or CTOs. Being a technical leader is way more complicated than being an individual contributor. You have to deal with all the complexity and uncertainty, but you can’t do anything yourself and rely on your team instead. But someone has to do it.

From Engineer to Reluctant CTO

Once upon a time, an engineer named Dragan lived in the heart of the Balkans. Dragan was a brilliant software developer known for his problem-solving knack and ability to write clean, efficient code. He loved the thrill of tackling complex technical challenges and the satisfaction of seeing his code come to life.

One day, Dragan’s life took an unexpected turn. The CTO of his company announced his resignation, and the CEO, impressed by Dragan’s technical abilities and potential, offered him the position. Dragan was flattered and excited by the opportunity but also very anxious. He knew that the role of a CTO was very different from that of an engineer, and he wondered if such a significant change was right for him.

From his new role’s early days, Dragan fought with a steep learning curve. He was no longer immersed in code but juggling many responsibilities, from strategic planning to team management. He missed the hands-on technical work he loved as an engineer so much.

Dragan also found himself feeling isolated in his new role. As an engineer, he was part of a close-knit team, working together to solve problems and build solutions. But as a CTO, he was often making tough decisions alone. He missed the connection with others from his engineering days and the shared sense of accomplishment when the whole team solved a challenging problem together.

Moreover, Dragan struggled to think differently, as the new role required. As an engineer, he was used to diving deep into problems and spending as much time as needed to find the perfect solution. But as a CTO, he had to consider the bigger picture, balancing the desire for technical perfection with the realities of business constraints.

The Common Challenges in the Transition

The struggles Dragan was experiencing are common for those transitioning to the role of a CTO. I remember myself feeling this way, too. Being an engineering leader means a broader range of responsibilities and a shift away from hands-on technical work.

People who deeply enjoy the technical aspects of engineering and prefer to focus on problem-solving and coding will be happier as engineers. Deep inside, every CTO misses the coding days. However, we all must grow, and this broader strategic role is extremely rewarding for those willing to take on leadership and management responsibilities.

The decision to transition is highly personal and depends on your career goals, skills, and interests. I researched what accomplished CTOs think about this. Here are a few highlights of the challenges and differences.

  • In a post by Shekhar Gulati, he shares his transition experience to a CTO role. He mentions that there were times when he considered going back to being an individual contributor. He describes the role of a CTO as challenging and lonely and emphasizes that it involves a lot of on-the-job learning.
  • Vadim Kravcenko, who became the CTO of a small company, shares that the transition made him work harder than ever before. He had to manage a growing list of responsibilities that didn’t fit on a single to-do list.
  • In a post on LinkedIn, Andrew Raymond discusses the transition from engineer to CTO and highlights that engineers must fully understand what it means to be a CTO, including what they will have to leave behind. He mentions that the engineer in you may want to spend as much time and resources as possible to solve a particular problem. Still, as a CTO, you must keep in mind the overall cost-benefit to the end result.
  • Katia Gil Guzman, in her article “From Software Engineer to CTO,” describes how her life changed completely after the transition. She had to unlearn some of her previous beliefs and train her brain to think differently. As a software engineer, she spent most of her time coding, but as a CTO, that was just one of many responsibilities

Key Skills and Mindset Differences

When it comes to leadership skills, ask yourself — do you get a kick out of mentoring others and helping them develop? Do presentations and public speaking make you nervous or excited? As CTO, you must motivate the team and share the engineering vision with everyone. The good news is that you’ll get to shape the culture into what you want. The downside — less time for heads-down coding work.

Take a good look at your experience across different tech domains for technical chops. Can you comfortably zoom out and get excited about high-level architecture? Making strategic tech picks for the company will be up to you as CTO. You’ll drive the vision, which is fantastic. But again, it does mean less hands-on keyboard time.

Business sense — this one’s essential. Can you connect the dots between technology and real business value? Running R&D requires some business savvy, too, like managing budgets. You get a seat at the executive table as a leader. But yet again, you trade some pure engineering work for it.

Now for risk management. How are you at planning for worst-case scenarios and coming up with contingency plans? CTOs have to be paranoid and watch out for potential pitfalls. You’ll need to balance innovation with pragmatism at times to mitigate risks. The stress of having the buck stop with you on tech risks comes with the territory.

Problem-solving skills count a lot, too. Do you geek out on finding solutions to really complex technical puzzles? That’s great if yes, but it’s not enough. You’ll have to deal with people’s problems and conflicts, and your people skills will often matter more than tech ones. You’ll get to flex your problem-solving muscles in new ways as CTO, which is fun but can also be high-pressure.

Lastly, be honest — are you genuinely passionate about technology and its possibilities? The CTO role demands that kind of enthusiasm. You must have a broad, long-term vision and be accountable for all technology decisions. It’s a big responsibility to have on your shoulders.

The CTO Role is About Leadership

The CTO role is a leadership role in the first place. As a result, you need to be comfortable working with people, managing and guiding them. You’ll also need good technical expertise in different areas and a good business sense to solve complex problems and make high-impact decisions.

This role comes with a lot of responsibility and stress because you don’t get to do anything yourself — you have to rely on your team and their tech expertise. It’s very different from an engineering tole and definitely not for everyone. But it is very rewarding because you get to decide how things are done and build a great product and an incredible team with a culture everyone will envy.

Originally published on Medium.com