5 Things I Will Never Do Again as a CTO or Senior manager

Becoming a good manager is not only about learning what to do. It is also what not to do. These are some of my hardest-won lessons as I write this as a diary to myself.

I will never again Be the Sole Agent of Culture Creation or Change

As a senior manager or CTO, I've learned that driving company culture isn't my primary responsibility. While I can and should influence the engineering culture within my team, overall company culture should be shaped and driven by the CEO. In a previous role as a non-co-founding CTO, I made the mistake of trying to take on the mantle of culture agent for the entire company. This role belongs to the CEO, and if they don't take it up, it's not my responsibility to fill that gap. My focus should remain on fostering a positive and productive culture within the engineering department, aligning with the broader vision set by the leadership.

I will never again Start Greenfield Projects with Microservices

For greenfield projects, I’ve learned the hard way that starting with microservices can lead to unnecessary complexity and overhead. Instead, I will always begin with a templated monolith and iterate from there. This approach allows for faster development and easier debugging in the early stages. As the project grows and the need for scalability becomes more apparent, we can then consider breaking the monolith into microservices. This strategy ensures we don't prematurely optimize and can adapt more flexibly to the project’s evolving requirements.

I will never again seek out 10x engineers

I’ve come to believe that the concept of a "10x engineer" is more myth than reality—hallucinations of Silicon Valley fever dreams and Substack newsletters. Instead of chasing these unicorns, I prefer to take a "Moneyball" approach, akin to Brad Pitt's character in the movie, and focus on building a team of solid performers who can execute consistently and predictably. This approach ensures that the organization can effectively absorb their output, and customers can handle the changes and deliveries we make at a steady, reliable pace. It’s about building a balanced team where each member contributes to a cohesive, well-functioning unit rather than relying on the perceived exceptional output of a few individuals.

I will never again Dictate How Things Should Be Done

I’ve learned that as a CTO, my role is not to dictate how my team should accomplish tasks, but to clearly define and enforce the desired outcomes. My focus should be on setting clear goals and objectives, ensuring everyone understands what success looks like. This empowers the team to leverage their expertise and creativity to find the best path to achieve those outcomes. By emphasizing results over methods, I foster a more innovative and motivated team that is aligned with our overall vision and goals.

Additionally, I understand that my team might not always know how to achieve these outcomes. Therefore, I support them by providing learning and development opportunities. This could involve buying them books, enrolling them in courses, or offering other resources that help them build the skills needed to reach our goals. Supporting my team in this way ensures they have the knowledge and tools necessary to succeed, and it demonstrates my commitment to their professional growth.

I will never again Blur the Lines Between Professional and Personal Relationships

No, I'm not talking about love-interests. That is kind of obvious and often outlined in company policies

I’ve learned the importance of maintaining professional distance with my team members. I will never again become close friends or deeply engage with them on a personal level. While building rapport and understanding is crucial, it is equally important to preserve professional boundaries.

From a psychological perspective, blurring these lines can lead to various issues. Personal friendships within a professional context can create:

• 🎲 biases
• 😉 favoritism
• ⚖ conflicts of interest

which can undermine team dynamics and decision-making. It also makes it challenging to provide objective feedback or make tough decisions that may impact those personal relationships.

Moreover, maintaining professional distance helps in preserving authority and respect. When the boundaries are clear, it becomes easier to lead effectively, as team members are less likely to question decisions based on personal feelings.

It is a balance, but it is not always easy to be empathetic and supportive as a leader while keeping the relationship professional to ensure fairness, objectivity, and the ability to lead without personal entanglements clouding judgment.

Like everything, you usually "fail forward" – meaning that you get better at this over time. You get better at setting boundaries. Maybe, just maybe, you begin to understand why some in leadership seem aloof. The make small appearances at company events. They keep a low profile when outside the context of work. The are kind and gracious and engaging to a point, but there is a distance by design.