Extreme Ownership: How to Be an Exceptional CTO

9 min readJan 16, 2023

How to Be an Exceptional CTO, Chief Technology Officer, Tech Leader

In this article, we will focus on the leadership skills and traits that are essential for a CTO. While technical skills are important, they vary depending on the company and technology used.

The CTO position requires a unique set of leadership skills, known as “The Dichotomy of Leadership”. CTOs must balance opposing traits such as being confident but not cocky, courageous but not foolhardy, and competitive but a gracious loser.

This concept of “The Dichotomy of Leadership” is inspired by the book “Extreme Ownership: How U.S. Navy SEALs Lead and Win” by Jocko Willink and Leif Babin, which emphasizes the importance of balancing opposing traits in leadership.

In this section, we will explore the different aspects of leadership that CTOs must navigate in order to be successful in their role and how they can improve their skills.

The Dichotomy of Leadership

The concept of “The Dichotomy of Leadership” refers to the idea that leaders must balance opposing traits in order to be successful.

This means that a leader must be able to balance being assertive and decisive with being humble and open to feedback, for example. It’s about finding the right balance between different qualities and being able to adapt to different situations.

It’s about understanding that different situations require different approaches and being able to navigate the different aspects of leadership.

1. A good CTO must be confident but not cocky

Confidence is the belief in one’s own abilities, qualities, and judgment. A confident CTO is able to lead their team with conviction, make difficult decisions, and communicate effectively with other executives and stakeholders.

A confident Chief Technology Officer:

Has belief in their own abilities, qualities, and judgment
Can lead their team with conviction
Makes difficult decisions
Communicates effectively with other executives and stakeholders
Admits when they are wrong and learns from their mistakes
Gives credit to their team for their successes

A cocky Chief Technology Officer:

Has an overbearing attitude and overestimation of their abilities
Makes decisions without considering input from others
Doesn’t admit when they are wrong
Takes credit for the success of their team, while not taking responsibility for the failures
Insists on being the only one to make decisions
Unwilling to acknowledge contributions of the team

2. A good CTO must be courageous but not foolhardy

Courage is the ability to face difficult situations with bravery and determination. A courageous CTO is able to take risks, make tough decisions, and inspire their team to do the same. A foolhardy CTO is reckless and act without thinking the consequences and may ignore important information.

A CTO that is courageous but not foolhardy:

They are willing to take calculated risks and make difficult decisions to achieve the goals of the company.
They are able to anticipate potential problems and plan accordingly.
They are able to handle pressure and uncertainty and remain calm in difficult situations.
They are willing to admit when they are wrong and take responsibility for their decisions.
They are able to make bold moves while still considering the potential consequences of their actions.

A CTO that is foolhardy:

They are willing to take unnecessary risks without considering the potential consequences.
They are not able to anticipate potential problems and may make hasty decisions.
They may become reckless and make decisions that put the company at risk.
They may not be able to handle pressure and uncertainty and may become easily overwhelmed.
They may be unwilling to admit when they are wrong and take responsibility for their decisions.

3. A good CTO must be competitive but a gracious loser

Competitiveness is the drive to be the best and achieve success. A competitive CTO is driven to achieve success for their team and company, and is always striving to improve. A gracious loser is able to handle defeat with dignity, learn from mistakes and move on.

A CTO that is competitive but a gracious loser:

They strive to win and achieve the goals set for the company, but also recognizes and respects the achievements of their competitors.
They are able to learn from their mistakes and losses and use that knowledge to improve their own performance.
They maintain a positive attitude and encourage the team members to keep working hard even in the face of defeat.
They celebrate the wins of the team, but also find ways to acknowledge and celebrate the successes of other teams or companies.
They are able to maintain a healthy balance between striving for success and being humble enough to admit defeat.

A CTO that is not a gracious loser:

They have a difficult time accepting defeat, and may blame others for their losses.
They may also become bitter and resentful towards their competitors.
They may have a negative attitude, and may discourage the team members from trying again.
They may also be unwilling to acknowledge the successes of other teams or companies.
They may be unable to learn from their mistakes and losses, and may repeat them in the future.

4. A good CTO must be attentive to details but not obsessed by them

Being attentive to details means paying close attention to the small but important aspects of a project or task. A CTO that is attentive to details is able to catch potential issues and improve the overall quality of the work. Being obsessed by details means getting lost in minor aspects of a project or task and neglecting the bigger picture. An obsessed CTO may become bogged down in minutiae and lose sight of the overall goals.

A CTO that is attentive to details:

They pay close attention to small but important aspects of a project or task.
They are able to catch potential issues and improve the overall quality of the work.
They make sure that the final product meets the company’s standards and the client’s expectations.
They are able to balance the attention to details with the bigger picture and the overall goals of the project.

A CTO that is obsessed by details:

They get lost in minor aspects of a project or task and neglect the bigger picture.
They may become bogged down in minutiae and lose sight of the overall goals.
They may focus too much on small details and miss out on major issues, causing delays and setbacks.
They may also be too perfectionistic and delay the launch of the product or service.

5. A good CTO must be a leader and follower

Being a leader means taking charge and guiding the team towards a common goal. A CTO who is a good leader is able to inspire and motivate their team, and make difficult decisions when necessary. Being a follower means being able to take direction and guidance from others. A CTO who is also a good follower is able to listen and learn from others, and work well in a team.

A CTO that is a leader:

They take charge and guide the team towards a common goal, setting clear objectives and providing a vision of success for the team.
They inspire and motivate the team to achieve the goals and build a culture of excellence.
They are able to make difficult decisions when necessary, even when it means going against the status quo or facing resistance.
They also lead by example, making sure that they are always pushing the boundaries of innovation and quality.

A CTO that is a follower:

They are able to take direction and guidance from others and are open to feedback and constructive criticism.
They are good listeners, and able to pick up on cues from the team and other stakeholders.
They work well in a team, and are able to collaborate effectively with other team members and stakeholders.
They are able to learn from the experience of others and are not afraid to ask for help when needed.

6. A good CTO must be quiet and not silent

Being quiet means being able to listen more and speak less, and think before acting. A CTO who is quiet is able to take a step back and consider all options before making a decision.

Being silent means being unresponsive and not engaging with others. A CTO who is silent may be perceived as disengaged or uninvolved, which can negatively impact the team and the company.

A CTO that is quiet:

Before a meeting, they take the time to review the agenda, gather input from the team, and prepare any necessary materials. They are active listeners during the meeting, and take notes to ensure that all relevant points are considered before making a decision.
They also make sure that the ideas and opinions of the team are heard and take into account before making decisions. They also give the team members the space to speak and express their ideas.

A CTO that is silent:

They don’t engage in the team’s conversations or discussions, and are not present during team meetings. They also don’t give feedback or provide guidance when asked.
They also don’t communicate with the team members, stakeholders, and upper management. This can lead to a lack of direction and a lack of trust in the team and the company.

7. A good CTO must be close with the team but not too close

Being close with the team means having a good relationship and being able to connect with team members on a personal level. A CTO who is close with their team is able to understand their needs, provide them with the necessary support, and create a positive work environment.

Being too close with the team means becoming too familiar and losing the necessary distance to effectively lead and make important decisions. A CTO who is too close with their team may struggle to maintain a professional relationship, and may be unable to make decisions that are in the best interest of the company.

A CTO that is close with the team:

They have a good relationship and able to connect with team members on a personal level.
They understand their needs, provide them with the necessary support, and create a positive work environment.
They are able to communicate effectively and create a culture of trust and transparency in the team.
They make sure that the team members are on the same page and work together to achieve the goals.
They maintain a level of professionalism and ensure that no team member is given preferential treatment.
They set clear boundaries and ensure that the team knows who is in charge.

A CTO that is too close with the team:

They become too familiar and lose the necessary distance to effectively lead and make important decisions.
They may struggle to maintain a professional relationship,
They may be unable to make decisions that are in the best interest of the company.
They may also be too invested in the personal life of the team members and neglect the professional aspect.
They may also give preferential treatment to certain team members and create favoritism.
They may forget to establish a clear chain of command and create confusion among the team.

In conclusion, being a successful Chief Technology Officer requires a strong understanding of leadership and the ability to navigate the “The Dichotomy of Leadership”. It’s important to remember that the role of the CTO and the skills required will change depending on the size of the startup and the tech team. In early stage startups, the CTO may spend 80% of their time writing code and 20% involved in the strategy of the company. As the company grows, the CTO’s role shifts towards more strategy and mentorship, and less code.

One of the key ways to develop leadership skills is through learning and reading. Books like “Extreme Ownership — How US Navy Seals lead and win” provide valuable insights into leadership and teamwork that can be applied to the tech industry. It’s important to understand that the principles discussed in the book may be applied to business and leadership problems in general but the good understanding of the book is what made me to be able to share this knowledge in a context directed to Chief Technology Officers and Technology Leaders.

It’s also important to remember that there is no one style of leadership. Leadership style depends on your personality and how you feel comfortable applying these principles. It’s important to find a leadership style that works for you and your team, and to be open to learning and growing as a leader. In the end, the most important aspect of being a CTO is to lead your team to success while maintaining a healthy balance of all the required skills and attributes.