10 Common mistakes of first-time tech leaders

Tanaka Mutakwa
April 1, 2020
VP of Engineering

We'll start with a story:

Jane works as a software engineer at ABC Software Company. She is the most skilled software engineer on her team. She is the person everyone else on the team goes to when they need help to solve complex problems and she always comes up with high-quality solutions in a short space of time. 

Senior management at ABC Software Company recognizes Jane’s ability and decide to appoint her as the manager of her team. They call her into a room on a Monday morning and tell her she is getting promoted. Jane is now the manager of the team and going forward everyone should listen to her. 

A ceremonial handshake between her and senior management occurs and hopefully as part of that promotion Jane’s salary has been increased. Jane walks out of the room surprised but excited at the same time – this promotion is not something she expected at all. The next day Jane’s team is informed about the change in Jane’s title and responsibilities.

Jane comes into the office and for the first time in her career she has a whole team of people reporting into her. It does not take long for Jane to realize that the new technology leadership role is very different.

Jane was not well prepared for this new technology leadership role. She did not take part in any leadership training before the new role and she was not made fully aware of the expectations and challenges the new role would bring.

The exceptional skills for which she was recognized as an individual contributor are completely different to the skills she now requires to be successful as a technology leader. The time she spent as an individual contributor focusing on writing well-designed code does not translate into the skills necessary for understanding people, resolving conflict, or suddenly having to juggle more tasks than she can possibly achieve by herself.

Jane’s technical expertise, the knowledge, and skills that enabled her to excel as an individual contributor are decidedly less valuable at this new level.

Making the leap into tech leadership

Jane’s story is the typical story for a large number of individual contributors who are shifted into technology leadership roles. They are not ready for the responsibilities, expectations, and challenges of taking up a technology leadership role. This results in a lot of frustration for the new technology leaders.

They feel incompetent in their new role and long for the days when they were recognized for being good at something. The people who report into them also pick up on their new manager’s frustration and incompetence and in-turn are also frustrated because they are not receiving the support and career growth they require. 

Engineer vs Manager: competence and skills
Photo credit from the Good Manager, True Leader presentation by Pawel Brodzinski

In this article I will share common mistakes first-time technology leaders make when they transition into a new leadership role from being an individual contributor. I will then share how to avoid the mistakes for a higher chance of succeeding in their leap into technology leadership.

1. Coding full time

This is the most common mistake first-time technology leaders make. They default back into doing the work they are good at - writing code. Coding full time leads to not giving attention to all the other important responsibilities that come with a technology leadership role.

Things such as cultivating a good team culture, helping your direct reports grow their careers and managing conflict between team members. Ignoring these important responsibilities will over time lead to a failing team and disgruntled direct reports. If you are in a technology leadership role your first priority is the people who report into you and creating a great working environment for them. Operating as an individual contributor is secondary to having a team that is working well together.

It is ok to spend time writing code as a technology leader - and you will see I encourage it in the next point - but it is important to know it is not the highest priority item on a technology leader’s responsibilities and they need to balance that well. 

2. Not spending enough time writing code

On the other extreme a technology leader may find themselves not spending any time at all writing code. This is risky as they may lose all context of the issues their direct reports face on the ground in the codebase.

They may lose technical respect from their team who feel they are unable to discuss technical complex issues with their leader. Direct reports may also feel their leader is unable to set appropriate growth plans for them if they don’t have a good understanding of the technology the team is working on.

A technology leader must spend some time writing code with their team so they can empathize with the individual contributors on the challenges they face in the codebase. Writing code also allows a technology leader to keep up to speed with the latest technologies and keep their technology tool belt strong, despite now having multiple responsibilities that pull them away from writing code full time. 

3. Making all the technical decisions

Some technology leaders believe that once they are in a leadership role they should make all the important decisions for the team. This is a big mistake as it means the leader is the main bottleneck of the team. Nothing happens until the leader makes a decision.

Given that the technology leader will be pulled into many different directions they may not always be available to the team. The team spends a lot of time waiting for the leader to come back and make decisions. If the technology leader makes all the decisions for the challenging problems they are not empowering their direct reports and giving them opportunities to learn and grow. 

4. Forgetting about cultivating team culture

Individual contributors typically focus on writing their day to day code and delivering features. When there are conflicts between people in their team someone else figures out how to resolve the conflicts. When it comes to coming up with ways of working as a team or organising team building activities someone else makes that happen.

New technology leaders often fall into the trap of continuing to operate in the same way they did as individual contributors. They will leave team culture issues to be figured out by someone else. What every new technology leader needs to realise is that cultivating a great team culture becomes their most important responsibility as soon as they take up the role. They cannot leave that responsibility to someone else.

A great team culture is the root to success for most software teams, it cannot be ignored. 

5. Talking technology only

Individual contributors spend a lot of time with other individual contributors discussing technical topics to any level of deep complexity they wish to. Individual contributors can get away with mostly only interacting with other technologists. First-time technology leaders often make the mistake of continuing to only interact with fellow technologists and discussing concepts at complex technical levels.

This is a mistake because once someone is in a technology leadership role they become the face of the team to the rest of the company. They are likely to interact with people from other departments who are non-technical. First time technology leaders need to build good relationships with people across the whole company. They also need to learn how to communicate complex technical ideas in a simple easy to digest way for non-technical people. 

6. Saying yes to everything

The world of leading and/or managing talented technologists can be messy. The first-time technology leader will suddenly find themselves leading meetings, negotiating for resources, making strategic decisions, participating in hiring, and a whole range of other mission-critical activities that fall outside of the technical toolbox.

A common mistake is to say yes to every single request that arrives at a technology leader’s desk. This leads to two possible bad scenarios: They will either feel overwhelmed and stressed by the sheer amount of workload they have and end up not accomplishing anything. Or they will accomplish all the tasks they say yes to but they will be overworked and burnt out in a few months.

Good time management and prioritization is important for a technology leader. They need to learn what to say YES to, what to DELEGATE to others and what to say NO to. They cannot do everything. 

7. Assuming you need to have all the answers

First-time technology leaders often believe because they are in a respectable leadership role they must know everything and cannot expose any lack of knowledge they have. This is a mistake because it can lead to making up things or blatantly lying in discussions when asked questions or for opinions by their team.

One of the most important lessons for a first time technology leader to learn is that it is ok for them to say to their team “I don’t have enough knowledge about that topic.” As a leader being very open with your team shows that you are able to be vulnerable in front of them and builds trust. It also means that things you don’t have answers to can be explored by the team as a unit and create learning opportunities for the team. 

8. Isolating yourself and becoming lonely

The world of technology leadership can be very lonely. Especially for first-time technology leaders. They remember their days as an individual contributor where they used to always spend a lot of time with fellow individual contributors. Now they are in a leadership and they are pulled away from the individual contributors.

Perhaps because they now have many other responsibilities they cannot spend as much time with the individual contributors. Or because they now have a leadership title the individual contributors now view it as an us and them situation. The first-time technology leader can easily end up feeling isolated and lonely.

If they work in a bigger organization with other fellow technology leaders they must develop relationships with this new peer group. That peer group faces similar problems they will likely face and will be useful to have as people to discuss ideas with. First-time technology leaders should also look for people in leadership roles outside their organization who they can share approaches and discuss ideas with.

I’d encourage first-time technology leaders to identify someone who they trust who has been in a leadership role for much longer and ask them to be their mentor. It is really useful to be helped by people who have faced similar challenges and navigated them in the past. 

9. Thinking all people are the same

Individual contributors are obsessed with writing efficient code that eliminates any duplication. One function that can 'solve it all' given multiple different variables. First-time technology leaders can fall into the trap of trying to solve different people’s issues in the same way, thinking that if one solution for the same problem worked for one direct report they can use it for another direct report.

This is a mistake. People are different: they come from different backgrounds and have different motivations. What makes one direct report happy can make the next direct report angry. That is why we say leadership is challenging and messy.

The first-time technology leader needs to learn how to build good relationships with each of their direct reports. Understand them well. Build trust between each other. This is achieved over time in many ways but one of the most important trust building exercises is having frequent one-on-one check-in meetings with their direct reports.

Once a technology leader has a good understanding of their direct reports they are better placed to address each individual’s issues successfully. 

10. Not seeking feedback from your team

Individual contributors are often used to instant feedback from their work, through functions like monitoring failures and bug reports, and problems are solved relatively easy – meaning they get a quick sense of accomplishment. For technology leaders, feedback on their work takes much longer to arrive and it is often difficult to measure the impact of their work.

A technology leader can have a conversation with one of their direct reports today and the impact of that conversation only get realised over time.

It is important for the first-time technology leader to constantly seek and receive feedback from their team. This is the one way a technology leader can constantly keep track of how well they are doing and the areas they need to improve in. 

Making a successful leap into tech leadership

As an individual contributor, life is mostly about writing code and producing. You are excited about delivering features and seeing your software being used. As a new tech leader, your focus has to change. The transition requires a whole new set of skills and you have to learn to let go of what was expected of you as a developer.

Many technology leaders get the job by default. They are the best or most senior technologist and suddenly find themselves leading meetings, negotiating for resources, making strategic decisions, participating in hiring, and a whole range of other mission-critical activities that fall outside of the technical toolbox.

Leadership is a learnable skill, however learning about leadership in the technology industry is often left to chance. This often leads to frustration for both leaders and those being led.

It does not have to be this way––and I hope this article helps new technology leaders navigate this journey much more easily.

To close, some resources for first-time tech leaders and a video from the monthly tech leadership meetup in Cape Town that I co-founded for all of the reasons touched on in this article: