Transitioning From Vice President of Engineering to CTO

Problem

When I first stepped up into my role, the pandemic was in full swing. I kind of had to work around those circumstances, which honestly made things a lot tougher. Remotely, you can’t really meet or connect with people.

I would say that it worked out in the end, however. I worried about making too many assumptions and rushing into the role. I wanted to take some time to really understand things. When managing a remote team, lapses in communication can hinder productivity. What is the best way to get one’s thoughts across to a larger audience when I am not able to meet them and influence them in person?

Actions taken

The first step was understanding the role itself, both internally and externally. I reached out to folks that I considered mentors — previous bosses and other community members. I wanted their input on what they perceived as being my strengths related to this new role.

The community thing was really helpful. The second group that I reached out to was my group of peers. Mentors have faced these problems in the past, but peers are facing these problems right now, just like you.

The other thing was to understand what the role meant internally. It’s different for every company. I effectively had to ask all of my stakeholders what they needed from me as a CTO. I went to my CEO and other company heads like our data officer; this helped me to grasp all of their general expectations for me.

Being CTO is much more business-focused than being the Vice President of Engineering. Even though I had been in the company for a while, I had to spend some time learning what the business side entailed. I went through the financials of the company in order to understand our biggest business challenges. I wanted to be fully-aligned with what the company needed at the time.

Once I felt like I had a good understanding of what the role meant, I realized that it was also about proving myself. I worried about straining my relationships with peers who I now managed, as well as being able to keep up with my new, executive-level peers. The first couple of months were more about learning how to align myself with everybody’s expectations. What was the best way to work with all of these different folks in this new capacity?

I wanted people to know that I was worthy of their trust. Eventually, I made my way to a point where everybody on board was in alignment with the direction that I wanted to take.

Lessons learned

• All people are different. There is no way to fit everybody into one single framework or way of working. The first couple of months were really about understanding how to work with all of these different folks and what their priorities were. The next one or two months were about building my own philosophy about what was right for the company and what types of decisions that I needed to be making.
• When I first started, I went very heavy on the video chat aspect, especially at the beginning of the pandemic. This helped me make up for lost time with my team members.
• Building feedback loops also helped a lot, as well. Even quick surveys helped without those casual conversations that let you know what people are thinking. The surveys were not generic; they were tailored to each group within the company specifically. I think that helped to save me a lot of surprises. I was more tuned in to when somebody was feeling disconnected or unhappy.