What was it like becoming a manager?

When I finally said yes to the dress and became an engineering manager, everything changed.

I had just over 10 years experience as a Software Engineer when I took this career reset and something like 20~ years of programming experience. While I was able to bring a lot my skills along for the ride, it was starting over.

The First Day

The manager I was stepping in for had put together a 12 page document. I would refer to this document for the next 2~ years. It was kind of intimidating to receive it, as it provided the following information:

• A very heart warming welcome message. Thank you for this!

• General info about the team.

• Big list of projects, what’s in flight and upcoming work.

• Planning and staffing needs.

• Team processes and how things operate.

• People - where the risks are, how folks are doing, who needs what, who might struggle with the transition the most, etc. Also details about each engineer, she knew her people well.

I also had the chance to interview her before she left, and when I would ask her questions like “Where do you see the Design Systems team going in the future” she gave me a very detailed answer, and then 6 different links which had a ton of information. Entire roadmaps.

The notes I made from this meeting were 4 pages long.

I also received a 7 page “ramp up” doc from my mentor.

I was intimidated, to say the least.

These were already so much information, but of course the team had a Google Drive filled with hundreds of documents. Tech specs, project proposals, etc. They had a massive wiki filled with a ton of runbooks and descriptions of things. Github repos, a ton of them! All doing stuff, all important. There were Jenkins jobs and infrastructure built. The team owned internal websites. They had meetings with lots of different teams I didn’t know. This team also worked with Design, who had their own entire set of areas with their own documents and complicated inner workings.

So on my first day I took a deep breath, and I created a doc.

Everything went into that doc.

All the links, into the doc. Any new information? Into the doc. A task I needed to do? Into the doc.

It became massive very quickly. Before I abandoned it for a more robust system a few months later, it became 18 pages.

The first day came and went, and I survived. All the fears I had about it were unfounded. I met the team, I got to speak with me mentor, my manager, and I was off from there.

The First Month

I quickly realized that the organizational methods I had learned as an engineer were not going to serve me as a manager. There was just so much more information than when I was an engineer. There was in fact now 10 engineers worth of information, and like when I first learned to drive, it was so hard to know what to pay attention to.

1:1s began in earnest in week 2, and I was officially meeting with all 10 of my reports. One of the engineers had handed in her resignation before I started. To this day I’m not sure why, but I know that egotistically I assumed it was because I was leading the team. I was new, I had no idea what I was doing, and she was jumping ship before I crashed it. Very unlikely, but that was the story I wrote for myself in the early days.

As an extreme introvert who was afraid to do meetings with people — odd choice to become a manager I know — 1:1s ended up being the best part of the job.

I was very opinionated about 1:1s between managers and engineers, which gave me a great place to start: Here is how I view our relationship, what do you think?

As is common as a manager, everyone said that was great. And as is common as a manager, I had no idea if they were being truthful or sucking up. It was my first dip into the changes that come with leading a team.

The first month was hard, but not for the reasons I thought. It was the information overload that I struggled with, not the meetings. Even as an introvert who was very drained from meetings, the meetings were easy.

The First Quarter

I had my first hard lesson in ownership and stakeholder management when meeting with some executive stakeholders (VPs), who were reviewing our teams roadmap. I actually didn’t know what the teams roadmap was yet, but the design manager who managed the designers on the team had worked with the previous manager on it, and lead the meeting. One of my ethos of becoming a manager was not to change anything initially coming in. I didn’t have enough context to really own anything yet, I was here to learn and understand.

The executives were not happy with the roadmap.

I remember one part of that meeting where I was told by an executive that it’s my roadmap, so I have to have ownership of it. I had tried to give context that it was my first month~ on the team, and they were having no excuses.

I don’t fault them, but years later I don’t think I would have changed anything leading up to that meeting. I wasn’t going to evaluate and make a whole new roadmap in my first month, so I thanked them for the feedback and we moved on.

By the end of the first quarter, I had a chance to have my butt handed to me by execs, we got through an entire project cycle for projects I mostly understood, I had 2 people leave, and 1 more transfer to another team (we still chat!), I got to work through an annual compensation cycle and help with that, I got to run and do quarterly planning (for the upcoming quarter) with the team, and have some hard 1:1 conversations.

I got to meet and get to know my management group, and have interesting conversations about hard problems other managers were working through. I also got to share some of mine with the group, and get help and their perspectives on things.

I got to work through level calibrations, and learn about the other side of career planning and progression.

It was a hell of a first quarter.

And then my 5th child was born on Christmas Eve.

Paternity Leave As a Manager

At Yelp we get 8 weeks fully paid for paternity leave, at least in Canada. We can take longer, but you only get paid by employment insurance. I won’t go into how much that is, but it’s peanuts. I am the sole income for my family, so I only did the 8 weeks.

That is a long time to be away from your team, especially when you have only been managing them for 12 weeks. But that was part of the deal. My manager (ie director) knew going into this that at some point I would be out for leave. My team also knew and I talked to them about it.

This transparency was super helpful in planning for while I was gone.

We arranged for another manager to cover while I was out, and it went very well.

I came back more tired than ever (did you know babies are hard??) but it was nice to be in routine. On my 21st week as — but only having 12 weeks of experience — I was back home, leading my team, and taking ownership of that roadmap.