At Asbury Agile, Bitly’s Sean O’Connor Talks about Transitioning from Developer to Manager

Developers, UX designers and other members of the New Jersey tech community gathered in Asbury Park on Oct. 2 for the 2015 Asbury Agile Web Conference. As its website says, Asbury Agile is a friendly, informal, single-track conference for web professionals and students that is held annually.

In a humorous afternoon session, Sean O’Connor, lead application engineer at Bitly (New York City), discussed his transition from developer to manager. He provided some real information for programmers and designers considering such a move.

O’Conner said that he joined Bitly about three years ago as a programmer, writing code every day. He began doing some mentoring, helping members of the team with lessons learned, and working with members of the data science team.  After a management shakeup about two years ago, he had to decide whether or not to accept more of a management role. This route may not be right for everyone, he cautioned.

“You will no longer be working with coding and machines. It turns out that humans are … squishy and even more fickle [than machines], but also awesome and exciting. … You are going to have to be much more deliberate when you speak. …You can’t revert or omit when you upset somebody on your team.”

If you are doing your job as a manager, you won’t have time to code, he noted. During the summer of 2015, for example, there were entire weeks when he didn’t commit any code. “Earlier in my career, that would have been terrifying,” he noted.

Also, this is a career change, he cautioned. You are going down a completely different path from the one you were heading down before. You will be developing a different set of skills that won’t overlap with your former skill set. Your goals, on which you will be judged by your peers, will be completely different. “There is much more focus on people and much more focus on the team, and not so much on what eventually ships,” he said.

Making the choice to go down this road wasn’t easy. However, the best piece of advice O’Connor got was to “optimize for my happiness.” He advised the audience to figure out what will make them happy if they get more of it. “Ask yourself, what is it about your job that you love, what keeps you coming back.  Is it learning about new tools, libraries and systems?” Then you might not be the right candidate for management. 

On the other hand, “one of the things that get me excited is creating tools that help people do their jobs,” he said. “For me, personally, coding is just a means to an end,” and a team of several people will be able to help reach that end sooner.

 If you decide to be a manager, he added, you want your team to be excited and motivated.  “Management is a learnable skill, just like coding is,” he told the group. People transitioning to management have a lot of resources to learn from. Finding mentors can be important, too.

First, he noted, you can draw from your own experience. Look at the strategies of the good managers you’ve worked for, and at the techniques they’ve used that worked, he urged.

Remembering that management is about relationships is the key to being a good one, he noted. Build trust with your team, he said. “I don’t know if you’ve ever had a boss you don’t trust, but it is awful and it’s not sustainable. Similarly, if you have people on your team that you don’t trust,” you have to figure out what to do. You have to build trust between you and those who report to you, and among the members of your team.

You also have to know your team members as individuals: What makes them excited and what makes them scared?  What do they want to work on? Where do they want to be in five years? Having this understanding will go a long way toward figuring out what you need to do to make them happy and productive.

Communication is also important.  “In my experience, the best thing you can do is having one-on-one conversations with your staff. I have five people I manage. I have at least a half-hour one-on-one conversation with each and every one of them every single week.”  During those conversations, a manager can find out what is working and what is not.

Another thing that is important is being empathetic. If you can put yourself in the other person’s shoes, “the crazy rhetoric they are saying starts to make a lot of sense.” Also, it helps avoid a lot of drama, he noted.

Once you have a clue of how your team is doing, you can start to plan, O’Connor said. “For example, in this particular group of human beings, they apparently step on each other’s toes each day. That’s not helping anything. Let’s figure out a plan to stop them.”

He added that sometimes the team gets busy and needs him to pitch in and do the day-to-day work. But that can become a horrible cycle, as then he’s not doing what he should be doing to manage the team. “Which means, we are going to get less done,” he said.

Sometimes you have to just say, no, we can’t do that this week. “None of this is easy,” he pointed out, but it’s much better than the alternatives.

O’Connor noted that he continues to struggle with one aspect of management. He said that he wears his own emotional state on any particular day on his sleeve, and that might not be good for the group.

“I am a terrible actor,” he said. “So if I have a personal problem at home,” if the dog was sick, for example, “I may come in miserable and low energy.”  However, doing that “sucks the energy out of the team. … Just because I’m having a bad day, my team shouldn’t be less productive.”