8 Boston Tech Leaders Share Advice for Engineers Transitioning Into a Management Role

by Olivia McClure
September 21, 2020
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At some point in their career journeys, many software engineers will be granted the opportunity to take on a management role. And while there are many benefits of having a management position, many engineers can find it hard to transition from being an individual contributor to an engineering manager. 

There are some significant differences between being an engineer and an engineering manager. While software engineers interact closely with the code, managers often don’t come close to it. For engineering managers, satisfaction comes from seeing their team as a whole succeed and helping each member grow within their careers. 

While becoming an engineering manager requires hard work, there are various ways to more easily navigate the transition. Built In Boston recently checked in with leaders at eight Boston tech companies to discuss the challenges they overcame when becoming engineering managers and share their advice for those transitioning into the role. 

 

Gokul Subramanian
Head of Perception Engineering

Anduril builds hardware and software products that solve complex national security challenges. As head of perception engineering at Anduril, Gokul Subramanian spearheads the company’s creation of defense technologies. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

Individual contributors (ICs) that shift into management roles have to learn an entirely new skill set, which can definitely be challenging. For example, before I wrote any programs professionally, I had written thousands of programs in school or in my own time. Before I solved any engineering challenges professionally, I spent years training to be an engineer in school. So the skill of being an engineer or writing software programs comes naturally to me as an IC. 

In engineering, when you shift from IC to a manager, day-to-day engineering isn’t your job anymore. Your job is to ensure your team succeeds and that they have what they need to do their job effectively. While it might be easier to just write a new piece of code or solve a technical challenge yourself, as a manager it is much more impactful to teach your team skills so they can grow as engineers themselves. As an IC transitioning to management, you often know exactly how to solve a technical problem yourself, but you must learn and take pride in helping your team grow and achieve.  

 

How did you overcome this challenge, and how has it shaped your approach to management?

My former boss gave me a great piece of feedback when I became a manager. He told me that he was no longer going to look at my accomplishments but rather the sum total accomplishments of my team. If my team was high-functioning, that would be considered success. But if I personally was completing project after project and my team was struggling, that was a failure on my part. The shift in mindset from my success to team success is absolutely critical as a leader of teams. It is easy to read books on how to be a successful manager, but in a practical sense, it is much harder to move behind the curtain to ensure you are putting your team’s success front and center.  

 

Take pride in the journey of becoming a better leader.” 

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

First, being a manager is a brand new skill. What made you great at your old job isn’t the same as what is going to make you great at your new job. Be open to new learning and development. Take courses, read books, reach out to mentors and, most of all, be prepared to put in as much effort as you put into becoming a great IC. Take pride in the journey of becoming a better leader. 

I would also encourage you to reach out to other engineering managers. Those are the people who will help you learn and grow. Watch what they do and how they manage teams, and have conversations about what works for them and what doesn’t. Often your “first team” is the other managers across the company, not the team you directly lead. These are the people who are learning the trade alongside you and can help you learn and grow. 

Lastly, tend to your own garden. You want to have a little "garden" for yourself where you continue to practice your individual contributor skills because the thing that makes you a great engineering manager is being up to date with the latest technology. If you are out of date, you are often providing bad advice to your team or are unable to relate to the problems they are experiencing. So, it’s a good idea to carve out time for yourself. A project which is relevant to your organization but outside of the critical path is often a great opportunity to keep your skills sharp. 

 

Christopher Buchino
Sr. Director of Advanced Engineering

Interactions is an AI company dedicated to changing the way brands and consumers communicate. Christopher Buchino, the company's senior director of advanced engineering, oversees the development of AI-driven customer service products. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

I was relatively early in my career when I stepped into a management role. I ended up going from being an individual contributor to building and leading a team of around twenty, including other managers. For me, the hardest part of moving into management was learning how to delegate. I used to be told over and over by a previous manager that I was taking too much on and that I needed to lean on my team more. Being responsible for several concurrent projects, I knew that if I didn’t delegate tasks effectively I was going to become a bottleneck, yet this was still extremely difficult to do. Delegating means giving up a degree of control over details and trusting your team to execute. Sometimes this does not come naturally to an engineer who is used to researching and solving problems with a high degree of autonomy, and I struggled with it early on. Years later, I still need to resist temptations to do too much myself.

 

I’ve become a better manager as I’ve learned to delegate and not deprive my team of the opportunities to step up to the plate.”

How did you overcome this challenge, and how has it shaped your approach to management?

Oftentimes, experience is the best teacher. In my case, I learned to delegate by doing — practicing, failing at times and learning from it. What I’ve realized is that a manager is not only doing themselves a disservice by taking too much on, but they can be hurting their team as well. At Interactions, one of our core values is “We Create Opportunity,” and as managers, we should be giving our team members opportunities to stretch themselves, take on more responsibility and grow professionally. I’ve become a better manager as I’ve learned to delegate and not deprive my team of the opportunities to step up to the plate.

 

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

The most important thing I would say to a new individual-contributor-turned-manager is that being an engineering manager does not just mean that you go to more meetings and conduct one-on-ones with your team, but you get your real work done with individual contributions (typically off hours). Being a good manager is the real work, and it can be difficult at times. Someone once told me that the hardest part of building software is not the engineering but the people, and I’ve found that to be true as well. Getting to know your team, building two-way trust and ultimately helping them be successful can be hard work, and the answers to these kinds of challenges are not ones you can easily find on Stack Overflow. I’ve found that finding a mentor who has experience managing engineers really helps. It is so rewarding when you are leading a team that is motivated and working well together, and you experience the impact of it.

 

Robert O’Toole
Engineering Manager

Toast develops technology that helps restaurants increase revenue, improve operations and delight their customers. As an engineering manager at Toast, Robert O’Toole plays a large role in the development of products at the company. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

Transitioning to management has a longer reward cycle than an individual contributor. When you write code every day, you feel fulfilled by the act of successfully building something new. You make progress on a feature or fix a bug that was causing pain for the customer. You don’t get that same instant gratification when you’re the manager who maybe wrote the ticket to fix the bug or helped to define the feature. Your satisfaction comes during the one-on-one with an engineer where they are elated about how they are growing, during a demo day where they are sharing the end result with you, or in a sprint retro when you successfully landed the sprint.

 

How did you overcome this challenge, and how has it shaped your approach to management?

The longer feedback loop took some getting used to. There were days where I would be in meetings all day and feel like, “What did I do today?” I would have to look back and realize that there were lots of mini wins throughout the day. There are small accomplishments like getting interview feedback in before the debrief, helping to unblock a team member, reviewing some code, hearing how your team member is growing in a one-on-one, or contributing to a slide deck.

 

Don’t be afraid to lean on your team members for support.”

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

Don’t be afraid to lean on your team members for support. Time management is something you need to work on as a manager. You can’t do it all and will need to delegate most tasks. You will have to switch context quickly, and your calendar will be mostly full, so long-form tasks have to wait until you get that window of time. You will find yourself doing things like replying to the 10 Slack messages you received while you were in back-to-back meetings. You are sometimes the go-to person internally for your teams, so you will field questions from other team leaders, help them solve hard problems or find the right person to answer the question for your team. Delegation is a skill in itself and a powerful way for you to scale yourself across the team. 

 

Laura Stone
Lead Site Reliability Engineer

Klaviyo offers a marketing platform designed to help online businesses accelerate revenue using channels they own like email, web and mobile. Lead Site Reliability Engineer Laura Stone plays a part in helping businesses easily store, access, analyze and use transactional and behavioral data. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

The biggest challenge I faced during the transition to engineering management was changing my perspective on success. As an individual contributor, it was clear to me what success looked like: produce value for the company by building "concrete" things (features, processes, etc.). These "things" had clear and binary definitions around what "done" looked like (and thus what success looked like). There were also fairly quick feedback cycles on whether or not I had accomplished what was spelled out. Feedback was bountiful and a main indicator in whether or not I was doing well. Lastly, I could go out on my own and ensure I accomplished my goals or give others direct advice from my past experience that they could apply to solve problems.

It took time for me to understand that as a manager, success is more nebulous and requires a more holistic mindset to achieve. It is no longer about my direct success but instead about doing what I can do to ensure each person on my team is set up for success. It is not my responsibility to prescribe how others do things, or even know all of the answers to their problems. It is instead about asking better questions to encourage creative and new solutions and making sure expectations are clear for what they need to do by when. And when things are going well, I don't always get a lot of feedback.

 

How did you overcome this challenge, and how has it shaped your approach to management?

My perspective on success changed as I learned to embrace the ambiguity of being an engineering manager and to organize and classify that ambiguity. I went from having clear structure and expectations as an individual contributor to a more fluid role that has to adapt to the needs of my teams and organization. To help shift that mindset, I sought out information about what was expected of engineering managers in the industry as a whole. I read books from leaders in engineering management (e.g. Resilient Management by Lara Hogan, The Making of a Manager by Julie Zhuo, Managing Humans by Michael Lopp) and participated in Slack groups targeting engineering leadership (e.g. Rand's Leadership Slack). I learned that different companies expect different things from engineering managers. Some expect people with this title to function as more of a technical lead that oversees architecture and technical changes, while others expect more of a team lead, someone focused on growing people and building high-performing teams. All of this helped solidify my ideas on what makes a good leader and how I can apply those ideas to my current role and company.

 

Having a clear north star for yourself will help you navigate the uncertainty and longer feedback cycles of working with humans.”

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

I want to give two pieces of advice to someone who is transitioning into their first engineering manager role. First, understand why you are making the transition and what skills you want to improve by taking on the new role. It's important to understand where you're coming from when making the transition because being an engineering manager requires developing different skills than those required of an individual contributor. Working primarily with people and their growth, it can be hard to know whether or not what you're doing is working, as well as whether or not you are doing well. Having a clear north star for yourself will help you navigate the uncertainty and longer feedback cycles of working with humans.

Second, get help! While having a north star will aid in navigating the loneliness of being an engineering manager, it is also great to have others you can talk to about what you are going through as you navigate this change. Consider the other engineering managers at your organization as your "team.” You are all in this together to make your company successful. It is also useful to seek out advice from engineering managers at other companies who can give you a fresh perspective on how to tackle organizational challenges.

 

AJ Jenkins
Engineering Manager

Kyruus is a healthtech company dedicated to enabling a better, data-driven approach to patient-provider matching. As an engineering manager at Kyruus, AJ Jenkins helps fulfill the company’s mission to transform how patients access care. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

Becoming a careful communicator. As an engineer, I had only focused on being a clear communicator, but as a manager, you need to be a careful communicator, too. One of the first mistakes I made as a manager was asking my team, “Has anyone seen Jenn? I wanted to talk to her about something.” That’s a harmless question if it comes from a teammate, but when someone hears that their manager wants to talk to them about some unspecified thing, that can cause unnecessary confusion. There has been a learning curve on being a careful communicator.

 

How did you overcome this challenge, and how has it shaped your approach to management?

This is still something that I’m trying to get better at, but I’ve definitely made progress since I started working as a manager. Unfortunately, this wasn’t something I paid attention to when I started, so I’ve improved by making mistakes and learning from them. Thankfully, I work in an organization where people are comfortable sharing feedback, so I got a lot of feedback from my manager, reports and peers whenever I made a mistake so I could learn from it and try not to make the same mistake again. It also helps to share important updates over video calls so you can see people’s body language to gauge how well your message is being received. If people seem confused or upset, try to think about why (or ask them), and then try something new next time.

 

As a new manager, you’ll make mistakes, and that’s OK.”

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

As a new manager, you’ll make mistakes, and that’s OK. No matter how many books or blog posts you read, you’ll inevitably find new ways to make mistakes that you had never considered before. Management is a very different type of job than engineer, so people are expecting you to make mistakes. You just need to make sure you do two things when you do make mistakes: give a genuine apology and do your best to avoid making the same mistake in the future.

 

Phil Morris
Senior Engineering Manager

EzCater operates the world’s largest online catering marketplace. Senior Engineering Manager Phil Morris helps further the company’s mission to make businesspeople more productive and drive revenue for caterers and restaurants. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

An early challenge was learning how to delegate, knowing that accountability rests on my shoulders. Through my experiences as an engineer, I became very confident in my engineering abilities and always felt in control of my own performance and contributions. Leading a team required me to recognize that the team must be successful for me to be successful. This would be impossible without building bidirectional trust and confidence with my team, allowing me to delegate effectively.

 

My value is not measured by my abilities but in how I can help my team maximize its abilities.” 

How did you overcome this challenge, and how has it shaped your approach to management?

I realized that in order to delegate appropriately, I’d have to do everything possible to ensure those on my team were set up for success. I considered the strengths and aspirations of each team member and thoughtfully paired them with the right opportunities. I learned how they like to learn, how they need to be supported and how to celebrate their accomplishments. I did this with each person. We built trust and confidence as teammates. We learned how to communicate with each other. We learned how to win and grow together. We built the foundation for great working relationships where delegation became my desired approach. I remember the first manager who did this with me. He saw my potential and invested in my growth by providing opportunities and guided support. As a manager today, my value is not measured by my abilities but in how I can help my team maximize its abilities. This realization changed my approach to leadership.

 

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

For someone entering their first engineering manager role, my recommendation is to invest in each member of your team. Build relationships based on trust, honesty and integrity. These relationships will provide you the space you need to grow as a leader with their support.

 

AJ St. Aubin
Engineering Manager

EdX serves as an open-source online learning destination, offering high-quality courses from 140 universities and institutions worldwide. As engineering manager at edX, AJ St. Aubin oversees the company’s efforts to increase access to high-quality education. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

The single biggest challenge I faced transitioning from individual contributor to engineering manager was learning when to step away from the code and toward supporting and empowering my team. As a technical manager, when you are presented with a challenge it is easy to fall back on your technical abilities to solve it, but this is not always what is best for your team. As a leader, you have to learn when to step back and support your team in overcoming the challenges they face. Delegation is hard and requires trust built from providing your team with the opportunity to show you they can handle anything.

 

How did you overcome this challenge, and how has it shaped your approach to management?

To overcome the challenge of learning when to delegate I had to learn that I could not do it all by myself, that my value was not in the code now and to trust my team. At one point, the balance between trying to be a good manager and continuing to contribute at the same level I was as an individual contributor became overwhelming. I brought this up to a mentor at work, and they asked me what the smallest task was that I could do that would help my team be more successful. It turns out that it was not coding. I began to see that my actions to unblock my team were much more valuable than a line of code.

 

Seek out opportunities to learn and practice leadership skills like you would technical skills.”

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

The most important piece of advice I would give to someone transitioning into their first engineering manager role is that they should treat their leadership skills and abilities like they do their technical ones and find mentors to help. Never stop learning. Seek out opportunities to learn and practice leadership skills like you would technical skills. Spend the first year, at least, with your head down building up your leadership toolbox by reading, taking courses or participating in other learning experiences that will help shape what leadership means to you.

 

CarGurus uses data and technology to transform how shoppers find cars and how sellers find buyers. Manager Mayur Sharma spearheads the company’s efforts to give people the tools they need to confidently find, buy, finance or sell a car. 

 

What was the single biggest challenge you faced during the transition from individual contributor to engineering manager?

There have been many, but the biggest one I would say was the fear of becoming less technical by delegating more. As an individual contributor who really cherished solving complex problems and building scalable solutions, I knew it was going to be challenging to stay away from code. It also meant that I had to learn to self-evaluate differently and that my performance isn’t based on my output alone but also includes my team’s performance.

 

How did you overcome this challenge, and how has it shaped your approach to management?

Fortunately, CarGurus had multiple new manager training programs at various stages of my transition that made me self-aware and think about this even before I formally stepped into my new role. I try to be hands-on when I can, but I have trained myself to know when to step back and delegate more. I also periodically ask for feedback from my team and from my manager to help me self-evaluate since the feedback loop for managers is generally much longer than for individual contributors.   

 

Be patient with yourself.” 

What's the most important piece of advice you'd give to someone who is transitioning into their first engineering manager role?

Be patient with yourself. There will be days when most of your time will be spent in meetings and that might give you a sense that nothing was accomplished. But know that work is still getting done, just that metrics for success have changed.  

 

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