How 3 Software Engineers Navigated the Challenges of Becoming a Manager

Three software engineers share how they’ve navigated the challenges that come with stepping into a managerial role. 

Written by Stephen Ostrowski
Published on Sep. 10, 2020
How 3 Software Engineers Navigated the Challenges of Becoming a Manager
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Scaling the engineering ladder can be an exciting ascent, where the chance to shape strategies, mentor junior colleagues and effect significant organizational impact presents itself at successive levels. 

Simultaneously, that elevation brings with it a suite of attendant challenges. 

“You’re now accountable for the team’s contribution as a whole, helping drive strategic planning and execution, giving your reports feedback and building career development plans, plus a host of other new responsibilities,” Alexander Perry, engineering manager at Irvine-based cannabis platform Weedmaps, said.

 

Route
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Not only must engineering managers contend with additional, expanded duties, but they must also strike the right balance between leading and outright directing. 

“By telling people what to do, you may create an unintended dependency. The team needs to develop the ability to act independently and make good choices,” David Castellanos, senior software engineering manager at El Segundo-based cybersecurity provider Rapid7, said.

Ultimately, Rafael Costa of Santa Monica-based package tracking app Route said, managerial success is bolstered by open, sincere leadership. 

“If your team knows that you genuinely care and truly want them to succeed, they will excel in their respective roles and, in turn, increase the overall success of the team,” Costa said. 

Below, the trio of managers shared the challenges they faced as they assumed managerial duties, how they tackled them and how others might do the same. 

 

David Castellanos
Senior Manager, Software Engineering • Rapid7

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

The change from being a contributor to a leader and facilitator. Being a contributor allows an engineer to have a lot of say within the project. At times, being a leader feels like the opposite.

In order for the team to give its best performance, I need to empower them to make the choices and take the actions that best fit with the problem at hand. I need to be there to make sure that the team is aligned with the goals and mission of the company, while allowing them to see how to best achieve them. Sometimes, more guidance is needed; however, the people and team that I work with want to succeed and excel, so all they need is a nudge in the right direction and clear targets.

 

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

I am still overcoming this challenge. Fundamentally, I understand my role and function for the team. The challenge is to make the choices and actions that lead to the best outcome for the team; however, that’s not always clear. I need to be able to empower my team to design and implement solutions, offer guidance, and, when needed, weigh in on technical direction. There is a fine line between offering guidance and telling people what to do. Even if you’re right, by telling people what to do, you may create an unintended dependency. The team needs to develop the ability to act independently and make good choices. 

Also, being involved in tactical matters takes focus and time away from the manager’s ability to plan and coordinate, which is the core of the role. Common sense says that I should understand the bigger picture and give my teams direction in a way that is actionable. In practice, you need to review your performance and make sure you are doing it in an effective manner. The best way to do that is to have peers and managers that offer help, guidance and lots of feedback, as well as the opportunity to fail and succeed within reasonable parameters.

There is a fine line between offering guidance and telling people what to do.”

Whats the most important piece of advice youd give to someone who is transitioning into their first engineering manager role?

Transitioning into engineering management is an honor and privilege. But, to be clear, the role is not a more influential version of a software engineer. Software development is a human endeavor, and being a manager means understanding people and their needs, strengths and weaknesses. You’re in charge of a team, but are also responsible for them. To get people engaged, you need to motivate them, play to their strengths and help them overcome or mitigate their weaknesses. The team’s successes are your success, but their failures are also yours. Since you’re not coding —  or shouldn’t be —  you need them in a way that they don’t need you. Take care of your team, because it’s the right thing to do, but also because you will need to depend on them.

 

Rafael Costa
Software Engineering Manager • Route

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

Definitely hiring. Staffing a team isn’t an easy task, especially when you work at a company with an incredibly high hiring bar. We move quickly here, but making the wrong decision on a hire can drastically impact culture, productivity and overall team morale. As a manager, it’s my responsibility to evaluate candidates on their experience, trajectory, work ethic and if they’d be a culture fit with the team. 

 

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

First, trusting that I knew exactly what success looks like for my team. Coming from that perspective, it was easier to understand what to look for, given that I had just been held accountable for those same goals and expectations not too long ago. I took some time to listen to the engineers on our team in order to understand what was lacking and the pains they were experiencing. Once I fully understood the needs, I worked closely with our hiring teams to define the job descriptions and ideal candidate profiles so that everyone was aligned from the top down.

Actively listen, be transparent and always be open to suggestions.”

Whats the most important piece of advice youd give to someone who is transitioning into their first engineering manager role?

Understand that, as a manager, your main job is to serve your team. Be conscious of individual pressures, needs and challenges by working closely with each member. Actively listen, be transparent and always be open to suggestions. If your team knows that you genuinely care and truly want them to succeed, they will excel in their respective roles and, in turn, increase the overall success of the team.

 

Alexander Perry
Engineering Manager  • Weedmaps

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

Understanding the level of abstraction I needed to operate at. As a lead or senior engineer, your purview is very much in the weeds. You are still contributing code, doing extensive code reviewing, technical decomposition of tickets and technical documentation. Although the variety of activities may be broad, it is still fairly narrow in focus on the code and application: Does this app do what we ask it to do, when we ask it to do it? 

When transitioning to management, you’re now operating at a much higher level of abstraction. You’re now accountable for the team’s contribution as a whole, helping drive strategic planning and execution, giving your reports feedback and building career development plans, plus a host of other new responsibilities.

 

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

What quickly became apparent to me was that if I was managing down, I was not adding as much value to the team in their execution, and, at the same time, they were more exposed to externally introduced thrash. Building trust with the engineers, and learning to “hold on loosely, but don’t let go,” meant I could spend more time managing up and across to ensure the team was on the most productive path toward achieving our business and technology goals. Learning to align on and set expectations for the engineers meant they could step up as leaders, self-organize and feel more empowered to generate results. As their manager, you can focus on clearing blockers and defining the long-term vision to minimize surprises that would disrupt their work.

When transitioning to management, you’re now operating at a much higher level of abstraction.”

Whats the most important piece of advice youd give to someone who is transitioning into their first engineering manager role?

Find a mentor. There’s a lot to learn, and even more that the industry as a whole is still figuring out, due to the dynamic nature of modern software development. Having one or more mentors to talk to will give you insights into techniques they have used, their relative effectiveness and their learnings. This should also help alleviate some of the imposter syndrome you’ll likely feel, because you’ll get more of a glimpse behind the curtain and see that you are not the first person — nor the last — to encounter these challenges.

 

Responses have been edited for length and clarity. Images via listed companies.

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