The Value of Letting Go: Engineering Managers from Peloton and RocketReach Share The Advice They Wish They Heard

The transition from individual contributor to leader can be turbulent. RocketReach CTO Jeremy Livingston and Peloton Engineering Manager Jennifer Barry sat down with Built In New York to share the tips they wish they had heard as new leaders.

Written by Jenny Lyons-Cunha
Published on Mar. 16, 2023
The Value of Letting Go: Engineering Managers from Peloton and RocketReach Share The Advice They Wish They Heard
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Leadership is not a straightforward endeavor.

It’s common for technical leaders to feel they must do it all — compassionately manage their reports, shepherd projects to the finish line, generate the next great engineering epiphany. But complete control is impossible. 

“In any complex organization, a leader must delegate enormous amounts of control,” writes technology and innovation expert Neil Chilson in an article published by Entrepreneur

In their efforts to be exceptional, he continues, new managers often face burnout, missed deadlines and dropped batons. 

It’s a fate that befell Peloton Engineering Manager Jennifer Barry when she transitioned from individual contributor to leader. 

“During my initial weeks as a manager, I was wrapping up my existing engineering work while also taking on new priorities of managing projects and people,” Barry recounted. “I was super excited to get involved in everything myself — but this made for a packed schedule that was impossible to balance.”

RocketReach CTO Jeremy Livingston echoed a similar dilemma. 

“Had I found ways to remove myself from the critical path earlier, I would have prevented delays with our projects, helped the team learn more quickly and illuminated gaps in our organization much sooner,” Livingston said. 

In their growth as leaders, both Barry and Livingston learned the art of letting go. 

“When I delegate tasks, it gives my team opportunities to grow while giving myself time to focus on team strategy and culture,” Barry said.

Livingston agreed, noting “Success in your new role shifts from what you personally accomplish to what the team accomplishes.” 

Conversation with both leaders makes one thing clear: Effective managers lead with delegation and healthy trust in their team. Built In sat down with Barry and Livingston to learn more about the advice they wish they knew when they made the leap to leadership. 

 

Jennifer Barry she/her/hers
Engineering Manager • Peloton

Peloton is an interactive fitness platform that serves a community of more than 6.9 million members in the United States, U.K., Canada, Germany and Australia. 

 

What is one piece of advice you wished you’d received when first starting out as an engineering manager, and why?

The importance of delegation and leaning on those around you. I started at Peloton as a senior software engineer and transitioned into the engineering manager role.


What steps have you taken to implement this lesson in your own work as a manager? And what impact has that had? 

Even though I am still in my first year of management, I’ve learned that leaning on the great team of people around me at Peloton is a win-win situation. 

I’ve learned that leaning on the great team of people around me is a win-win situation.” 

 

This is evident when dealing with bugs. I used to directly pick up issues that I knew how to solve. Now, I encourage team members to investigate issues and come to me with questions. This allows them to get a deeper understanding of how our system works and frees up my time to plan for future projects. 

Delegation is a skill I will continue to improve as I continue to grow as a manager at Peloton.

 

 

Jeremy Livingston

Powered by an expansive and trusted collection of contacts, RocketReach connects professionals to new opportunities and empowers sales, recruitment and marketing teams. 

 

What is one piece of advice you wished you’d received when first starting out as an engineering manager, and why?

I wish that I would have been encouraged to find ways to remove myself from the critical path of software delivery as early as possible. When I transitioned into management, I tried to maintain my same level of contributions as an individual contributor while also adding new management responsibilities into the equation. This ultimately led to me doing a poor job at both.

When you pursue a move into engineering management, you are taking on a fundamentally different role. 

Remove yourself from the critical path of software delivery as early as possible.” 

 

There are still many ways that engineering managers can — and should — stay close to the technical work of their teams: Engaging in system design sessions, participating in code review, pairing with their teams and absorbing low-urgency and distracting work. All of these contributions allow managers to stay technically sharp and well-informed without being a barrier to delivery.

 

What steps have you taken to implement this lesson in your own work as a manager? And what impact has that had?

In the spirit of removing myself from the critical path, I strive to create teams that can operate autonomously and are empowered to make decisions on their own.

As your management career progresses, the predictability of your day becomes a lot less certain. Ensuring that teams have a clear understanding of why we are pursuing certain initiatives and are aligned around the end goal gives them the context to make informed decisions on their own. I find that this approach helps people feel trusted and appreciated, which contributes to strong relationships with leadership and the rest of the organization.

Recently, at RocketReach, we rolled out a bottoms-up goal-setting process for our product and engineering teams. Our teams collaborate cross-functionally to create quarterly goals and solicit feedback from senior leadership throughout the process. This process has been a major boost to engagement and has helped us find more creative ways to solve our largest customer pain points.

 

Responses have been edited for length and clarity. Images provided by included companies and Shutterstock.

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