How Should Engineering Leaders Think About Their Career Growth?

Jerry Li
Jerry Li
Sep 11, 2018 · 9 min read

As engineering leaders, we spend plenty of time helping individuals on our teams think through their own career growth. But how should we think about and plan our own careers?

At a recent event with the San Francisco Engineering Leadership Community (SFELC) hosted at Affirm, we got together to discuss this issue, with a keynote and a panel discussion.

Keynote: A Framework For Planning Engineering Leadership Careers

Allen Cheung (Senior Director of Engineering at Affirm), our keynote speaker, provided a framework for thinking about a manager’s career growth. Allen himself started as an individual contributor (IC) at companies like Tagged and Google, before transitioning up the ranks of management at Square, Counsyl, and currently, Affirm.

Allen Cheung delivering they keynote

To start, as a manager planning your career, you should introspect. Where are you in your career right now, and where do you want to go? Allen points out that there’s a balance. While it helps to be thoughtful about your career path, the Donald Knuth saying “premature optimization is the root of all evil” applies just as much to careers as it does to technical systems.

After deciding on the direction you want to go, it helps to make sure you have alignment with your organization and your manager. You should understand what your company and your manager need you to do, and you should make sure your manager understands how you want to grow. You can then work with them on having a plan to get there that also fulfills their needs. Otherwise, you might end up spending time on skills or activities that help you grow but don’t get you promoted, or vice versa.

Next, you have to factor in learning. The growth path is never smooth and continuous; at some points in your career, you will hit rough patches that require you to acquire new skills. For instance, the ability to manage other managers is pretty different than the ability to directly manage ICs. Allen recommends two books, The Manager’s Path by Camille Fournier, and The Leadership Pipeline by Charan, Drotter, and Noel.

Finally, it is important that you reflect. You know where you want to go, you have alignment from your company, and you have taken time to learn. Are you growing at each step along the way? You should have a continuous process of doing things that are “hard” for you, then doing those hard things until they become trivial.

After his talk, the audience also had a few questions for Allen:

What are some tips for managers who want to grow but stay hands-on?
Allen said that a common answer to this question is that managers can code in their spare time, but that can eat into your family time and may not be realistic. Ultimately, there will always be trade-offs. At many companies, it might be difficult to both continue growing while also staying very hands on. As a manager, you can try to find organizations that have roles that allow you to have as much growth and as much hands-on exposure as possible.

Many great opportunities come from networks? How can you build a network while being super-busy?
It starts by putting yourself out there. Communities like the SFELC are a great place to meet other people. There are a bunch of slack channels around for engineering managers. Grab coffee with people you meet, and talk to them about a topic you’re thinking about.

What are the top three things that you try to find in an engineering manager when you interview them?
Allen said the top three things he looks for are:

  • Eternal curiosity and ability to learn and adapt. Especially people that can scale up as the company scales up.
  • A degree of self-awareness that allows you to know what you need to learn.
  • Technical ability, but not necessarily the ability to code or get into technical details. Technical ability for managers means being able to converse with and mentor other engineers, especially senior engineers. Not having that ability places a cap on how much a manager can grow.

Panel: Charting Career Paths

Next, we hosted a panel on the same topic, moderated by Dan Pupius, CEO of Range Labs and former Head of Engineering at Medium. The panel was composed of several senior engineering leaders that have crafted their own path and helped other engineering leaders advance their career:

From left to right: Souvik Das, Maria Latushkin, Rolf Jensen and Dan Pupius

While we recommend you watch the panel for the full effect, we’ve highlighted some of our favorite quotes.

What does it mean to optimize career growth?
It’s a very individual question — you need to figure it out yourself. Ask yourself: What do you want? Do you want money, title, influence, recognition? But once you know what you want, a big part of it is being opportunistic. Look around you and see what opportunities there are for you to make a difference.

When taking on a more senior role, should you stick with your current company or switch to a new one?
It really depends on the circumstances, but at a high-level, it’s an easier transition at your current company, where the complexities are known, the people are known, the domain you’re operating is known. That helps to build confidence as you’re taking on a more senior role. But sometimes an opportunity comes up at another company that’s hard to pass up.

If I’m promised a promotion at my current company within some time-frame, but the timeline keeps getting delayed, what should I do?
It’s important to understand why the timeline keeps getting delayed. Sometimes, there are valid reasons, maybe there was a manager change. Are you being passed over, but your manager doesn’t have the courage to tell you? Are there circumstances that are changing at the company? You have to dig into the true reasons.

What conditions provide the best opportunities for personal and career growth?
The key thing is to make sure that your core values are aligned with your organization and your team.
Maria: Any time my company is going through significant change. Sometimes they are good changes and the company is doing well, and you can learn a lot. Sometimes the company isn’t doing so well, and you learn from all the chaos. Positive and negative changes both provide opportunities for growth.

How do you support the growth and failure of leaders in your organizations?
Stretching yourself and your team is important. It’s like having sore muscles after a workout, that’s how you know you’re getting stronger. One technique I’ve found valuable is to have agreed upon “stretch goals” that really push people beyond their limits, but agree that they are stretch goals that might not be met.
Rolf: You have to give people space to fail, and support them through that, as long as they are trying and have the best intentions.

Should engineering leaders code?
The subject matter of an engineering manager is fundamentally engineering. You need to understand the subject matter at a fairly good level and understand the trade-offs in different decisions. One technique I’ve found is being involved in production incidents since it helps to understand what’s going on. That said, we have to understand that our role has changed and we are no longer engineers. It’s a different profession.

What advice do you have for people transitioning from managing ICs to managing other managers?
The biggest challenge is communication. What you say gets transmitted through other people, and less directly. You have to invest in proper feedback and communication loops. You have to always set really clear expectations. Sometimes you might not be saying what you think you’re saying. Secondly, you have to learn to let go. Your manager reports will have their own way of doing things, and you have to give them enough leeway to operate in a way that’s different than how you would operate.
Rolf: Another big part is choosing the right leaders. Who is ready to manage? Who has the right energy to propel a team forward?

As a manager, how do you deal with stress?
I recommend everyone read the stages of burnout, and learn to recognize the signs of when it might be happening.

How do you get your reports to give you honest, critical feedback as a manager?
It helps to start small and make sure it feels safe. Have a regular cadence. It helps to try and make the feedback seem less consequential to make the communication feel safer.
Rolf: There are a lot of structured ways to get 360 feedback. But an important thing is for you to be authentic, and be open about when you do something wrong. That helps create a safe space for others to give you feedback.
Dan: Trust is such an important part of building the foundation. I’ve seen a problem of conflict avoidance across many companies we’ve worked within the industry. You have to work on your culture, and set deep feedback cycles across your hierarchies.

How do you feel about democratic vs authority-based decisions?
It is our responsibility as leaders to decide when to use one style or the other. A lot of companies go through periods where democratic decisions will give the best outcomes, but sometimes bigger or faster changes are required, and that might require a more top-level decision-making structure.
Maria: I believe in alignment, but that doesn’t always mean agreement. It’s important to set expectations about who is responsible for a decision. That decision-maker should align others on the reason behind their decision, even if not everyone agrees.
Souvik: Disagree and commit is a pretty key principle. You can’t always have consensus.
Dan: Models like RACI can help. Organizations usually have multiple hierarchies beyond the reporting chain.

Any tips for new managers?
A lot of us became managers by accident, or just doing company growth. It’s survivable. But I think it works a lot better and you can become effective faster if you invest in training. Two common themes I’ve seen catch new managers by surprise are prioritization and communication.
Souvik: Practice the craft. Look for mentorship. Find leadership programs. Trust yourself and your team.
Rolf: As a manager, you don’t have the same control you had as an IC. Your levers are now people, not code, and people are not code. People have emotions, hopes, dreams, and aspirations. These people have to work effectively as a team, and you have to give them room to make decisions.

Breakout Session

Following these sessions, we held a breakout session for more peer-to-peer dialog between members of our community.

Resources from the event


Thanks Ragini Holloway, Ashley Nair and the Affirm team for hosting us at your beautiful event space with great food and wine!

Thanks Allen Cheung, Souvik Das, Maria Latushkin, Rolf Jensen and Dan Pupius for taking time out of your already busy schedule to share your learnings with us!

Thanks Osman (Ozzie) Ahmed Osman for helping make this Medium post a reality.

San Francisco Engineering Leadership Community (SFELC) connects software engineering leaders across the world. If you’re interested in connecting with other engineering leaders and sharing learnings, please follow us on Twitter and Medium, and join our community!


Engineering leadership publications by SFELC

Jerry Li

Written by

Jerry Li

Empowering Engineering Leaders



Engineering leadership publications by SFELC

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