December 5, 2019
August 16, 2021

Talking Talent: Engineer Your Career

Isabel Strijland

How to Scale from an Engineer to Engineering Manager

On November 26th, we had the pleasure to host yet another Talking Talent event. The topic of it was: ‘How to Scale from Engineer to Engineering Manager’. We kept it close to home, by inviting Engineers and Engineering Managers to gather at Contentful — a company behind a headless CMS. The speakers all followed a different path while scaling into management:

The evening started out with an exercise, where Ben Lowdon focused on the importance of communication when building happy teams, for example by games that facilitate learning and putting yourself into the shoes of a trainer or coach instead of a manager. A big point that Ben made was that these skills he required to be an effective manager can be learnt as much as any coding language or framework.

Kevin Barnett from Contentful opened the floor with his first challenge: not having fun. He described that the simple truth about moving from being an individual contributor into management is that you don’t get to play with the LEGOs anymore:  

‘Your job is no longer about programming or building software, but about people and building teams. If that doesn’t sound appealing to you, maybe it’s probably not the right time or even the right path to get into managing people.’

The first time he went into people management, he couldn’t stop playing with the LEGOs. He continued contributing code and working on projects which quickly extended his workday into regular nights and weekends.

‘I cancelled 1-1s to fix bugs and meet deadlines. I put almost zero thought into the development of my direct reports. My work as a software developer and manager suffered as well as my own personal health and well-being.’

The second challenge is that of criticism, followed by learning how to criticise the work and not the individuals. His move to Berlin and working with diverse, international teams meant that he had to make adjustments on how to give and receive criticism.

‘I quickly learned that exporting the United States’ culture of feel-goodery and sugar-coating any criticism was too easily lost in translation. People did not understand when I was praising and when I was being critical because it pretty much sounded the same. I now had to learn how to be much more direct and sugar-free with my criticism just to make sure it was clearly understood. [...] Consider that if your work is now all about people than by definition that means you now trade in criticism about decisions and behaviours. This cuts much closer to your self and ego.’

The third challenge would be handling ambiguity. There are many reasons why working as an individual contributor is awesome but if we had to choose one, it would be this: you have very fast feedback on whether or not you’re being productive. Fix a bug, finish a user story, ship a feature, remove technical debt. Just hearing those words sounds nice, right? This provides such a good feeling about our work and it usually takes anywhere from a few hours to a few weeks to get that feedback which keeps us wanting more.

‘If it sounds like I need to enrol in a 12-step program, you’re not wrong to think that. It is very difficult to kickback from the addiction of fast feedback knowing you’re being productive.’

As a manager, this feedback loop extends to months, quarters, sometimes years. Decisions you make today on a team’s process or any influence you have on someone’s performance will likely take a while before you understand the impact if any. And you have to be okay with that. Similarly, you will start receiving questions like what’s next or you might be asked to explain a future vision of something. As we all know from software development, the cone of certainty expands as a function of time — estimations and delivery become less certain the further into the future you look.

People are very complex and much less predictable than any software system. The inputs and variables are almost limitless. The problems you need to solve with your direct reports will involve other people and factors you have very little control over.

What can you do to face these challenges? Kevin thinks the most important ability of an Engineering Manager — and probably any Manager — is managing stress.

‘What really helped me to learn how to manage stress was understanding the concept of Anti-fragility, although it required reading Nassim Taleb: not to be afraid of stress. Stress can be a good thing so long as you have time and space to recover from it. Being mentally and emotionally fit is similar to physical fitness in that it requires exerting and pushing yourself in order to become stronger. It also means that you absolutely require recovery time in between these metaphorical workouts. If you have that, you can embrace the suck in your career and push forward knowing that the next stressful moment will be even easier to manage.’

Next up was Kathrin from Asana Rebel with a particularly inspiring story. She talked about how much of an introvert she used to be, and how previous roles had lacked personal development and how she had avoided people generally and did not enjoy interacting with them. Her changes came about as the organisation she was with at the time implemented Agile (something she was not originally a fan of), and she needed to adapt to how she worked. Ironically she became the Scrum Master, which pushed her out of her comfort zone and became the best thing that ever happened to her. Doing this talk is pushing her again and important in her role as Engineering Manager.

This story resonated a huge amount with the next speaker’s focus. Dennis Winter spoke about putting yourself outside of your comfort zone. It will be difficult, awkward, and challenging, but will always result in the biggest improvements and learnings. Dennis shared that on the day he went from Individual Contributor to Engineering Manager, peers started to treat him differently, he took problems home, he had to worry about people now instead of code. Taking care of yourself, your personal development and open communication is key in overcoming these challenges.

And our last speaker, Florentina Arsinte, gave some really interesting personal approaches, starting with the quote that moving into an Engineering Manager role felt like:

‘spinning a bunch of plates, while riding a unicycle, in the rain... with people throwing tomatoes at you.’

She highlighted the difference in how your days will look and talked about going with the flow. As an Engineering Manager, you see the behind the scenes in a way you did not an engineer. Things will change and just happen a lot more, things can seem much more uncertain, but she advised, you just have to go with it!

‘Generally, I structure my day after the calendar. When I’m not in meetings, I work on the items from my notebook, unless someone drops by my desk for an ad-hoc talk. Once in a while I also check Slack messages and emails. And that’s it. If I have back to back meetings in one day, then I have back to back meetings and get to the other items the next day or reschedule something, in case of emergencies. And my team comes first.’

She took the same approach as Kevin and stated the possibility to debug people like you debug code.

‘Speaking of debugging people, as an engineering manager you have to talk to people, a lot, every single day. And not just talk, but, coach and mentor people, helping them find solutions, handle conflict…you know, all those things that make us human. So, how did I figure this out? Well, by doing what I do in all new situations — read. I did a lot of reading on the topic of self-awareness and it really did help me a lot in figuring out how to handle tricky situations.’

She stayed focused by figuring out what her core values and North Star guiding principle was, and then basing decisions and actions in any given case around these. Focussing on people and making them happy was one and the values related to it: kindness, courage and integrity.

In the panel, we continued on the notion to focus on people, as we discussed what success looks like in the role of EM. Kevin states that it is defined by the success of your team, the growth and if they reach their goals. Having a people-first approach and setting a purpose for the team accelerates that success.

'I believe that happy, informed, and productive humans can build amazing products' — Florentina.

Furthermore, building diverse teams is on top of mind to all engineering managers, as it allows the team to communicate about a broad amount of topics. How EM’s deal with this diversity? Start with creating a great hiring process, make sure you adjust to your team, keep an open line of communication, see the best in people and trust them. (additional readings would be The Culture Map by Erin Meyer and the Unconscious Bias by Facebook).

Also, Kevin closed down the evening with a warning to not go into management too quickly or too late:

'The moment you realise you master the craft of engineering for 95%, you can either try to focus on perfecting the last 4.9999% or make a step into management.’

If you are an engineer scaling into a manager, or an individual in any other department looking to make the step to managements, the learnings and challenges found in this article, can be used as guidelines to make this decision for yourself:

  • Be a trainer or coach, rather than a manager (this you can learn)
  • Stop playing with the lego’s and focus on management
  • Accept criticism in your team
  • Get used to the ambiguity and stretched feedback loop
  • Learn how to manage stress and don’t be afraid of it
  • Step out of your comfort zone - it will help you scale faster
  • Focus on your personal development and that of your team
  • Set your North Star and core values and use them in every decision you make
  • Go with the flow!

Be sure to join our Meetup group to keep an eye out for our next event.

Thank you!

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