Photo by Sajjad Ahmadi on Unsplash

Software Engineering Manager: Year Two

David Faizulaev
Chegg
Published in
4 min readApr 16, 2024

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If you are curious, the title is a nod to the “Batman: Year One” comic, which is awesome btw :)

Approaching my second year as an engineering manager, I decided to take some time to reflect on what I’ve learned during this time. After looking back on the differences between the first year and now and let me tell you…there are a lot.

There are differences in decision making, management style, project planning and much more.

I decided to discuss this topic with other engineering managers at Chegg, particularly those who assumed their role around the same time as I did. It was cool to see that almost every manager had similar insights, so I’ve compiled a list of tips for new engineering managers and team leads embarking on their journey, with the hope that it will make their beginning easier.

  • Don’t commit to anything on the spot: It sounds weird, but I’ll explain. There will be cases where you’ll be asked to commit to a certain date, feature scope etc. It can be a face-to-face meeting, Zoom call, email or Slack message with a product manager, project manager or other partners.
    — Give yourself the time to think the ask through and to consult with the team, a colleague or your manager if needed. It’s better to give a comprehensive answer than answering on the spot and then realizing how off the mark you were.
  • Make Mistakes: On the subject of “off the mark” you will make mistakes, quite a few actually. Do the best you can to learn from them. Take action items, ask for advice on how to tackle similar cases. Ohh and a spoiler — you’ll still make mistakes, like underestimating development time and missing design flaws to name a few that’s just life.
  • Keeping Context: You’re going to work on a lot of tasks with a lot of people in various roles. Find the best way to keep context of the team’s status, per task, per project, etc. Make sure to have all important dates, milestones and commitments made there as well.
    — I use a Google sheet doc to track the team’s tasks per quarter, including important dates, and their respective LOEs (with LOE standing for ‘level of effort’) as well as team vacations.
  • Backlog: As an Engineer I didn’t really understand why a team’s empty backlog was a bad thing. Naively, I thought an empty backlog showed that the team had finished all their tasks or were about to. But not having a backlog is a bad thing. A backlog indicates that the team has scope and a roadmap forward. A lack thereof affects the team’s motivation and outlook on their role and impact in the company. So, make sure to always have a backlog!
    Collaborate with product managers, the CTO, group managers or other partners to get more work for your team.
  • The Art of Delegation: Learning to trust your team and delegate effectively is like realizing you don’t have to run the whole race yourself. You’re not admitting defeat; you’re empowering your team. This boosts your teammates’ growth and frees you to focus on strategic planning. Remember, delegation is not about shedding responsibility; it’s about enabling others to flourish.
  • Setting Expectations: Just like in a good relationship, clarity and communication are key. Setting clear roles, responsibilities, and expectations isn’t just administrative work; it’s the foundation of a high-functioning team. Be like a tour guide: clear about the journey, transparent about the challenges, and enthusiastic about the sights (goals) you’ll visit together. And yes, this extends beyond your team to stakeholders, too!
  • Take a Break, it’s Okay: Working without breaks is like being a superhero who forgets they can fly. Taking time off isn’t a sign of weakness; it’s a strategic retreat that lets you come back stronger. Just as you recharge your phone, you need to recharge yourself. Learn to rest without feeling guilty about not checking emails or Slack messages every five minutes. Your brain (and your inbox) will thank you.
  • Speak Less, Listen More: As you grow in your role, you realize your words have weight. Learning to filter what you say and being cautious about the promises and pressures you create is crucial. Imagine your words are like social media posts: Oonce they’re out, they can’t be taken back. So, think before you speak, and remember, sometimes the most powerful thing you can do is listen.
  • You’re Not the Star of Every Show: There’s beauty in recognizing you don’t need to be in every meeting or decision-making process. It’s like accepting you’re not the lead singer in every song. Give others a chance to shine, and you’ll see a harmonious team performance that might just surprise you. This not only reduces your stress but also fosters a culture of trust and mutual respect. Just make sure to get the relevant context back and see if there are any action items you need to handle or can assist with.

I hope that armed with these insights, you’re better prepared to lead confidently and effectively. Embrace these principles and watch as they not only change your approach to leadership but also the dynamics of your team for the better.

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