Learnings from my first 90 days as an engineering manager

One day, I was an individual contributor, and the next, I was a manager.

I was still the same person, just now with a team that needed a manager who could take care of them from day one. In the first 90 days of my transition to management, I kept a journal to document my wins and opportunities. These are the challenges I encountered that I didn’t anticipate when I took on the role.

• Confidentiality. In 1:1s, I strived to create a safe space where my teammates could share their challenges with me. In the team, I worked with individuals through performance gaps and conflict resolution. Keeping secrets has been a significant emotional burden.
• Preparing, giving, and receiving feedback. Handling feedback was daunting, especially in the beginning. I worried about how the feedback would land, and how my teammates would perceive my feedback and me. I struggled with reports getting defensive over feedback, but it was also challenging to receive feedback without getting defensive because of my insecurity.
• Decision making. A lot of folks looked to me for information, and to make fair decisions. Everything down to how I presented myself was a decision, to begin with. The vocabulary I used, the jokes I endorsed, and the way I recognized and penalized my reports represented the company culture. My stress level went up. I also struggled with making idempotent and fair decisions.
• Managing change. I transitioned into management in the same team where I had been an individual contributor. I felt the need to build up my credibility quickly. Some of my former peers had concerns when I first stepped into the role. Most folks welcomed the change, but it still took time to adjust to the new relationship.

With the learnings from this experience, I want to share with you five handy techniques you can use to navigate these challenges. 

Setting expectations early

Before setting expectations with the team, I encourage you to set expectations for yourself. It took me months to establish and to come to terms with what the role entails. 

My current expectation is to ‘get better outcomes from a group of people working together’ – a quote from The Making of a Manager by Julie Zhuo. I aim to achieve this by ensuring that the team delivers quality output efficiently, and meets our stakeholders’ needs in the short term. I also facilitate the team to run the right processes, communicate with organizations effectively, and focus on the business goals. 

Helping the team short-term is one dimension of my responsibility. If I only follow the short-term expectation, I could probably achieve results just from putting a lot of pressure on the team. 

Here is where the long-term goal comes in. My long-term goal is to build a diverse and inclusive team where the team’s ideas are heard, refined, and implemented. To reach this, I give the engineers space to develop skills for their development, and the team’s future needs. I evangelize for the company in the industry, and I hire the best people for the team. That way, we can build a sustainable team and long-lasting business.

Next, let’s talk about setting expectations with the team. Early on, I was extremely hesitant to set them, thinking that it would sound condescending and that the team would find it awkward. The reality was that expectations were there whether we liked it or not. If we didn’t make them explicit, they would still exist implicitly. And not discussing expectations would only result in a mismatch of them. When I saw opportunities where folks could improve, it wasn’t easy to provide feedback. By whose standard were they not doing a good job? If I didn’t explicitly discuss the criteria of doing a good job, then the feedback wouldn’t be fair or as just as it could be.

A conversation about unmet expectations or underperformance sounded daunting, but it was all the more critical. The following scenario has stuck with me. At a quarterly review, a teammate thought they could move up the engineering levels at multiple dimensions. But I had to tell them that, quite the contrary, they were not performing at their present level. The issue though was that we had not had an open conversation about what it meant to meet expectations in the first place. This resulted in a mismatch of expectations. My teammate was disappointed, and they possibly lost trust in me. If I had a candid discussion earlier with them, I could have avoided a nasty surprise, and given them more time to improve.

Expectations go both ways. Discussions on whether I met my reports’ expectations were also helpful. Some folks expected me to be more hands-on with project management, others expected me to be more transparent with company news. I would encourage open conversations with the team to align their expectations of me. This made it easier for them to deliver feedback to me. These discussions enabled me to establish a trusting relationship with the team in the long-term.

Delegation

Early on, I received advice to ‘delegate often’, but it was easier said than done. Here is what I struggled with. I was ultimately accountable for the deliverables of the team, even when things went south. How can this be reconciled with delegation?

These are the steps that were missing, and that I run with now:

1. Carve out responsibilities for teammates. Set expectations with them early on (see above). Align the engineer on what great work should look like.
2. As the engineer executes the task, coach the engineer through any challenges that come up.  Help unblock them and connect them with the right people to set them up for success.
3. After the engineer completes the task, verify the results. Do a retrospective with them, and get their perspective on what went well and what could be improved. Then give feedback. 
4. If they accomplished great work, celebrate the win with the team, and vouch for their work up the management chain. If not, take accountability for the failure, but also hold the engineer accountable for the areas where they could improve. Next time, support them through improvements in subsequent assignments.

With these steps, you can delegate responsibilities, and help the team grow along the way.

Identifying my values

With the transition to management, I got a wider exposure to the company. Other leaders asked me for my opinions more often. I was the representative of my team in some meetings. When making tough choices, I think about the values I don’t compromise on. I take a people-first approach. During COVID-19, business needs were urgent to attend to. Though at the same time, with office closure in place and subsequent isolation, the people weren’t doing well at all. For me, offering more 1:1 time, sharing mental health care resources, and encouraging the team to take days off were my priorities.

It is important to reflect on the values that mean the most to you. What is non-negotiable for you? Autonomy and authenticity? Or creativity and courage? It is a magical experience to work at a place where you genuinely identify with the company values. Your decisions will likely get backed. Decision making is low-friction. However, if your values clash with those of your company, your stress level will increase. Say you thrive with authenticity, but are expected to withhold information from the team often, you might want to consider changing organization.

Practicing self-care

Most management books I have read had a self-care or self-management section. Every time I came across this chapter, I skipped it because I wanted to get to the “real” content. This was a mistake. I learned that only when I know how to prioritize taking care of myself over work priorities, can I be the best manager for my team in the long run.

I used to think that showing my emotions at work was unprofessional and weak. As a lead, I felt that I had to stay positive at all times to support the team. As a woman in tech, I cared a lot about how I was perceived in order to counteract the stereotypes. The last thing I wanted was to appear as though I was unable to manage my team efficiently due to being emotional. However, that was not the best path for myself or the team. I missed out on opportunities to be vulnerable with my team and for them to be vulnerable with me. Over time, I have learned that having emotions and showing emotions is human. Staying true to how I feel and supporting others to navigate sadness, anxiety, and disappointment was really the courageous thing to do.

How to get help

Getting quality feedback as a manager requires a more thoughtful and deliberate approach. There is a power hierarchy between a manager and their reports. When I stepped into management, before the team and I had the chance to establish a trusting relationship, the team took on a risk when they were giving me feedback. They might have been afraid of retaliation. It could also be more difficult for folks from certain cultures, like mine, to share feedback with their manager. (I am originally from Hong Kong. In my culture, I would be perceived as disrespectful by disagreeing with someone who is more senior than me.)

It didn’t help that in the early days, I was insecure about myself. With insecurity came defensiveness. When my reports brought up potential problems in the team, I sometimes struggled to accept them humbly. I let my ego get in the way. Giving feedback to their manager was already hard for my team. And my defensiveness didn’t help the team surface their problems. 

How about my team delivering feedback to me through my manager? The reasons why I wouldn’t only rely on this method are as follows:

1. My manager could be tackling multiple responsibilities and might not meet with the team often. Therefore feedback could be delayed, and opportunities to improve when most needed could be missed.
2. My reports might find delivering feedback to me through a skip-level meeting daunting, particularly if I have a good relationship with my manager. My team members could be fearful of my manager disagreeing with their opinion, resulting in harming their own career in the org.

There are no shortcuts to getting candid feedback from the team. You must work to establish an open and trusting relationship with your engineers. With time, using the five tools in this article will help.

Another source of feedback is through peer teams and departments. What does the product team think about the recent launches? Is there friction with the sales team over committing to delivery dates? How is the team being perceived by other groups in engineering? Establishing a good cross-team network will give us pointers on how to improve the team.

Finally, I work from Lara Hogan’s advice to build a ‘Manager Voltron’ (see her article). I have multiple responsibilities and objectives. No one person can give me all the feedback I will need to succeed. I contacted experienced managers throughout the whole company to coach me through challenging work scenarios, and I now do role plays with them before I need to have tough conversations with my reports. I read management books and feel mentored that way. I would also encourage you to hire a leadership coach to help out if needed.

Conclusion

Transitioning from an individual contributor role to a management role was a big change for me. Setting expectations early, delegating responsibilities, identifying my personal values, practicing self-care, and getting help from my ‘Manager Voltron’ helped me navigate through these challenges. There is a lot to learn on the leadership path, but the reward comes when the people flourish and fulfill their potential, bringing the whole team up. Meanwhile, hang in there. You’re not alone in this journey of becoming a manager!