Answering some common engineering leadership questions

After multiple speed coaching sessions during LeadDev London in June, Lena and Mathias share some common questions they get from engineering leaders, and some steps to take to help.

Leadership roles can be very lonely. Finding community and a sense of belonging by hearing what others are struggling with can help you learn how to be a more effective leader. Last month, during LeadDev London, Lena and Mathias ran Speed Coaching sessions, where attendees could  get coaching on issues they are facing, or just listen in to learn from others. 

In addition to fostering a sense of belonging, these sessions also help leaders get ideas for addressing the challenges they’re facing, take away practical ideas, and learn from experienced coaches to hone their own coaching skills. Here, we want to share some of our London highlights with you, with all coaching questions having been anonymized.

Questions from senior leaders (Head of, Director, and VPs of Engineering)

How can I get better at delegation? 

The problem: An engineering leader struggles with rolling out a significant development program across their organization of 180+ engineers. 

They’ve been wanting to delegate aspects of it out among their direct reports, but have had difficulties identifying suitable individuals. They’ve also been using various prioritization techniques to focus their own work on the most important goals, but still don’t have enough time. 

The coaching conversation and takeaways: In our conversation, this engineering leader realized that they were hesitant to set clear expectations with their direct reports out of a desire to not to be overbearing. They resolved to set more explicit expectations and work with their direct reports on how they manage up and push information to them.

The engineering leader will also rethink how they’re scoping out the problem that they want to delegate, starting with breaking it down into smaller chunks that can be owned by others.

As it’s been challenging to identify suitable individuals to delegate to, they’ll direct their attention towards building a reliable organizational system that they can trust, instead of over-indexing on finding “the right people” to delegate to. This could include steps like creating better visibility into progress across the organization through shared metrics, and encouraging their direct reports to work more as a “first team”.  

How do I create and roll out a career growth framework for engineers? 

The problem: An engineering leader running a department of 50+ engineers wants to create and roll out a career growth framework for all engineers.

The coaching conversation and takeaways: We explored what problems they want to solve through this career growth framework. They highlighted their engineers being unclear about what their internal career progression could look like, wanting to foster a stronger feedback culture, and a desire to uplevel performance and accountability across their organization.

Building and rolling out a framework like this can take time; Lena pointed them to resources like progression.fyi, as well as the work she’s done with organizations like CircleCI on to conceptualize as well as roll out engineering growth frameworks. 

While they’re working on the growth framework, the engineering leader wants to collaborate with their managers to start more focused career conversations with all engineers and get development plans in place for everyone.  

Cultural aspects like a strong feedback culture can be supported, but rarely fully addressed by a formal growth framework. The engineering leader took away the action to start focusing on building a stronger feedback culture, by encouraging feedback across their teams and holding managers accountable for giving and asking for feedback more regularly. 

How can I progress from a senior leadership/management position?

The problem: A coachee wants to progress in their career as a manager of managers, but their company isn’t providing them with any guidance. They wanted to understand how they could find out what they can and need to do to work towards a more senior management position.

The coaching conversation and takeaways: Things do get wonky in many organizations when it comes to a growth trajectory for directors. The path is undefined and higher-ups tend to not be able to provide much guidance. This was a challenge for several coachees. One in particular was wondering how they could find the kind of projects that would allow them to work towards that next level of leadership and influence.

Working your way further upwards will usually require you to focus more and more on the impact of your work on other teams and other departments. As you approach your work, start considering where your interaction points are across those boundaries.

We suggested that they start talking to people around them, whom they have overlap in their work, understand what’s important to them, build up influence, and work on projects that have a positive impact not just for their team, but also for others.

Some coachees brought their peers to our sessions, which served as a great starting point for better peer support. For lack of a clear path or educational resources, it can be helpful to work together to figure out what they can do to progress. Setting up a manager support group is a great way to learn from each other.

We also suggested they find folks within and outside of their organization who already work at that next level, to talk to them and figure out what work they took on to get to their level. These conversations can provide input and inspiration for a conversation with their manager.

Questions from engineering managers

How can I position myself as a new manager with a non-technical background taking over a new team? How do I get the team members to respect me? 

The problem: This person moved into management less than six months ago. Their background is in project management, and while they have a good understanding of engineering, they’re not an engineer themselves. They just took over a new team and are concerned about how they’ll manage to fill the big shoes of their predecessor in the role. The team already mentioned that they miss their former manager, an engineer-turned-manager with a strong technical background. The new manager has spent a lot of time thinking about how to best emulate the team’s former manager.

The coaching conversation and takeaways: The manager wants to spend time with their team on understanding what they really need at this point in time. That’s not been possible so far, and we realized that the manager has therefore filled this void with their own assumptions and projections about what the team may need. 

The engineering manager realized that they’re currently bringing a lot of their own insecurities and concerns into this new endeavor. They’re – understandably – not very confident yet when it comes to managing teams, and are questioning their abilities especially given their different background. We explored how they can connect more to the skills and strengths that they bring to this role, especially given their experience managing complex projects.

How can I provide feedback to a manager who doesn’t take feedback well and takes credit for my team’s work?

The problem: A manager of several teams reports to a boss who doesn’t take feedback well and who’s difficult to work with, not just for them, but also for their peers. Our leader has found it challenging to work for them, especially as they tend to take credit for other people’s work, including that of our coachee.

The coaching conversation and takeaways: We asked what our coachee has already tried. They’d shared feedback with the higher-ups, but their boss is delivering on business results, while also burning out the team. They hadn’t yet shared with the higher-ups how much the team suffered. In the recently changed market conditions, our coachee said, retention and team health have taken a bit of a backseat. Pressure is high and to leadership, their boss seems to do well.

We suggested a staggered approach, on a scale from least escalation to highest. They could start with things that have the lowest chance of upsetting the status quo too much. We warned that retaliation is always a risk and offered that it’s useful to find a few steps that provide little surface for it.

This could include reframing the feedback to the manager to highlight the dangers of burnout. Next level could be giving that feedback to higher-ups. Then to ask teams to work normal hours and to highlight to the higher-ups that delivery so far has been based on an unhealthy pace. Then they could group together with other peers who are also suffering to make their case, maybe first to the boss, then to the higher-ups. And so on, until they reach the last step they’re willing to take. For some, this could mean leaving. Others might stay but keep their head down. The staggered approach maintains an awareness of the increasing dangers of escalating this further.

How can I build an effective feedback protocol with my manager, after they gave me critical feedback on something I did months ago?

The problem: My manager recently gave me some critical feedback on an incident that happened months ago. Back then, I had no explicit expectations outlined for me, so I didn’t know how I was being measured, let alone that my manager disagreed with my approach. How do I tell them that this wasn’t helpful?

The coaching conversation and takeaways: Our coachee was frustrated that their manager hadn’t told them sooner. They wanted to talk to them and wondered how they could convey just how frustrating it was. We suggested there could be a different opportunity here, one that could help strengthen the relationship that got a dent through this incident. Voicing their frustration might feel good in the moment, but it puts at least one person on the defensive and instantly shuts down the conversation, avoiding any productive outcome.

We suggested that our coachee could approach their manager about this incident, simply stating the facts, that they were surprised by the delayed feedback and then to focus on how to change things from here on out. They could ask their manager what their expectations were, how they can be sure to meet those expectations in the future, and what their future protocol should be for sharing both work and feedback on it early enough that there are no surprises. This conversation can be all about tightening these loops, avoiding a similar situation and frustration in the future.

Final thoughts

We always sincerely appreciate the openness and trust that everyone brings to these coaching sessions. To us as coaches, it’s an honor to be trusted with challenges that engineering leaders face, and work through them together. It was especially heartwarming to see the community come together to listen to each other and learn. At times, the room was filled with over 50 people at once. Many leaders mentioned to us the benefit of hearing what others are dealing with. 

Even if you weren’t able to join us at LeadDev London, you can find community in the LeadDev Community Slack. And always remember: no matter what you’re struggling with, you’re not alone in this.