Demystifying managing managers

Transitioning from a manager to a manager of managers is harder than it looks. Here are some common misconceptions about making the step up in your engineering career.

When I stepped into a manager of managers role, I naively thought this would be an easier transition than from individual contributor to engineering manager, and I was wrong!

Here are some common misconceptions to consider and the differences to expect to help you make an informed decision.

To be or not to be?

“I bet I’d love my manager’s job!”

Is managing managers the right next step for you? In order to begin answering this question, I suggest closely observing what your manager does day-to-day, and ask yourself if you would actually like your manager’s job.

I have seen enough people who loved being engineering managers (EMs) that hated being directors. One common reason is that you are no longer part of the team where the hands-on work happens. You are now further away from the action and you operate outside of teams through complete indirection. This can be a tough pill swallow for some and may not be what gives them joy after all.

Maybe the aspects that you like about being an EM do not translate into managing managers at your company. It’s important to understand what this role actually means in practice. You will learn this best from observing your leaders, rather than their job descriptions.

If you find that you like being an EM but aren’t sure about this next step, talk to your manager about how you can continue to grow on this path without being pushed into managing managers. Emily Nakashima at Honeycomb advocates for having multiple career paths open for engineering managers, and I highly recommend exploring this in your company as well.

“But I don’t want to be middle management anymore!”

Another common sentiment I hear from EMs is that they want to move into managing managers because they are sick of being middle managers. Well, unless the next step at your company is being the CTO, it’s likely that you will continue to have a non-trivial amount of middle management work in your next role.

When you are an EM, you are responsible for your team to your manager, but now as a manager of managers, you are responsible for multiple teams and their leads to your manager. The layers may have shifted, but you will still be managing between them.

“But I want more responsibility!”

Wanting more responsibility is natural for ambitious engineers. However, I think a common misconception here is that having more responsibility equates to having more control, but this does not necessarily apply here.

You have to actively give up control to be successful as a leader of leaders. You are now a multiplier through complete indirection, and this means you will not be as involved in technical decisions and the day-to-day work, while having many new stakeholders.

You have to give your leads your trust and autonomy, otherwise you will hurt the very people you are trying to help succeed.

Finding your anchor

Now that we have explored some common misgivings, it’s important to identify whether your motivators align with the role. For me, I found that I was excited about growing leaders, strategy and planning, org structure, staffing and stakeholder management.

I wasn’t excited about some topics, such as budget management, and that’s okay too. It may not be realistic to expect to like 100% of your job. If you explore the role and find that there are key aspects that interest you, and you are aware of the common pitfalls as discussed, then this might be a wonderful fit for you.

What will change?

You need to go deeper

One of the biggest changes when you step into this role is that you are no longer just responsible for one team, but multiple teams and their leads. You not only have to gain the trust of your direct reports, but the direct reports of your direct reports. You also want to get their honest feedback about how your organization is performing to help you best support your leads. How do you go about this?

I would recommend starting with observing what rituals already exist that you can leverage, and what makes sense to put into place. For example, I find demos, knowledge sharing spaces, skip-levels and all-hands meetings great spaces to build trust and also to receive feedback. I go through RFCs (Request for Comments) and post-mortems as it gives me insight into technical decisions and how engineers collaborate with each other. Team health check surveys are also invaluable tools in checking the health of your organization.

However, beware of power dynamics when navigating these rituals. For example, not everyone might want to have a skip-level meeting with you (I know, that hurts), perhaps it causes them anxiety or they have a lot on their plate, but will feel pressured into accepting your meeting invite due to that power dynamic.

Absolutely leverage organizational rituals to help you build trust with your organization and receive feedback, but be mindful of power dynamics!

Your beloved 1:1s

Another change to expect in your new role will likely be your 1:1s. Typically as an EM, your 1:1’s focus on the individual and their topics. However, as a manager of manager’s, your 1:1s might now focus on topics of an entire team(s) and not just your direct report.

You will likely have to revisit the format, duration and frequency of these 1:1s and actively encourage your EMs to prioritize themselves over their teams in them. This is because if they don’t put on their oxygen mask first before helping others, then it will be very difficult for them to have high performing, healthy teams.

You are being watched

For me, this was the most terrifying change, as I was now being watched like never before. This is fair, as we tend to hold our leaders to higher standards, and there is now an increased power dynamic. Words and actions matter more now, and I had to be more intentional about them. What helped me here was to write down my thoughts and verbally run through them before engaging in important communications. This helped me put my best foot forward.

And while this change is terrifying, this is also an amazing opportunity to use our power for good. For example, let’s say you are in a post-mortem and you notice an engineer blaming another engineer for something. It’s both what you do and don’t do in this moment that matters as a leader. If you stay silent, you are normalizing this in your engineering culture. However, if you use this opportunity to set expectations about running blameless post-mortems, then you have just used this power to move the organization in a positive direction.

Every interaction is an opportunity to shape the culture, and that makes the anxiety of being watched worth it for me.