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Advice from 3 Engineering Leaders on Becoming a Manager of Managers

October 24, 2019
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The transition to becoming a manager of managers requires an entirely new set of skills: hiring, onboarding, and coaching engineering managers are fundamentally different jobs than hiring, onboarding, and coaching engineers. Leading other managers becomes much more about guiding teams, communicating in terms of broad themes of work, and proactively calibrating with peers to stay connected and aligned.

In this panel discussion, three engineering leaders embraced the challenge of learning to manage engineering managers. Rich Archbold, Senior Director of Engineering at Intercom; Charity Majors, CTO at, and Ian Nowland, VP, Engineering - Metrics and Alerts at Datadog came together to share their own experiences of making that transition, what they look for in future managers of managers, and what makes the work so rewarding for them. The discussion was moderated by Marcus Blankenship, Technical Leadership Coach at

Presented here are some of the key takeaways from the panel discussion, which you can still watch in full here (or listen to the audio on Soundcloud).


What are the defining differences as you start to manage managers?

Ian: To me, managing managers really comes down to building delegated relationships where each person knows their role and can give feedback within it. That's very different for me than even managing senior engineers. When you have engineers reporting to you, you get a long way just relying upon intuition and telling people what to do. Managing managers, there is this give and take between their freedom and me wanting to give it to them, while mediating a story that makes everyone happy. Rich has the smoke metaphor I’ve heard him use.

"The more you try and drive and influence, the less effective you're actually going to be. Everybody wants change, but nobody wants to be changed."

Rich Archbold Sr. Director of Engineering at Intercom

Rich: Yeah. One of my former managers told me that being a manager of managers feels like being somebody who herds smoke. Your job is to get the smoke from one side of the room to the other end. The more you actually try and push it, the more your hand goes through and creates a backdraft. You're like, "How can I try and create this gentle, steady momentum that guides people and guides this team in one particular direction?" The harder you try and force it, the more you try and drive and influence, the less effective you're actually going to be. Everybody wants change, but nobody wants to be changed. Empowering coaching tries to let everybody feel like the change is their idea.


Often, being a manager of managers means leading people who are more experienced than you. What was that like in the beginning?

Rich: Scary. Going from being an IC to being a manager is a really big transition. We recognize that people are actually doing a different job now, so they access training courses beforehand and are well prepped and generally well supported. And when you're undergoing that transition from being a manager to being a manager of managers, I think it's again a very different job and a very different skillset, with a whole new set of behavior patterns. There’s different variants, which have their own additional sets of problems—like, if you're managing somebody who has more experience than you, or you're managing somebody who has skills in a different functional area than you. If you are a software manager and now you're managing security engineers or IT engineers or PMs.

"When we're managing managers, everyone else has their own intuitive way of doing things. The way that you solve your problems doesn't work. You have to figure out how to help someone else use their own strengths to solve their problems."

Charity Majors CTO at

Charity: Almost by definition, you're managing people who are way better at their jobs than you are at their jobs. Rich is the person who told me this, and it finally made it click for me: most of us managers—not all of us, but many of us—are very intuitive people managers, right? As we manage our first teams, it just kind of works and we don't really have to think about it too hard. Then when we're managing managers, suddenly everyone else has their own intuitive way of doing things. The way that you solve your problems doesn't work. You have to figure out how to help someone else use their own strengths to solve their problems. Intuitively.


There’s the idea that leaders have a certain amount of capital, and they have to be aware of how they spend it with their reports. For instance, you might get once or twice a year when you can tell someone directly what to do, instead of guiding or coaching them. But how do we earn our capital at this level?

Charity: Doing what you say you're going to do, and being seen to be effective. It is actually performance. A lot of times, people will only believe you if they see you do what you said, right?

I feel like a lot of people expect there to be some magic formula and there just isn't. But one idea that I have constantly given short shrift to, and I'm still not very good at, is learning how to manage up. It feels like sucking up or curing favor that I violently reject. But it matters. If you don't have a good relationship with the people above you, you're not going to be able to effectively advocate for your team when it counts.

Ian: Charity, you mentioned a magic formula. I'm going to give you the magic formula that I use. It’s absolutely not mine. I don't know which leadership book I read it in (editor’s note: our research points us to The Trusted Advisor by David Maister). But the formula is, your influence comes from credibility multiplied by reliability multiplied by intimacy, all over self-interest. How credible are you? Do people think when you speak that you actually know what you're talking about? Are you reliable? Are you going to do what you say you're going to do? Are you willing to create intimacy with people? Do you actually meet one on one with them?

I think reliability is an amazing skill and discipline that is underrated. And I think so much of what we do is just showing up over and over again, grinding it out, doing what say say you're going to do. That is just so underrated but so powerful. Then the intimacy bit—admitting when you're wrong, telling people when you're actually burnt out. Asking for help. Actually getting to know people and meeting them where they are. And then when people see that you're actually willing to work hard to make them successful rather than to make yourself successful? I think it’s underestimated.


How do you know if someone will be a good manager of managers? Are there key behaviors or indicators that you look for as you consider moving people into that role?

Ian: I like to start seeing from people that they are comfortable succeeding through influence. Very early on as a manager of engineers, you can often get away without really influencing. People just look up to you and really listen to you. So you know people are high-potential when you see them actually influencing their peers. They're often visible upwards. And those are great characteristics, because those are what the job is going to require. Also, seeing that people are happy with that ability to influence, because the job itself is more frustrating. You don't get the hits of success anywhere near as fast through influence as you do through doing it yourself.

Rich: I'd say the first thing is I want to see somebody be an excellent frontline manager. People actually need to be excellent at the job at hand and be recognized as a role model by their peers. Their peers have to look up to them and go, “That person does it really well. I feel like I could learn something from them.” And the next thing I want to see is really good stakeholder management. I need to know that, if we actually give you more scope and more teams, I can trust you to send up the flag and notify me about only the stuff I need to know. I'm going to trust you to take care of everything, always knowing that I can rely on you to call in the right people when it’s needed.


Managing engineering managers is not all just rainbows and unicorns, right? You have long-term feedback loops. You often only hear the bad stuff, and successes are hard to define. I would love to hear from you all: why the heck do you do it?

Ian: I’m an engineer who loves solving hard problems. But at a certain point in my career as an engineer, I wasn’t sure if new problems were going to be that different. The thing about being a manager is you are always learning about people. You're always learning about yourself. And that sense of growth, that I'm getting better at it, is actually what keeps me going. It's super energizing for me to say, "Hey, I see the world better than I did six months ago."

This sense of personal growth motivates me, where I know other people are much more interested in solving hard technical problems for their sense of personal growth.

"The thing about being a manager is you are always learning about people. You're always learning about yourself. And that sense of growth is actually what keeps me going."

Ian Nowland VP, Engineering - Metrics and Alerts at Datadog

Charity: To be clear, I'm perfectly happy as an engineer and I planned to go back to being an engineer at some point. That was the entire plan when I started this company. It got sideswiped. Starting a company was something that I did out of necessity because there was a problem that needed to be solved. Ian, you said you were motivated by personal growth. I'm motivated by doing what I feel needs to be done. This is why I've always been in operations. Whatever it takes to achieve that goal, I will figure out a way to do it.

Rich: My motivation I think is pretty similar to Ian's. I'm very driven by personal growth. I'm driven to take on harder and harder problems. That desire for personal growth and pressure to perform are some of the things that drive me on. As I got into my career, I realized I was a much better people manager that I was an engineer. I'd say the people management turned into a calling for me rather than a job. Helping other people to grow their careers or avoid burnout or advocate for more money for their families—I feel like it is actually how I do good in the world.

You can watch or listen to the full panel discussion on Becoming a Manager of Engineering Managers with Rich Archbold, Charity Majors, and Ian Nowland.