The One About Managing Managers

About 6 or 7 years ago I made the move from a series of small companies to Skype in Stockholm. I joined as a Senior Software Engineer but quickly moved into a Dev Lead role leading half of the team (about 5 people). I was still hands-on coding for the majority of my time but spreading my wings as a line manager. This post isn’t about the transition from being an individual contributor (IC) to line manager, it’s about the next step after that: managing managers.

I was Dev Lead on Skype for Windows Phone, Skype for Xbox One and then Skype Qik before moving on to the Engineering Manager at GroupMe (acquired by Skype some years before). At this point, I was managing all 4 of the client development teams (about 15 individuals) and still trying to be hands-on in one of them, too. Understandably, it wasn’t long before I realised that I couldn’t manage that many people and fulfil the Engineering Manager role as well as still write code and I left coding behind. However, I was still managing ICs.

About 18 months ago I joined Skyscanner as a Senior Engineering Manager fulfilling the role of Tribe Engineering Lead (read more about the Squads and Tribes model over at Spotify Labs). Apart from a few ICs, I was now responsible for more squads and I was managing people who were themselves in that Dev/Squad Lead role. This post is about what I’ve learned so far from the mistakes I’ve made that’s different when you manage other managers.

Realising the Value You Bring

You might have learned this as a Dev Lead, or you might still be kidding yourself, but as a manager of managers, you really have to accept that the value you bring is different than it was when you were an IC. As an IC it was all about the code. As a Dev Lead you were still writing code, but increasingly the value you brought was in the mentoring, guidance and support of the people that reported to you. As a manager of managers, you’re highly unlikely to be writing code, it’s all about the people. Supporting them, guiding them, coaching them and passing on the infinite wisdom you gained while doing that job yourself. You really do have to accept that or you’ll find yourself wondering what it is you’re here for!

Staying Connected

When you manage a team of ICs, you may have one or two people that are remote (or even your whole team!), but even so, you’re all working together on the same thing from the same task board and you all know what everyone is up to. As a Dev Lead, your 1:1s are with the people that you work with day in, day out. I don’t have experience of being a manager of managers anywhere else, but here at Skyscanner I’ve managed teams in 5 different countries so far and I currently manage 5 squads in 3 different countries and 4 different offices. The individuals that I manage (with a few IC exceptions) are themselves Squad Leads responsible for their own squad and the individuals in them. This introduces two challenges:

  1. I’m not in the same office as everyone.
  2. I’m not directly involved in the day-to-day work of everyone.

As a manager of managers, your span of control has increased, but so has your distance from the “front line”, in my case geographically as well! You need to find a way of staying in touch with your wider organisation, not just the people that report to you, otherwise, you’ll lose trust and credibility. There’s no silver bullet here and you’ll probably need to do a number of things. I’ve tried various things, but what’s working really well for me at the moment is:

Regular Skip-Level 1:1s

I currently have 4 half-hour slots in a week and work my way through the entire tribe getting to everyone roughly every 5–6 weeks, which is long enough for things to have moved on since our last chat but not too long. I try to make use of face-to-face time for these 1:1s where possible, but use video calls to ensure that the meetings happen.

The first time I started the process I focused on getting to know each other, our backgrounds, interests and what has brought us to where we are today career wise. Now, I try to focus the first half on what the individual has been working on so I have an appreciation for their contributions and what they actually do (remember, it’s not a status update), then the second half is about giving them the opportunity to voice any concerns or ask any questions. I always make time to ask for feedback on whether there’s anything I could be doing better, but more on that later.

Office Visits

As I mentioned above, my tribe is spread across 3 countries and 4 different offices. First of all, make sure you’re “winning the home game”. Any teams that you have in the same office that you’re located in should really get the benefit of you being there. Secondly, don’t leave anyone out. I visit a different office each month in a rotation and publish my travel plans for everyone to see. It’s worth reminding people when you’re coming, though. If you miss out an office or leave it too long between visits, the people there will soon start to feel like you don’t care or that they’re not important enough.

When you do an office visit, clear your calendar so that you can make sure you make the most of the time that you’re there; don’t just carry on your usual calendar from a different location. Have face-to-face time with your direct reports, with the squads in that office and with other people in the company that you don’t normally get to see. It never hurts to take people out for a meal or drinks, too. Maybe have lunch with a team, maybe have drinks with your direct reports, or maybe have coffee with a colleague. Building personal relationships is important, but especially when people are remote.

Status Updates

As we all know, good 1:1s (with directs or skip-level) aren’t about status updates, they’re about the individual. When you’re a Squad/Dev Lead you’re aware of what your team are doing, so you’re already aware of status through daily stand-ups, etc. When you manage managers, being that level removed means you need to find a way that works for you and your teams on reporting status. I’ve tried a weekly update meeting, but focus and engagement quickly dropped. I’ve also tried async pre-reads for those meetings but found that pre-reads invariably weren’t read. In my current tribe, each squad publishes an internal blog post every 2 weeks which covers what’s been achieved and what they’re expecting to do next. I’m finding that this blog post format provides a rich and engaging update with enough detail to be useful without going into too much depth. As with all things, what works in one place, might not work somewhere else 😏

Trust and Autonomy

The level of indirection that comes with managing managers means that you can’t (and shouldn’t) be involved in the day-to-day activities of any one team. You have to trust the teams and allow them the autonomy to deliver what’s asked of them, but offer support when needed or asked for. You might not even have direct hands-on experience of the specific technologies in each of the teams, so you need to ask the right questions to probe, challenge and guide, but in a non-threatening way to ensure that your teams feel trusted and empowered. It’s not about telling people what to do or how to do it, it’s about using your experience to help guide and support them.


Self-reflection is one way to determine what you’re doing well and where you can improve, but your own assessment doesn’t necessarily reflect that of others. With broader scope comes a greater number of people and that extra level further away means that it’s harder for you to appreciate how your actions are perceived. Being proactive in both giving and seeking feedback and fostering an open feedback culture will really help.

I always make a point of asking for feedback at the end of 1:1s, whoever they’re with and I make sure I give praise and feedback where applicable as soon as possible.

To take advantage of feedback you need to have an open mind: The mind is like a parachute, it only works when it’s open

You’re Still Part of a Team

When you’re a Dev Lead, you have the support of your team around you; you’re in it together. When you’re managing managers it’s easy to feel like you’re on your own, but it’s important to realise that’s not the case. No one person has all the answers and you’re still all in it together; your direct reports and your teams. In the case of Skyscanner, our tribes are lead by a team of (usually) 3 representing Product, Growth and Engineering. In my case, my line manager is outside my tribe and even outside my broader group, but I’ve always got my fellow tribe leads to talk to and work with as well as my peer tribe leads, so I’m never on my own.


Of all of these, I think staying connected is the one that took me the longest to come to terms with and find a good solution for. The skip-level 1:1 and office visits are working really well for me so far and I’ve had good positive feedback on this approach, but obviously your mileage may vary.

If you’re a manager of managers and have other tips, I’d love to hear them 😃