Senior Engineering: Give Them Time To Find Their Own Stretch

This blog post is brought to you by a random dream I had in December.

As I reflect more on what it means for me to be considered a senior engineer, I find myself picking up answers from my own dreams as well. In a dream this past December, I felt myself being at the office (which, given the situation, is definitely a dream state) but also in particular I found that I was hosting a number of people from my old high school.

As it turns out it’s well possible that the reason why I dreamt of my old high school is because I was talking with my wife about how I would like there to be an organization that would reach out in schools such as that one. But that’s not what the dream was about. And it probably was helped along by having seen a Boston Legal episode about high schools the night before.

In the dream, I was being asked by one of the visitors what would I would recommend them to do, so that more of their students would be successful, and work at big companies. Small aside: there were three of us from my high school, and my year, working in Google when I joined – as I understand one of them was in New York and then left, but I was never really in touch with him – the other guy was actually in Dublin the same as me for a while, and I knew him well enough that I visited him when he moved away.

What I answered was something along the lines of: just don’t fill them of homework that takes them time. They won’t need the homework. They need to find something they can run with. Give them time to find their own stretch.

This is likely part of my personal, subjective experience. I generally hated homework from the beginning, and ignored most of it most of the time, if I could get away with it (and sometimes even when I couldn’t). Except when the homework was something that I could build upon myself. So while on most of the days I would be coming home from school and jump on Ultima OnLine right after lunch, other times I would be toying with expanding on what my programming teacher gave me or, as I told already, with writing a bad 8086 emulator.

But it reminded me of the situation at work, as well — “stretch” being a common word used to refer to the work undertaken by tech employees outside of their comfort zone or level, to “reach” their next goal or level. This plays especially into big tech companies, where promotions are given to those who already act as the next level they’re meant to reach.

While thankfully I only experienced this particular problem first hand a few times, and navigated most of them away, this is not an uncommon situation. My previous employer uses quarterly OKR planning to set up the agenda for each quarter, and particularly in my organization, the resulting OKRs tended to over-promise, by overcommitting the whole team by design. That meant taking on enough hi-priority tasks (P0 as they are usually referred to) to take the whole time of many engineers just to virtually keep the lights on.

Most of this is a management problem to solve, particularly when it came to setting expectations with partner teams about the availability of the engineers who could be working on the projects, but there’s a number of things that senior engineers should do, in my opinion, to prevent this from burning junior engineers.

When there’s too many “vertical” stakeholders, I still subscribe to the concept of diagonal contributions – work on something that brings both you, and many if not all of your verticals, in a better place, even when you could bring a single vertical to a much better place ignoring all the others – but for that to work out well, you need to make the relationship explicit, having buy-in from the supported teams.

The other important point is just to make sure to “manage upwards”, as I’ve been repeatedly told to do in the previous bubble, making sure that, if you have juniors in your team, they are given the time for training, improving, collaborating. That means being able to steer your manager away from overcommitting those who need more time to ramp up. It’s not a hypothetical — with my last manager at my previous role, I had to explicitly say a few times “No, I’m not going to delegate this to Junior Person, because they are already swamped, let them breathe.”

As I said previously, I think that it’s part and parcel of a senior engineer job to let others do the work, and not being the one concentrating the effort — so how do you reconcile the two requirements? I’m not suggesting it’s easy, and it definitely varies situation by situation. In the particular case I was talking about, the team was extremely overcommitted, and while I could have left a task for Junior Person to work on for a quarter or maybe two, it would have gone to be an urgent task afterwards, as it was blocking a migration from another team. Since it would have taken me a fraction of the time, I found it more important for Junior Person to find something that inspired them, rather than something that our manager decided to assign.

Aside: a lot can be written about the dynamics of organizations where managers get to say “I know they said the deadline is Q4, but nobody believes that, we’ll work on it in Q1 next year.” The technical repercussion of this type of thinking is that migrations drag along a lot longer than intended and planned, and supporting the interim state makes them even more expensive on both the drivers and receivers of the migration itself. Personally, if I’m told that Q4 is a deadline, I always tried to work towards migrating as many of the simple cases by Q3. That allowed me identifying cases that wouldn’t be simple, making requests to the migration drivers if needed, and left Q4 available for the complex cases that needed a lot more work. If you don’t do that, you risk assuming that something is a simple case up until the deadline, and then find out it’s another quarter worth of project work to address it.

Of course, a lot of it comes down to incentives, as always. My understanding of the state of it before I left my previous company is that the engineers are not evaluated directly on their OKR completion, but managers are evaluated on their team’s. Making that clear and explicit was itself a significant life improvement I would say — particularly because this didn’t use to be the case, and I was not alone in having seen the completion rate as being a fantasy number that didn’t really do much — much has been written by others on OKR and planning, and I’m no expert at that, so I won’t go into details of how I think about this altogether.

Keeping this in mind, another factor in providing stretch to more junior engineers, is to provide them with goals that are flexible enough for them to run with something they found interesting — leaving your task as the senior person to make sure the direction is the right one. To give an example, this means that instead of suggesting one specific language for implementing a tool, you should leave it up to the engineer working on it to choose one — within the language choice the team has accept, clearly.

It also means not requiring specific solutions to problems, when the solution is not fully fleshed out already. Particularly when looking at problems that apply to heterogenous systems, with different teams maintaining components, it’s easy to fall into the trap of expecting the solution to be additive – write a new component, define a new abstraction layer, introduce a compatibility library – ignoring subtractive solutions — remove the feature that’s used once every two years, delete the old compatibility layer that is only used by one service that hasn’t been ported yet. Focusing on what the problem to be solved is, rather than how it needs to be solved, can give plenty of room to stretch.

At the very least this worked for me — one of the tasks I’ve been given in my first team was to migrate between two different implementations of a common provider. While I did do that to “stop the fire”, I also followed up by implementing a new abstraction on top of it, so I could stop copy-pasting the same the code in ten different applications. I maintained that abstraction until I left the company, and it went from something used within my team only, to the suggested solution to that class of problems.

The other part that I want to make sure people consider, is that deciding that what you were assigned is not important and that there’s better things to do, is not a bad thing. Trying to make it harder to point out “Hey, I was assigned (or picked up) this goal, but after talking with stakeholders directly there’s no need to work on it” is just going to lead to burnout.

To go back to the continuous example of my last team at the previous employer, I found myself having to justify myself for wanting to drop one of the goals from my OKR selection – complicated by the fact that OKR completion was put on my performance plan – despite the fact that the area expert already signed off on it. The reason? We were in a month already in the quarter, and it seemed to late in the game to change our mind. Except the particular goal was not the highest priority, and the first month of the quarter was pretty much dedicated full time to one that was. Once I started poking at the details of this lower priority goal, I realized it would not gain anything for anyone – it was trading technical debt in one place to technical debt in another – while we had a more compelling problem on a different project altogether.

Again, all of this does not lead to a cookie-cutter approach — even senior engineers joining a new space might need to be told what to do so that they are not just wasting air for a while. But if you’re selecting tasks for others to work on, make sure that they get an opportunity to extend on it. Don’t give them a fully-detailed “just write the code for this very detailed specification” if you can avoid it, but rather tell them “solve this problem, here’s the tools, feel free to ask for details”.

And make sure you are around to be asked questions, and to coach, and to show what they may not know. Again from personal experience, if someone comes to you saying that they’d like advice on how to write design docs that pass arbitrarily complicated review processes, the answer “Just write more of them” is not useful. Particularly when the process involves frustrating, time-consuming synchronous reviews with people wanting you to know the answer to all their “What if?” questions without having heard them before.

In short, if you want your juniors to grow and take your place – and in my opinion, you should want that – then you should make sure not to manage their time to the detail. Let them get passionate about something they had to fix, and own seeing it fixed.

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