(Please don't share)
I have been an "engineering director" for a while now. In my current job I run about 1/5 of the engineering organisation. Together with my product partner we are responsible for 1/3 of the company's bottom line.
I never intended for this to happen. When I was promoted to the pre-director level in my previous company, I told myself and anyone who asked, "this is it". The path to director seems unnecessarily grueling, plus I've heard a few ppl saying "director is the first level that you are sided with the company instead of your team", and to me back then that reward does not sound very appealing.
However 6 months after my promotion, I was thrown into the job market unexpectedly, and somehow did an interview really well, and soon after I found myself staring at my new contract, with "Engineering Director" on it.
It's been quite a ride since I started. I'm having surprisingly more fun than I expected. I also found myself learning new lessons at a faster than ever pace, which is refreshing.
It takes discipline to be effective at this levelI haven't worked this hard since my first job in tech.
To be 100% honest, in the past 5 years, I rarely worked at 100% capacity. Often I was able to deal with things as they happen, and still frequently have time to either slack off, or tinker some 20% projects.
I quickly realised this time it's different. I was practically forced to work at maximum throughput, 40 hours a week, from week 1.
And I realised it is extremely easy to be carried away by constant flow of events, to just operate reactively all the time, to work nights and weekends frequently, but to have no results.
One of the best decisions I've made this year, is to read Effective Executive before starting this job. It taught me the principles and tactics to stay effective at a role like this.
Ultimately, the real lesson is it takes discipline to choose to be effective every hour, every day, every week. Be intentional in how you spend your time, what decisions you are making, and how you are communicating. It's the only way to be truly effective at this level and above.
(I quote lessons and snippets from this book so frequently that people joke about my "effective" lingo in the company now, which I see as a positive thing.)
Value first, aptitude secondThis is a direct quote from Sam Altman. I don't fully agree with how OpenAI operates, but I agree with this line of his.
I had 2 performance problems on my hand when I joined; one I was strongly hinted that I should exit them quickly, the other was referred to as "high potential" once the "small" problem is fixed.
The results couldn't be any more different: I was able to turn the first one around, but left with no choice on the second one after much effort and struggle.
Reflecting back, the root cause driving completely different outcomes is value, in this case being open to feedbacks. The first individual, while aptitude wise may not be the most outstanding (but is perfectly capable at their current level), is extremely open to feedbacks and would take immediate actions. With the second individual, every feedback and coaching attempt would turn into a lengthy and tiring debate.
The derivative lesson from this, perhaps a bit painful, is my own leadership team have to fully trust me. I simply cannot afford any mistrust in the leadership team. And once mistrust is there, I cannot afford taking the same time and energy to fix it compared to when I run a much smaller team. Because any trust and value misalignment means a significant portion of my org (that reports to them) would be misaligned with me. And every second counts when that happens.
Once there is a value mismatch, often the best way is to move on quickly, instead of trying to change how someone is wired fundamentally.
Thinking back, I had a very similar case in my previous job, where I made the mistake of trying really hard to save it, which only brought me prolonged high level of anxiety, and is totally not worth it.
Black swan events are going to happenA few months into this new job, I was hit by a "black swan" event. Note I am not calling every unusual event a "black swan" event: a few years ago, my product partner went out to get lunch, got hit by a bus, and sadly passed away a few days later. This is my definition of the extent of a black swan event.
The latest event came at a really bad time where I was already spinning more plates than ideal, and it immediately added significant new workload overnight. My initial reaction (apart from feeling deeply sorry for the individual) was, "jeez, what are the odds", and I even went around seeking external validation, asking my managers "am I being unlucky or is this normal", and everyone assured me yes I am indeed being unlucky.
Then one day I realised: as my org size grows, these seemingly very unlikely events, are just going to happen. If I put on the CTO hat and look at the whole company, there are 2 other black swan events going on. They are no longer an anomaly given a sufficiently big org size. I need to accept that new reality and consciously plan for them.
You will be quoted often, so get used to itI actually don't think "watch what you are saying" is the right lesson here, but rather you need to have the guts to own your words. And have the guts to say you are wrong when you are wrong.
You are primarily a resource allocatorI command 20% of the whole company's engineering resource, and I am the engineering director accountable for the most ambitious expansion plan the company has to date. From day one I knew my primary job is to allocate all these resources well, such that combined they propel the company forward in a maximum effective manner.
This is very different to my past roles where my primary role is a combination of growing individuals and making sure team executes well. While it still can be rewarding at times, it's definitely not as satisfying.
When I was job hunting, I told every company that I want a seat at the decision table -- I no longer want to fall victim to some decisions made behind closed doors. I have that seat now, I am naturally good at it, and I thoroughly enjoy every second of it. I can't really explain why, perhaps a bit related to how "type A" I am, or how I still dream to run my own business one day, or how I enjoyed commanding the court being the point guard.
I love it.
"Team vs company" divide turned out to be okayI realised very quickly this is not as big a problem as I feared it might be. Working in a mission-driven company definitely helps. It's extremely easy to motivate your teams when they can see how their work directly translate into company outcomes, which translates into both better user outcomes and better financial outcomes for themselves.
Be a good human
As soon as I joined, I set out to have a 30min 1/1 with everyone in my org. It took 3 months but was a very worthwhile investment as I learned so much about everyone. What surprised me though, is multiple people have told me, "you're the first director that has come talk to me".
I'm a data nerd, when observing incidents I would jump straight in and help run data queries. A manager told me in private that that might be seen as "not trusting engineers". I was mortified and went to apologise to the engineer running the incident and said I would stop doing that, his response: "absolutely not! It's refreshing to see a director actually wanting to help."
Over time I start to realise: I operate in quite a different way compared to some other senior folks. I'm very quick to show concern, care, curiousity, vulnerability. In a way you can say I tend to forget I'm "someone important-ish".
This has come full circle for me: when I first became an engineering manager, I mainly operated out of intuition: I cared for my team, and wanted to see everyone succeed. I ended up committing several classic mistakes such as adoping "us vs them" lingo, and tried too hard to be liked by everyone. I built a loyal and high functioning team, but perhaps not the most self-sustaining one.
Since then I have read quite a few books on the subject, tried to act more like a "professional manager", with a mix of success and failures.
Fast forward to today, I am once again letting my true self show in my work, and I feel liberated. This is not to say all the past readings and learnings and "actings" are useless, rather they have helped me internalise the lessons and experiences, and enabled me to be genuine, without falling into old traps.
I do believe everyone finds their own way of being effective. For me, at the end of the day, honesty, genuinely caring and being curious are still meaningful and valuable. And they are way more important to my core identity than any professional titles I carry.