Ask HN: What was the biggest leadership challenge of your career?

Second point, sure. That's the ideal. But it's not always going to happen, and you need to be able to deal with that situation to be a well rounded manager and leader. IMO.

The company I own got hacked and our database was stolen, containing basic user and company data for 100,000s of users as well as some partial card data. From the moment I discovered the breach (browsing logs after an unexplained brief outage), for the next 3-6 months, my life did not belong to me, but to insurers, forensic investigators, regulators, the police, credit card companies, press/media, and thousands of customers who emailed and called about it. Suddenly my life went from two or three people I would regularly interact with a couple times per week, to dozens of people who were involved in the crisis response, cleanup, and 'remediations' who I would speak to multiple times per 16-18 hour day.

Around the same time, I lost some close friends very suddenly - one to cancer, another to old age. And there was the whole pandemic thing. I still haven't been able to grieve properly about that.

You read about data breaches happening almost every week to various companies large and small, and mutter about how careless they were, or worry about whether you were personally affected. But from the inside, it is a totally different story for those involved (if they have even an ounce of genuine remorse and concern, as I did). Behind the scenes, they are an absolute shit-show. The truth is we had been careful and the hack was due to a compromised vendor, not our own code or networking, but I felt massively responsible and like the worst person in the world. I worked the 16-18 hour days in part to assuage my own guilt, but also because I had nobody else that could. The one saving grace was having good cyber crime insurance (which, I note, is now far more expensive than before - I'd pay it many times over, though).

I'm still not over the incident, and have regular therapy (and regular nightmares) with many days spent unable to really focus on anything. Burnout is real, PTSD is real, and I don't know if I will ever feel truly safe again - I certainly feel that I need to get myself off the internet as soon as possible, and away from any kind of business leadership role. I just cannot ever face something like that ever again.

Thanks

This led to quite a few rushed learning experiences for myself, since I hadn't had the same years of mentorship that you'd usually expect.

* Learning how to balance mentoring team members and how to be hands off. It's easy to get into the position where you're spoon feeding the team or haven't built their confidence up. You become the bottle neck and overworked. On the flip side, if you are too hands off, then the important implementation details slip through and you miss out on things you should know, but are not getting bubbled up. It's a hard balance that I still struggle with, and I don't know if any resources truly cover it.

* How to manage under performing employees is a struggle. For example I've had a very senior team member who was struggling with personal issues and it was causing their output at work to be riddled with issues. However we had nobody to cover his areas of expertise and he refused to take time off. Trying to balance this while managing the rest of the team was a real nightmare, which involved pushing them on to lower risk tasks and absorbing more of the load myself till they could work through their issues.

* Setting culture is a difficult one too. Team culture is often top down and leaders need to be aware that everything they do trickles down. However often the negative aspects amplify greatly over positive ones. While I would never compare myself to someone like Linus Torvalds, you can see this in how people try and emulate his negative characteristics (heated project comments) without understanding context or seeing his positive moments. Similarly I was known to be very critical in code reviews, though I went to lengths to soften my feedback and was never harsh. However over time I noticed several junior devs were emulating the criticality of my reviews without picking up on the softening and positive aspects of my reviews. This led to several scenarios where they'd bully other devs in code review and attribute it to my review culture. Anyway again this is something I find difficult to deal with. People naturally amplify negativity and the only way I've found so far is to be vigilant and counter their adopted behaviour early. Whether that's intervening in code reviews, or providing regular work culture refreshers, it is something that's required to maintain a healthy culture.

* On to specific examples of issues I had to struggle with. A lot of the devs on my team were not great at body hygiene. Some didn't bathe regularly. I was literally being asked not to send people to meetings . The only solution was to ask HR to send a strongly worded notice to the whole company to remind them about hygiene and taking some folks aside to gently suggest some mitigations for their hygiene. It was rank.