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

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

#81

Earlier quoted context omitted.

How can this be accomplished? I take great pains not to get involved in my employees' personal lives. When they call out sick, I never ask why. While I do ask if "they need anything", they never have to tell me what they are sick with, or if they are even not sick and just need a day. I assume they are adults who are competent to manage their own time. I once worked with a manager who would always ask for details lik…

I don't think it's prying to care about your employees and want to make sure they are ok. Asking for at least first level details should be done IMO.

What do you consider first-level details? It’d be super put off if my boss asked me if I had a fever when I emailed in sick.

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

#82

Learning to let my go of my ego and trust... Understanding that delegating tasks, instead of doing them myself, was of the utmost importance the more people I managed... especially, greenfield work. Literally: do not steal the fun. This also means inherently trusting people, and if you can't do that you shouldn't be working with them. two important notes about that: 1. If you just thought of someone you can't trust i…

[deleted]

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

#83

(Throwaway account.) 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…

Thanks for sharing your perspective. I would definitely feel the same (or worse) if I was in your shoes.

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

#84

I'm in it right now. I thought I've been doing a good job and suddenly I'm being attacked from all angles. I'm having someone help me, but it honestly even feels like they're attacking me. The hardest part is that it feels like i'm being forced to let go of my compassion and empathy for others in order to succeed.

Me too man -- It is isolating. My superiors are generally helpful but my reports (who were previously my peers that I got along with personally) expect a lot from me now and it's hard to figure out exactly what/how I should deliver.

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

#85

I was CTO of a company under investigation for both securities fraud and some other misdeeds. The CEO was definitely sketchy. When I tried to talk (many times) about the pressure and stress I was feeling he would alternate between throwing chairs (seriously!) and offering me various pills and alcohol. I couldn’t even quit because then I would have to foot all my own legal bills which would have bankrupted me. I was s…

> and truth be told I wasn’t exactly a saint either

lmao. rich people are hilarious. this isn't a "leadership challenge." this is you almost facing the consequences of your actions and then getting out of it and being successful despite the fact that you (by your own admission) were probably guilty. too bad you weren't caught -- then you may have actually learned something.

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

#86
post #13

Accepting that I was seen as a leader. I've never wanted a leadership position, I just wanted to build cool shit. I'm good at it. At some point in my career (I've been doing software for 22+ years professionally) people started taking me really seriously. I could no longer make certain jokes and I had to be careful about my opinions because they were taken (in many cases) as "the right thing to do". So I got in all s…

The jokes things is something I realized too. Not because I ever tell off-color jokes, but because I realized certain people felt compelled to laugh. And others would then quietly roll their eyes, not at me, but at the exaggerated reactions. It was causing small divisions on the team. When I just had peers and made a stupid pun, my friends/coworkers would just groan and tell me not to quit my day job. But when people…

As a person who finds the blatant tail wagging pretty annoying, I think a good way to address this from the boss's perspective would be to not being seen basking in the fake adulation and keep an even keel. That keeps the ass-lickers in check and sends the signal, to those who are not, that merit still trumps such shenanigans.

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

#87

(throwaway) I'm a developer at a fairly small company. I never really wanted to be managing people but after some internal drama a bunch of stuff was moved around and I found myself in charge of the team I had been on while we looked for a permanent manager. One of the devs who now reported to me decided that this was the best time to demand a raise- not just a cost-of-living increase, which are scheduled, but an amo…

No, that was the correct response.

If anything, you should have fired him intentionally yourself when he went over your head. He isn't looking to work with you or the team, he's actively seeking to undermine you; at that point his presence is a negative, not a positive.

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

#88
I was leading a team of thirty five people in the US and India and working weekends and holidays powering through a death march of one terrible release after another. I got a lot of accolades for work; called out at town halls and even a hand written letter from our CTO thanking me for everything I'd done.

Things were slowly improving as we collected metrics to improve poor code quality and shoddy releases that were killing us all. (This predates SRE/devops by a decade.) The AD teams had no choice but to add some quality control but still things weren't perfect.

At the end of our third year of this five year project the project manager who worked with me on one portion of what we did was promoted to executive director but I was not.

Within a few days of learning I was passed over for promotion I also accidentally discovered my grandfather had died of cancer. I didn't even know he was sick! No one in the family told me. I just found out about the funeral when someone asked me if I planned to attend.

While at the funeral I made plans to have dinner with my younger sister and to go to Las Vegas with my grandmother. Soon after my sister was dead, killed in the line of duty as a police officer. A month later my grandmother was dead from open heart surgery.

The whole time this was happening people were coming up to me at work asking how did that guy get promoted instead of you? How, indeed. The challenge for me was staying motivated and putting on a happy face for employees and not quitting. Frankly if I'd been able to I would have.

The part that makes me laugh now is at the time we still did exceeds, meets, needs improvement stack ranking. My boss told me if he had made me exceeds I would have gotten the promotion but he couldn't because of politics: the guy who sponsored the fellow who did get promoted managed to get my ranking knocked down so I wasn't competing with his fellow for ED. To top it off my mentor dropped me: he said if I was no longer an exceeds it was a waste of his time.

Despite falling into a black pit of depression I powered through the motions of being a people manager but frankly I couldn't take any part of managing careers of others any more when I knew the system was so broken and I had wasted years away from family and friends. My solution was to go back to being a hands on technical person: I transfered to our internal IT group and started over. I'm back to leading teams and getting kudos from the top of the house but still if I'm honest I feel like I failed my biggest challenge by choosing to just move on. On the other hand I'm certainly far happier and no longer ignoring family and friends to work 80-100 hour weeks. On balance that's probably for the best.

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

#89
The challenge I faced earlier was to get things executed ( expected outcome) from different teams. When I found my first follower , the one who really buys my vision and takes it down, things started to roll faster. This might give you an idea of first followers.

https://youtu.be/fW8amMCVAJQ

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