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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?

#91

Post by matco11 »

throwaway78594 wrote: post #76

(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…

Amazing of you to share this. It will get better. You will feel better.

I understand how you feel now, but (I am sure) very many people out there would rather trust their data to (a future) you given how careful you have been, how much you have cared, and how much you have learned from this.

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

#92

Post by peterlk »

anonymouse008 wrote: post #70
rubyn00bie wrote: post #44

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…

So, you must have really good hiring methods... do you mind expanding on those too?

"Hire slow and fire fast". I've never seen a company that had not made several bad hires. The difference was the speed at which they were willing and able to identify them and remove them. You shouldn't trust someone the moment you bring them on, but I do believe that should be able to imagine yourself trusting them.

A general rule for me is that you should know within the first 2-4 weeks whether you've made a bad hire. This is a bold statement, but my experience is that this time frame will give you enough time to get a gut check (super vague, but there are too many different patterns for me to articulate here). If your gut says no, that will stick with you, and your gut will likely become a self-fulfilling prophecy anyways.

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

#93

Post by murukesh_s »

throwaway78594 wrote: post #76

(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 the experience. I understand your pain. It would be helpful if you can name the vendor, or if it's too dangerous to reveal, just name the industry/vertical of the vendor? it could help others avoid the vendor..

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

#94

Post by cutemonster »

trs8080 wrote: post #85
throw_jail999 wrote: post #34

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.

> almost facing the consequences of your actions

No, but the consequences of a seemingly sociopath CEO's actions.

Your reply was one of the worst things I've read here on HN the last weeks. Saying such things to someone who was, back at the time, thinking about suicide.

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

#95

Post by hummerbliss »

rubyn00bie wrote: post #44

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…

"Learning to let my go of my ego and trust…”

This is the quality I learnt to look for in a leader (I am not a leader but worked under few good ones).

I also noticed how good leaders never take things personally. They quickly move on and not hold grudge. I am amazed how good leaders are able to do that and in doing so inspire me to do the same.

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

#96

Post by [deleted] »

cutemonster wrote: post #94
trs8080 wrote: post #85

Earlier quoted context omitted.

> 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.

> almost facing the consequences of your actions No, but the consequences of a seemingly sociopath CEO's actions. Your reply was one of the worst things I've read here on HN the last weeks. Saying such things to someone who was, back at the time, thinking about suicide.

[deleted]

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

#97

Post by camjohnson26 »

technofiend wrote: post #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…

The politics game is a stairway to nowhere. Good on you for getting out of it, even the ones at the top are always worried about losing it, it’s much wiser not to play at all.

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

#98

Post by arendtio »

darkerside wrote: post #45
rubyn00bie wrote: post #44

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…

As someone who suffers from the same neuroses, I would push back on some of this a bit. If you haven't built trust with every person on your team, that doesn't make you a shitty manager. The more people you can work with and trust, the more effective you may be as a manager, but don't let a counterexample serve as proof positive that you suck. Trust is a two way street. Sometimes people underperform for other reasons…

> Sometimes people underperform for other reasons that have nothing to do with you.

You can still try to find out what causes their behavior (by showing interests into their perspective) and may be able to help them and therefore the team.

- If they have a different perspective, it should be helpful to listen to their perspective.

- If they have a bad day, it will go away.

- If they have family or health problems, you might not want know the details, but simply knowing that a person is going through a difficult time might give you enough information to know how to improve the situation.

Even if you are not the cause of the situation, you might still be able to improve it as a manager.

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

#99

Post by rand846633 »

cutemonster wrote: post #94
trs8080 wrote: post #85

Earlier quoted context omitted.

> 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.

> almost facing the consequences of your actions No, but the consequences of a seemingly sociopath CEO's actions. Your reply was one of the worst things I've read here on HN the last weeks. Saying such things to someone who was, back at the time, thinking about suicide.

[flagged]

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

#100

Post by takeda »

rubyn00bie wrote: post #44

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…

Eh, that describes exactly my last job (which wasn't bad, I liked my coworkers, but my last manager made it a horrible experience), worst job I had so far.

He wasn't bad as an engineer, but he had this crazy OCD to a point that even keys in YAML file should be ordered alphabetically.

He had his vision how things should be, and how he would implement them.

First, he was not happy that my solutions were done differently than what he would do.

Then, when I learned about that he wasn't happy and tried to do it the way he wanted by asking him question about it he told me that I required hand holding and as a senior should not need that. Yes I'm senior, but not a mind reader.

I would think that someone who majored in psychology would be better at something like that, but I guess the only thing he learned in psychology class was Socratic method, which he constantly overused when talking to others.

He though he was being clever but only made me think (because I couldn't say it to his face): "just fucking tell me what the fuck you want me to do"

Ugh, I'm so glad I don't have to deal anymore with this BS.

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