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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?

#131
A mark of a good leader is that their team runs really well without them. It should also run just as well when they are around.

Always be looking to take your ego out of the situation. You are there to facilitate the success of the team it’s individual members.

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

#132
post #112
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.

Wow. Looking to hate on the first thing because they're successful.. confirm your twisted worldview that success is robbery to make your feel better how you haven't made it. Nice try...

Hate is a strong word but he did say the CEO did something sketchy and he is not a saint. We all know US regulators dont have teeth anymore and so lot of bad guys escape with no punishment or a slap on the wrist.

So there is a possibility that in a perfect world he could have gone to jail.

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

#133

Are you preparing for an upcoming interview?

It is the annual creative writing exercise known as appraisal time at many organsiations, including mine. Why not get some inspiration from HN?

Actually this year has never been easier for appraisals, all successes have been despite the great covid challenges, all failures and delays are due to the terrible covid disruptions.

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

#134
post #102

Earlier quoted context omitted.

If requirements were provided and person didn't fulfill them, they did a bad job. If requirements were fulfilled, but you aren't happy with the result, then you did a bad job.

This happened to me this past week. I built exactly what the spec said. They came back and said it all looks good, except we expected this to be that. Um, nothing about that was in the spec, nor was it ever mentioned verbally in a meeting. Making the change from this to that will require everything to be redone since it requires fundamental changes. I would have built it differently had it been communicated to me fro…

A key skill of a senior developer is a sixth sense for this kind of unspoken requirements, and asking questions to flush them out. Not always possible, of course.

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

#135
I was climbing up the ranks as a dev of a web agency. The owner just got into the startup scene abroad and wanted to be part of it. So he spun up a separate company, and I ended up as a lead dev there. And as the senior dev I ended up with the CTO role.

No experience with that whatsoever, and no support structure to lean on as we were basically one of first gen IT startups in my country. No established processes and we had to invent them as we go. I had read zero books on technical leadership and didn’t know anyone who I could talk to. Didn’t know which books I even had to read as there wasn’t anyone to talk to. HN was my only solace.

I was working like crazy and putting out fires, but instead of helping my colleagues I leaned too much into doing the technical challenges myself.

And it all came crashing down when I went on a long overdue summer vacation. On the first day I start receiving emails in the form of “um we seem to be having a problem, not sure how to deal with it”. It kept escalating day by day, and at one point the CEO just told me “sorry mate but we need you back” and I had to cut my vacation by half and get back to work.

On the bus ride home I kept thinking “never again” and when I got back took a _much_ more serious effort to make sure I wasn’t the single point of failure and actually be a CTO.

Read some books, took some steps back, mentored people, and most importantly actively took less challenging things so others could shine too.

And it worked, I mean I wasn’t that great a leader I’m sure, but there wasn’t a problem that my team couldn’t handle without me afterwards.

Ended up quitting a couple of years later as I was burned out and not happy with the direction of the company overall, but the team is still there more than five years later and growing.

What I learned was that you have to take new responsibility seriously and try to teach yourself for it, not expect things to just “work out”.

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

#136
post #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.

This is a nasty thing to say to someone who is talking about the circumstances of when they considered suicide.

It doesn't matter if you think it's true, or if you think the person deserves it, or any of that. It doesn't matter if they're rich.

In the end, you are the asshole. You are the one dunking on someone's toughest moment in life. If you can do it to them, you can do it to anyone.

It's not justified "because they're rich". The same idiotic logic is used by pompous jerks who litter "to give janitors something to do" or who treat waiters like shit "because it's their job". Maybe you're reading that thinking "that would never be me" but, I've got news for you, that IS you. Just a different flavour of it. The person on the other end is human and you treated them like dirt.

You tried to shit on someone who shared their lowest moment in life. Let that sink in, deep.

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

#137

(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…

Having been promoted to managing a team I was previously a part of, I feel your pain.

If it helps, consider that this person might have tried exactly the same ploy with whoever was in your shoes. I'm sure they had some issues going on in their life, and issues with the existing management that you inherited unknowingly.

Management stress is real. Part of it comes with maintaining confidentiality, whereas a disgruntled employee will rant and get things off their chest.

I won't say it's 100% about the role and not the person, since that's dumb - interpersonal relationships are real and significant. Equally, it's not 100% about the individual. FWIW, and taking your description at face value, I think your response was appropriate and theirs was not.

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

#138
Kudos: Compliments, highlighting successes, lauding positives.

Within a 11 year span of working in same but large company, once you’ve mastered the resource management, the hardest leadership skill is kudos ... toward your upper management, ... knowing when to let yourself down and have your boss get the kudos instead.

- IMHO, the ADHD workers are the easiest to managed (trick is gaslighting their focus into a hard problem that highly interest them for them to tackle). My Kudos are often brushed off but still required to be dispensed tactfully.

- Laziest workers are definitely the hardest to narrate a path for task completions. Kudos are rarely a good tool for shaping of the lazier’s task path and too easily overused toward increasingly diminishing ROI.

- But upper leadership kudos requires letting go of your own greed, avarice, possessiveness, ... in many words to shorten, the real power in leading.

Harder still is making the your middle boss of many middle bosses look the bestest of the best. Even to a point of moving his name in front of your invention patents.

That was a strong sign that this rat treadmill isn’t for me and that I truly have the entrepreneurial skill to strike out into a smaller company and startups.

I excelled there as well but the happiness factor was way better.

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

#139
post #135

I was climbing up the ranks as a dev of a web agency. The owner just got into the startup scene abroad and wanted to be part of it. So he spun up a separate company, and I ended up as a lead dev there. And as the senior dev I ended up with the CTO role. No experience with that whatsoever, and no support structure to lean on as we were basically one of first gen IT startups in my country. No established processes and…

Thanks for sharing your story.

I‘ve had/have a similar experience. No seniors here to learn from but got it up to top performance with reading (joelonsoftware was a great inspiration back then), investing lots of time (but rarely overtime) and being ambitious.

I believe you also learned that you shouldn‘t be the single point of failure. I‘m still actively working on that. Though it‘s hard to relay to others if they just can‘t get it done or don‘t share your ambitions, vision or views of quality and customer focus. But there‘s always hope.

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

#140

Having an unstable teammate on a project I led. Long story short, they: (a) saw things in terms of them being persecuted, and took critique of their work or approach deeply personally (b) tended to see things as us vs them, and not a two-way street, where both sides bore responsibility. And that sometimes crappy things happen with no malace. (c) resented other's success at the company, and thought that the 'successfu…

Early in my career I witnessed a our company’s founder being able to literally convince anyone in their vision.

It was very subtle and masterful, you would see people trying to tell him of their problems, and an hour later leave believing they got their way, only to have agreed on the exact opposite, and being happy about it.

I was too young then to fully appreciate and learn from it. It was probably something like what people were saying about Steve Jobs’ “distortion field”.

He would sit and listen quietly, try to figure out what you were passionate about. He would himself get excited about _that_ too, and then slowly move the direction to seeing the world from his point of view.

After a while I got to know the guy pretty well, and I am sure he was not a sociopath and there was no malice in it. He was genuinely interested in people’s opinions and wanted to help them, he just had a grand vision and managed to find purpose for people in it. He was something like the embodiment of what the book “How to win friends and influence people” was about.

What I believe now is that there is a way to talk to almost anyone about their issues and help them overcome them. Every time I have trouble resolving issues like that I would try to go back and think “what would this person do”. Usually helps.

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