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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?

#151

Post by tluyben2 »

chris_j wrote: post #129
tluyben2 wrote: post #22

Having to tell my team that our product, their baby, had to be rewritten (because our competitors were gaining on us and we had accrued too much tech debt: new features took forever and the result was slow performance wise) and then motivating them to work on that rewrite with the same enthusiasm as the old product. There were over 200 people working on it and it almost went wrong because a lot of people kept trying…

What motivated you to rewrite it rather than fixing the debt in the old product?

It was a ~8 year old mix and mesh of tech was not really fixable. We also got too many requests for enterprise clients for Java. And that would have been impossible. We more than doubled in revenue after the rewrite because now we could go for fortune 500 countries.

It was a different time: the product was a combi of perl, php, c++. And then the business world, at least here, went over to java backends.

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

#152

Post by jariel »

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…

This is good advice for many but it's not nearly as universal as it's implied.

There are people who don't live up to the mark in terms of quality and that's that, and in those scenarios it would have little to do with trust.

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

#153

Post by emodendroket »

I’ve found it a challenge and adjustment to get used to mentoring junior employees. I am entirely self taught and the temptation is to get annoyed at kids who don’t know something that seems basic because, you know, how did you miss this with your fancy education or whatever. But that’s not fair and not helpful.

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

#154

Post by emodendroket »

deedubaya wrote: post #32

I accepted a remote lead position at a startup. Interviews had gone great. I gave my notice at my soon-to-be old employer and made the transition. Along comes my first day and surprisingly, it’s mostly radio silence. CTO, my boss, doesn’t respond to my emails, doesn’t answer the phone. I call the CEO and he promises to sort it out. Fast forward a week or two later, something is obviously up. Long story short, the boa…

The first project I ever had to deliver I had nearly no programming experience and the boss I had who was supposed to mentor me quit right when I started. A lot of excitement.

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

#155

Post by emodendroket »

chasd00 wrote: post #67

When I was a young kid me and some college friends started a software shop (very early 00’s). It became clear a friend was not making it and only producing obstacles rather than progress. I was nominated to fire him because, and I’m not joking, “he trusts you the most”. So I fired him and he never talked to me again. That was about 20 years ago. Edit: the company lasted maybe 2 years and barely fed us at all

Well, to try and look on the bright side, a lot of my close friends I’ve just fallen out of touch with and I didn’t have to fire them.

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

#156

Post by christophilus »

juancn wrote: 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…

I’m similar, but my conclusion was to work for very small companies. I’m currently at a company with 3 devs, 100% remote, each in wildly different time zones (almost evenly distributed around the world), and with only one meeting per week. I’m quite happy.

I just never have managed to enjoy leadership in the official sense. Natural leadership, e.g. being looked to for advice, generally followed is one thing. Official leadership, e.g. meetings and planning is for the birds in my book.

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

#157

Post by emodendroket »

PoachedSausage wrote: post #133
firstfewshells wrote: post #125

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.

I often wonder how much influence anything I write on those really has on anyone.

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

#158

Post by noir_lord »

juancn wrote: 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…

> Leaders lead even when they don't intend to.

"Lead, follow, or get out of the way." - Thomas Paine

Falling into leadership means that people respected you enough to either follow or at least get out of the way.

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

#159

Post by teddyh »

lostcolony wrote: post #87
whirlingdervish wrote: post #47

(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.

> you should have fired him intentionally yourself when he went over your head

Is escalating an issue a fireable offense?

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

#160

Post by marshmallow_12 »

feoren wrote: post #124
cutemonster wrote: post #94

Earlier quoted context omitted.

> 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.

Do you really not think accomplices to a crime ever deserve to face consequences for the crime? It sucks what OP went through but I'm not going to say a bank robber shouldn't go to jail because he's real sad about the whole thing.

again there's a vast gulf between one who steals money through dishonesty and one who steals with voilence. (granted if you have been screwed over you may disagree)
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