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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?

#121

Post by bob1029 »

sopooneo wrote: post #26
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…

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…

This kind of thing is why we don't do daily standups anymore. The gradual psychological grind of the same, forced interpersonal dynamics every 24 hours can get to be incredibly oppressive.

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

#122

Post by [deleted] »

matco11 wrote: post #91
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.

[deleted]

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

#123

Post by goto11 »

fighterpilot wrote: post #101
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…

> When people don't deliver what you expected, it's because you did a shitty job of communicating it to them. Why is this necessarily the fault of the manager's communication skills? Sometimes the person sucks beyond repair and needs to be fired. If you have a competent person who didn't deliver what you expected, then yes, it's probably the fault of the manager's communication. Not so for the lower-end of that compe…

In management you can't really deflect responsibility downwards.

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

#124

Post by feoren »

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.

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.

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

#126

Post by fighterpilot »

goto11 wrote: post #123
fighterpilot wrote: post #101

Earlier quoted context omitted.

> When people don't deliver what you expected, it's because you did a shitty job of communicating it to them. Why is this necessarily the fault of the manager's communication skills? Sometimes the person sucks beyond repair and needs to be fired. If you have a competent person who didn't deliver what you expected, then yes, it's probably the fault of the manager's communication. Not so for the lower-end of that compe…

In management you can't really deflect responsibility downwards.

I'm not trying to suggest that. I'm suggesting an accurate diagnosis of the mistake that was made by management.

In the case of my example above, it was a failure of management to hire a sufficiently competent person, or a failure to fire the person when their lack of competence became apparent. It wasn't (in my example) a failure to communicate requirements properly.

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

#127

Post by raverbashing »

dillondoyle wrote: post #30

My career is young. I'm only (just about) 32 but own a small agency with a partner. This election cycle was tough. We tried to grow in 2019 with more staff than we'd ever had. We've always had a leadership problem of trying to transfer skills from the top down to help lift up employees that don't already 'have it' - especially (braggart time) me and my partners skills as I think our uniqueness as a firm is tied to my…

> losing a key employee to another agency - the same agency the mistake employee landed at

I've worked with those "mistake employees" and if they landed somewhere else that's probably the last place I would want to go.

Though to be fair everybody can make mistakes, and you would have to access if it was lack of skill, lack of attention, "impedance mismatch", or maybe it was the general climate that was making this employee less effective.

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

#128

Post by globular-toast »

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…

I don't think trust is something you can just decide to do. It's like loving someone or believing something. You either trust them or you don't.

Is your advice to pretend you trust them? Some kind of "fake it til you make it" approach?

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

#129

Post by chris_j »

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?

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

#130

Post by chris_j »

giantg2 wrote: post #59

I feel like it's hard to say. I'm a midlevel dev, so I have no real authority. I was in charge of elevating some code when I first started. I screwed it up and had to spend 6 hours redeploying while the team waited. It did not feel good telling everyone about the situation. It turned out ok in the end. I was the ASC for a team (actually 6 teams across 2 departments). The application had a serious vulnerability that r…

There are a couple of terms here that I'm not familiar with.

What is "elevating code"? (I'm trying to work out of autocorrect has screwed up the word "deploying".)

What is an ASC?

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