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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?

#61

Post by giantg2 »

29athrowaway wrote: post #17
throwarayes wrote: post #3

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…

In the "Big five personality traits" model, you have: 1. Openness to experience (inventive/curious vs. consistent/cautious) 2. Conscientiousness (efficient/organized vs. extravagant/careless) 3. Extraversion (outgoing/energetic vs. solitary/reserved) 4. Agreeableness (friendly/compassionate vs. critical/rational) 5. Neuroticism (sensitive/nervous vs. resilient/confident) Excessive neuroticism (aka emotional instabili…

Wow, I feel like I fit both sides of 4 out of the 5 categories depending on the context.

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

#62

Post by giantg2 »

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."

This happened to me. It led to some problems though. People from other teams would contact me as the tech lead (was a midlevel dev acting as tech lead) and ask me to do stuff in PRD. I'd like to help, but only official tech leads are granted that access...

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

#63

Post by de6u99er »

Quitting my last job. My emoloyer comitted misuse of public funds in my last project through kickback fraud, despite me warning them to not try to pull this off in my projects. Thing is, that I never wanted to do anything illegal at work because I don't want anyone to have leverage over me and blackmail me into doing more unethical things.

It only afterwards turned out to be a challenge. I didn't have an alternative job offer at the time of quitting, and shortly after my last day at work the pandemic started.

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

#65

Post by ISL »

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…

For the first point -- I believe that OP wants the manager to extend trust as a mechanism and path toward both a trusting relationship and short-term performance.

For the second -- it is on the manager to know enough about the reasons affecting their report's performance to be able to adapt before the team underperforms. (and it is on the report to surface that information quickly so that the team isn't compromised)

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

#66

Post by beachy »

throwarayes wrote: post #3

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…

I've often thought about how easy some issues must be to deal with with the US's "fire at will" regime.

In my country you really can't fire anyone without a major HR process that saps everyone's energy and morale.

In your case it sounds like everyone would have better off if this person had been fired early on in proceedings.

Once I made someone redundant, which can be a back door mechanism for firing in some circumstances. He just wasn't cutting it. I felt ghastly afterwards.

I ran into him months later and he told me he had no hard feelings, and the shock of it had made him reappraise his career path and he had made his way into a job which was much better suited to his skills. He was far happier.

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

#67

Post by chasd00 »

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

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

#68

Post by rickpower »

Being decisive. Nothing is ever perfect.

If you continue to lead, at some point, its going to feel like all the walls are crashing down around you and your team.

Your path forward will most likely not be perfect, but it is a path, and the team will look to you. Be open to ideas and feedback, but I'm talking about when nobody on the team knows what to do because it feels everything has failed.

Pick a direction, start running, and scream "this way!"

It's your job to say "Get to the choppa!" if that is what the situation calls for. Nobody else is going to do it.

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

#69

Post by Chozenlaruso »

ISL wrote: post #65
darkerside wrote: post #45

Earlier quoted context omitted.

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…

For the first point -- I believe that OP wants the manager to extend trust as a mechanism and path toward both a trusting relationship and short-term performance. For the second -- it is on the manager to know enough about the reasons affecting their report's performance to be able to adapt before the team underperforms. (and it is on the report to surface that information quickly so that the team isn't compromised)

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 like "oh you have a headache? Do you have a fever?" While I think his intentions were good, and that he just wanted to show concern and even offer support or advice, I always found the questions incredibly invasive and a violation of my privacy.

My team knows that I will always listen if an employee wants to share details of their personal lives (upto anything that crosses the line of appropriatness for work), but I would never pry.

So, in this example, I would never know an employee is struggling with a personal issue, unless they broached the subject with me.

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

#70

Post by anonymouse008 »

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?
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