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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?

#221
post #215
post #104

Earlier quoted context omitted.

> At some point I finally embraced it and actively started figuring out what kind of leader I should be. Can you expand on this? I'd love to hear your thoughts on this. What sort of leader did you become? I don't even know what kind of leaders there are.

I don't want to be a manager (I don't care about dealing with salaries and such). I'm a tech lead. I care mostly about the personal growth of my team, I firmly believe that if I help them be the best they can be, the world will be a better place (even if it means losing some of them because they realize they want to do something else, the world will still be a better place). This means sometimes giving advice, someti…

Thank you for taking the time to reply and share your knowledge.

I think I'm on the edge of becoming a manager of sorts in the next couple of years. I don't know if I'm ready or even willing but it's the only way to progress in my career.

I'm in similar boat as you, I'd rather be doing the coding. But at the same time I love working with others.

Thank you again

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

#222
Honestly? Now. Invested heavily in a venture in China for 4 years then COVID hit and being locked out of the country for a year while paying rent on two properties (one major and industrial) and having my team denied return visas due to altered government regulations while being blackmailed by an equipment supplier (court case pending) and then having to tear my family including young kid out of a comfortable western lifestyle to return to factoryland via 2 weeks quarantine in a hotel room we couldn't choose, then six months of fighting to hire a new team due to an impossible HR market. Finally I have found some good people to work with and things are returning to normal, but the kicker is I have world leading contactless food preparation and retail technology which is nominally in demand but I can't get ears to any decent investors presumably because we are a pre-market cross-border venture active in China, which nobody likes under the current political climate, despite securing 1:1 foreign government investment matching to re-shore and world class advisors. Need a decent forward break soon! This is leadership for family and company simultaneously. Could write a book or three already and only 50% in according to Bezos' "most overnight successes" formula (10 years).

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

#223
One of my team members, and a long-time friend, committed suicide. We were a small team of five, then of four. Although we were a fully distributed team, we were close.

I called each of the team individually, and broke the news. I will never will get out of my head the inconsolable moans of his junior engineer he had been mentoring.

There was a fair amount of pressure from “leadership” not to divulge any details, but fuck that. They needed to know he was an recovering alcoholic and on-and-off-again manic depressive, and that there was nothing they could have said or done that would have made a difference in the final outcome.

Transparency that builds trust has never failed me, whether why a coworker committed suicide or why our backlog priorities changed overnight, or why we chose to use GraphQL over REST.

Listen deeply to your people, so you can understand them deeply, so you can empower them fully,

I failed with my friend because I wanted to believe the lies that addicts tell so well. If you are listening closely enough to your people’s words and actions, and you put aside wishful thinking and blind optimism, as well as lazy skepticism, then you’ll know what they need. Then your job is simple: get them what they need. But I missed his warning signs because I was more focused on the success of the startup than on the success of his life. Never again.

Management is an important role in many organizations. But in a small startup people need to manage themselves. What they need are leaders who listen carefully, communicate clearly, and create a culture of transparency and trust by exemplifying both.

People talk about transparency in the same way people talk about a just-war: that the rules only apply up until the point your principles may cost you victory. But what’s the point of transparency — of pro-active honesty — if “well, in this situation discretion is more advisable” is actually the principle most valued?

Human beings matter the most. If the choice is between your company failing and the well-being of your people, a decent person and a good leader chooses their people every time.

This doesn’t mean you can’t fire people. If they aren’t performing, then they are in the wrong place, and deserve to be somewhere else where they can develop. Firing a person means we made a mistake in hiring, and it’s incumbent upon us to see what we can do to rectify that mistake,

I could go on, but you probably get my point. A company is nothing without people. So take care of them, even and especially when it hurts.

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

#224
post #168

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 guy who sponsored the fellow who did get promoted managed to get my ranking knocked down so I wasn't competing with his fellow for ED." You're working at a toxic place and putting your own self worth up to them for measurement - this is not healthy. People out of school until age 35 sometimes have a hard time truly separating their work from their professional identities, something we could all work on. So sorry…

Thank you.

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

#225

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…

Thanks for sharing. Had a somewhat similar experience to yours that your comment took me back to. I used to lead a global team of 80+ devs at a senior management level. I inherited my team which was an absolute train wreck with a poor track record of poor performance who delivered nothing causing much angst to the business. Over 3 years, rebuilt the entire team, let go of these who brought toxicity/incompetence, set…

Thank you for sharing that.

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

#226
post #159

Earlier quoted context omitted.

> you should have fired him intentionally yourself when he went over your head Is escalating an issue a fireable offense?

When done in bad faith, yes. This wasn't "I have an issue, my manager didn't address it", this was "I have an issue with my manager. He's an idiot. You shouldn't have made him manager. You should have made ME manager", etc. There is nowhere to go with that. There is no way to fix that. There is no way to ignore that. And the employee is going to be killing team morale more and more the longer they stay at that compan…

But suppose that the person made manager really is an idiot. You have now defined the situation such that merely bringing that fact to the attention of the higher-ups is a fireable offense, with no other recourse.

Also, making this a fireable offense only makes the complainer instead stay quiet, but they will still be “killing team morale”. So is that better?

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

#227

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 p…

> Kudos: Compliments, highlighting successes, lauding positives. I think advices can be without providing proper context can not only be counter-productive, it can also create toxic cultures. I've been part of a company where the CTO was a very self-help guru type "positive" person. There were compliments, positivity, motivation etc. everywhere. There was no bar for excellence. Everything was excellent to begin with.…

Agreed.

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

#228
post #226

Earlier quoted context omitted.

When done in bad faith, yes. This wasn't "I have an issue, my manager didn't address it", this was "I have an issue with my manager. He's an idiot. You shouldn't have made him manager. You should have made ME manager", etc. There is nowhere to go with that. There is no way to fix that. There is no way to ignore that. And the employee is going to be killing team morale more and more the longer they stay at that compan…

But suppose that the person made manager really is an idiot. You have now defined the situation such that merely bringing that fact to the attention of the higher-ups is a fireable offense, with no other recourse. Also, making this a fireable offense only makes the complainer instead stay quiet, but they will still be “killing team morale”. So is that better?

If the person made manager is an idiot, you go to upper management with proof, focusing on particular actions, and you do it in a careful way.

"Hey, I wanted to raise up my concerns about X. I mentioned it to (manager), but I'm not entirely certain I communicated it effectively. If we don't do Y, Z will happen". Expect upper management to talk to the manager about it, and expect the manager to try and downplay the concern (or if they're treacherous, express outrage that you didn't talk to them about it; have proof of the conversation if that's a concern). If it doesn't lead to change and blows up, it will be noticed.

Better still - if you have anonymous surveys (most companies do), lambast the manager there (politely), and you place the impetus to change things on upper management there (provided a majority on the team agrees).

The reality is that upper management put the manager there -because they trust them-. They barely even know you. That's the reality. You can still talk to them, but you can't come off as though you're trying to undermine your manager. If upper management's response is to tell your manager "deal with it", you clearly came across as trying to undermine your manager; you're a problem. You just made it so it's your job or your manager's, since you just burned that trust, and in a public way that upper management is now aware of. A good manager will fire you because of the effect you're going to have on team morale. A bad manager will fire you because they feel threatened.

This isn't about what is hypothetically better, this is about what the reality is. The reality is that management is all about trust (really, working in groups is all about trust); upper management has to trust middle management, and middle management has to trust the ICs. Your bypassing your manager is going to look like a breach of trust with your manager (i.e., why didn't you talk to them and work it out with them?). Your claims may be right, but being right doesn't equate to being effective, nor does it excuse being stupid in what you do about it. This guy not only doesn't sound in the right, he also was stupid in how he approached it.

As a slight addendum, too - the reality is that managers that are 'stupid' may still be valuable to higher ups. The business is not evaluating managers the same way ICs are. If the manager makes a decision, overruling the ICs, and the ICs raise their concerns about the decision (NOT the manager), carefully, politely, and the decision leads to a bad outcome, upper management will notice. But I've had decent managers who were technically a bit clueless, but who knew to let the ICs make the decisions themselves; the team succeeded. You can have stupid managers who still run effective teams; if they're actually bad managers, upper management will notice. It may or may not be before you've made plans to leave yourself, but the reality is you can't force a manager to be replaced; you can only work to move yourself (to another team, or to another company), or wait for it to be noticeable and be careful to control the narrative.

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

#229
post #226

Earlier quoted context omitted.

But suppose that the person made manager really is an idiot. You have now defined the situation such that merely bringing that fact to the attention of the higher-ups is a fireable offense, with no other recourse. Also, making this a fireable offense only makes the complainer instead stay quiet, but they will still be “killing team morale”. So is that better?

If the person made manager is an idiot, you go to upper management with proof, focusing on particular actions, and you do it in a careful way. "Hey, I wanted to raise up my concerns about X. I mentioned it to (manager), but I'm not entirely certain I communicated it effectively. If we don't do Y, Z will happen". Expect upper management to talk to the manager about it, and expect the manager to try and downplay the co…

> do it in a careful way.

Sure, that sounds more reasonable. Your initial description could easily be interpreted as “If you go over the head of your immediate manager for any reason whatsoever, you are a liability to the company and deserve to be fired immediately”, which is mostly how I read it. Certainly, an employee must be careful when engaging the company in non-orthodox paths, just as you say, but employers must also be careful in how they communicate the possible options available to an employee; if what employers say comes across like my quote above, an employee can feel trapped and easily become disgruntled in a situation when upper management would actually want to be informed of said situation.

The onus is on upper management to make sure that employees feel safe enough to actually inform upper management of something management would like to be informed about, which includes counteracting middle management, since the incentive of middle management is to try and make sure that employees never ever go over the head of middle managment for any reason at all.

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

#230
post #229

Earlier quoted context omitted.

If the person made manager is an idiot, you go to upper management with proof, focusing on particular actions, and you do it in a careful way. "Hey, I wanted to raise up my concerns about X. I mentioned it to (manager), but I'm not entirely certain I communicated it effectively. If we don't do Y, Z will happen". Expect upper management to talk to the manager about it, and expect the manager to try and downplay the co…

> do it in a careful way. Sure, that sounds more reasonable. Your initial description could easily be interpreted as “If you go over the head of your immediate manager for any reason whatsoever, you are a liability to the company and deserve to be fired immediately”, which is mostly how I read it. Certainly, an employee must be careful when engaging the company in non-orthodox paths, just as you say, but employers mu…

Very first thing I said - "When done in bad faith".

Sounds like you were perhaps arguing against a strawman? I never said don't ever go to upper management, nor that there is never a reason to go to upper management. Just that if someone goes to upper management the way this guy did, the right response is to let them go, that they are a liability to the team, the manager, and the company at that point. Honestly to themselves, too, but that's not on the manager to fix.

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