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Ask HN: What is the thing you've did as a manager that you regret the most?
47 points by serko on Nov 21, 2022 | hide | past | favorite | 31 comments
It is similar to https://news.ycombinator.com/item?id=33675112 but about being a team leader, operations manager, or project manager.

Currently, I am moving from being an individual contributor to a management position. And I constantly have this thought in the back of my mind that at some point I'll do something dumb and let down people that I am responsible for. It's illogical because through the last couple of years I have substituded the manager for weeks without any issues. But I understand that this is a normal reaction for anyone who is facing something new

So I thought that the HN community with all its experience has something to share on such topic

Thanks in advance




Never managed, but I strongly recommend reading Extreme ownership. It's a very good book.

As someone who's been through a few managers. Please please give feedback, and not that yearly review stuff. Managers have a very hard time doing that, especially when it's needed. If you don't give people feedback, then they can't push back on the feedback (tell you things you don't know or don't know you don't know) or address it. The end result is a loop where they are stressed which harms their ability to work, and then you treat them with increasingly lower levels of respect, which stresses them out more, which makes them less able to function until you get into a situation where you soft fire them (move them to an unimportant team or project) or PIP them.

Also for the love of god, don't talk shit about any employees on any team. It will immediately be assumed that behavior is pervasive which will make a person question who is shit talking about them or if management respects them at all.


This is spot on.

In addition to giving feedback, I think it's also important to ask people for their opinions regularly. This gives the employee the sense that they are valued and that what they are doing matters. This is the fuel that great employees are powered by.


+1 Great book if you are looking to be a leader. Other leadership books I would recommend are:

To Risk It All: Nine Conflicts and the Crucible of Decision

Execution: The Discipline of Getting Things Done


Read it, great book


This is good.


My biggest regret by far is managing a (formerly extremely productive) remote team that developed incredibly toxic indirect communication spirals which just got worse and worse and worse.

I also deeply regret ever being a middle manager when it is not my area of strength or interest and don’t plan on doing it again. Ever. If I can avoid it.

I learned that middle management is the worst place to be in any corporate environment. Especially in this environment of contraction.

You can “get it” from below (your direct reports rebel and try to undermine you). You can get it from sideways: Your peers trying to take you out. You can get it from above, your management changing to people who don’t get along with you or feeling threatened and trying to get you.

And you can get it from combinations of those things: Your direct reports and your managers teaming up on you. Your peers and your direct reports teaming up on you. Etc.

How did I find this out?

Because every combination of this happened to me. My management started fighting with each other and then it started trickling down to me directly.

I tried to ignore it but my manager wasn’t covering me so I tried to cover myself. That triggered more fighting and less trust and more politics.

And my direct reports were angry at me because they didn’t know what was going on and neither did I.

It just got worse and worse and worse and worse and worse. Like a fractal of awful.

To this day I do not know what I could have done better or how to fix it. I tried to stay out of it, but it was like this awful toxic stench that stuck to everything and everyone.

Everyone absolutely hated each other and it was so rotten and no one could get out and no one could leave.

There were multiple factions competing with each other and no one trusted each other and everyone was sneaking around trying to cover their tracks.

In retrospect I should have quit and joined a startup.

My advice?

Don’t be a middle manager.


I'm sorry to hear about your experience in that role. That sounds pretty awful.

That being said, it also sounds like a toxic overall environment, independent from the middle management role (eg. from MoM to (Senior) Director in big corps). Allow me to maybe try and redeem the role just a little bit.

By my own metric, I've been in middle management for over a decade now, and by most accounts probably pretty successfully so. Here's a couple of take aways for folks who are thinking about such a career path. I don't think any of this would've salvaged your situation though.

- Even more so than a line manager, you will benefit greatly from becoming good at transitive gratification. Learn to see other folks' (usually your team) success as a source for your own happiness and achievements. This has both contributed to my sense of achievement and happiness but also helped me learn that credit being split is usually still worth more than half.

- Appreciate the challenge. I've walked into problematic teams/organizations more than once, full knowing, because I wanted the challenge. Sometimes I succeeded and the teams became happier and more productive (which often has causation in either direction). Sometimes I most decidedly did not succeed. It's just like with technical challenges that way. Just try to gauge whether or not you have the support to see it through and drive change. Again, just like in a technical project.

- I've had the luxury of largely working in environments where most people, engineers, managers, executives, etc were reasonably competent. It has been rare that execs were true bullshit artists. Obviously that helps, but most importantly it makes the following feasible: be genuine. You can't always provide 100% transparency because context matters, but you can try to get as close as is safe for folks. State your intentions. Never lie. Treat political backstabbing harshly. Just, well, act with integrity. In my experience, with enough tenacity, this eventually makes it much easier to have your teams' respect. Knowing you can get transitive gratification makes that so much easier. This probably breaks down at the latest around an org size of several hundred where folks can't experience you as an individual anymore.

- Be a bit of a shit umbrella but not in a load bearing way. This is a special case of the previous point - if you try to protect your teams from the latest executive fire drill, but for some reason you fail to deliver on it while insulating the teams right up to the breaking point, it'll be so much worse when it all punches through at once. Equally, you won't get the thing done that is required, eroding your own management chain's trust in you. Bonus: by being transparent to your leads and involving them gently, you give them an opportunity to practice your succession.

- Do not skimp on performance management. Be principled. Don't play favorites. Give feedback early. Be empathetic in how you deliver it, and how you act on it. But don't let that be your excuse for not doing it consistently. It's hard. Exhausting. Often awkward when either party isn't used to giving/receiving it. But it's not unkind or doesn't have to be. Having had a great manager who was willing to give me difficult feedback has saved me from failure more than once. When one of my reports, whom I had done a PIP with, got promoted a few years later, I was happier than if I had been promoted myself. If you do this well, folks on your teams will better understand expectations. If you do it with empathy, they will build trust in you. Good people from elsewhere will be happy to join your teams because they see folks' development. It really can be a virtuous cycle.

- Develop a keen sense for how power distance changes relationships. Treat people with respect regardless of their seniority or lack thereof. That 23 year old intern also brings their unique experiences. Never talk down on anybody. But also never forget that power distance creates severely imbalanced relationships. As much as it may pain you, be very careful about becoming personal friends with your reports. It can work, and has worked for me many times, but there's little more crushing than learning that it was less than genuine. They themselves may not even realize it at the time.

- The move from engineering manager to indirect manager is, for many people, more subtly challenging than when they first became a manager to begin with. It's an insidious change where you can get away with little adjustment of approach for a while. That's usually a straight path to become a horrible micromanager. (Been there, learned the lesson.) I must have asked nearly a hundred candidates in interviews about how they experienced this transition and this is by far the most common pitfall. Instead, build out a trust-but-verify approach, letting go of some details, giving your leads leeway to explore solutions, while creating a set of metrics and controls/reviews that will alert you when you need to step in to help.

That all being said, in the spirit of this thread, I've made a lot of mistakes along the way, and continue to do so. Some mistakes I regret (others I recognize as source of learning). The management mistake I probably make the most frequently is: not doing performance management early/consistently enough. If you let it go for a while because it's exhausting, or because you're not confident enough, or simply because it's no fun, then it just becomes more and more difficult and unkind to the recipient. I still fall into this trap sometimes. Is it their performance? Or are my expectations just not calibrated in this new org I just moved to? ...

But the biggest, most hurtful mistake so far surely has to be a case where my instinct had told me that somebody was toxic, but my hubris won out, thinking I can salvage them for their talent. It even appeared to work for a while, my hubris making me provide them with increasing amounts of sponsorship, which they reciprocated with ever increasing success (they did have talent). Fast forward another year, I've allowed myself to think of them as a friend. Transitive gratification goes into overdrive. Finally managed to establish them as a peer, splitting my own organization in half. The day they became a peer, they basically stop talking to me. Within a month our now mutual manager concludes that the person wasn't ready (did I mention that I over-sponsored them?) and folded their org back into mine. Toxicity back in full swing. Eventually they rage quit by deliberately (I think) getting themselves fired for talking about internals on Twitter. On the way out, they blamed me for all bad things. Wow, did I mess that up, good intentions be damned. Hope they're alright now.

Anyway, I hope that there's still folks willing to try out a middle management role for the right reasons. We all deserve better management. :)


Avoiding difficult conversations and waiting too long to deal with a people-problem. People-problems are the biggest drain on my energy and enthusiasm for work.

The first time I dealt with one, it was awful. I was close to quitting myself. But once I got through it, it was like night and day how much better things were immediately. Now having been through it more than once, I know what it’s like and how to deal with it and how to get through it and move on to the next thing.


yeah, that's a difficult one, then you are only substituting you don't have to deal with tasks like that


A few years ago, as fresh IC/Manager hybrid with a couple juniors, I found myself with a junior who wasn't growing well relative to other hires (same team, different team, hires from colleges mostly, some bootcamps too). The two of us didn't talk about performance or contributing or engagement enough. I raised some alarms with my management peers and my manager, but I think it was too late. We transferred them to another team, hoping another team (less independent, more team based), environment, industrial vertical, new manager would foster some growth. A few months later the company let them go.

About a year later, they asked me for a recommendation and I said sure, I will do my best. A recruiter called me, I tried responding via voicemail but no follow up ever came around.

I really struggled to identify weak performance back then. I gave everyone the benefit of the doubt. I also kept the topic at bay for too long. My regrets include my slow response, but my regrets extend to the unknown, if I helped ruin this kids career.

You really do need to ask how they're doing, how they think they're doing, and if you have any concerns, air them early so there's time to change.


Sorry I'm struggling, but when you say they, you mean the junior?

Anyhow as you say, performance was not there and the other team quitted as well. There's that.


Have you looked them up to see how they’re doing, career-wise, now?


A few months ago I did try a LinkedIn search but their profile hadn't updated with new activity.


I’m only 3 months into the same journey but having difficult conversations up front I’ve already learnt is really important. There’s also a way of framing it. For e.g. “I need you to” rather than “you are not doing this and it’s a problem”

For e.g. there’s a developer on my team who my boss managed previously and gave the impression that being a senior dev was not a huge amount of work and he could reach that milestone by Christmas. My boss was very hands off because he had something like 20 reports plus a full time software engineering manager job and contract shit to deal with.

I took over the team started managing him and it became very obvious very quickly that he wasn’t at the same standard as our other senior devs. So I had to make it clear very quickly that for e.g. this is a rough skills matrix of what we expect for each level and you can do the coding OK, but you don’t seem able to write tests for your language of choice, and you often start randomly working on things that we’ve not agreed in the sprint, etc. etc.


Not sure if relevant to you, but I came to tech from manual labor in the midwest, so my work ethic was probably skewed. I found my team incredibly whiny and rather lazy. I fired the laziest one after catching him sleeping for the however many'th time.

Not long after, I realized I was setting expectations way too high and had the 'time to lean time to clean' mindset too fresh in my head. I regret being such a brainwashed hardass, and firing that guy, and hope he landed on his feet elsewhere.


What do you mean by "sleeping"?


Physically fall asleep in his chair, usually on quiet mornings.

It might sound bad on paper, but all the crap I've seen since WFH and forced COVID WFH since makes that look and feel extremely benign.


Not to make you feel worse, but falling asleep at work can be caused by a health issue, for example sleep apnea. In the future I would recommend approaching this with your employee as a health issue first rather than as a laziness issue.

Manual labor is usually paid hourly with bonuses for overtime. Unless you're keeping a close eye on the workload to make sure not only the entire team but also each team member is treated fairly, you can expect people to do things that resemble slacking off, to manage their own workload. If you randomly require the whole team to work weekends, the person who put in a solid 40 hours during the week loses out compared to the person who left early when they could. If the whole team is sometimes required to stay until 6 or later to fix some crisis, the person who shows up at 9 sharp every day loses out compared to the person who drifts in around 9:30 or 10.


IDK man, straight-up sleeping at work sounds pretty wild lol, unless, as the other poster mentioned, it was the symptom of a real health issue.


My Dad is straight up the biggest work-a-holic I've ever met. Constantly works 12-16 hour days, weekends, etc. Says he loves it. Came out of retirement to work more. I don't understand it but he's happy.

I got some of my friends jobs at work through him and it got brought up to me that he fell asleep at work quite a lot. Was hard to hide because he snored really loud. Was pretty embarrassing to me. Either way, long story short, he had exactly what the other poster was talking about sleep apnea. Got diagnosed, got a c-pap(?) device and guess what, no more falling asleep at work. Probably saved his life as well, as he's already had a heart surgery.

Either way, I pretty sure he's the most non-lazy person I've ever been around. :)


I took on 2 teams.

I had formed, recruited and managed a very successful team for a year or so, we worked great together, like clockwork. Nothing is perfect but it's the tightest team I've ever worked on to date. Another team was constantly causing issues for us and other teams, they were a problem. They let the manager of that team go (unsurprisingly) and so I offered to take over that team while they found a full-time replacement.

My thought was to make things better for my team and others by putting this team on the right path but it wasn't to be. The team needed to have some people replaced, but I was hesitant to do so right away as I was learning about their domain. Overall this just took time away from my main team. I eventually got completely burned out and was very stressed. So much so that I eventually decided to go back to being an individual contributor. Looking back, my greatest accomplishment of my career thus far has been forming that first team and leading it, we did some amazing high impact things.

So I guess, morale of the story is to not take on too much. Or think that you can always replicate success with a different group of folks.


Question to folks who respond and experienced managers: how do you deal with peer managers who're not as supportive and out to get you?

Context: I joined a startup and I'm leading a new function for this org. While I have decent relationship with all others, one of my peers is far less supportive, demonstrates his value/("we made this call before you joined") at every opportunity, and even wanted to push through some of the tasks/projects on me/my team where we need not be owner but partners.

Management is supportive of me as well but said peer has a stronger rapport and I don't want to be finicky about this to the management.

How do you rightfully pushback in this scenario then?


> leading a new function for this org

Odds are that other manager thought they would get that function or was somewhere in the process of getting that function and now you have it.

One approach might be to sit down in a one on one and talk about how everyone wants new thing you manage to succeed and ask details about how they would approach new function, what they might be looking for and some background history about decisions, etc. I think establishing common ground of "we all want this to be awesome" and "I'm here because there is so much work to do in this space its a separate team" should be pretty straightforward at a startup/small company.


Honestly I think this is a pretty common problem. Management can be a very competitive branch of the tech organization. There’s only so many positions and everyone (mostly) is motivated and wants to be next in line.

If you’re comfortable and don’t want to make a move, don’t worry about it. But since you’re asking, I’m assuming you have some ambition. You’ve got the play the game. Show your value to the organization. Act like the individual the role asks for. Advocate for yourself and your team. It’s hard at first, but gets easier.


When I was a new manager, I had a problem employee. He was very bright, but very lazy. He wasn't self-motivated and was always doing everything in a mediocre way.

I ignored the problem for a long time, which caused friction within my team.

I eventually had to fire him when the situation got very severe.

The mistake I made was not addressing it right away.

I think that now, how to fire (or better stated, "manage up or out") your first employee as a new manager is one of the most important things you have to figure out how to do right.

The next time I had a problem employee, I got on it right as soon as the problem was clear. Saved me and everyone around me lots of grief.


I didn't trust my instinct and hired a guy that was a pathological liar. Almost ruined the whole company. This was during the dotcom bubble and programmers where hard to come by. My company didn't pay as well as the (soon to be bankrupt) flashy dotcom firms. I really needed people and I let myself think "OK, he is odd, but maybe it's just my bias".

His office soon turned into a dump, he didn't show up to important customer demos ("Oh, I told you I was going to visit my sister", "I got a bad allergy after vaccination, I'm in the hospital."). He could spend weeks not producing anything, and have very elaborate excuses. Some periods in the beginning he did really good work. So I had to weigh the pros and the cons of keeping him. And maybe I wanted to avoid a conflict. I was young and had never met a person that could lie and cheat without feeling bad.

The worst was that he blamed his co-workers for everything. People wanted to leave. And I, as the middle manager, was caught between caring for the team, getting the work done and be accountable for the managers above me.

I should have ended his employment after a week. There where enough bad signs.

One day he just disappeared. We were worried and went to his house. It was empty. Never heard from him again. After a month his office phone rang. It was his mother. I had to tell her that he was missing. "Oh, not again", was her reply.

When recruiting, listen to your instincts. And be proactive when a team member is not functioning. One person could ruin a team.


Did the person do anything specific during the interview process that suggested the problems you ended up having? Just thinking someone is "odd" can be the result of, as you say, bias.


He looked like he was right out of bed. But it was mostly a feeling. I had recently hired a high school dropout and an immigrant who barely spoke our language. Both turned out great. Did not have the warning sounds go off during their interviews.

That period was strange. I got applicants with Microsoft certification in SQL Server who couldn’t explain the simplest SQL query.


Team leader. I was too happy to hire a person who, in retrospect, has resonated with me personally more than was the best person for the job. I wish we interviewed more. It wasn't a big issue - the hire was still ok, but the realisation still haunts me.


I've learned that putting on airs and having a lot of pride are not conducive to good management.

Humility is.


I wonder if Elon musk is on hn




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