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

• adverbly 5y ago
  Follow up question: What attracted you to our company, and how did you find out about our job listing?
• throwarayes 5y ago
  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 'successful' person was only successful because management supported them unfairly in a way my colleague was not supported. My colleague perceived themselves as a secret failure for not doing what the other person was doing. They also thought others telling them they were successful was not genuine. (d) lacked a kind of self awareness, and tended to take over meetings with their grievances and upsetness. They couldn't see that other team members needed to discuss their own issues, or with the issues they brought up, that other people also had valid emotions and points of view on them they needed to hear and appreciate. The time we worked on it as a leadership team went beyond having difficult conversations. I've had difficult conversations, where you talk about someone leaving a job, or someone's difficult behavior. You give it in a loving, compassionate way. Some people can get defensive, maybe upset, but will hear the feedback and take some time to digest it. Even when they're upset, they take some part in the responsibility for the feedback they hear. This person, assumed off the bat, you were going to attack them. They couldn't see the compassion you were trying to bring. They froze up and got defensive. They tended to carry their own narrative of how they were the victim, and didn't take responsibility for their side of whatever they were having a problem with. I give credit to our leadership team that we kept at it. We didn't accept this person's sometimes abusive behavior. We tried, and frankly, by letting others know it was not OK, and that we kept our focus on it, it helped the rest of the team understand that "yes we get there's a problem here". We wanted to help the person. We gave them lots of opportunities for improvement and to do the kind of work they said they wanted to do. We gave them coaching and their own time to develop their own interests into new business directions. After trying and trying, probably helped a bit through some coaching, this person realized the company wasn't a good fit for them, and they left on their own accord. This was a good outcome. Though I wish there was some way to have accelerated it and/or let the person go so they weren't as destructive to the team.
  • uh_uh 5y ago
    Sounds like quite the nightmare. Was the person at least technically competent in their role?
    • jansommer 5y ago
      When someone is that kind of person, they likely don't have many relationships, but a lot of time. I'd be surprised if that person wasn't good at their job, and if not, what motivated grandparent to put so much effort into trying to heal what seems like a fundamental distrust in other people.
    • ohazi 5y ago
      I think I understand why you phrased it like this, but using "at least" here might be read as implying that technical competence can excuse these issues. It can't. I can understand management being hesitant to fire someone technically competent, but this kind of disfunction can tank the productivity of an entire team of otherwise technically competent people, as OP alluded to at the end of their comment.
      • apozem 5y ago
        Completely agree! Something I realized lately is if you don’t ha e soft skills, it literally makes you worse at coding. I always knew you needed them to be a good employee, but it wasn’t until I worked with a “senior” without an ounce of social grace that I realized lacking soft skills makes you worse at writing good code. The “senior” didn’t solve the application’s problems because they didn’t care to ask. They thought they knew everything. They didn’t spread their knowledge onto the rest of the team. Instead, they spent their time working on a half-baked idea no one asked for. They would get stuck on a problem and never ask for help, a junior mistake. My hot take is you need some minimum of social skills (doesn’t have to be a lot!) to be “technically competent.”
        • nickthemagicman 5y ago
          Don't business analysts figure out what would solve the applications problems and the engineers code it?
• seneca 5y ago
  Having a severely unperforming, and sometimes belligerent, employee that couldn't be fired because of HR reasons. His work was horrible, and his responses to feedback was to become hostile. Not only was he dead weight, he destroyed the team's morale and hurt their relationships with other teams. The team looked to me to solve the issue and couldn't understand why he wasn't being fired, and I couldn't tell them "I'm not allowed to fire him". I spent months working with him on improvement plans, coaching, and mediating with no improvement, and in the end managed to shake him off in a RIF. I stayed long enough to repair the team's morale and strengthen the hiring process, and then quit as I had completely lost faith in the company.
  • xmprt 5y ago
    What reason did HR give for you not being able to fire him? I think at least some members of the team would be understanding. Also, I'm not sure if you tried this, but I've heard in cases where you can't fire someone, you recommend them for internal transfer and give the other manager good reviews of them. It's a bit scummy but it's the most positive outcome for the team.
    • seneca 5y ago
      > What reason did HR give for you not being able to fire him? I don't want to ignore the question, but it's a sensitive topic and I'm not sure bringing it up would add to the conversation. > Also, I'm not sure if you tried this, but I've heard in cases where you can't fire someone, you recommend them for internal transfer and give the other manager good reviews of them. Yes, I actually had a peer recommended this as well. In the end, I decided against it as I felt it was unethical. I didn't want to get rid of a problem by becoming one myself.
      • jawns 5y ago
        I don't think you need to divulge any sensitive details, but unless this is a "one in a million" occurrence, it's possible that others might be faced with a similar situation in the future, so it might be useful to share at least some broad details. Was HR concerned that it would lead to legal problems, e.g. an ADA violation or a claim of discrimination against a protected category? Or was it more like a nepotism issue? As a manager, I would likely handle those in different ways.
• ykevinator3 5y ago
  Having to smoke out a brilliant but toxic employee. He was a 10x guy but ruined everyone's day constantly. I have learned the power of working with nice people, even if they're not as good as the genius.
  • colinmhayes 5y ago
    Nothing a good toke can't fix.
• andrew_v4 5y ago
  "Non-contrubuting ideation" - people from other groups without real skin in the game who don't want to take responsibility for anything but insist on providing input on how it's done, and often have some political standing to do so. This has come up again and again in many roles. For me personally, I am really bad at handling this. Sometimes it's fine just to meet with people an hear their ideas (which can obviously be helpful). But other times I have had to basically say that if this other person wants to run the project, they're welcome to it. I'm aware that a lot of this is my fault and some people are much better at diplomatically handling this kind of situation. At the same time, I have led some very successful projects by taking a stand and burning political capital by keeping armchair quarterbacks away from the project.
  • nickthemagicman 5y ago
    Is political capital a real thing for managers?
    • deleted 5y ago
      [deleted]
    • refenestrator 5y ago
      If you're taking stands all the time, you're the cranky person who's hard to get along with and you'll be in real trouble the first time something goes wrong. Have to pick your spots.
    • jawns 5y ago
      Absolutely -- although it's less manipulative than the phrase implies. It just refers to building up some level of trust, respect, and goodwill over time by being an honest, decent, and caring person. Then, when you find yourself having to make a decision that you know is the right call, but might not be well received, that trust and respect you've built up can be useful in helping your team digest the decision.
  • schoolornot 5y ago
    Try assembling a document that covers how outside teams should interact with yours during project planning. Build some red tape into the process like requiring they write their own documents, go through a review process, get approval from a department head, present a demo of what they want done, etc. No good deed goes unpunished with some people. It's so unfortunate because we're all in this together.
• juancn 5y ago
  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 sorts of trouble, because I didn't want the leadership at the time. At some point I finally embraced it and actively started figuring out what kind of leader I should be. After that point, it has gotten a lot easier. I even started enjoying it. Leaders lead even when they don't intend to. So if you're one (willing or not), you should take the responsibility do your best to make the team thrive. I think it as: Company > Team > Self in terms of goals, if I cannot accept that, I'll move on to a different gig.
  • sopooneo 5y ago
    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's annual reviews are in your hands, it's a different story. I think it's perfectly fine to open a meeting by lightening the mood with humor, but I feel compelled to generally reign it in.
    • noisy_boy 5y ago
      As a person who finds the blatant tail wagging pretty annoying, I think a good way to address this from the boss's perspective would be to not being seen basking in the fake adulation and keep an even keel. That keeps the ass-lickers in check and sends the signal, to those who are not, that merit still trumps such shenanigans.
    • bob1029 5y ago
      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.
• chucky_z 5y ago
  I'm in it right now. I thought I've been doing a good job and suddenly I'm being attacked from all angles. I'm having someone help me, but it honestly even feels like they're attacking me. The hardest part is that it feels like i'm being forced to let go of my compassion and empathy for others in order to succeed.
  • mcrider 5y ago
    Me too man -- It is isolating. My superiors are generally helpful but my reports (who were previously my peers that I got along with personally) expect a lot from me now and it's hard to figure out exactly what/how I should deliver.
• tchalla 5y ago
  People with a black or white binary thought process. “We either do it or we don’t”. There’s no room for options and implications. I have to constantly remind to move towards options and implications (with assumptions). Thus, shifting the conversation to a probabilistic decision making that includes on opportunity costs. In this scenario, there’s more than one hypotheses and there’s no dominating “winner take all” option.
  • schoolornot 5y ago
    My personal experiences is that a lot of people get stuck "in the gray" because of indecisiveness or an unwillingness to exert the effort to POC something. I prefer that strongly opinionated minds demonstrate their ideas work or fail and move on to the next prototype than hold endless conversation.
    • austinjp 5y ago
      Genuine questions: Are you in a management position? How do you reconcile the shades-of-grey people with the black-or-white people? What are the strengths and weaknesses of each position, and how do you harness the strengths and manage the weaknesses? Do people change type depending on the situation, or is a grey always a grey and a b/w always a b/w?
  • sergiotapia 5y ago
    Sure there are shades but ultimately as a leader you need to assist your team is making a decision and going forward with it. Your team is there to shade it and give you all the options, even decide on the options. But you are there to break the stalemate and give your team confidence in execution.
• nojito 5y ago
  Understanding that bad leaders focus on under performing team members and that great leaders focus exclusively on team productivity.
  • cocteaus 5y ago
    This is nuanced and underrated.
• tluyben2 5y ago
  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 to shove parts of the old product in making everything slow and buggy. But it worked out in the end and we came out of that really well. Edit: my colleagues did not actually get really motivated until we deployed our first client on the new system which did make the whole thing very stressful for me because it was too much of an uphill battle. Once deployed, it was so much more performant and so much more stable that we all saw we would be spending far less time fixing bugs or trying to squeeze out performance: that changed everything.
  • giantg2 5y ago
    How did you get people to listen to your suggestion to rewrite, or did you have that authority? I made similar suggestions to my boss about a system once. They basically told me it would never happen and to stop thinking about stuff like that so I could focus on the day to day stuff. Well, 2 years later and they outsourced that entire group to a company who will end up rewriting the system...
    • tluyben2 5y ago
      I was the CTO.
      • giantg2 5y ago
        Edit: this comment misunderstood the parent
        • detaro 5y ago
          CIO and CTO ar quite different roles, so why do you think how your company does it has any relevance to what tluyben2 has done? Why do you think they are talking about your company?
• nickthemagicman 5y ago
  Younger in my career, I used to think managers had it easy. Now I realize I don't want that job for any amount of money.
• dillondoyle 5y ago
  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 work in particular (which my parter is very good at picking up) especially tech & a certain unique vertical of advertising. It's hard to find employees with multi-skillsets and experience to run things themselves using our tools. especially in politics not a lot of people come in from the outside, and there is low tech skill from the inside. With larger staff we tried to do more training, tried to build stronger team mindset. That I think that's our biggest weakness and leadership challenge. Still is. An example from this cycle of it not going well: A big problem is mistakes. Our work is hard, long hours, stressful clients making last minute decisions. One staff member in particular made a large amount of mistakes - and big ones. More importantly didn't seem to learn from them. Lost us important clients and reputation. So come end of cycle we usually have to downsize payroll. Choosing who is tough. This year had to decide do we prioritize team cohesion and moral at the cost of mistakes (and our reputation is a big potential issue)? Or do we try to go with more skilled employees who are also more likely to leave, especially without the larger team bonding. Or i guess third option do we take a larger risk than usual in having larger cash loss during down period. We went with higher skill. Well I think it just bit us, losing a key employee to another agency - the same agency the mistake employee landed at. It's not a coincidence. though to be fair in our business we usually lose people after 2/3 years anyways so maybe just stings more than a disaster of decisions. Hiring is also a leadership challenge for everyone it seems. It's almost random given the few we hire which all look promising which ones end up excelling. We need to improve learning skills to be more bottom up if we want to grow. But another leadership challenge: I'm also not sure it's our best path forward. we might be more profitable and successful staying smaller and being top heavy.
  • geoduck14 5y ago
    This was really good to read. Thank you for sharing.
  • redelbee 5y ago
• paulryanrogers 5y ago
  Turning down a promotion I felt too inexperienced to accept. And a close second: convincing others that I'm ready now, after learning what makes good technical leadership yet without having a recent role on my resume.
• deedubaya 5y ago
  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 board fires the CTO, making me the most senior engineer in the company. Yikes, but ok. The contract with some of the consultants are up a week or so later, and they choose not to renew. Weird. The only other FT engineer quits. Uh-oh. I’m now the only engineer. I had to learn a new product and code base. The support backlog was long. I was getting called into sales calls. If I had lived in a tech hub, I would have quit. But I didn’t, I lived in a remote mountain town and finding this remote job took months. I ended up lasting about 18 months. It was a learning experience, but horrible on my body, relationships, mental health.
  • qazxcvbnmlp 5y ago
    Yep - I dealt with that once. My life got considerably less stressful after I quit.
  • cutemonster 5y ago
    > finding this remote job took months It can be that hard to find remote jobs? (I never tried.) Can I ask how much work experience (eg years) did you have at the time? I'm glad you could get away from there eventually. (Hmm you found another remote job?)
  • emodendroket 5y ago
    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.
  • z77dj3kl 5y ago
    Hope it was those leaving that were sketchy and not those left! Sounds hard as it was already.
• chad_strategic 5y ago
  -USMC -Combat Tour -Enlisted -Officer CWO2 retired Best/Worst job ever. After that everything is a walk in the park. I will say after working in web development, software engineers are a unique breed and are difficult to integrate into a team. I believe this an issue because of the demand for developers and the amount of knowledge they control. Luckily, I don't work in the web development world anymore.
• throw_jail999 5y ago
  I was CTO of a company under investigation for both securities fraud and some other misdeeds. The CEO was definitely sketchy. When I tried to talk (many times) about the pressure and stress I was feeling he would alternate between throwing chairs (seriously!) and offering me various pills and alcohol. I couldn’t even quit because then I would have to foot all my own legal bills which would have bankrupted me. I was so stressed I considered suicide despite the damage it would do to my fiancée and family. I didn’t see any way out of the situation and had convinced myself I was going to jail and my career was ruined. There were all sorts of suspicious emails, and truth be told I wasn’t exactly a saint either. I wound up finding a therapist who specialized in criminals and those going to jail. He listened to my story and gave me very good advice, and said worst case I would go to low-security prison for a few months. He didn’t think (from his professional experience) that I would do any time, and to relax. We wound up settling with the regulators, I left the company on semi-good terms, and eventually the company got acquired for the biggest exit of my career! And I am very happy I did not kill myself (as are my now-wife and kids). The silver lining is normal stressful situations don’t rattle me anymore. I have ice in my veins given what I went through. I am now a CTO of a respected company.
  • geoduck14 5y ago
    Woah. That is some serious perspective! Thanks for sharing
  • whimsicalism 5y ago
    It sounds like you were also struggling with anxiety writ large, not including those very stressful circumstances!
  • austinjp 5y ago
    Oh boy. Sounds like hell. Very glad you're through the other side.
  • trs8080 5y ago
    > 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.
• rubyn00bie 5y ago
  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 instead of thinking about how you can give more trust to people, you just had your ego stand in the way of mutual success. You are a shitty manager, and today is hopefully the first day of you recognizing that and learning to trust. 2. When people don't deliver what you expected, it's because you did a shitty job of communicating it to them. What seems obvious to you after 45 minutes in a meeting with three other people already prepared for the topic will most of the time seem obvious to no one else. If it does, I can almost promise, their vision of it is totally different than yours. Learning to work through the defining the problem (that includes asking "does this problem exist?") and then guiding solutions (we have x days, engineering hours, etc available) to ensure they meet the needs of the business. If no one but you delivers things correctly, you're a shitty manager, and today's hopefully the first day of you recognizing you need to learn to communicate and trust. Not many people are lucky enough to be told so plainly it's their ego, but it's your ego that causes your team to fail. Maybe it's your boss's ego that's causing you to fail... I was told plainly to my face to not let my ego get in the way of the goal... and yeah it punched me in the gut too, so if you're hurting, or in denial know it's okay. We all have to grow, it's worth it.
  • darkerside 5y ago
    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 that have nothing to do with you. They may have a different perspective, or they may just be having a bad day. Or they may have family or health problems affecting them. Or, they may actually just no longer care or not be good at their job.
    • 5y ago
• whirlingdervish 5y ago
  (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 amount of money that would have made him the highest-paid person on the team by a lot. (He was on the lower end of both seniority and performance.) He was threatening to leave, and after talking to my superiors I basically just said "sorry, you aren't getting that, I don't want you to leave but if you do I will be happy to give you a good reference." That didn't go over great and he emailed the whole C-suite trashing me and telling them essentially what a mistake it was that I got tapped to lead the team over him. The CEO just forwarded the email to me and said "deal with this." We'd had a pretty good relationship before, (or at least I thought we did) but all attempts to sit down with him and figure out how we could work together ended with him just making it clear that he was not going to play ball. He stopped showing up to work for awhile and sent his notice not too long after, and eventually we hired a real manager (which was always the plan) and I went back to writing code. Even though I don't know what I could have done differently I still feel bad and think about it a lot.
  • qazxcvbnmlp 5y ago
    Sounds like you did the right thing and they needed to go.
  • lostcolony 5y ago
    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.
    • teddyh 5y ago
      > you should have fired him intentionally yourself when he went over your head Is escalating an issue a fireable offense?
• austinjp 5y ago
  My boss took me and my team out when there was a bit of ill-feeling brewing for reasons I can't remember. He bought everyone a few drinks, and asked what everyone's problems were. The issues came tumbling out with frankness. I kept my mouth shut, but generally agreed with the team. My boss, without warning, pointed to me and said basically "austinjp will take a note of all this and sort it all out" then left. I had no budget, no control over any of the issues, no authority outside my team, no time... nothing. It was made clear to me that there would be no support in any way. I was young(er) and tried my best but it was a shitshow. I have never felt more exposed and thrown under the bus. A couple of similar situations were enough to grind down my resolve and I became as disillusioned as everyone else. When the inevitable redundancy was offered I took it and left without hesitation. Still bemused by how absolutely amateurish and vindictive the situation became. So I didn't "overcome" it, clearly, but it helped me realise a few things. Firstly, that nobody has any idea what's going on in anyone else's head. God knows what my then-boss thought of me, but it clearly wasn't much, and it clearly didn't match how I thought I was perceived. Secondly, once things are toxic it's almost impossible to turn things around. A couple of other people at the same place acted very poorly too, around the same time. Looking back, maybe I should have just quit. But it wasn't easy to see the wood for the trees. Third, stick up for yourself and for others. Don't be an arsehole. Everyone's dealing with their own demons and people in authority should constantly try to remind themselves of this. Support each other and grow together. Fortunately most people aren't arseholes, even if some occasionally act like they are. I haven't always got those elements right, but at least I'm aware of them. So I guess what I overcame to a small degree was my own professional shortsightedness! :)
• newlead 5y ago
  (throwaway) As a new team lead, coming up with a roadmap, and not being able to subdivide a project into independant parts that can be worked on in parallel by different team members.
  • SkyPuncher 5y ago
    Sounds like you're putting too much of this process on yourself. Your reports should be able to work 5his out among themselves with you helping.
• giantg2 5y ago
  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 required multiple people to address. I brought up the issue with my boss - not prioritized. Talked to my department head next. They told me they weren't going to address the issue because they have a backup system. So I added if they ever tested the system or had documentation on how to restore from it - nope. So I did all I could do. All the tech leads were shocked when I talked to them about it. No way was I going to own the security for that POS system, so I posted to a different area of the company. I worked as a tech lead (unofficially as I'm only a midlevel dev - seeing any issues with this company so far?). Oddly enough, I don't remember any serious issues even though this was the most authority I was given (took really, the others have me their trust/approval/etc to lead them). I had a great team and we were able to overcome a few challenges and provide business value while performing some major technical upgrades.
  • chris_j 5y ago
    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?
    • giantg2 5y ago
      I use elevate and deploy interchangeably sometimes. The package or files are already deployed in the test region, so you are elevating them to the next region (PRD). You could deploy the same code to the test region again, which wouldn't be an elevation since it's already there, and deploy would make more sense. ASC is Application Security Champion. Essentially the role requires some internal security training then you are responsible for following the processes to identify and remediate vulnerabilities.
      • chris_j 5y ago
• de6u99er 5y ago
  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.
  • cutemonster 5y ago
    > I didn't have an alternative job offer at the time of quitting, and shortly after my last day at work the pandemic started What happened after that? If I can ask
• allsystemsgo 5y ago
  Not being given leadership challenges, or if I take on a leadership challenge my manager takes credit.
• chasd00 5y ago
  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
  • emodendroket 5y ago
    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.
• rickpower 5y ago
  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.
• dnndev 5y ago
  Leading without the backing of management Quit the job Found a job that allowed me to have the resources and flexibility to truly lead (not simply have the title)
• throwaway78594 5y ago
  (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, and thousands of customers who emailed and called about it. Suddenly my life went from two or three people I would regularly interact with a couple times per week, to dozens of people who were involved in the crisis response, cleanup, and 'remediations' who I would speak to multiple times per 16-18 hour day. Around the same time, I lost some close friends very suddenly - one to cancer, another to old age. And there was the whole pandemic thing. I still haven't been able to grieve properly about that. You read about data breaches happening almost every week to various companies large and small, and mutter about how careless they were, or worry about whether you were personally affected. But from the inside, it is a totally different story for those involved (if they have even an ounce of genuine remorse and concern, as I did). Behind the scenes, they are an absolute shit-show. The truth is we had been careful and the hack was due to a compromised vendor, not our own code or networking, but I felt massively responsible and like the worst person in the world. I worked the 16-18 hour days in part to assuage my own guilt, but also because I had nobody else that could. The one saving grace was having good cyber crime insurance (which, I note, is now far more expensive than before - I'd pay it many times over, though). I'm still not over the incident, and have regular therapy (and regular nightmares) with many days spent unable to really focus on anything. Burnout is real, PTSD is real, and I don't know if I will ever feel truly safe again - I certainly feel that I need to get myself off the internet as soon as possible, and away from any kind of business leadership role. I just cannot ever face something like that ever again. Thanks
  • b0afc375b5 5y ago
    Thanks for sharing your perspective. I would definitely feel the same (or worse) if I was in your shoes.
  • matco11 5y ago
    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.
• dagmx 5y ago
  I was in an odd situation where I was supervisor for teams on major projects after 4.5 years in the industry, at 26. This was a fairly large company in our domain. This led to quite a few rushed learning experiences for myself, since I hadn't had the same years of mentorship that you'd usually expect. * Learning how to balance mentoring team members and how to be hands off. It's easy to get into the position where you're spoon feeding the team or haven't built their confidence up. You become the bottle neck and overworked. On the flip side, if you are too hands off, then the important implementation details slip through and you miss out on things you should know, but are not getting bubbled up. It's a hard balance that I still struggle with, and I don't know if any resources truly cover it. * How to manage under performing employees is a struggle. For example I've had a very senior team member who was struggling with personal issues and it was causing their output at work to be riddled with issues. However we had nobody to cover his areas of expertise and he refused to take time off. Trying to balance this while managing the rest of the team was a real nightmare, which involved pushing them on to lower risk tasks and absorbing more of the load myself till they could work through their issues. * Setting culture is a difficult one too. Team culture is often top down and leaders need to be aware that everything they do trickles down. However often the negative aspects amplify greatly over positive ones. While I would never compare myself to someone like Linus Torvalds, you can see this in how people try and emulate his negative characteristics (heated project comments) without understanding context or seeing his positive moments. Similarly I was known to be very critical in code reviews, though I went to lengths to soften my feedback and was never harsh. However over time I noticed several junior devs were emulating the criticality of my reviews without picking up on the softening and positive aspects of my reviews. This led to several scenarios where they'd bully other devs in code review and attribute it to my review culture. Anyway again this is something I find difficult to deal with. People naturally amplify negativity and the only way I've found so far is to be vigilant and counter their adopted behaviour early. Whether that's intervening in code reviews, or providing regular work culture refreshers, it is something that's required to maintain a healthy culture. * On to specific examples of issues I had to struggle with. A lot of the devs on my team were not great at body hygiene. Some didn't bathe regularly. I was literally being asked not to send people to meetings . The only solution was to ask HR to send a strongly worded notice to the whole company to remind them about hygiene and taking some folks aside to gently suggest some mitigations for their hygiene. It was rank.
• technofiend 5y ago
  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 killing us all. (This predates SRE/devops by a decade.) The AD teams had no choice but to add some quality control but still things weren't perfect. At the end of our third year of this five year project the project manager who worked with me on one portion of what we did was promoted to executive director but I was not. Within a few days of learning I was passed over for promotion I also accidentally discovered my grandfather had died of cancer. I didn't even know he was sick! No one in the family told me. I just found out about the funeral when someone asked me if I planned to attend. While at the funeral I made plans to have dinner with my younger sister and to go to Las Vegas with my grandmother. Soon after my sister was dead, killed in the line of duty as a police officer. A month later my grandmother was dead from open heart surgery. The whole time this was happening people were coming up to me at work asking how did that guy get promoted instead of you? How, indeed. The challenge for me was staying motivated and putting on a happy face for employees and not quitting. Frankly if I'd been able to I would have. The part that makes me laugh now is at the time we still did exceeds, meets, needs improvement stack ranking. My boss told me if he had made me exceeds I would have gotten the promotion but he couldn't because of politics: 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. To top it off my mentor dropped me: he said if I was no longer an exceeds it was a waste of his time. Despite falling into a black pit of depression I powered through the motions of being a people manager but frankly I couldn't take any part of managing careers of others any more when I knew the system was so broken and I had wasted years away from family and friends. My solution was to go back to being a hands on technical person: I transfered to our internal IT group and started over. I'm back to leading teams and getting kudos from the top of the house but still if I'm honest I feel like I failed my biggest challenge by choosing to just move on. On the other hand I'm certainly far happier and no longer ignoring family and friends to work 80-100 hour weeks. On balance that's probably for the best.
  • camjohnson26 5y ago
• yogrish 5y ago
  The challenge I faced earlier was to get things executed ( expected outcome) from different teams. When I found my first follower , the one who really buys my vision and takes it down, things started to roll faster. This might give you an idea of first followers. https://youtu.be/fW8amMCVAJQ https://youtu.be/fW8amMCVAJQ
• moneywoes 5y ago
  Title rings like a Amazon interview question tbh
• therealslimslug 5y ago
  Dealing with an abusive CEO. I joined the company as a dev and quickly got promotes to a PO/Teamlead position. To be honest, it was everything I could have wished for, and I felt very lucky - fantastic colleagues, exciting product, cool tech, modern ways if working, and the team I would lead had some fantastic individuals and a positive attitude. I was assigned to a newly formed team in charge of a new revenue opportunity. The project was the CEO’s little baby, so I was a bit nervous of how his involvement would be, but so far there were no red flags. I had heard some comments from colleagues about him - he seemed to come up in conversations a lot - but nothing major, I thought. This was my first management role and I felt completely overwhelmed. I got a large amount of responsibility on top of still doing my previous dev work. Managing felt a lot like what I imagine being a preschool teacher is like. Coming in with grand ideas of wanting to help the team be the best it can, having high ambitions... and then drowning in the sheer practicalities. Misunderstandings, people with different wills, tantrums, power struggles... I wanted to be an empathic and supportive team lead, but my manager colleagues who were much more direct and strict seemed to be moving along and through conflicts faster (not true, I learned later). I was proud of always putting the welfare of my team first. Later a member would tell me he decided to decline a move to another team for that reason, so at least I did something right. But instead of focusing on learning to become a good manager, problems with the CEO started right off the bat. I went on a short vacation, during which he had summoned my team, upset and wondered what the hell is going on, ordered them to do the exact opposite of what I had tasked them to, then grabbed me on my first day back to berate me and tell me I should listen to him because he knows better than me. His behaviour came in waves. If things appeared to be going well, he was your best friend and generally hands-off. The moment he smelled what he perceived to be trouble, problems began. Eventually I ended up permanently on his bad side due to a long series of drama. This is the point I learned the company had hired a leadership coach who spent 99% of his time helping managers deal with the CEO and his antics. Up until this point I had thought I was getting on his bad side due to my behaviour or results. Now I was slowly starting to realize that everyone who reported to him had a similar experience. I started to have a feeling of constant dread. He was unpredictable and could react suddenly to anything in any manner, often with ferocity. There were groups of people spending significant time trying to control his outbursts. He would usually be apologetic after, and claim to have learned a lesson, but the next day it would be back to the same old. Things started to take a toll on my personal life. I was drained, agitated and exhausted from work, and brought those emotions home. I had to see a therapist. We also had our first child around this time. Then I started getting weekend calls. The worst was a sunday morning call from him starting with ”I just had a great idea”. The great idea was to throw my last two weeks of planning in the trash, smash my team together with another team, have both team leads lead the team together (which naturally lead to an instant power struggle) and add some unrealistic expectations to the mix. Funnily, I was still telling myself that perhaps this was normal. Then we had a salary discussion. When I joined I had been promised a percentage raise after the first year, otherwise I would have taken another offer at the time. He told me that despite getting good feedback, I am actually performing bad (I asked him to back it up with statistics which I knew existed - he answered that I should just trust him because he knows better) and could not give me the raise. I didn’t really care about the money, but at this point I felt that, if I can’t even trust him on his word, it’s impossible for me to work for him. He lied as usual when challenged and claimed he had never promised the raise, except this time I had written proof on the promise and asked him to honor it. He reacted about as well as could be expected. Anger and tantrums. Incoumd tell he wanted to fire me on the spot. Since that’s not possible here, he demoted me and sent a multi-paragraph rant email to multiple parties explaining how we had both agreed that if i’m not the best employee in the company in two months that I would cease to be employeed. After I replied that we had not agreed to that, I was offerer a moderately-generous exit package. I took it without hesitation. An hour after taking the offer, a colleage stopped me in the corridor and asked ”What happened, did you get some good news? You seem a lot calmer than usual.” I realized it was true - all my anxiety was gone. I felt relief. Don’t let yourself get treated badly chasing a career. I’m back in a dev position elsewhere and couldn’t be happier.
• firstfewshells 5y ago
  Are you preparing for an upcoming interview?
  • PoachedSausage 5y ago
    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.
    • emodendroket 5y ago
      I often wonder how much influence anything I write on those really has on anyone.
• italicbold 5y ago
  A mark of a good leader is that their team runs really well without them. It should also run just as well when they are around. Always be looking to take your ego out of the situation. You are there to facilitate the success of the team it’s individual members.
  • d0paware 5y ago
    This is a very underrated observation. I've seen teams where all code reviews pass through one or two individuals. The "core developers" become a bottleneck to all changes, even if they offer the best feedback available. The team eventually leans on them as a crutch to catch all problems, progress grinds to a halt as everyone is waiting for their code to be reviewed by X, the core developers don't get any real work done, and the rest of the team never levels up because they don't learn lessons that sometimes are only learned the hard way in production. Good leaders know how to "let go", delegate, and recognize when they're becoming part of the problem.
• seer 5y ago
  I was climbing up the ranks as a dev of a web agency. The owner just got into the startup scene abroad and wanted to be part of it. So he spun up a separate company, and I ended up as a lead dev there. And as the senior dev I ended up with the CTO role. No experience with that whatsoever, and no support structure to lean on as we were basically one of first gen IT startups in my country. No established processes and we had to invent them as we go. I had read zero books on technical leadership and didn’t know anyone who I could talk to. Didn’t know which books I even had to read as there wasn’t anyone to talk to. HN was my only solace. I was working like crazy and putting out fires, but instead of helping my colleagues I leaned too much into doing the technical challenges myself. And it all came crashing down when I went on a long overdue summer vacation. On the first day I start receiving emails in the form of “um we seem to be having a problem, not sure how to deal with it”. It kept escalating day by day, and at one point the CEO just told me “sorry mate but we need you back” and I had to cut my vacation by half and get back to work. On the bus ride home I kept thinking “never again” and when I got back took a _much_ more serious effort to make sure I wasn’t the single point of failure and actually be a CTO. Read some books, took some steps back, mentored people, and most importantly actively took less challenging things so others could shine too. And it worked, I mean I wasn’t that great a leader I’m sure, but there wasn’t a problem that my team couldn’t handle without me afterwards. Ended up quitting a couple of years later as I was burned out and not happy with the direction of the company overall, but the team is still there more than five years later and growing. What I learned was that you have to take new responsibility seriously and try to teach yourself for it, not expect things to just “work out”.
  • m_st 5y ago
    Thanks for sharing your story. I‘ve had/have a similar experience. No seniors here to learn from but got it up to top performance with reading (joelonsoftware was a great inspiration back then), investing lots of time (but rarely overtime) and being ambitious. I believe you also learned that you shouldn‘t be the single point of failure. I‘m still actively working on that. Though it‘s hard to relay to others if they just can‘t get it done or don‘t share your ambitions, vision or views of quality and customer focus. But there‘s always hope.
• egberts1 5y ago
  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 problem that highly interest them for them to tackle). My Kudos are often brushed off but still required to be dispensed tactfully. - Laziest workers are definitely the hardest to narrate a path for task completions. Kudos are rarely a good tool for shaping of the lazier’s task path and too easily overused toward increasingly diminishing ROI. - But upper leadership kudos requires letting go of your own greed, avarice, possessiveness, ... in many words to shorten, the real power in leading. Harder still is making the your middle boss of many middle bosses look the bestest of the best. Even to a point of moving his name in front of your invention patents. That was a strong sign that this rat treadmill isn’t for me and that I truly have the entrepreneurial skill to strike out into a smaller company and startups. I excelled there as well but the happiness factor was way better.
  • johncena33 5y ago
    > 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. Everyone was congratulating themselves not only for doing the miniscule things, but also for bringing in a good team spirit. The whole culture ended up being a participation trophy culture. All the good employees left the company, and the medicore ones were still doing the same thing last team I heard. This toxic positivity has become very popular in pop cultures. Unfortunately it's all appearances, underneath the positivity is the thriving mediocrity.
    • egberts1 5y ago
      Agreed.
• anotheryou 5y ago
  You asked for the hardest, no good solutions to those: - dev with low self-esteem causing social issues: problem ongoing, helping though: speaking about it, more focused tasks he can take ownership over and finish without that much communication and trouble. - dev generally not nice to people (and not that compenent): people started avoiding him and he quit... Should not have come through the probation period, but I wasn't in change of that (see next point). (it's also not that easy firing someone in germany btw) - ownership of product and progress, but no say in direction (which changed every 2nd week) and not officially team lead: I quit.
• emodendroket 5y ago
  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.
• yowlingcat 5y ago
  Loneliness, learning how to exert soft/passive power and patience. As you move further up leadership, your social circle of peers necessarily and naturally becomes smaller. For those of us who get a lot out of the social aspects of work (the team sport as you said), this can make something that you'd otherwise celebrate rather bittersweet. Exerting soft/passive power has been the major long-term challenge, I think. Learning how to exert action at a distance requires a lot of finesse, a lot of listening, and more scanning than printing, so to speak. I'll be the first to admit that I lacked some of that when I began; still do now, really. You have to think about things as an analyst, an evangelist and an investor, rather than a do-er. There's a lot of education, persuasion, and sermonizing involved, even if it's primarily in recruiting others to work your ideas or to join your team to work on theirs. Leadership is about people; people can be messy and fickle, so leadership challenges involve things that can be messy and fickle. Finally, patience has been the most subtly challenging part of all of the above. When you're more alone and need to exert soft power to be effective, you need patience in spades, and you very likely may lack it. I certainly do. The impatience that was such a virtue to me as an IC has bitten me as a leader. I've had to learn the hard way that patience regarding challenges isn't a nice to have -- it's a necessity, and without it, I'll fail. That said, I think I have enjoyed a lot of tailwinds that have made much of my early leadership challenges a non-issue. I'm pretty self-aware and am more motivated by winning than being right, so I've not had too many challenges with stupid unforced errors on my end. I like talking to people and enjoy fixing their problems to make them happy, so management and leadership has large component of real fulfillment to it that I don't have to fake just because it takes my career forward. I've spent a lot of time in necessarily cross-functional technical roles at startups in my early career, so it's never been hard for me to empathize with leaders in other divisions and be an asset in effectively translating technology into their business goals. But even with all of those tailwinds, leadership is /hard/. Beyond the day to day challenge of increased responsibility, decreased agency, and thinner safety nets, it's just plain mentally tricky in so many ways I could conceive of but not fully appreciate until I began my own journey. The highs are high, but the lows are really, really low, painful and traumatic even. I never questioned whether I should be doing what I was doing as an IC. But as a leader, that questioning became a lot more prominent. And it had very little to do with how well I was objectively doing according to the CEO (which was "very well"). I think it is just the nature of the beast.
• sitkack 5y ago
  Managing up is a thankless fools errand. Managing a team shouldn’t be a political drama.
• contingencies 5y ago
  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).
• wildermuthn 5y ago
  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.
• saddington 5y ago
  the hardest leadership challenge has also been the hardest professional challenge... i cofounded a venture-backed startup with my brother. a few years in, i had to fire him. too many details to unpack here, but, gratefully he's found footing and is happy building something else. i'm still running the venture although we are running out of time / money. (i'm not sharing that last point for sympathy; i understood the risks and i'm prepared to face the end, just like the beginning.) overcoming it? honestly, i just pressed on; what else can you really do? i got therapy, counseling, to work through the difficult patches and i invested in myself a bit more so i could find peace with it all. i realized that i had a pretty serious co-dependency issue and now i'm clear-headed in a way i've never been. so, the result has been net-positive.