Having an unstable teammate on a project I led. Long story short, they: (a) saw things in terms of them being persecuted, and took critique of their work or approach deeply personally (b) tended to see things as us vs them, and not a two-way street, where both sides bore responsibility. And that sometimes crappy things happen with no malace. (c) resented other's success at the company, and thought that the 'successfu…
Ask HN: What was the biggest leadership challenge of your career?
31–40 of 238 posts
Re: Ask HN: What was the biggest leadership challenge of your career?
#32Along 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.
Re: Ask HN: What was the biggest leadership challenge of your career?
#33Best/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.
Re: Ask HN: What was the biggest leadership challenge of your career?
#34I 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.
Re: Ask HN: What was the biggest leadership challenge of your career?
#35Having an unstable teammate on a project I led. Long story short, they: (a) saw things in terms of them being persecuted, and took critique of their work or approach deeply personally (b) tended to see things as us vs them, and not a two-way street, where both sides bore responsibility. And that sometimes crappy things happen with no malace. (c) resented other's success at the company, and thought that the 'successfu…
Maybe other teams are better at dealing with him.
Re: Ask HN: What was the biggest leadership challenge of your career?
#36I 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 s…
Re: Ask HN: What was the biggest leadership challenge of your career?
#37I 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 s…
Re: Ask HN: What was the biggest leadership challenge of your career?
#38Re: Ask HN: What was the biggest leadership challenge of your career?
#39Having an unstable teammate on a project I led. Long story short, they: (a) saw things in terms of them being persecuted, and took critique of their work or approach deeply personally (b) tended to see things as us vs them, and not a two-way street, where both sides bore responsibility. And that sometimes crappy things happen with no malace. (c) resented other's success at the company, and thought that the 'successfu…
I've been in the position of managing this person. After a lot of effort and too much time I realised I really couldn't do anything for him. I am not in the business of fixing gaping personality issues. And any work related coaching was impossible due to his victim mentality and inability to accept feedback. Some people asked if your engineer was technically gifted. For me the answer is it doesn't matter . The toxic…
When I started as a lead I devoted a lot of time and energy to someone who was underperforming and difficult to work with (and whose self-perception didn't match reality) when I should have devoted myself more to engineers who were doing well and receptive to feedback.
Re: Ask HN: What was the biggest leadership challenge of your career?
#40"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…
Is political capital a real thing for managers?