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

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.

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 attitude always undermines any technical contributions they makes. Even a talented asshole just ends up taking on more and more critical projects, which widens their sphere of negative influence.

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.

Anyone tries to do that to me and I'm out. Thats the road to a competitive and shitty management culture.

You can try and create a bubble of goodness in your own team, but you still exist in a sea of shit. Eventually that sea will drown you.

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.