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

What was your biggest leadership challenge of your entire career? How did you overcome it? What happened then?

(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.

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.