Ask HN: What was the biggest leadership challenge of your career?
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&#x27;d done.<p>Things were slowly improving as we collected metrics to improve poor code quality and shoddy releases that were killing us all. (This predates SRE&#x2F;devops by a decade.) The AD teams had no choice but to add some quality control but still things weren&#x27;t perfect.<p>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.<p>Within a few days of learning I was passed over for promotion I also accidentally discovered my grandfather had died of cancer.  I didn&#x27;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.<p>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.<p>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&#x27;d been able to I would have.<p>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&#x27;t because of politics: the guy who sponsored the fellow who did get promoted managed to get my ranking knocked down so I wasn&#x27;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.<p>Despite falling into a black pit of depression I powered through the motions of being a people manager but frankly I couldn&#x27;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&#x27;m back to leading teams and getting kudos from the top of the house but still if I&#x27;m honest I feel like I failed my biggest challenge by choosing to just move on. On the other hand I&#x27;m certainly far happier and no longer ignoring family and friends to work 80-100 hour weeks. On balance that&#x27;s probably for the best.