The deadline had passed by a few days.
A former Reonomy employee wanted to exercise vested options. He had worked at the company for about a year, but his request arrived just after the exercise window had lapsed.
My first reaction was blunt: that is wild. Why wait? Why let it lapse?
My second reaction was to argue that we should try hard to find a way to allow the purchase. The legal question mattered, and the company had done nothing wrong. I agreed with that. The documents had a deadline and the request missed it.
Still, a person had put in a year of work and was now days late. Losing the entire value over that gap did not feel honest or like strong judgment to me. We did not have a close personal relationship, so this was not about doing a favor for a friend.
I asked the opposite question: why would we refuse if there was a lawful way to say yes?
There were other company obligations in the background, and I did not want to improvise around signed agreements. I suggested letting the lawyers handle the structure and tell us what was possible. If allowing the exercise required reaffirming existing commitments, they could sort that out properly.
The legal review eventually confirmed that the window had lapsed. I had no objection to a direct conversation afterward, but I was not the lawyer and I did not control the final answer.
This was not a job description I could rewrite before hiring somebody. The person had already worked, left, and missed a written deadline. My position stayed the same: check the documents, get the legal answer, and do not pretend that legal clarity makes the human part disappear.