2. The day before This starts to get problematic. You really need to know with whom you’re meeting and how big a problem it is to reschedule the day before. There are some people who live locally to you and you know don’t have calendars full of meetings every day (I actually wish I didn’t. I want to be on Paul Graham’s “Maker’s Schedule” but as a VC this is quite hard.) If I KNOW it is somebody with whom I can more easily reschedule then we’ll reach out to them and see whether it’s OK. We usually try to re-slot them in quickly. We try to be very accommodating on timing. Often if they were going to come to my office I’ll offer to go to theirs to make it up for rescheduling so late. I assume that I owe them one.
And if we need to reschedule the day before it’s usually for a very compelling reason. It’s often because I have some last minute unplanned travel. If it really is a problem we’ll often stick by our initial commitment.
3. The day of the meeting- It better be a great freakin’ reason like travel problems, you’re sick or there’s some burning issue you can’t avoid. And obviously it is far worse if you were the person who had scheduled the meeting. In this case it warrants a personal email (or better yet a phone call) from you and a Herculean effort to reschedule the meeting.
Recently a team flew to meet me. They came from New York. I assume that they also had other meetings in LA but they really wanted to meet me. I had been introduced by a friend. Their plane had to land in Las Vegas unexpectedly to refuel. I had no other open slots to meet them that day and they missed their window. So I ended up doing a dinner meeting because I know what it’s like when you travel to meet somebody about fund raising and might not get to have the meeting after all.