Sounds like the right kind of questions to ask, but without more concrete data on what questions your predictions were off by how much, it is hard to give any better advice than: if your gut judgement tends to be 20% off after considering all evidence, move the number 20% up.
Personally me and my partner have a similar bias, but only for ourselves, so making predictions together on things like “Application for xyz will succeed. Y will read, be glad about and reply to the message I send them” can be helpful in cases where there are large disagreements.
Sounds like the right kind of questions to ask, but without more concrete data on what questions your predictions were off by how much, it is hard to give any better advice than: if your gut judgement tends to be 20% off after considering all evidence, move the number 20% up.
Personally me and my partner have a similar bias, but only for ourselves, so making predictions together on things like “Application for xyz will succeed. Y will read, be glad about and reply to the message I send them” can be helpful in cases where there are large disagreements.