Regarding "Dates have a % confidence", has anyone else used this system in practice? How has that worked out? Do current project management tools allow you to put a confidence interval next to estimates?
Anytime I'm tasked I make sure I understand exactly what's expected and when it's due. I get it in writing until we've established trust. Then I deliver.
I'll agree to work that I know, barring any unforeseen circumstances, I can accomplish in two weeks. Thirty hours. Ninety hours? Whatever it takes to complete the work.
I would ask people that were agreeing to work, that if they were comfortable quitting their job or refunding me all the contract money if they failed. Sometimes they would say yes, other times no, other times they would look at me with bewilderment. I would ask them only to take on work that they knew they could complete. Sometimes they would adjust the estimate, and I would thank them for it. Everyone wins when people hold their word. There have been times when I have had management, very upset, demanding to know why I did not complete a task. I asked them if I ever agreed to it? They would say no. And I would say then, why would you expect me to complete it?
While I do not ask for a percentage completion, I look for a binary response. We can adjust the scope, we can adjust the timeline. We cannot adjust the completion status after the deadline has elapsed.
I have agreed to work not knowing how to do it, only with the confidence that I knew I could get it done, or subcontracted out at zero gain.
As for project management tools to capture this, no. I did develop my own team tracking methods. We had a internal facing fail board. If you failed, you made a public note. This was encouraged. We fail, we learn, we do not lie. Others would ask, how did you fail? We would tell a story and we would all learn. The goal was to have less fails than days in the week.
For instance, just today I was asked when I could finish a task. I answered "I'm 80% confident I can deliver in two days". If I leave my confidence measurement off of that and just say "two days", it could lead others to make inflexible schedules and a delay could derail things. Giving a confidence level gives them an additional bit of information that can be very useful.
Sometimes, I've said something like "80% chance of 2 days", and the response was "what would it take to make that 90% (or whatever)." That's also very valuable, because then we can have a realistic discussion about tradeoffs/prioritization in scope or quality to gain more certain scheduling.