Decision-making can be a tricky thing, in a number of ways.
First, you have the issue of determining when you have enough information to make a solid decision. As Josh Kaufman said in The Personal MBA, “no decision, large or small, is ever made with complete information“. How do you even know what “complete information” looks like?
Second, you have to be able to remember that a good decision might have a bad outcome, but that doesn’t mean it wasn’t a good decision.
So how do you know when to stop debating and make a decision? Former US Secretary of State Colin Powell had a pretty simple formula for it:
“Every time you face a tough decision you should have no less than forty percent and no more than seventy percent of the information you need to make the decision”
It’d be foolish to try to make a decision with only 20% of the info you need, but you’ll also likely waste a lot of time if you constantly strive to hit 100%. The unspoken challenge with his advice is knowing the scale of the information. If you only have 20% of the total information, how do you know what 100% looks like in order to know that you’re at the 20% mark?
The best solution there is likely to simply make more pots — just get more reps under your belt. The better you understand your area of expertise, and the more times you’ve made a decision (whether it failed or not), the chances of you getting the next one right will only go up.