This is very thoughtfully put and really should be the test before anyone puts their time / money into someone else. Thank you for putting in the time and effort into writing this. It shows that you really do care.I'm not sure if I can do a good job of quantifying it here, but I'll try (kinda like the fact that I played professional poker for a long time, but it's really tough to explain how I pick up tells from other players)...
Some things I tend to see:
- How much work they've put in before they come to me. If someone wants me to hold their hand starting from the day they decide to try a new endeavor, they probably won't be successful. There are LOTS of resources out there to help you learn the basics of starting and growing a business, investing, real estate or whatever it is you want to do. If you don't have the initiative to learn everything you can on your own before you ask for help, you're probably either too lazy or too undisciplined to make it as an entrepreneur. Those who spend a few months learning absolutely everything they can and only come to me when they hit an insurmountable roadblock are the ones that will often make it.
- The questions they tend to ask. The depth of questions is a big tell in how someone thinks. If someone asks me to lunch and asks a question like, "What's the best tip you have for a new investor?" or "What do you wish you would have known when you started?" I know that this person is unlikely to take much action. If they ask pointed, detailed questions that are actionable and help them overcome issues they're facing, they are much more likely to have the personality where they are willing and able to solve hard problems, and that's an indicator for success.
- How they treat me. If it's all about them, and they are happy to use me for however I can help them, they aren't going to be successful. They'll attempt to use other people as well. If they are more concerned about providing me value than they are about me providing them value, they are more likely to have the mentality of offering value to others, which goes a long way towards entrepreneurial success. It's amazing the number of people who practically beg me to have lunch or coffee with them, and then expect me to drive to where they are or to split the cost of the meal. And no, it's not about the money.
- Their level of empathy. This is a weird one, but I've noticed a tremendous correlation between those who are empathetic (can put themselves in other people's shoes and can understand the thoughts and feelings of others) and those who go on to be successful entrepreneurs. Maybe it's confirmation bias on my part, but in my opinion, this is one of the best predictors of business success.
- Their previous success and dedication. With anything. I like to ask people about their past jobs, hobbies and what they do in their spare time. If someone has had a successful career or has played an instrument for a long time or is a skilled woodworker or has collected stamps for 20 years -- those are traits of someone who has the ability to dedicate themselves to something. Many people just jump from thing to thing and don't have the ability to dedicate themselves to anything. Those are the ones who will do the same with a business or their investments -- they'll abandon ship as soon as a little bit of work is required.
Those are the big things I can quantify. Obviously, there are a lot of things we can glean from people that is harder to quantify -- confidence, intelligence, drive, etc. -- and those things play a huge factor as well.