I was asked to provide career coaching feedback on a new employment opportunity, so I worked up these questions. These questions are equally applicable to a startup or other business opportunity, with suitable modifications around manager / company / product or services .
Ask the questions before you become emotionally invested in the opportunity. Once you get past that line, your emotional investment will color or skew your perceptions to the point you will not be able to be objective about the answers.
Use as many objective, fact-based data points as possible, and keep a log or spreadsheet that rates and weights the answers.
Questions #1 – #3 are absolute show stoppers.
It can be possible to overcome #4 if you can see a clear path to obtaining the necessary skills, etc. Most entrepreneurs get to where they end up by answering “Yes, I can do that,” to every challenge and figuring it out as they go along. That approach does not disqualify you for opportunities, but you need to be honest about how that changes your risk profile.
The answers will never come back all positive, but the goal is to have the majority of the answers to questions 5-11 come back positive. Some negative responses, such as those around customers, products and services, etc., may provide leverage points for negotiations.