The second skill/trait (not in order) I try to look for in entrepreneurs is if they are confident, but not arrogant. I actually dont think there’s a fine line as many people suggest. To me, most people clearly fall more into one bucket – lacking confidence, confident and over confident / arrogant.
I first observe how they introduce themselves. If I get a historical perspective (from them time they were born with some folks actually), and a list of milestones, that’s one thing I note. If there’s a lot of name dropping – I was at IIT, XYZ was my professor, ABCD is my uncle, etc., that’s something else I keep in mind. A list of specific accomplishments that are relevant to the conversation is another thing I am always looking for. I wont detail which ones are those that leave me with a positive and others that I am already sensing alarm bells go off, since that’s subjective. I have written before about the best way to introduce yourself in a positive manner.
Mostly thought what we are looking for is the way entrepreneurs address questions. So, depending on the situation, we use questions as a tool to gauge the boundaries and contours of their confidence.
Asking questions about what their biggest failures were, or things they learned from their experiences at previous companies they worked for helps.
- What do they say about the competitors when we bring them up?
- How they answer questions about their “perceived” shortcomings or flaws after we do reference checks?
- How they address the “market size is to small”, “you dont have a strong team” and other questions about their business model?
Typically a confident person is accepting and objective and an overconfident person (or a person lacking in confidence) will look for excuses and rationalize their behaviors.
I dont think it is important to be prescriptive about how to answer these questions, since most people will end up answering and also evaluating these differently, but it is one of our 21 criteria.
I know that you have your own way to judge if people are confident and not, what do you use to figure that out? I’d love to know.