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What is the Number One Skill for Investors?

by | Sep 13, 2023

I can’t get past that brand-new feeling of starting a new school year in September. There is still a bit of excitement left in buying a new sweater or notebook. Since it is ‘Back to School’ season, I wanted to discuss what is one of the top skills you need to cultivate as an angel investor.


Curiosity is your top skill as an angel investor. After all, our minds are a muscle, and curiosity is the mind’s exercise. Curiosity stimulates learning, helps us communicate better with one another, and helps to fuel innovation. Where would we be if no one asked, “Why?”

As an angel investor, you spend much of your time speaking with people who make these big claims with big hockey stick graphs. You cannot afford to take every conversation at its face value. You must learn to discern between the good and the bad and the fact and fiction.

Curious people ask questions. And they ask good questions. Good questions help to broaden our perspective and our set of options. Now, what I’m about to say is controversial, but there absolutely is such a thing as stupid questions. Let me explain.

A question is only a strategy for inquiry and must, therefore, have a purpose or intention if we want to evaluate its quality. A lousy question doesn’t have purpose or intention. Bad questions are vague and confusing. Bad questions are leading or use double negatives. Bad questions are biased and start with assumptions.

A stupid question is also a question that is never asked. Questions are powerful tools, and a curious investor asks questions with depth. 

Here are a few tips to implement during your September Angel Group Meeting to ask better questions to get better answers.

💡Be Clear: Ask your question with as much clarity and purpose as possible.     Explicitly state what you’re asking of people.

💡Be Concise:  Be brief and specific when asking your question. A good rule of thumb is if it takes more than 30 seconds to ask the question, then it is too vague.

💡Be Open: Ask open-ended questions rather than closed ones. Open-ended questions leave more room for discussion. These questions don’t allow for a simple “yes” or “no” answer. Open-ended questions may also lead to follow-up questions, which help you dig deeper into the topic.

💡Be Confident: Open, relaxed body language projects strength and control. Asking questions confidently helps put the questionee at ease and helps to build trust.

💡Be Listening: Active listening and curiosity are complementary skills. Active listening requires you to listen, reflect, and ask follow-up questions to dig deeper. When we listen with interest, we create a space for meaningful connections and deeper comprehension.

Be a good listener,” Dale Carnegie advises in his 1936 classic How to Win Friends and Influence People. “Ask questions the other person will enjoy answering.

As you incorporate these tips into your September Angel Group Meeting, remember that as an angel investor, you should cultivate curiosity every day- but so should the founders you invest in. Curiosity is closely tied to our ability to tackle complex problems and creative problem-solving. Curiosity is the key to innovation.

This post came from the September edition of the AIO Newsletter. Want to get your own copy delivered to you every month? Subscribe here

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