How to Ask Better Questions as an Entrepreneur

If you can Google the answer, don’t ask the question.

We asked the members of the 2020 Female Founders 100 for their best advice about winning and thrilling customers. These are the highlights.

When was the last time you outright asked for what you wanted?

If you can’t think of a recent example, chances are, you’re lacking one of the greatest assets that could determine your success as an entrepreneur.

I have found asking smart questions is a superpower that can be used to inspire greatness within you. Knowing how to inquire curiously teaches you about other people, engages you in a way that talking prohibits, and sets the precedent that asking questions is not a weakness, but a powerful asset. 

When you are willing to step out and ask others, and yourself, bigger questions, you pull out bigger answers. Here is how I grew the mindset of asking tough questions strategically.

1. Know what you truly want.

Before you ask anyone else for anything, ask yourself the hard questions first. The better you get to know yourself, the more self-awareness you have, and thus, the greater your ability to ask for what you want.

One way to do this is by questioning yourself “why” over and over. This practice will get to the heart of what you want, and likely show you a faster and more effective way to get there. You may think you want a $1 million business, but when you ask why, the real desire will present itself. It could be a craving for freedom with your time or attaining a certain status in society, both of which don’t necessarily require a specific $1 million milestone.  

One of my favorite questions to ask is: “How can I make twice the money with half the effort?” If you ask yourself questions this specific, everything else falls by the wayside and what you want will be more easily attained.

2. Find people you want to ask specific questions.

If you want to get anything in life, the knowledge and blueprint likely already lies in someone else’s mind. And the tool to gain that value is in asking questions. The thing is, you don’t want to ask just anyone. Study people you strive to emulate, who have done things you dream of doing, and are living the life you want.

I started a podcast as a passion project but found it was the best tool to improve asking the right people insightful questions. Every week, I have an hour with a powerful and admirable person. Asking them cookie-cutter questions wasn’t going to help me or my listeners. To make the conversation worthwhile, I dig into what particular insight they can share that will make my life better. Again, this couldn’t be possible if I didn’t know what I wanted for a better life in the first place. 

Instead of being broad, I get specific. “What do you do for fun?” is replaced with “What activity brings you the most relief after a long day of work?” And instead of asking a closed question like “When did you start your business?” I create space for a story with something more like “What was the biggest influence that inspired you to start this business?” A general rule of thumb is if you can Google the answer, don’t ask people the question.

3. Connect the dots.

At conferences, virtual or in person, I am consistently blown away during the Q&A portion of a presentation. Students and attendees could take this opportunity to get really nitty-gritty, but instead, ask things like “What are the three things you would suggest for anyone trying to be successful?” or “How did you make $1 million?” They were trying to take universal principles and apply them to their niche cause and mission. But the reality is, this way of asking questions won’t drive you forward. If anything, it will weigh you down with endless input to sift through. 

To ask good questions, connect the dots between what this person has done that you admire, and what you are working toward. Use these commonalities to then ask questions. This could look like understanding the roadblocks you’re hitting that they may have gone through and targeting the conversation in that direction. It also goes back to asking them why they made certain decisions or took specific actions. Although their particular experience may not identically mirror yours, why they made a decision likely shows the multiple variables impacting their choices that you should be aware of.

Stop brushing the surface, and learn how to ask the right questions. You never know where the answer to your problem may lie.

© Inc. 2020

Related Articles