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4 Steps to Asking Influential People Great Questions as an Entrepreneur

Written by: Kelisha Mills, Executive Contributor

Executive Contributors at Brainz Magazine are handpicked and invited to contribute because of their knowledge and valuable insight within their area of expertise.


I started listening to thought leaders on the Clubhouse app. I love this app because you can hear valuable information daily from celebrities and experts for free. You also have the unique opportunity to speak directly to these experts when you are invited to the stage to ask them a question relating to the topic chosen. Now, imagine you have thirty seconds to ask Oprah or Kamala Harris a question about success or business. What on earth would you ask them?


I was fortunate to be invited to the stage to ask a question to some influential businesswomen. I live in the Caribbean, and my question was how to market my product in the US while living internationally. However, I beat around the bush so much with irrelevant chatter that my question was not straightforward. This prompted the amazing and accomplished Forbes Riley to interject. She noted that, after all I had said, she did not get what the real question was. I felt horrible but empowered to do better. This caused me to research “how to ask great questions in the presence of influential people.” Not only will you pique their interest, but you will immediately be put on their radar as someone who is focused and knows what they are about.

When you ask great questions, you...

  1. Get clear on what is important to you. You’ll receive advice and solutions to your challenge.

  2. Become a better thought leader through increased knowledge from a mentor

  3. Become connected with the expert who brings opportunities for future partnerships

  4. Spark an intelligent conversation that elevates your awareness of a topic.

In my research, I found the definitions for the word “question” were quite interesting. The Merriam Webster Dictionary notes a question is:

1. An interrogative expression is often used to test knowledge.

2. A subject or aspect in the dispute or open for discussion.

3. A subject or point of debate or a proposition to be voted on in a meeting.

4. An act or instance of asking.

5. Torture as part of an examination.

6. Room for doubt or objection.

In essence, the question asker is in a state of not knowing. However, the way they seek the answer can be good or bad.

As business owners, especially women entrepreneurs, we can sometimes find ourselves on the bad side, meaning we are constantly questioned. Most of the time, it’s by our children, spouse, friends, family, and especially when it comes to funding. Therefore, when it is our time to question someone else, we have difficulty expressing ourselves. It happens to me when I’m in rooms I feel I'm not qualified to be in. So, let's learn how to ask great questions!

1. Get clear on the purpose of your question

Why do you want to ask this question? Whose progress is it relevant to? What benefit will the answer bring to you, your clients, or your network? Is the atmosphere right to ask this question? Believe me. Some people ask questions knowing very well that they know the answer, only to rebut with intellectual concepts to make themselves look smarter than the person they ask. I have seen this time and time again at conferences and meetings. The ethical approach would be to think about what you don’t know about the topic at hand and formulate your question that would:

a. extract the deep thoughts of the person

b. spark further dialogue on the topic

c. brighten the spark in their eyes and allow them to express their passion

Questions that can achieve this response from the influencer will cause them to share more than they usually do in public settings. This gives you the power to be the initiator of insights from the person and places you in an advantageous position in terms of being on the same level as them, even for a moment.

2. Introduce yourself in less than 30 seconds

This is also known as your elevator pitch. When you are in a setting with high-quality people, you have a golden opportunity to let them see how beautiful and smart you are. So, if you skip over your name and what you do, you can lose the chance to connect with other persons in the setting who may be interested in your product or service. In 30 seconds, you should state your superpower and be relatable. Every setting is different, so your pitch should never be static or rehearsed word for word. Gain the skill of assessing the room and make assumptions about the person you are talking to by finding out all you can about their likes, dislikes, hobbies, family, and business. This truly sets you apart because it shows that you have done your homework. This also increases your “likeability.”

3. Leave the door open for other valuable contributors

Sometimes we have blinders on and look only towards the person we are asking the question. This closes the door towards others who have aligned businesses that can be very profitable if connections are made. To leave the door open, thank the person for answering your question and leave a call to action that is appropriate for the room, like, asking them to “slide into your DM’s on Instagram, or to connect with you on LinkedIn.

4. Find a way to store or repurpose your newfound knowledge

So, what are you going to do with this information? Are you going to keep it for yourself or share it with others? Are you going to write an article or record a podcast? Find ways to share what you have learned. Sharing is indeed caring. This would increase your title as a thought leader. I have seen, especially on Clubhouse, that those persons who ask great questions go on to be called upon by the very influencer to host and moderate their rooms.

I hope this article was helpful. I’d love to connect with you! Slide into my DM’s and let me know what the thing that stood out the most to you was.

Follow Kelisha on her Facebook, Instagram, Linkedin and visit her website.


Kelisha Mills, Executive Contributor Brainz Magazine

Kelisha Mills is a wife, mom of 4, author, speaker, and Entrepreneur (BSc. Entrepreneurship) for over 13 years. Kelisha specializes in life makeovers for mom entrepreneurs, helping them gain the clarity and confidence they need to find symmetry to run a successful business and have quality time with their families.



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