Asking questions is an important part of growing as a person and as a business. In the business world, there is a common misconception that asking questions is a sign of weakness and that you’re not smart enough. That is not true. Studies have shown that asking well-thought-out questions is a sign of intelligence. It’s also one of the traits successful people have in common.
Asking the right questions to entrepreneurs can lead you to the business or career of your dreams. It also offers you an opportunity to learn from other people’s mistakes so you don’t repeat them. It’s also the quickest way to learn what works and what doesn’t.
You’ll learn:
Want to learn from the best? You better be ready to ask questions. Great mentorship starts with sharing information and getting insights. When you ask questions during your sessions, you’ll be able to make the most of your mentor’s expertise.
Some ways that asking questions for entrepreneurs can boost your mentorship relationship include:
In particular, when you think of questions to ask successful entrepreneurs, you’ll be getting practical business advice to start or improve your own.
How you conduct and carry yourself when you’re speaking with your subject will go a long way to influencing the outcome of your interview.
If you’re interviewing an entrepreneur you particularly respect or consider of higher status (in the grand scheme of things), it’s important that you treat them as an equal, regardless of any pre-existing feelings you might hold. To come off as subordinate or timid will color their opinion of you immediately. This will likely diminish the quality of the conversation as a result.
Conversely, if you’re interviewing a new or younger entrepreneur - one that hasn’t [yet] reached the pantheon of the globally famous and mega-rich - you should likewise afford the same amount of respect and cordiality you would reserve for anyone else.
Regardless of who the subject is, it’s only right that you arrive at the interview properly prepared. You must have conducted sufficient background research to allow you to engage in a real conversation. A genuine back-and-forth will demonstrate to the interviewee that you are worthy and respectful of their time.
And, as the interviewer, it’s up to you to set the mood of the meeting, as well as the agenda. Know what you want to ask, know why you want to ask it, and arm yourself with sufficient knowledge to pick up on where the entrepreneur might take the conversation.
When you ask questions with clear intent, you won’t get distracted during your conversation or interview. Knowing why you are asking certain questions will help you stay focused, and you’ll be able to gather valuable facts or opinions that you actually care about. It will also help you avoid asking unnecessary questions just to fill the time.
Try to listen to the person you are talking to and understand what they are saying. Being a good listener will help you ask questions the other person will enjoy answering.
When asking questions, try to use a neutral tone and avoid asking potentially leading questions. Try to keep your questions open-ended to get the best possible answers. Open-ended questions can sometimes provide you answers you didn’t expect.
It’s important that you structure your questions. General questions should be followed by more specific ones, ask only one question at a time and use something from the answer as a lead to the next question.
If you want your questions to be dynamic, think about these specific categories and ensure that you don’t ask too much of one type of question:
These are questions that don’t move the needle forward and may even provide awkward periods of silence as the entrepreneur or founder tries to think of what to say next. The best questions to ask successful entrepreneurs are ones that will allow them to provide a wealth of valuable information.
Many entrepreneurs are pressed for time and energy. Asking vague questions that don’t have a clear purpose in mind can be more frustrating than helpful. Remember here, you want to find value from their wisdom and build a foundational relationship with them. Asking generic questions won’t cut it.
Therefore, this goes to say to take these sample questions with a grain of salt. Make sure they fit within the context and the wheelhouse of the entrepreneur.
Here are the best questions that you can ask an entrepreneur. Don’t forget to put your own twist on them to make them your own and in line with your purpose.
These are great first questions to warm-up and get at ease with one another. They help with creating a friendlier and more comfortable atmosphere that will encourage the other person to share information with you.
Asking entrepreneurs personal questions can offer you a great insight into how they see entrepreneurship and what tools and tactics are they using to achieve the entrepreneurial mindset. You can also ask questions about dealing with failure staying focused when times are difficult, etc.
Feel free to ask questions about their business. After all, business-oriented questions to ask entrepreneurs are very important as building ventures is what they do for a living. You can also ask about tips for scaling a business and how they network as an entrepreneur.
Pick your mentor’s brain with questions for successful entrepreneurs. These questions get to the heart of the habits and mindsets of the scrappiest of entrepreneurs. You can ask questions for successful entrepreneurs that will give you a look into their daily lives and help you cultivate an entrepreneurial spirit.
Asking anybody about finances has the potential to drift into awkward territory. So when enquiring about finance-related topics with an entrepreneur, ensure that the questions remain legitimate informational queries and don’t cross the border into the realm of being inappropriate or even downright rude.
“So, how much are you worth?” for example, is a complete no-go.
Here are ten appropriate questions that you can go ahead and ask a financial entrepreneur instead:
If you’re carrying out an interview with an entrepreneur via a podcast, then you must account for the fact that this conversation is no longer for an audience of one, but an audience of many.
A podcast interview, as opposed to a one-on-one conversation for the purposes of mentorship, will often have different desirable outcomes for both the interviewee and the interviewer.
The podcast host will be looking to inform and entertain their listeners just as much, if not more, than they will be seeking to improve their own knowledge base. The interviewee might well be much more focused on raising awareness of their company, or promoting a new product, over teaching important business lessons to whoever is conducting the interview.
All of this should be determined prior to the interview taking place, either with a preliminary call or an e-mail/text exchange. This allows all participants to agree on an agenda and subjects to be covered. This way, all active participants can achieve their own respective goals and everything is in place for the recording to go smoothly.
Some pertinent questions to ask entrepreneurs on your podcast include:
When interviewing a small business owner it’s important that you pay them as much respect as you would if you were interviewing Elon Musk or Mark Zuckerberg.
Many contemporary industry titans started as small business owners, from Richard Branson to Howard Schulz (Starbucks) to Ralph Lauren.
You should always keep in mind that most small business owners care for their business as much as larger ones do and your conduct with them should show that you appreciate this fact.
Good questions for small business owners include:
These questions will provide you with some general information about their company. You can ask about the company’s name, headquarters, vision, mission, goals, and the future of the company. You can also ask more detailed and in-depth questions regarding how they are running their business.
Having great leadership skills is vital to entrepreneurial success. You should ask entrepreneurs questions about building their teams and managing them to get results. Company culture is a big factor in creating a sense of purpose and motivating teams to do great work. Ask about both managing issues, as well as promoting values on your teams.
Landing your dream job starts with understanding the job search process. Lean on your mentor’s industry experience to get to know what hiring managers are looking for and how to stand out in the applicant pool. You might also ask an entrepreneur questions about interviews, cover letters, networking and more.
Knowing how to use technology can make a difference to your business. You should ask entrepreneurs questions about technologies, platforms, apps, etc. that further business goals and allow for innovative new projects.
People love to talk about themselves and things that happened to them and entrepreneurs are no different. Don’t hesitate and ask about memorable events that happened to them. You can even ask some more in-depth personal questions. Those in-depth questions will provide you with even more valuable answers. Don’t be afraid to ask questions that require a bit of critical thinking.
Questions are just the start of any great mentorship relationship. As you get to know your mentor and define your career goals, you can start turning questions into actions. If you asked questions about the job search process, try scheduling a mock interview for practice. Or if you’re interested in undertaking an entrepreneurial project, set up a due date to get initial feedback from your mentor.
While questions for entrepreneurs can help guide your mentorship sessions, you should also define key actions to improve your career potential. Be sure to ask your mentor about any next steps that he/she recommends for you.
In this guide, you learned how to ask the right questions and what questions to ask an entrepreneur to keep you motivated and inspired. Entrepreneurs love sharing their knowledge and experience so don’t let the fear of rejection stop you from asking questions.
The road to establishing a successful business can be rocky and tricky to navigate and sometimes we all need help to overcome obstacles. If you feel stuck on your business journey, a business mentor might be the answer you’re looking for. Learn how to choose the right mentor for yourself and your business. Having a good relationship with your mentor can help you grow professionally and personally.
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