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11 Questions To Ask a Mentor About Business
by Brett Farmiloe
January 2, 2024
Black woman working on laptop smiles at man using tablet

The business world can be a challenging place to navigate. Having a mentor who knows the ropes is a great resource. As a business professional constantly making decisions, what questions should you ask? 

Knowing what questions to ask will make all the difference in your successes and failures. 

To gain a better understanding, we asked 11 thought leaders to share their opinions on business questions to ask a mentor.


1. What are your tricks of the trade?

Ask them for tricks of the trade from their own experience. What unique situations have they found themselves in that generated a change or adaptation in the way they run their business? Sometimes, you will be able to learn these lessons through your mentor without having to make the same mistakes.
- Court Will, Will & Will

2. What are my areas of weakness?

This question is difficult because it forces us to admit that we don't have it all together and challenges us to improve our behavior. Business owners might have a blind spot when it comes to their weaknesses, and by bringing in an objective observer, such as a mentor, they will be able to see the full picture.
- Monica Eaton-Cardone, Chargebacks911 

3. How are you currently increasing business growth?

What are you doing to increase business growth despite the challenges of the pandemic? This question can go a long way to help struggling entrepreneurs keep their heads above water. A good mentor will most likely share insights that will help you choose the right marketing strategy, organizational model, and the best remote work policy for your business.
- Chioma Iwunze, Time Doctor

4. How are our finances looking?

The questions I have had the most trouble with during these strange times are how much cash we should be hoarding, if we should pay off our debt in full or keep balances to hold onto money, and when this will all be over. We want to be ready for this to end so we can hit the ground running with all of our back-burner projects completed and new marketing strategies ready to go.
- Ben Walker, Transcription Outsourcing, LLC

5. What’s your input on the nitty-gritty and the overall vision?

Business owners should be willing to take both the nitty-gritty of daily business as well as the overall vision of their company before a mentor. Some of the questions that could lead to great conversation include:

  • If you could improve my mission statement, what would you change?
  • What should I do about a particular employee causing strife in my organization?
  • How do I create a culture of responsible leadership from the top to the bottom of my organization?
    - Alex Azoury, Home Grounds

6. Start with a story or two about yourself.

Initially, ask the mentor to tell you a story or two about themself. Something which they feel could be useful for you to hear. Once you've broken the ice, use situational questioning to decipher how you should proceed with a problem you have. Try to be as specific as you can and indicate the importance of the problem(s) you're trying to solve. For example, my boss asked me to pick up another two tasks for my current remit. Right now, I'm working at 100% capacity as I'm still ramping up, how do I say no to this? Once you've gotten to know your mentor a little better, you can ask them for input on what they perceive your strengths and weaknesses are and what skills they believe you are missing to level up.
- Ahmed Mir, Nature and Bloom

7. What would you do in X situation?

An answer to such a question reveals the thinking process behind the decision-making of such a person. Getting to know the mental models that the mentor uses can get you on a fast track to becoming an independent business owner and a mentor to someone else.
- Jakub Kliszczak, Channels

8. What is your input on this life-changing business decision?

Don’t be afraid to ask for their input in making large, potentially life-changing business decisions. Share as much information as you’re comfortable with, and have them walk through possible choices with you. You’ll find that having a second mind work through problems with you may be just what you need to stay calm.
- Vanessa Molica, The Lash Professional

9. What are your failures?

When discussing business with a mentor, it is important to ask about their failures. Failure in one aspect or another will happen to every business owner, but there is a chance certain ones can be avoided by learning from the mistakes of your mentor. It is great to ask about the success and how they get to where they are, but to set yourself up for success, ask the hard questions and learn how to avoid certain mishaps.
- Peter Babichenko, Sahara Case 

10. What key lessons have you learned throughout your career?

Mentors in business are a great way to help you level up. My favorite questions are fairly basic yet effective. What key lessons have they learned throughout their career? Also, ask them to ask questions about what they see your strengths and weaknesses to be. What areas can you improve on? My advice is to start with these questions and let the relationship naturally develop from there.
- Erika Acorn, Tempe Chamber

11. Is there anyone else I should talk to?

Mentors aren’t one-stop shops for all things advice-related. But, great mentors do have a healthy Rolodex of connections who can help provide advice a mentee is seeking. Anytime I meet with a mentor, at the end of the conversation, I ask if there is anyone else I should talk to about an issue that my mentor and I have discussed. Inevitably, there’s always an introduction to be made and more insights to be gained. 
- Nikitha Lokareddy, Markitors

About the author
Brett Farmiloe
Brett Farmiloe is the Founder & CEO of Terkel, a Q&A site that converts insights from small business owners into high-quality articles for brands. Brett Farmiloe Founder & CEO,
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1165 Herndon Parkway, Suite 100
Herndon, VA 20170

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