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 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

Every industry has unwritten rules and hidden shortcuts you won't find in any business book. Ask your mentor about unique situations they've encountered and how these experiences shaped their business practices. Their hard-won insights could save you years of trial and error.

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

Remember, acknowledging weaknesses isn't self-criticism; it's identifying opportunities for growth and improvement. Ask your mentor for concrete examples and actionable steps you can take to strengthen these areas. 

3. How are you currently increasing business growth?

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

A mentor can share a current approach for scaling, including specific tactics that are working right now. Ask about potential customer acquisition strategies, operational improvements and how to adapt to market changes. Learn their decision-making process for choosing which growth opportunities to pursue and which to pass on. Their insights can help you develop a more robust growth strategy tailored to your business.

4. How are our finances looking?

The questions I have had the most trouble with during difficult economic 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?
- Ben Walker, Transcription Outsourcing, LLC

Financial management goes beyond basic accounting. Ask your mentor about strategic financial decisions: How can I balance reinvestment versus cash reserves? What financial metrics should I prioritize? When should I seek outside funding versus bootstrapping?

A good mentor can help you understand the nuances of financial planning, including how to prepare for both opportunities and challenges. They can also share insights about managing debt, optimizing cash flow and making strategic investments in your business's future.

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 and 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 that 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

Building rapport with your mentor is crucial for a productive relationship. Ask them to share experiences that shaped their business philosophy. This approach not only creates trust but also provides context for their advice.

7. What would you do in X situation?

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

When presenting scenarios, ask them to walk you through their thinking step by step. What factors do they consider? What risks do they evaluate? Which principles guide their choices? This insight into your mentor's thinking can help you develop your own decision-making framework. Pay attention to how they balance intuition with analysis and weigh different stakeholders' interests.

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

Ask your mentor to help you evaluate different scenarios and their potential outcomes. Their experience can help you identify considerations you might have missed and anticipate potential challenges. 

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 certain ones can be avoided by learning from your mentor's mistakes. It is great to ask about their successes and how they got 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

Experienced business owner's answers often contain surprising insights about business and leadership. They could reveal fundamental truths about business success that aren’t limited to a specific industry niche or background. 

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

You’ll get the most from these questions by listening actively, taking notes, and following up on the advice you receive. A mentor's guidance is only valuable if you put it into action. Don't be afraid to ask for clarification or specific examples, and always come prepared with context about your situation. The right questions, asked at the right time, can transform your business journey and help you avoid costly mistakes on your path to success.