If you’re lucky enough to find a great business mentor, you want to make the most of their experience and willingness to help you. It’s unlikely they will drive the mentorship, so it’s up to you to ask questions and pull information out of them that will help your business grow and make you an effective business owner.

So what are the important questions to ask a business mentor that can help you and aren’t just casual conversation?

What Should I Be Doing Better?

Your business mentor has likely looked at your business, how you run it, and has ideas on what they would do in your situation. So it’s essential to ask the question of what you’re doing that they think is worthwhile, but that needs improvement.

It will start the conversation on a positive note with advice to improve things you’re already doing in the business.

What Mistakes Do You See I'm Making?

Understanding what mistakes you’re making from an outside perspective can be crucial; whether it’s internal mistakes with your hiring practices or something around how you market your business, anything you’re doing that could hinder your business is essential.

It’s also an opportunity to see how your mentor finds problems and looks at solutions, which is an important skill you want to learn from them.

What Should I Not Be Doing?

This question will help highlight what you are doing that is plain wrong in the eyes of your mentor. It will also help find some quick wins that you should instantly stop and not fix or work around it. Finding problem areas could introduce some ideas around areas that your business is trying to work in that it shouldn’t, or maybe you’re spreading yourself too thin and need to pull in your focus until you grow larger.

Anything that stops your business from growing or drawing in new customers, and even something that your mentor predicts will happen if you keep on a particular path, will be interesting.

What Are My Weaknesses?

Where does your mentor see weakness in you that you can improve? It’s not about attacking you; it’s about finding not only how to improve your business but how to improve yourself as a business owner. 

Are you highly technical but have poor customer interaction skills that turn potential customers off. For example, perhaps you join sales meetings but can’t effectively sell to customers. Identifying your weaknesses can lead to thoughts or questions on improving your weak areas to do a better job.

What Do They Link to Your Current Financial Situation?

What does your mentor think of your current financial situation and what approach or strategy do they advise? It’s essential to know and understand where someone with experience sees your business going if it continues in its current direction.

Should you try to expand and open up new markets, or should you try to sell off and wait out the current financial issues? Are there some hard decisions you need to make about employees, equipment, or even physical locations you own?

What Do They Regret Not Doing Earlier?

What does your mentor regret not doing sooner within their own business, and does that relate to your business? It’s an opportunity for an open-ended question about growth or changes that could be made within your business sooner rather than later. 

It could even be professional changes they made or wanted to make for themselves; maybe they regret not bringing in critical people sooner to take on jobs they just weren’t suited for.

How Do They Spend Their Time Each Day?

Understand how your mentor spends their time, what tasks they do, what they feel are essential things within their business, and what they delegate out to people. 

You can use this to create your only daily task list and consider if you should still be doing everything you currently are. Building a business relies on trust in other people to do their jobs and one of the key things you need to keep control of.

How Should You Set Yourself Apart From Competitors?

In almost every situation, you’re going to have a competitor that may be taking your customers or taking the lion’s share of the market. Your mentor can provide information on what they did to set themselves apart and make customers choose them over their competitors. 

In a follow-up question, you can ask if they think that approach would work for your business or what ideas they have around to set your business apart and above competitors. 

What Organizations or Associations are They a Part of?

Networking with other business leaders, especially in your industry, can be important to understand what others are doing or as a way to build more business through those connections.

See what organizations or associations your mentor belongs to, and see if they think you should join or investigate further. 

What Was Your Biggest Mistake in Your Business?

You may get a single answer or multiple answers on mistakes made, but it’s interesting to know what mistakes your mentor made to see if you’re doing the same or even could potentially make them in the future.

Follow up and ask what the outcome of the mistake was, how they handled it, and if they learned anything or made changes based on that mistake. It’s an exciting way to see how your mentor deals with failure so that you can learn from their mistakes as well.

What Technical Skills Do You Believe are Important?

It’s an interesting way to see what your mentor thinks about keeping up with the technology or the skills required to do the nitty-gritty work within your business. Do they think you need to move into a leadership and business role only to forget your earlier career?

Focusing on both the business and technical aspects can be daunting, so where should your focus be, and how much do you need to keep learning in both areas.


Your business mentor wants you to succeed and wants to impart their knowledge to you. They’re not fallible, but they have the experience you can learn from. So make sure you’re asking as many relevant questions as you can but taking the time to absorb the information and see how it relates to your business.

Ask follow-up questions on your primary questions to see what else you can draw from your mentor. Ask very open-ended questions to start with and drill down as you want more information or as your mentor wants to provide more details.