6 Must-Ask Questions for Your Mentee to Maximize Your First Conversation


When you first enter into a new mentoring relationship, it can be difficult to know where to begin.

As a mentor, you’re aware of the skills you have to offer, but you need to be able to assess how your expertise can be best applied to support your mentee’s goals.

It is also important for you to gain critical insights to help you familiarize yourself with your mentee’s business offerings, as well as their obstacles and goals.

To guide you through this process, we’ve identified six key questions designed to get the conversation started.

When asked in the following order, these questions provide a great framework for determining your mentee’s business challenges—which in turn, can help you deliver better guidance as a mentor.

Question #1: Why do you do what you do?

This question is intended to help your mentee clarify and articulate their purpose in starting and operating their business.

It’s easy to lose sight of the answer to this question in the day-to-day of running a business. Asking this question can help your mentee center themselves in remembering what inspired them to begin with.

If you need to dig deeper, some supporting questions could be:

  • What drives you to do the work that you do?
  • Why are you in your business area or field?
  • What initially inspired you to launch this business?

Your mentee’s answer should help reveal their passion for their profession and is a great place to start your mentorship.

For example, Vivian, an entrepreneur who is launching their own food truck, might say something like: “I want to share my love for authentic Cajun food with my community.”

Always keep the answer to this question front and center as you work together to solve your mentee’s challenges.

Question #2: Where do you want to go from here?

This question is designed to unearth your mentee’s aspirations and identify their business objectives. What is their ultimate goal?

For Vivian, the answer could be something like “I want to launch my food cart successfully and become popular in my community. Eventually, I would like to raise enough money and build a customer base to open my own brick and mortar restaurant.”

Keeping in mind the long-term goal will help you set short and medium-term goals together.

Question #3: What are you currently doing well that’s helping you get there?

This question is a great way to pinpoint your mentee’s core strengths and decide what areas your expertise as a mentor will be most beneficial.

You might also want to ask your mentee:

  • What are you naturally good at doing?
  • What do you enjoy doing the most?

Your mentee’s answers might surprise you. Are they great at motivating a team? Do they have a budgeting superpower?

Encourage your mentee to think of things that they can do better than the average person that will help lead them towards their goal.

Vivian might say something like, “I love cooking Cajun food and people love eating what I make. I also really like engaging with my customers on Instagram and at the food cart.”

Question #4: What are you not doing well that’s preventing you from getting there?

You must first identify obstacles in order to overcome them.

Chances are, your mentee already has a pretty good idea of their own weaknesses and the challenges that are standing in the way of their goals—that’s why they are looking for a mentor to offer guidance.

Encourage your mentee to conduct an honest assessment of what’s preventing them from reaching their goal.

For example, Vivian might say, “I’m having a hard time keeping up with my books. It’s hard for me to stick to the budgets I create. I’m also having a hard time delegating tasks to my staff. I love my work and want to make sure everything is perfect but I’m working 80 hours a week. I know I can’t keep this up for too much longer!”

Question #5: What can you do differently to overcome those challenges?

This question is about helping your mentee prioritize the right things.

People have a natural tendency to focus on the things that they do best (i.e. their answers from question three) and spend less time addressing their weaknesses (i.e. their answers from question four).

For example, Vivian is very likely focusing their energy on their cooking and Instagram, rather than tackling their budget and delegation.

Similarly, if your mentee is an amazing web developer, they would probably much rather focus on that strength than let people see their poor leadership skills.

The problem with this tendency is that while your mentee may boast a phenomenal work ethic, if they are not focusing their hard work on the areas where they are struggling they will be very limited in their progress toward their goals.

Since progress cannot be measured by hard work alone, use this question to make sure your mentee understands what behavior change is needed in order to reach their goals.

This will be a great place to start building some goals to work on together.

Question #6: Where do you need the most guidance?

Now that you’ve tackled the first five questions with your mentee, the answer to this question should reveal itself much more easily.

You’ve illuminated your mentee’s overall goals and honed in on the challenges they face—now, it’s simply a matter of aligning those areas with your specific skills, expertise, or resources.

Going back to our example of Vivian, they need the most guidance in creating a practical budget and implementing tools to make sure they are sticking to it. They also need advice and tips for delegating their work and hiring the right people to take some of the workload off their shoulders.

These questions provide an excellent first step toward building a successful mentoring relationship, helping you effectively assess how and where you can really help your mentee and their business. By going through this exercise together, you can better define a mutually productive path forward.

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