3. Assess the entrepreneur's project

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. You also need to gain critical insights to help you familiarize yourself with your mentee’s business offering, 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 this 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. What drives them to do the work that they do? Why are they in the business that they are in?

Your mentee’s answer should help reveal their passion for their profession. For example, a mentee who is launching their own food truck might say something like: “I want to share my love for authentic Cajun food with my community.”

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

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

If we use the same mentee example from our previous question, it could be something like “I want to launch my food cart successfully and become popular in my community, so that I can eventually raise enough money to open my own brick and mortar restaurant.”

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

This is a great way to pinpoint your mentee’s core strengths. What are they naturally good at doing? Motivating a team? Sticking to a budget? Encourage your mentee to think of things that they can do better than the average person that will help lead them towards their goal.

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

It’s important for your mentees to recognize their weaknesses and the challenges that are standing in the way of their success. Of course, no one likes dwelling on the negative, but you can’t overcome obstacles without first identifying what they are.

Encourage your mentee to conduct an honest assessment of what’s preventing them from reaching their goal—whether it’s at a company or individual level (or both).

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

This 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, if you are an incredible soccer player, you’d much rather show off that capability than let people see you struggle in a baseball game.

Similarly, if your mentee is an amazing web developer, they’d 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 right things, they will be very limited in their progress.

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.

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

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 their 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.

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.

Next: Propose mentoring structure