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Mentoring Best Practices

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Getting Started

Mentoring an entrepreneur, small business or nonprofit owner is a great way to give back and develop your own business, teaching, and leadership skills. Here are a few tips for getting started.

Identify Your "Superpower"

Your superpower is the thing that you do best. Maybe you have a wide array of business skills and can help an entrepreneur get his or her organization off the ground. Or, maybe your superpower is more specialized, and you can help someone with a marketing plan or finances. Whatever you have to offer, be confident in this ability and assess how your expertise can be best applied to the entrepreneur’s specific situation. With that said, be clear about your core competencies, and how much weight should be given to advice within and outside these competencies.

Ask Questions

Sometimes, mentoring is as simple as asking key questions. In formulating their answers, entrepreneurs are forced to get to the heart of their business problems and articulate their most pressing needs. When asking questions, make sure to actively listen to your partner, respond in clear and simple language and always be sensitive to their specific personal and professional circumstances. It is also important to be direct and thorough in your feedback. Remember that “do not” is at least as important as “do”.

Don’t Take the Simple Stuff for Granted

One major mentoring hurdle that you will likely encounter is the challenge that comes from stepping into your entrepreneur’s world and discovering how different it is from your own. If this occurs, it is important to resist the urge to second-guess yourself and instead remember that you have diverse skillsets that can be immensely helpful even if you aren’t completely familiar with their work.

For example, entrepreneurs are often so close to what they are doing that they struggle to make effective management decisions. From a higher vantage point, you can provide valuable insights into key competencies like personal organization, prioritization and goal setting. You can also be a great help to your entrepreneur by simply listening, gathering information and providing positive reinforcement.


Questions to Ask the Entrepreneur

We've identified six key questions that can help to get your mentoring relationship moving. When asked in this order, these questions provide a great framework for determining your entrepreneur’s business challenges—which in turn, can help you deliver better guidance as a mentor.

1. Why do you do what you do?

This question is intended to help your entrepreneur 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? Their answer should help reveal their passion for their profession.

2. Where do you want to go from here?

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

3. What are you currently doing well that’s helping you get there?

This is a great way to pinpoint your entrepreneur’s core strengths. What are they naturally good at doing? Motivating a team? Sticking to a budget? Encourage them to think of their own “superpower” and how that will help them attain their goal.

4. What are you not doing well that is preventing you from reaching your goal?

It’s important for your entrepreneurs to recognize their weaknesses and the challenges that are standing in the way of their success. Encourage them to conduct an honest assessment of what is preventing them from reaching their goal—whether it’s at a company or individual level (or both).

5. What will you do differently tomorrow to overcome your challenges?

This is about helping your entrepreneur 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 answer to question four). The problem with this tendency is that while they 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. Use this question to make sure they understand what behavior change is needed in order to reach their goals.

6. How can I help? / Where do you need the most help?

Now that you’ve tackled the first five questions with your entrepreneur, 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.


Entrepreneur Evaluation

Entrepreneur Evaluation

In addition to the six key questions, you and your entrepreneur can fill out the following evaluation together. This is a quick and helpful way to analyze the value of their business to their customer and provides an overall diagnosis of what areas of their business require the most focus, (indicated by a low score or low value to the customer).

After conducting this evaluation you might find that your entrepreneur needs help in one or more areas. Remember to choose to address the area(s) where you have the most expertise and feel the most comfortable.

Download the Entrepreneur Evaluation Worksheet