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How to be a Mentor

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In business, we hear about mentorship a lot. Many entrepreneurs attribute their success to the quality of their mentors, and often these mentors can help you avoid mistakes and accelerate your success. But unfortunately, being a great mentor is a skill that people just assume exists. It’s uncommon that people teach how to be a great mentor.

This lesson dives into what a mentor is, and how to mentor someone. Combined with our lesson on how to receive mentorship, you will have a grasp on how to begin these mentoring relationships from both sides, and how to avoid some of the most common pitfalls.

What is a Mentor?

“Mentor” is a broad term, ranging from someone who helps with primary school mathematics to a business advisor. Here, we’d like you to think about a mentor as an individual who helps another individual think in new ways, reframe their perspectives, and grow their business successfully. What does this definition really mean? That anyone can be a mentor: experts, customers, peers, family and friends. As long as they’re all helping an individual rethink their assumptions, they can all bring different value to the table.

A mentor is someone who asks and answers questions. But here’s the difficulty: there’s nothing worse than answering the wrong question well. Mentors need to understand how to mentor in order to provide constructive feedback and develop a solid relationship with their mentee. A mentor is someone who is trying to develop curiosity, the joy of learning, and the confidence to try new things in their mentee. A great mentor is also asking critical questions that cause the mentee to question assumptions and think clearly, unhindered by preconceptions and a false sense of security.

The qualities that each individual mentee will desire in their mentor change from person to person. Each mentor-mentee relationship is unique, so different qualities will work for different people. When we asked our audience of entrepreneurs, here are some of the qualities that they said they look for in a mentor:

  • Knowledgeable
  • Good listener
  • Domain expertise
  • Great network
  • Personally relateable
  • Desires a real relationship
  • Honest and trustworthy
  • Cares about your project and accomplishments
  • Accessible

It’s always good to have an understanding of what qualities pertain to you, so you can understand what you’re bringing to the table as a mentor. But you can be plenty of things without understanding how to mentor someone, so read on!

How do you mentor someone?

Mentoring, as we said earlier, is a skill that’s not often taught. However, we’d like to give you some tips for maintaining a positive, healthy relationship with your mentee that will benefit both of you. Always remember that the relationship between a mentor and mentee should be a positive, healthy and beneficial relationship for both of you.

Set Expectations

The first thing that you should do with any prospective mentee is have a conversation about what you’re both bringing to the table. List out the qualities that you have that you think could be beneficial to the mentee, and they should do the same for you. What do you know that’s useful? What experience do you have that could shed some light on the mentee’s problems?

It should be a dialogue, and there should be some form of mutual contract, whether that’s formal or informal. Often, mentors and mentees start out by having a discussion without setting expectations, and so neither of you know what you’re looking for, or what your expectations of each other are. Set up an idea of how often you’re going to meet or talk, and what the mentee needs help with. Share where you think you can be of assistance, and think about how your network can serve the needs of the mentee.

Here are some questions you can ask of yourself and the mentee:

  • Where is the mentee coming from? What’s their background? What’s their company?
  • What are they looking for? Where do they need help?
  • Are you going to be a fit? Do you have the right qualities, experience, network, time, and other resources to help this person?
  • Are they really looking to receive the gift of mentorship? Or are they just looking for the answer to one question?

Learn How They Think

One of the most important jobs of a mentor is to learn how their mentee thinks, and help them expand their viewpoint. Break them out of the pattern that they’re in at the moment. If they’re struggling, you’ll need to learn what their thought processes are to understand what the struggle is.

Think about different types of learning when you’re analyzing the way your mentee thinks. Some people are visual in their thinking, whereas some people are logical, and others are free-form. Work within that framework until it isn’t working anymore, and then break it! Push your mentee to frame their ideas and questions in different ways when they’re struggling.

Ask Questions

Our favorite piece of advice to both mentors and mentees is to ask questions! Asking questions, rather than just giving answers or talking in circles, will help both of you think in new ways that will break the patterns that are causing difficulties in the first place. Think about what’s better: answering a mentee’s question, or asking them questions so they can answer themselves? Ask them questions! It’s always better if a mentee can come to a solution on their own, with your assistance.

You have to start somewhere in the relationship, and it’s often best to start with questions. Mentees usually have a very specific idea of where they want to start. They may not know what the right context is, or how to ask the right questions, but they know they need help in an area. As a mentor, it’s your job to ask them questions and bring out the difficulties.

If someone asks, “Do you think the right answer is A or B?”, don’t answer! Often, the right answer is ‘neither,’ or ‘both.’ Instead, ask questions in response, and help them figure out how to test and validate for the right answer. Even if you thought A was better than B, that might not be the right answer for them and their company. They know more about their company than you do, so let them answer questions themselves! You’re trying to enable what we call an ‘aha!’ moment, where the mentee is able to come to conclusions on their own, navigating what’s best for their business with your assistance.

When you’re asking questions and breaking out of the box in terms of thinking, try some of these methods and tools:

  • Asking the market
  • Talking to customers
  • Brainstorming
  • Online research
  • Discovery and exploration
  • Fieldwork and in-person research
  • Surveys
  • Landing Pages
  • Frameworks

Open Your Network

One of the most valuable parts of mentorship is having access to a larger network. If you don’t know the answer to a question, or aren’t sure how to help your mentee, try opening up your network to them. It’s okay to say that you don’t know the answer to a question. But, do you know someone that would be able to help with that? What other resources, besides your knowledge and experience, can help your mentee? Where can they go to learn more about a specific subject?

Change Their Perspective

One of the other helpful tips, after learning how they think and asking questions, is figuring out where the mentee is stuck, and helping to change their perspective. The mentee may not know where they’re stuck, or what kind of context they should be looking at. Pull away from the problem and try to help your mentee reframe the question.

Ask questions about framing, even if they seem irrelevant. Even if the mentee thinks there’s a context for their difficulty, maybe the problem is better understood by taking a different view, or abstracting away from the problem. You may even ask them, is this actually a problem? Or is this an opportunity to change something, and do something different?

You can also ask them, how did they get to this issue? Is it a pattern that happens often? Is the mentee concluding the same things and having the same problems? Take a look at reframing the process by which the mentee makes decisions, not just the decisions themselves.

The Difficulties of Being a Mentor

One of the great difficulties of being a mentor is figuring out when a relationship isn’t working, and why. Sometimes, you’ll feel like you’re putting a tremendous amount of energy into helping somebody, and they’re not even capturing it. Even if they don’t realize it at the time, you’re trying to feed them some valuable frameworks, knowledge, and experience, and the mentee isn’t processing it at all. This experience can be really discouraging.

Often, the difficulty in the relationship is because you haven’t had a conversation about your expectations up front, or you don’t feel like they’re listening to you. Setting expectations, and making sure that the mentee is open to the gift of mentoring, can avoid these problems from the beginning.

However, if you find yourself in a difficult situation with a mentee, there could be a few problems. Often, mentors feel as though mentees aren’t truly listening, so encourage your mentee to ask questions and take notes during your conversations. Sometimes, you might just not get along! There isn’t much you can do if you don’t get along, in which case you should gently end your relationship.

If you think the relationship is salvageable, try recording and reviewing regularly. Share with your mentee what you’ve learned, and have them share what they’ve learned as well. Ask questions about your relationship, about whether or not it’s working for both of you, and if you’re helping. If the relationship isn’t working, it won’t fix itself! Try keeping up regular check-ins to make sure that you are on the same page as your mentee.


Being a mentor can be difficult, but it can also be incredibly rewarding. Giving back to less experienced entrepreneurs can be enjoyable and inspiring, as long as they’re willing to receive the gift. Don’t assume you know how to mentor just because you’ve been an entrepreneur before! Instead, learn from some of our tips above, and have regular conversations about your relationship with your mentee. You’ll be a great mentor in no time at all!

Think about using some of our frameworks throughout Startup Secrets to facilitate the conversations with your mentees. We’ve built those frameworks to be flexible to many businesses, and it can often be a great starting point for your conversations. If you have any questions or want to share some of your mentorship experiences, comment below, or check out our forums!

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