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One really important element in personal development is having a mentor. I think most people have access to really good people, they just struggle to maximize those relationships. A lot of people direct message me on social media asking me if I will mentor them. One of the first things I think is, You have so many good people around you that you aren’t utilizing. What makes you think that I have all the answers? What I realize is, a lot of people don’t know the right questions to ask their mentors.

I have 14 points, I know those are more points than normal, but they’re all valuable. These points will help you establish a real and vulnerable relationship with your mentor. Sometimes, we’re taught that being vulnerable as a leader isn’t good, it shows weakness. However, there is a lot of proof that this is not true—being vulnerable as a leader is important. If you’re interested in reading more about the culture of leadership, I highly recommend the book, The Culture Code: The Secrets of Highly Successful Groups by Daniel Coyle.

14 Questions to Maximize your relationship with your mentor

  1. What used to be your biggest weaknesses?

    I like this question because you can instantly learn from your mentor’s mistakes. It’s going to help you understand what this person had to work through in order to excel in the position they’re in and it allows you to start working on that right now.

  2. What are you most proud of?

    This question helps you understand the most important part of the journey for that person. I know, everybody has a different journey and we’re all doing things for different reasons, but I think the answer will help you put the most important things into perspective. Sometimes we focus too much on the money or something else. But, when somebody tells you there has been so much more in their journey that is significant, that they are proud of, there’s a lot to learn in that.

  3. What are my strengths?

    This question is an opportunity for you to build belief in yourself. If you came to me and asked what your strengths were, and I was honest with you and said, Your heart. You have such a big heart. You wear it on your sleeve, people can tell you’re genuine and you’re caring, and you draw people into your authenticity. If I tell you things about yourself that are already true, it will remind you why you can win in business. You will leave that conversation believing in yourself and thinking, I can win here because I do have a big heart.

  4. What are some of my blind spots?

    I think asking this question is so important is because we all have blind spots. You’re driving a car, you look over your left shoulder and there’s a blind spot. It’s a spot you can’t see but everybody else around you can. That’s a blind spot – something you’re doing on an ongoing basis that’s affecting you but only those around you can see it. I recommend that you get close with your mentor or somebody that you trust and ask what they see your blind spots to be.

  5. What’s the number one thing that I have to improve on for me to see some dramatic results?

    This is the one thing where if you don’t change this, you probably won’t see any results. A lot of us have one thing that if we just tweak, it would help us move forward significantly. Obviously, there are a lot of things that we have to get better at, but most of us have one issue that ties into the blind spot. It’s the one thing that if you got better at you would start seeing results almost instantly.

  6. How am I viewed by others on the team?

    What’s my personal brand within this organization, within this team, among my colleagues? As vulnerable as this question can be, it’s also empowering because you have the opportunity to change your brand. For example, if Pepsi wanted to change their brand, they would go to their marketing team and think about some things they can do to tweak the brand. Just the same, you can go back to the drawing board, consider what you’re representing that you want to adjust, and work to change your brand accordingly.

  7. How am I viewed by my leadership?

    This question goes beyond what your colleagues or teammates think to how you are viewed by your leaders. If you want the opportunity for upward mobility, to be put in a leadership role, to be given more responsibility it’s important to know how you are viewed by your leadership.

  8. What areas of my communication can be improved?

    Everything starts with communication. The number one reason teams start to break down is poor communication. We can all get better at communication – so why not ask what areas of your communication can be improved. There might be one or two areas you need to get better at. There might not be any but, it’s important to ask.

  9. Am I a coachable person?

    Are you only coachable when it’s convenient? Everybody is coachable when it’s easy, but it’s important to consider, have you been coachable when it’s been inconvenient for you. Remembering to receive feedback and take it to heart is important, even when it’s hard.

  10. Can we roleplay a couple aspects of me doing business?

    Let your mentor watch you do business tasks. Practice your presentation in front of them, take a few phone calls, do a pretend interview, pretend to close a sale, ask them to evaluate you. This forces you to completely expose yourself, all of your insecurities and allows your mentor to evaluate you and your business completely.

  11. If you were me, what would you be doing?

    Today, tomorrow, on an ongoing basis, daily, hourly, ask your mentor how they would be thinking and what they would be doing. Once in a while, people ask me this but very few people take my answer seriously. It’s one thing for you to ask this question but you have to take the answer to heart if you want it to make a difference.

  12. Can you recommend some specific books for me?

    Your mentors know what you’re going through because they’ve been there. They’ve also gotten through it. A lot of them are probably well-read and a lot of them are probably personal growth fanatics because, that’s what leaders do. Ask your leader, what you could be doing to self-improve and they will give you resources to do that.

  13. Who else would you recommend I connect with?

    There’s a lot of people that are around you that you might not recognize that you should connect with, but your mentor knows because they know your story.

  14. How can I help you?

    Do you know how rare this question is asked? Your mentor is the one that’s emptying themselves all day for your development, for you to walk into that relationship and ask how you can support them, that’s a big deal. It creates a higher level of respect and shows that you care how they’re doing and you care about their well-being. It shows that you’re not just there to take from them but you want to give back.

Imagine building an organization, whether it’s a small team or it’s a huge company, imagine building this organization that’s real, vulnerable and it feels safe to ask the kinds of questions I just listed. Can you imagine what that would do to the culture of your company? Can you imagine what that would do to the culture of your team? The goals you could set and accomplish as a team? I think that’s a team that would be a force to be reckoned with. A team focused on openness and vulnerability, on asking each other great questions.