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What are the Best Questions to Ask a Real Estate Mentor

Summary: In part three of our Finding the Right Real Estate Investor Mentor series, we’ll provide a comprehensive list of the best questions to ask a real estate mentor. Topics include: relationship-building, self-awareness and skill-building questions to ask your mentor. Along with what not to ask a mentor.

If you are looking for a mentor or your mentorship has become stagnant, consider going to your next meeting armed with a list of relevant questions. A mentee should never show up and expect the mentor to put in all the work. While a mentorship is like a student-teacher relationship, it is not meant to only be a lecture series. As someone trying to learn and develop skills from an expert who is willing to share, it’s vital to ask the right questions, in the right way, at the right time.

Questions to Ask a Mentor First

It’s extremely important to start off your mentorship on the right foot. Just like any relationship, you should start slow and build from there. Making a good first impression will likely set the tone for the entire relationship.

Think about it…you aren’t going to ask someone you just met to help you move (at least I hope not). You are going to ask your family and closest friends. Because moving…well sucks. And chances are you have helped your family and friends in the past, so it’s appropriate to ask.

Consider starting with the following questions:

  • How do you spend your time?
  • What do you wish you would’ve known when you were just starting your career?
  • What are some of the bigger mistakes you made when you were just starting out?
  • What used to be some of your greatest weaknesses and how did you improve on them?
  • Is this where you thought you’d end up?
  • How can I help you?

Relationship-Building Questions to Ask Your Mentor

Any sort of relationship has personal elements to it. Even a boss-employee dynamic involves sharing personal aspects of life. Asking questions that lead to sharing stories is an excellent way to build a relationship, relate to each other, and create overall trust. It also shows an interest in who this person is, outside of a business environment. 

Some examples of relationship or rapport builders could include the following:

  • What are you most proud of?
  • Where is the coolest place you’ve ever traveled to?


Aka Family, Occupation, Recreation, and Motivation. These are the four universal rapport-builders.

  • Do you have any kids?
  • What do you like to do for fun?
  • What are some things that motivate you?


Find a mentor you feel comfortable bouncing ideas and scenarios off of. Presenting a situation or problem to your mentor because you value and trust their advice has mutual benefits. You win because you are receiving advice from someone you trust. Your mentor wins because they get to share their experience and knowledge, while feeling validated by your trust. 

Situational questions might include the following: 

  • What would you do if you were me?
  • What would you do in situation X, Y or Z?
  • How would you suggest I navigate this situation?

Questions to Ask a Real Estate Mentor

Next is a list of real estate specific questions to consider asking your mentor: 

  • How long have you been investing in real estate?
  • What investment strategy have you had the most success with?
  • How did you find your investing niche?
  • What are your long-term goals within the real estate industry?
  • What do you think is the best way for a beginner to get started in real estate investing?
  • What specific things do you look for in an investment property?
  • What REI technology do you recommend?
  • Do you recommend any helpful resources as an investor?
  • How do you feel about investing in property out-of-state?

Self-Awareness Questions to Ask

These types of questions can be difficult to ask. They can sometimes be even more difficult to answer. Asking a question about yourself that you may not like the answer to, says a lot about your dedication to growth. Don’t be afraid to ask yourself and your mentor some tough questions. 

Consider the following self-awareness questions to ask:

  • Where do you see my strengths and what do I need to work on?
  • How do you think others perceive me?
  • What am I doing wrong?

Skill-Building Questions to Ask

Assuming your mentor has certain skills that you would like to learn and emulate, make sure you’re asking specific skill-building questions. 

Consider the following potential questions: 

  • What is your approach to risk-taking?
  • This is my financial situation, if you were in my shoes, what would you do?
  • How do you make sure a project stays on budget?
  • How do you determine the difference between a good deal and a bad deal?

Questions to Ask Down the Road

Because building a relationship between you and your mentor takes time, I would suggest holding off asking certain questions until rapport and trust has been established. You don’t want to present yourself as entitled or assuming. Asking too much, too early on can put a quick end to any mentorship. 

Consider the following questions when the time feels right: 

  • Who else would you recommend I connect with?
  • Continually ask, How else can I help you and add value?

Questions Not to Ask a Mentor

Again, every situation is different so use your best judgment. My advice is to avoid asking super broad questions. Be specific, thoughtful and purposeful in the questions you ask your mentor.

Consider the following questions “off-limits” to ask your mentor: 

  • Do you have any advice for me?
  • How did you get where you are?
  • Would you introduce me to ________?

Next Steps...

When it comes to the best questions to ask a real estate mentor, there is no “best” answer. Make a list of questions to ask, that are relevant to your situation, before each meeting with your mentor. Every single interaction with your mentor should be productive and efficient. 

A great way to ensure further communication and meetings with your mentor is to say, “If a question comes up, can I follow up with you?” Don’t leave a mentor meeting without setting up a future encounter.

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