Are you wondering what questions to ask a real estate mentor?

This article is for you. I’ll share the best questions to ask before you start working with a mentor and while working with them so that you can achieve your goals as fast as possible. 

Want to learn more? Read on.

What are the top 10 questions you should ask a real estate mentor? 

10 million Americans have invested in at least one property. However, what many miss is that they could get results much faster if they worked with a coach or mentor. 

After all, 97% of people surveyed say their mentor was valuable to their business. 

And if you’ve been considering hiring a real estate mentor, you’re much more likely to buy a property that is profitable – because you’re working with someone who has done it themselves. 

That’s something my own students say all the time. That they were stuck in analysis paralysis but once they got the support they needed, they finally took action – and built investment portfolios that generate five, six or multiple six-figures per year. 

But before you start working together, you want to know if they’ll be the right fit for you. The questions below will help you understand more about your mentor’s background, experience, and approach to real estate so you can decide if they’ll help you achieve your goals.

What inspired you to get into real estate?

Understand your mentor’s journey. Can you relate to them? This will help the mentor-mentee relationship.

For example, my inspiration was my grandpa, who was able to retire early and provide for his family. 

Often, my clients resonate with this message because they want to build a portfolio to support their family and spend more time with them.

What are the biggest lessons you’ve learned in your real estate career so far?

A mentor who is honest about their successes and failures is more likely to help you get results in your business.

For instance, I’m open about the fact that my first few years as a real estate investor weren’t that easy.

Because of mistakes I made, I lost $30,000. Today, I have a portfolio that generates multiple six-figures and let me quit my job – but it wasn’t always so!

Why is now a good time to get into real estate?

You want to work with a real estate mentor who is passionate and knowledgeable about the industry. They could be a good fit for you if they can provide an insightful answer that fits your situation.

You should also ensure they are also actively building their portfolio so they can provide up to date insights, perspective, and recommendations.

What does your daily life look like as a real estate investor?

Many people get into real estate investing without a clear picture of how their life could change. Ask your potential mentor what their daily life is like and see if that matches with your quality of life goals.

What real estate investment strategy has worked for you? 

Some real estate investors prefer high-risk commercial properties. On the other hand, investors like me prefer single-family student housing properties. See if the mentor’s approach works for you.

For instance, I wouldn’t work with someone who wants to invest in multifamily properties – that’s not the strategy I focus on.

How long have you been a real estate investor?

Simple question but understanding your mentor’s experience is crucial before working with them.

Let’s say someone has invested in real estate for a year. They might have gotten lucky if they’ve made good investment decisions in that time – and they probably don’t have a system you can use to grow your own portfolio.

What advice do you have for new real estate investors?

Asking this question tells you what your mentor’s priority is when it comes to mentoring new real estate investors like you.

Does their approach work for you?

Do they even work with newbies?

How do you stay motivated and overcome challenges in real estate?

Real estate can be challenging. This question will tell you exactly how they overcome challenges and can help you overcome them too.

What should you look for when buying an investment property?

Real estate investors have different approaches. Some look for renovation projects and others want turnkey properties. This question helps you understand your mentor’s approach to buying property.

What mistakes should I avoid as a new real estate investor?

Learning from your mentor’s mistakes can help you avoid common pitfalls and give you confidence to navigate your journey.

For instance, I created a video on the top mistakes new property investors make here:

So those are the best questions to ask a real estate mentor. Now let’s dive deeper.

10 questions to improve your investing skills

If you’re new to real estate investing, your mentor will help you improve your skills and knowledge. Here are some good questions to ask them:

  • What are your thoughts on real estate courses? What should I look out for to identify good real estate mentorship opportunities?
  • How do you finance your real estate investments?
  • What advice do you have for building a successful real estate investment team?
  • Can you share examples of deals that didn’t go as planned? What did you learn?
  • What books, courses, or resources would you recommend for learning about real estate investing?
  • What key metrics do you use to measure the success of an investment over time?
  • How do you improve your properties and investment strategies over time?
  • What exit strategies do you recommend for real estate investments?
  • What platforms, technology, and tools are you using?

10 questions to overcome your challenges

These questions help you understand your mentor’s approach to challenge and risk:

  • What are your main challenges as a real estate investor?
  • Can you share an example of a significant challenge you faced in your real estate career and how you overcame it?
  • How do you manage risk?
  • How do you manage stress while running your business? Can you share strategies for dealing with market downturns or economic uncertainty?
  • What resources or support systems do you rely on when facing major challenges?
  • What challenges am I likely to face as a new real estate investor and how can I avoid them?
  • How have economic downturns or market crashes changed your long-term investing strategy?
  • How do you keep a positive mindset when setbacks happen in the real estate market?
  • What have you learned from past failed opportunities?

For more on mindset, check out this video on building confidence as a real estate investor:

10 questions to ask about real estate trends 

These questions will help you understand your mentor’s approach to trends:

  • How do you stay informed about market trends?
  • How do you adapt your investment strategy in different economic conditions?
  • What emerging trends are you currently observing in the real estate market?
  • What impact do economic factors have on your investment decisions in the current climate?
  • Are there financing trends or challenges investors should be aware of?
  • Can you share examples of successful investments that were informed by current market trends?
  • What role do demographic shifts play in your investment strategy?
  • How do changing interest rates impact your investment strategy?
  • Do global events influence your real estate investment decisions? If so, how?
  • What are the best specific property types or markets to invest in right now?

10 advanced real estate investing questions

Once you’ve started investing, a mentor can help guide you through the challenges. Here are some advanced questions to ask a real estate mentor:

  • How can I manage my real estate investment business more efficiently?
  • How can I optimize my current portfolio for better returns? What advice do you have on tax planning and optimization for my real estate investments?
  • How can I manage my properties better and find great tenants?
  • How do you navigate regulatory changes impacting the real estate industry?
  • What strategies do you recommend for building a personal brand in real estate?
  • How do you determine the right timing for buying and selling properties?
  • What skills and knowledge should new investors focus on to get to the next level?
  • How can I diversify my real estate portfolio for a more sustainable strategy?
  • What marketing strategies do you recommend for finding tenants?

Next up: What not to ask a real estate mentor.

What not to ask a real estate investing coach

In theory, there are no right or wrong questions to ask a real estate mentor. But there are types of questions you should avoid. 

In short, focus on specific questions. Broad questions are hard to answer and won’t give you any value. 

Instead, think about the specific help you need and ask your coach to figure it out with you.

Here are some examples:

Don’t ask: “Why isn’t my investing strategy working?”. 

Instead, ask: “I’ve gone over my investment strategy, and I notice ABC. What steps can I take now to still reach my goal?”

Don’t ask: “Is now a good time to invest in X property/area?”

Instead ask: “I’ve been doing some research on ABC and it looks like a good opportunity. Could we look at the data together?”

Don’t ask: “Does the X strategy work?”

Instead ask: “I am interested in the X strategy and read ABC about it. In your experience, what are the pros, cons, and considerations of using this strategy over a different one?”

Always do the work and research first, then ask your mentor targeted questions to help you problem-solve.

Also, a great mentor will help you work through your limiting beliefs and tap deeper into those questions that will really help you.

Next steps  

There you have it! The best questions to ask a real estate mentor. 

A real estate investing mentor can help you find and profit from your investment much faster than if you tried to figure it all out on your own. But finding one isn’t easy.

I personally work with clients who want to achieve financial freedom and flexibility by investing in student housing. 

And you can read more about my approach to real estate investing here. 

Read more: 

How to Find a Real Estate Investment Mentor

Are Rental Properties a Good Investment? 

Is Now a Good Time to Buy Rental Property? 

About Ryan Chaw

About Ryan Chaw:
Ryan Chaw is a real estate investor with a multi-state and multiple six-figure rental portfolio, which he built on the side of his full-time job. Ryan also teaches others how to buy their first deal and quickly scale to owning multiple properties. Ryan also teaches others how to buy their first deal and quickly scale to owning multiple properties. Read more about Ryan here.