Newbies: You NEED to Overcome Your Fear of Asking Questions (& Looking Dumb). Here’s Why.

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I often write articles to appeal to the newbie investor. I do this because it is important that we continue to inspire those who have the ambition to face all their fears and persevere. I remember the many challenges I faced and hearing the stories of others who were willing to defy the external and internal odds to see their desires materialize. There are many challenges newbies encounter, such as financial constraints, lack of guidance and information overload. There is one thing that I noticed along my journey and which others stated was difficult to overcome. It was the fear of asking TOUGH questions.

For some this may not be a challenge at all, but for others understanding the importance of asking tough questions is essential.

Have you ever engaged in a conversation with your peers and someone makes a statement and it seems as though you’re the only one who does not understand or has limited knowledge of the subject matter? Sure you have, but what did you do? Most people will remain silent and try and figure it out along the way and be fearful to ask a question. I’m sure this has happened to you, but the truth is that those who are afraid to ask tough questions miss a great opportunity to learn.

Related: Newbies: These 3 Simple Steps Will Prepare You For Your First Deal

You may be asking, “Ok, what does this have to do with investing?” A lot!

Overcoming the Fear of Asking Tough Questions

Here are a few reasons you may be afraid to ask tough questions and what you are missing by letting this fear overwhelm you.

It is human nature to be non-confrontational. Because of this innate trait, we are limited in our opportunities to grasp a deeper understanding from those who we are doing business with.

Here is a real estate example: When speaking with sellers, most sellers have the demeanor of being confrontational (if you haven’t run into this, you’re obviously not speaking to enough sellers), and because of this demeanor, your natural instinct is to assume they don’t want to sell and they are tire kickers — and you think, let’s just get through the call. Due to your perception of the seller, you limit your conversation to a minimum and you do not ask the tough question. By not being consistent and asking all the tough questions, you miss an opportunity to get to the real reason why the seller is calling. I do understand some sellers just call to cuss you out, but if they are willing to engage you in a civil conversation, try and learn from them.

One of the hardest questions for me when speaking to a seller was asking them, “How much do you owe on your house?” In the beginning that seemed a little intrusive. Who would tell someone they don’t know what they owe? To answer your question, the majority of the sellers do not mind giving that information. It all depends on how you frame the question.

How about this approach? “Mr. Seller, do you have any liens or mortgages on the property? If so, are you current on your mortgage? If you don’t mind me asking, what do you owe on the property because I’m aware that the values of the property in that area fluctuate, and I want to make sure we are not going to have any issue with giving you the correct value or a fair offer.” A totally different approach, but you will still get the same result.

The Importance of Asking Questions as a Newbie

Another reason it maybe difficult for some to ask tough questions is because there is a fear of being judged or feeling you are in a place of vulnerability. Yes, that’s right. If you are a newbie and you are in a room full of seasoned investors, this can be a little intimidating.

I was talking with a new investor and he was stating that he has nothing to offer to the group, and he did not want the other investors to feel as though they were wasting their time working with him.

In a situation like this, it is important to ask as many questions as possible. Do not let the fear of being judged by others limit your possibility to learn from those who are willing to teach. I’ve read a ton of leadership books and one recurring quote that I’ve read in many different books that helped me tremendously is,“If you are always the smartest person in your group, you need a new group.” You cannot learn if you are always teaching.

Related: Everything Newbies Should Know BEFORE Seeking Out a Real Estate Mentor

Asking tough questions can help you greatly. By asking tough questions, you minimize your mistakes, you save money because you minimize those mistakes, and you can travel along your journey a lot faster.

Challenge yourself by asking tough questions to the following people: contractors, agents, sellers, buyers, brokers, accountants and escrow officers.

Try this and see what you learn. Just as with making an offer on a property, you never know what you may get if you don’t ask.

What are the most valuable questions to ask when you’re learning real estate?

Weigh in with a comment!

About Author

Marcus Maloney

Marcus Maloney is a value investor and portfolio holder of residential and commercial units. He has completed over $3.3 million in wholesale transactions. Currently, Marcus is a licensed agent who wholesales virtually in multiple states while building his investment portfolio. He has also converted some of his deals into cash-flowing rentals. Marcus holds seven rentals, two of which are commercial units. He’s even purchased a school, which was converted into a daycare center. His overall goal is to turn what is a marginal profit into a significant equity position. He leverages the equity by using the BRRRR (buy, rehab, rent, refinance, repeat) strategy to increase his portfolio without any money out-of-pocket. Marcus has been featured in numerous podcast such as the Louisville Gal Podcast, The Best Deal Ever Podcast, The Flipping Junkie, and many others. He contributes content regularly to his YouTube channel and blog.


    • Marcus Maloney


      I always try and make a friend when I am speaking with sellers because now may not be the right time but they will remember you when they are ready. This actually happened to me so I am speaking from experience. Follow up is key and when you follow up and make a good impression it is easier to get a deal done. Remember to keep moving forward no matter how small the steps are.

      “Enjoying the Journey”

  1. Cornelius Charles

    Great article Marcus. Working in the engineering field, it took me a long time to realize that there was not a single person who knew everything about a subject and that they all had to start from somewhere. And then i realized that most “experts” actually respected those who asked good, relevant questions and were eager to learn. Although this might be beyond the scope of this post, i would also add that you shouldn’t be afraid to say “I don’t know,” especially when you pair that with “But i will find out and get back to you.”

    • Marcus Maloney


      You are absolutely right we believe we have to have all the answers, I enjoy learning and being around those that know more than me because I know I will be able to grow in that kind of atmosphere. It took me some time to get used to it but it has helped tremendously.

      “Enjoying the Journey”

  2. Lari A.

    Thank you for the post, Marcus. I’ve been pursuing investing in earnest for just a few months now, and I have been guilty of being in the room with a host of seasoned investors, and feeling like I shouldn’t bother them with my newbie questions. I just tried to glean as much as I could from what they were saying, and after one particular REIA meeting, they all gathered in groups to discuss their deals. I didn’t want to take up anyone’s time, so I just left feeling more overwhelmed and confused than ever.

    My main dilemma is that I don’t have any funds of my own, so of course I’d like to wholesale. I’m comfortable with running numbers (ARV, MAO, CAP RATE %), pulling apples-to-apples comps, and have even stepped out boldly to view properties in order to become familiar with the process and to determine rehab costs. Still, the lack of a little guidance leaves me sitting on my hands, and then the frustration seeps in. I know that I could be really good at this if only I had a little guidance to help me recognize what a good deal really looks like, so that I can wholesale it to the list of buyers that I have.

    If there is ANYONE in Tampa (or St. Pete or Clearwater) who is willing to spend a little time with me, I would appreciate it greatly. Also, I will work for knowledge!


    • Marcus Maloney


      Great point, failure is inevitable but your resolve should be as well. We have to be like birds and just jump out the nest, I rather live a life doing what I love versus living a life of doing what I hate and living with regret because I was too fearful to step out on faith and make things happen. You have to have confidence in yourself. You are your greatest cheerleader right!

      “Enjoying the Journey”

  3. Ayodeji Kuponiyi

    Great post Marcus! I hope this article reaches all BP members. It’s funny how something so easy (yet hard) like asking questions on something we don’t know or understand ends up being the answer we need to get closer to our goals/dreams.

    • Marcus Maloney


      Ask and you shall receive right! In my day the saying was a closed mouth don't get fed. You have to ask questions in order to get where you need to go. At no time will you have all the answers.

      Thanks for reading.

      "Enjoying the Journey"

  4. Connie Cantillo

    What a great article, Marcus! And there I was, thinking I was the only one struggling with those fears. I feel better now. The important thing now is that I have to overcome that fear, be brave and go ahead and ask those tough questions, specially when you are surrounded by seasoned investors. I will most certainly take your great advise.

    BTW, I’m in the same boat as Lari above. I’m located in the Miami, Florida area, so if there is a “Karen” in this area, I’m willing to help out as a VA so that I can get that “Hands On” experience I need to start this amazing journey in the real estate industry.

    Thanks and have an awesome and productive week! 🙂

    • Marcus Maloney


      Thanks for reading, check out my response to Lari about finding a Mentor to get that hands on experience.

      Its good to know what you are afraid because then you know what battle you have to fight and what your enemy is. I rather know what I am up against versus stepping out blind. What is the worse that can happen someone tell you I don’t have time. Ok then move on to the next person that may be able to answer your question. In this business you will receive a lot of “NOs” I take 1 hour out of every day to listen to positive messages and I speak positive affirmations because constantly hearing NO can be discouraging. Step out and ask those questions, as soon as you do the sooner you will receive answers.

      “Enjoying the Journey”

  5. Torey Carden

    What an awesome post, thanks Marcus.

    I’ve been reading and learning from BP and getting the feeling of paralysis by analysis and I don’t want to just freeze and do nothing.

    I live in a very rural part of Southeast Virginia a small town called South Boston, Va if there is anyone near me that’s willing to reach out, I’m willing to ask the hard questions. This real estate journey is a must for me I have no plan “B” I have to be the one that break through not only for my immediate family but my extended family as well.

    I thank you in advance for whomever it shall be.

  6. Lisa Lam

    Thank you for this great post Marcus.

    I’m just wondering, I saw a few post where people have mentioned being in a room full of investors? How would I find groups or events like that in my area? I’m in the San Francisco Bay Area.

  7. Shane Casad

    A very nice article that hits spot on to how I feel, great job Marcus!

    This article not only highlights how I feel when having a verbal conversation but, even when here on BP. I am not as actively involved in forums as I should be as a newbie, out of fear that I might be wrong, or am asking the “wrong” questions. Your article made me feel much better, and is much appreciated!

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