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

by Marcus Maloney

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.

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.

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!

Interested in Finding out More? Reach out below

Shawn Ireland

Phone: 913-225-6231


Address: 1415 Main St. #823, Grandview, MO 64030


Facebook: @IrelandInvestmentsLLC/

Instagram: @irelandinvestmentsllc

Twitter: @IrelandLlc

Ireland Investments llc

This information is intended only for the use of the intended recipient(s) and it may be privileged and confidential. Please note that any views or opinions presented in this post are solely those of the author and do not necessarily represent those of the company. This is reposted information and is not original thought of Ireland Investments or anyone associated with the business.

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