What I learned about people from calling 300 per day for 9 months

Tyler Donahue
5 min readJan 31, 2018
Photo by Quino Al on Unsplash

I got my Real Estate license my Junior year of college in the hopes to make some extra money and slowly climb out of the hole I dug myself into — my the hole I mean student loans.

I didn’t know much about the industry but I figured I could score some wins by sheer call volume. I purchased software that auto-dialed phone numbers in a list and were able to make 200–300 phone calls per day while walking between classes and in my downtime. If I am being honest with myself, this didn’t get me very far when it came to succeeding in the real estate business. I saw some success because I called so many people, but in reality, I was spinning my wheels and moving nowhere; at least that is what I thought at the time.

It wasn’t until years later when I realized what I did to my subconscious by talking with so many people over the phone. I could make even the most resistant and reluctant individual feel comfortable talking with me in a matter of minutes. It really hit me when I got a call back from a voicemail I left.

The call went something like this:

Home owner: “Hi Tyler, I received a voicemail from you regarding my house”

Me: “Hi Mr. Home Owner, thanks for returning my call! Out of curiosity, did you call back all of the realtors that left you voicemails? I know it was more than just a few ha!

Home Owner: “Nope, I listened to all 35 voicemails and you are the only one I called back. Not because I want you to help sell my house but because out of all the voicemails I got, you by sounded like someone I could actually have a conversation with”

If you were wondering what I said in my “Expired Listing” voicemails, it went something like this:

“Hey mate, yes this is another Realtor leaving you a voicemail about your house. In the future make sure you get a Burner phone number when you post a public number, its a free iPhone app and it only costs 5 bucks a month per phone number and you can delete it as soon as your listing goes down. Anyway, if you are looking for a new representative, you can call back or text me anytime. 555–5555.

Sounds simple right. My focus wasn’t to sell him on how I could market his house but rather tell him how to avoid a nuisance he is currently dealing with in the future.

After this phone call, I did some reflecting. What am I doing over the phone that makes people feel comfortable with me? Have I learned something about people that I haven’t even realized? I organized this reflection below and identified a few things about people that tend to be consistent.

People are relationship-driven before they are sales driven.

You know that high performing salesperson in your office that seems to know nothing about the product or service they are selling?

People don’t necessarily want the person who is best equipped to solve their problem but rather someone who they can trust and someone they can authentically communicate with.

How do you earn someone's trust? After tens of thousands of conversations over the phone, I think the best way to earn someone's trust is to say something that helps them but is against your best interest. It can’t just help them, it also has to be against your interest. Sounds silly but it seems to work.

“Hello General Manager at Hyatt Hotels, I think our property management software could work for you for your franchises a and b reasons but XYZ Software has more accounts in your space so the on-boarding process will most likely be much simpler for your team.”

This might lose you the immediate sale but it will definitely earn you some trust points. Trust is a long term asset. So much so that it's on the balance sheet as “goodwill”.

People will spend more energy trying to avoid pain than gain pleasure.

This is the case for people and for businesses. It is tough to get their attention unless you are helping them avoid some sort of shortcoming or pain. So how do we get people to spill their beans? Get them to disclose the resistance and/or the discomfort they are feeling?

I have found that disclosing some of your own discomforts and asking for relevant professional advice can help people feel comfortable with sharing their own issues.

“Hello, General Manager, we have been struggled in the past with training hotel staff on using our new software. Do you have any advice when communicating with hotel staff? What workflow problems are you struggling with at the moment?”

Two things happened here, I showed humility/ weakness by admitting a problem and I asked for industry-specific advice that could help me with my on-boarding process.

Share > seek for advice > probe for discomfort

People feel more comfortable around those that show weakness and imperfection.

This showed up in my observations above when speaking about trust but its so unbelievably effective that I felt we should discuss a little further.

Have you heard the adage, “that's to good to be true”?

I think it comes down to the fact the people know its difficult for others to show weakness. They know it would have been easier to be less than 100% honest. So when you show weakness, something goes off in their minds that says: “If Tyler had the chance to lie in order to dodge an uncomfortable conversation, he would still tell the truth. This must mean, if he says something positive about himself, it will be true”

It isn’t easy to disclose weaknesses, especially in the workplace where strength is something highly regarded. No one wants to work with the weak right? Yes and no. No one wants to work with people who identify problems and weaknesses without actively working toward solutions. Show those weaknesses, but back them up with clear and defined action.

Hi 👋🏻

I am a friend, brother, son, writer, marketer, traveler, and entrepreneur. I like to work on relevant projects with people who inspire me. ​I may or may not be a stranger to you at this point. If we haven’t met or you want to learn more about me, read this 👉 Intro to Tyler Donahue




Tyler Donahue

Writer @TheHustle @thriveglobal | Founder @th3kindproject @essentialblankets