Over the past couple of years, I have had the amazing opportunity of mentoring dozens of startup companies from all around the nation. Mentoring is one of my favorite activities to do! With that said, I am the first one to say that, well, I used to suckkkkkkk at being a mentor.

How I learned that I was a crappy mentor.

Funny story actually. At the time, I did not know that I was a crappy mentor. I thought that I was pretty good. I know I have good advice to give. I have gone through some great lessons in my life. So what on Earth could I be doing wrong?

Here is my story of how I learned I was a crappy mentor.

I have been in a long distance relationship with my now fiance for 6 years. Over these 6 years, we have talked on the phone almost every night together. We share what we did that day, tell a funny story that happened, and talk about food, haha!

I remember one night about 1 year ago. Betsy, my fiance, had a pretty crappy day. On the phone that night, she started to tell me all about it. She started by talking about just how bad of a day it was, proceeded to who did what, then say why it happened.

Let me tell you something about my personality. I am a fixer-upper. When there is a problem with anything, I immediately interrupt to solve the problem. So, as Betsy was telling me what made her day so crappy, I interrupted a dozen times with a possible solution. Yeah, don't ever do that.

After only 5 minutes of talking together, Betsy hung up the phone on me...

Yup. The dreaded hang-up.

I can count on one hand the number of times I have had the phone hung up on me. When it happened, it really hit me. I had some real thinking to do....

I thought about it for a while, apologized to Betsy, and talked about it with her. This moment I learned a valuable lesson that would stretch beyond just our relationship together. I learned right then and there I was a terrible listener.


Yup. That simple, right? The biggest tip to being a better mentor is to listen.

When I first began mentoring, the sessions used to start with me talking the founder's ears off. I shared my expertise and how I could help them. Then, as they would share where they needed help, I interrupted to mentor mid-sentence.

Now, the first thing I do when I meet with a team is to start with a series of questions. Even when you are expecting a certain answer, ask the question anyway! I may ask 6 or 10 questions before I share a single bit of advice! It has helped on so many levels.

They are not as dumb as you think.

Every question that you ask, makes your advice that much better. Why? Because you are no longer assuming anything. You can give advice that directly impacts a problem faced by the team. Find out what the team already knows and skip it.

Example: A year and a half ago, I wasted a ton of time with a team that I was mentoring. I remember exactly how it went. I remember sitting down together and then team immediately asked a question. When they asked, I began to answer with little to no thought. No follow-up questions, I just jumped right into it. Turns out, after 5 minutes of me talking, the team looked at me and said, "yeah, we know". Oh, sorry? I didn't realize you already knew that.

Every heard of the 5 Whys?

When someone tells you a problem such as "why are our sales down this week?". Don't try to jump right into the solution with just that knowledge! There could be hundreds of reasons why you didn't make many sales this week.

When someone tells you a problem, simply say to them, "Why?". Then when they answer you, respond again with, "Why?". After that, again ask, "Why?", etc. This is known as the 5 whys. Asking "why?" 5 times to a broad problem will bring you to the root of the problem. As a mentor, you are not there to help fix broad problems. You are there to help move a team forward. Find the root of a problem together and then help them get over that small hurdle. It will help them dramatically!

(It doesn't need to be exactly 5 times you ask why. 5 is the magic number you could say. Most of the time, 3 - 5 is the number of times I ask "why?")

The night that Betsy hung up the phone on me, I had no idea how much of an impact that one moment was going to make on me. Our relationship together improved, my mentoring, friendships with others all improved. This is not just a lesson for being a mentor. This is a lesson for being a human being.

Listen. Then act. It makes a much bigger impact then you realize.