3 Ways to Finding and Having a 1 on 1 Conversation with a Mentor

A rule of thumb for being successful is to find a mentor who is successful and learn from them. Success leaves crumb trails. But, it seems as if anyone can label themselves an expert in anything. (I just updated my tagline to expert blog writer, yes, it’s that easy). But how do you find a credible source to mirror and learn from AND THEN get a chance to talk with them? I have a 3-step process that I have used to find a mentor to follow, mirror, and have conversation with.

First, let’s see how mentoring is defined according to our good friend Webster.

Definition of “mentor” according to Merriam-Webster

a : a trusted counselor or guide

Old School Mentoring

You seek out a senior professional in the industry you work in who elapsed some sort of monetary success. You offer to pay them for their counseling and guidance en-route to match their level of success.

Mentoring in 2017

You seek out an influencer on LinkedIn within the industry you are working in and immediately ask them for help or advice. WRONG! STOP! NO! This is what everyone is doing with no success.

This is not the way to find someone to mentor you in 2017. There’s a new way to search for a person you want as a mentor, a new way for them to mentor you, and a new way to have a 1 on 1 conversation with them (without paying).

Who will I have mentor me?

Pick a credible individual. I know what you’re saying “Ian, everyone is credible or an expert now. How do I choose someone legit?” Calm down! Like I said earlier, success leaves crumb trails. What I’ve found is that the most successful people give 99% of their path, insight, and coaching away for free. The free content comes in the forms of blogs, vlogs, and interviews. The 1% that isn’t free is usually in books. That’s right, books. Now why do these successful people give stuff away for free, you ask? Because successful people want to help others achieve success. So, when I’m looking for a mentor the first thing I look for is:

  1. Who has written a book in the area I want mentoring in?
  • Why a book? Because writing a book takes a ton of time. Also, writing a good book takes a ton of valuable information one can take away and better themselves with. So, if anyone is going to take that time to put all their knowledge down on 250 sheets of paper, all the while knowing it might not ever be read, well, they have my respect and enough of it to check out more of their work.
  1. How active are they on social media?
  • What does their following look like? Is your future mentor engaging with their following? Are they blogging, answering questions, or giving insight? If the person you want to mentor you is active on social and puts out content there is an astronomically better chance you will get them to engage with you.
  1. Choose 1 mentor……for now.
  • This is the fun part. If you have found someone you think would make a great mentor, do a little background checking. Anyone can write a book and be active on social but the real ones have started something and have grown it. They have actually done what they say they’ve done. I don’t trust anyone who tries to teach someone to do something that they have not yet done themselves. Once you’ve narrowed down who you want as a mentor, done the background legitimacy test, and are good to go, choose 1 and only one. For now, anyways. Baby steps.

Okay you have a mentor. So start having them mentor you.

Yes, you don’t have to contact them for help or advice. Remember the 99% free content your mentor puts out and the book they wrote? Start reading and start doing what they say to do.

Buckle up! It’s example time!!!

Let’s say you want to start a shoe company. Yes, like Nike. But you need a mentor because you don’t know where to start. Go grab Phil Knight’s book. Read it. Do it. He literally explains step by step how he created Nike. Let Phil Knight be your mentor.

Read all the posts he wrote in INC Magazine, the business articles, the interviews, and JUST DO IT. (See what I did there?)

You don’t need to meet these people face to face anymore for them to be your mentor. They put everything out there for you to follow. The only reason you haven’t done what they have is because you don’t want to do the work they have done. Everyone sees an overnight success but they don’t see all the overnights they’ve worked to become successful.

But, there is still that burning question you want to ask them they haven’t answered in ANY of their content. Here are 3 steps that I have personally used to have 1 on 1 conversations with a mentor of mine.


Follow all their channels and be active. Engage with them. Tweet, re-tweet, like, share, and anything else you can to be active with their content. When they post a new blog, read it, comment on it, and spread the word to your network. Trust me – they notice acts like that. Now don’t get this twisted as if all you need to do is like 1 post then you get to reach out with a question or conversation. No, this takes time. Plus, just liking a post isn’t enough.


Pose questions to start a discussion on the post they wrote. Bring other people into the conversation and be active with it. Get known in their space. Not creepily, though. Don’t go to Facebook or Insta and blow their notifications up because you just liked the last 374 pictures they put up. That’s the wrong way to get noticed and possibly a 1-way ticket to Blocked Town. Get noticed by being insightful and thoughtful. Bring their audience as much value as your mentor brings you. Over time they will start to notice the questions you ask or the input you have in a thread on their page. Trust me, they notice. And, if you have done as they said and are doing as they do, when they come to notice and check out your progress they see the hard work you are putting in and know they were a part of that and they feel grateful they were able to help a person achieve goals. Then they follow you. That’s where you want to be before step 3.

  1. Insightful questions asking for 1 piece of advice.

They followed you, now what? They know who you are and have made enough of an impact that they are generally interested in what you have going on. So, before you start jumping around like you just got a new puppy, do yourself and your mentor a favor and don’t message them the second they follow you. Maybe a thank you, but that’s it. Trust me it’s the greatest feeling in the world when you get followed by your online mentor but right now you need patience.

Keep repeating steps 1 and 2 for a while. Keep doing what they are doing, keep following their “written path” if you will. Remember they are still mentoring you at this point. After you feel comfortable enough to reach out to them mention a piece of content they wrote or a quote they wrote that relates to your question you still have. Ask if they would be able to elaborate a bit more. This part of the step is done in a DM or email. Getting to this point has taken me 3-18 months and even longer so don’t think of this as a 1 “like” and ask. They are flooded with thousands of DM’s and emails everyday so you need to do the work in steps 1 and 2 to get them to notice your name enough to answer back. Once they answer you back, the conversation is open. Make sure you are asking good questions – insightful questions that require an answer other than yes or no. At this point you have conversed with them and in my experience, they are always more than open to answering any other question you may have. Remember, it’s not all about you…give them value back. If you see something you think they might enjoy reading or see, share it with them. It’s not a one-way street.  

There you have it. My 3-step process to finding a mentor with the 3 steps I take to have a 1 on 1 conversation with them. I hope this helps you out. Good Luck!

-Ian Beaton-

Ian Beaton is a sales rep for Razor Tracking. He is responsible for prospecting, engaging, follow-up and closing and managing my own accounts. Having to do everything in a sales cycle; 1 of the most important skills he needs is sales development. Ian doesn’t get to the close without the 1st step in the sales process. He is his own SDR so he needs all the skills in this area to get his job accomplished.

Leave a Reply

Up ↑