A Beginner’s Guide to Mentorship

Dunny
6 min readJun 3, 2018

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The mentorship process is very similar to dating. Just like dating, you learn from experience what to do and what not to do; Just like dating, in most cases you learn the most from your mistakes; and just like dating, if you’re smart, you learn from the mistakes of others! I want to hopefully alleviate some of your heartache by sharing some of the lessons and insights I’ve learned from my experiences so that you can be ahead of the game. Let’s get to it.

One of my most memorable moments and lessons came early in my career when I directly asked an older colleague of mine who had a job title I wanted if he would mentor me. His response was as direct as my request: “How do I benefit from this?” My pride a little hurt, I thought about his question, and I’d like you to think about it as well.

As odd as it may sound, you must have something to offer in order for it to be worth their while. When you’re asking someone to mentor you, what you’re really asking them for is their time, their insight, and their network. In other words, this is an investment for them. Would you invest money in a company that showed no promise?

Lesson number one: Mentors need a reason to mentor you; they must see your potential.

This doesn’t mean you have to have it all together. It means you have to be heading in the right direction and have proof that you’re actively making moves towards your goals. If you tell me you want to be a professional boxer and you don’t even own a pair of gloves, I know you’re not serious. On the other hand, if you’re training everyday, going to fights, and actively tracking your progress, it shows determination.

Consider this in a corporate context. Let’s say you want to be a lawyer. A friend of your mom’s is a successful lawyer and someone you admire. Before you even express an interest in mentorship, you should have some proof that this is something you want to do. Being interested doesn’t mean that you like to entertain the thought every once in awhile or you enjoy the pats on the back when you tell others about your goals. It means you read a legal trade magazine every month and volunteer at a law-related non-profit in your city.

Don’t know where to start? That’s ok; it leads me to my next lesson.

Lesson number two: Ask your prospective mentors for advice, act on it, and then follow up!!!

This is such a simple principle that has a tremendous effect that I had to put three exclamation points. It works for several reasons but the most important reason is because hardly anyone does it.

Successful people get requests for mentorship all the time. One of the easiest ways to filter out the flakes is by giving them action items. People will dm me from time to time asking to learn about cryptocurrencies so they can get rich overnight. The first thing I do is tell them to read my other articles and then get back to me with any specific follow up questions or things they need further explanations with. This eliminates 99% of people and it keeps me from wasting my time. On the rare occasion that people do follow-up, I’m more than happy to respond to questions and continue the dialogue because they’ve shown some type of effort.

If your prospective mentor tells you to read a book, read the fucking book and ask them questions about it! If your prospective mentor sends you an article, read it and tell them what you found interesting about it! If they tell you about about an internship, a job, an organization, apply for it and let them know! You have to show commitment! Think Mr. Miyagi from Karate Kid.

Not only does it help you stand out, it makes them feel good! It’s like wow… they actually listened to what I said. Now I am more inclined to go out of my way because they went out of their way! This is powerful once you understand how far it goes with people because most people just want to be heard. By acting on their advice, you’ve now put them into a position to mentor. This leads me to my final lesson.

Lesson number three: Ease into the mentor-mentee relationship.

Going back to the dating analogy I opened with, you should think of the early stage of the mentorship process as the “talking” stage of modern day relationships. In other words, there’s no commitment and you’re just getting to know each other to see if you’re a good match. Remember, not everyone has the time to be a mentor and not everyone is cut out to be a mentor.

As you start filtering out prospective matches, you begin the courtship process. Invite them to meet for a fifteen minute coffee meeting where they talk and you listen (ask them about what’s going on in their industry). Call or text them from time to time with updates about your achievements or challenges. This is not the time for you to ask them to help you get a job or a recommendation letter. At this stage, you’re putting in the hours so that when the time comes that you need a reference, you’ve already laid down the groundwork so that the relationship is not one-sided and they don’t feel used.

Once the groundwork has been laid, it’s time to use my all-time favorite line: “You know, I consider you a mentor.” This is the professional equivalent of every man’s favorite question: “What are we?” Why? Because this type of non-committal expression forces your prospective mentor to define the relationship without making it awkward. Their response will let you know exactly how they feel. Responses will vary but most will be along the lines of “Wow, I appreciate you saying that. I’ve enjoyed getting to know you and guide you in your professional career.”

By taking this approach, they’ve become your mentor without you having to ask just like some couples suddenly find themselves living together. It starts by leaving a couple clothes items at their house, then your phone charger, then a toothbrush. By taking small steps and getting them invested in you, you can avoid the awkward conversation of asking someone directly if they’ll mentor you, and you’ve gotten to know them in the process. Asking someone who barely knows you to mentor you is a recipe for disaster.

Mentorship, like dating, is a process. If you put in the necessary time and effort, you’ll find yourself quality mentors who are willing to open up their schedule and their network to you. If you don’t, you may find yourself with a gang of low quality mentors or unread emails. Like relationships, the work doesn’t end once you’ve gotten that special someone. Routine calls and check-ins are important to maintaining the relationship because the worst thing you can do is be the type of mentee that only hits them up when you need something. Nobody wants to be a booty call mentor. These are connections you want to last for life.

Good mentors have the potential to accelerate your growth, your career path, and your success. Find them, keep them, and you’ll never go hungry.

Thanks for reading! My hope is that you got something out of it and appreciated the casual tone of the article. While this is my approach to mentorship based on my experiences, this is not THE approach. You have to find what works for you. My motivation for writing this was frustration with social media “experts” telling people they need mentors without telling them how. If the article is well received, I plan on writing more on the topic in the coming weeks. In the mean time you can find me on twitter @BitcoinDunny.

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