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Asking someone to be your mentor can be seriously overwhelming, and if you do it wrong, it can be super creepy. There’s a trick to how to ask someone to be your mentor, and it’s not a one-size-fits-all kind of situation. You have to be super self-aware, conscious of the reactions of others, and work with a plan.
I remember the first time I asked someone to be my mentor—epic fail. Fortunately, they only laughed and walked away, somewhat sparing my feelings, but it can be a total embarrassment when you ask someone to mentor you, only to have them freak out.
It’s important to carefully assess whether someone would be interested in mentoring you, if they have the time available, and whether you can offer them an incentive to mentor you. If you sum up the person you approach incorrectly, you could end up with egg on your face—the rotten kind.
So, here’s everything you need to know before you ask someone to mentor you, as well as how to ask someone to be your mentor and succeed.
What Is a Mentor?
A mentor is someone you look up to and who takes you under their wing, teaching you their methods and techniques to achieve the kind of success they have gained in life. Mentorship can be found in business, careers, and even in social presence.
The mentor guides you through different situations and learning opportunities so you can develop and grow as a person, while their words of advice help you steer toward victory. While a mentor isn’t someone who is perfect, they are someone who has lived and learned.
By mentoring you, they share their vast knowledge and experience, helping you succeed, because they let you stand on their shoulders of accomplishment.
Why Having a Mentor Is Important
Having a mentor is important as you get to learn from lived experience, which always trumps textbook learning. I recall the famous show, The Apprentice, in which contestants had to impress a very experienced businessperson and get them to choose contestants as their mentee or apprentice.
We learn from experience and from faults too, and if you can find someone who can mentor you, it means you get to draw on their experience, so you don’t have to make all the mistakes yourself. Having a mentor is like having a wise elder or consultant in your corner who helps direct your actions for maximum benefit to you.
A mentor needs to accept you as their mentee, and they need to know they will have a willing student, not someone who challenges their authority (or experience) or wastes their time and investment of knowledge. The value of having mentorship is that you have someone you can go to for learning and guidance.
Benefits of Mentorship
You would be surprised by the benefits of mentorship. For the mentee or the one being mentored, there are several benefits, including:
For the person who does the mentoring, there are also benefits to mentoring younger or less accomplished people through a learnership or even more unofficial mentorship like taking someone under their wing.
The person doing the mentoring benefits through mentoring because, in mentoring others, you:
7 Steps to How to Ask Someone to Be Your Mentor
If you consider asking someone to be your mentor, you need to think carefully and logically before you ask them for their advice and guidance, as not all people are interested in mentoring others. By asking in the incorrect manner, you may also come across as creepy and sleazy even.
By being prepared and clear about how you ask someone, your chances of gaining their mentorship guidance increases.
Here are the steps to finding and securing the mentorship of an appropriate mentor:
1. Decide What Kind of Mentor You Need and What You Want to Learn
Before you rush out there and ask someone you know who you think may be a great person to mentor you, decide what kind of mentorship you need. Remember, a mentor isn’t necessarily your friend. In fact, it may be better if they’re not your friend, as they’d be more able to give you constructive and objective guidance.
Assess what kind of mentorship you need. Having a mentor isn’t some social status you can claim to add to your social handles.
You are asking someone to invest their time, thought, and energy in helping you achieve a dream. If you don’t even know what you want to achieve, you are wasting their time (and yours).
It’s important to decide what it is you want help or guidance with. Sometimes, you may want a mentor because your life doesn’t feel like it’s on track. Assess what it is a mentor can do for you—they’re not there to fix you, but they can perhaps help you fix your own challenges and bring your life and ambitions back on track.
Example: If you are interested in transitioning from a full-time job to a career in writing, you may want to find a mentor to help you learn the best way to do this. In this case, you need to be clear about what you expect from your mentor. They’re not there to tell you what to do, but they can share their experience and tips with you.
2. Identify the Right Mentor for You
Now you know what you want from your mentor, it’s important to find the right mentor for you. If you want to be a successful businessperson, you probably can’t email Elon Musk and ask him to mentor you. Chances of him agreeing are slim, and he may operate at a level that’s way out of your business league.
Finding the right mentor for you is about identifying someone who achieved some of the success you are after whom you can approach for guidance.
If you are on step one, you don’t necessarily want to try to convince a mentor who is on step 15 already. They will perhaps not be able to fully and simply guide you as they’re already too far into the game of life.
But a person you look up to who is on step five or 10 may be a great person to approach for mentorship as they’re only a few steps ahead of you.
Example: You discover that a former colleague has made the same journey as you want to tackle, leaving their job to become a freelance editor. They are successfully surviving and paying their bills (with some money to spare), and they have a steady stream of clients. You consider asking them to mentor you on this stage of your journey as they have similar experiences, and they are still within reach as they (relatively) recently transitioned to freelancing.
3. The Conversation
It’s important to get as much information as you can in conversations with your mentor. If it’s someone you already know, you can call them up and ask them to have coffee and a chat, so you can get a feel of the water. It’s important to feel like you get them, and they get you, so you can create a beneficial mentorship relationship.
Ask questions such as how they learned their skills or what they see themselves doing in the next five or 10 years. Feel out their method and thinking paradigm, and when you are ready, consider your options.
If you don’t know the person you want to approach about mentorship, you will have to find other ways to connect, such as via email or on other social media platforms like LinkedIn.
Example: You invite your former colleague to coffee, and you gather as much information about the potential mentor’s past, their philosophy that guided them through challenging times, and their interaction with you. Chat about your plans, ask questions about the legalities of working from home, and talk about motivations.
4. Pre-Ask Self-Assessment
Now you’ve got your eye on a potential mentor, consider what you’d want to learn from them. You need to be aware of what you want to learn before you even consider approaching a potential mentor.
Your mentor won’t agree if you ask for something they don’t know about or if you don’t know what you want from their mentorship.
Next, decide what you can offer your mentor in return. No, I don’t mean how much you can pay them. Mentorship is usually not bought or sold.
Your mentor will want to know you are serious about this venture you want to start. They won’t want to waste their time or feel like you’re just toying with an idea. This means you need to be willing to put in the hours and do whatever they suggest to get to the same level of advancement as they’re at.
Example: Upon self-assessment, you realize you have two hours a week to spend with your mentor, and you have another four hours a week to work on any tasks they set you on your career shift. You have a small amount of savings you can apply to getting started on your career change, and you know you are serious in pursuing a career in writing.
5. The Ask
One of the best ways to fail at getting someone to mentor you is to simply ask them up front. Unless they specialize in mentorship (and probably have a fee for their services), you’re going to creep them out at least somewhat by just asking a stranger, “Hey, will you mentor me?”
Another downside to just asking them to mentor you is that it leads the conversation to a precipice where you may lose all confidence to ask them or ask any other mentor again. So, like asking someone out for a date, you need to work up to it.
When it comes to asking someone to mentor you, it’s a bit like a recipe —and you probably need to start with a little butter—the buttering up kind. Part of identifying the right mentor (step 2) is to research them and identify why this person would be ideal to mentor you.
Use the information to strike up a conversation. Everybody has an ego that likes being stroked—it’s human. Knowing how much butter (aka stroking) to use is important.
Example: Start by expressing to your potential mentor how much you admire something they accomplished. Don’t be a typical suck up in this; instead, be specific. If your mentor became a full-time author, then mention how much you enjoyed their books, and bonus points if you can mention something specific about an earlier book (showing you did your homework).
When the potential mentor has warmed a little to you, you can expand into telling them you want to transition from regular employment to writing full time too. They may expect you to ask them to check your writing samples, so don’t. Instead, talk about the process of moving from a boss-environment to an I’m-the-boss setup and ask about how they manage theirs (remembering to listen).
If you’re still sure you want to be mentored by them, you can move ahead and ask them to mentor you, making it clear you want their help with the process, not a freebee.
6. Follow Up
Great stuff, you’ve warmed them up nicely, impressed them with your eloquence and preparation, and when you ask, you don’t ask for the usual requests they may field. You are unique, interesting, and ready—a worthy mentor will be interested.
But people sometimes need to think, so don’t expect an answer immediately. However, keep the ball in your court. Take the initiative to ask if you could send an email to follow up in a day or two, perhaps asking for a business card or if they work through an agent, you can ask if you could forward an email to their agent.
Example: Wait a few days, then send a short but eloquent email to your potential mentor, again referring briefly to the specific request you made. Keep the email focused and short, showing off your analytical thinking skills.
7. Example of a Mentorship Ask
How you ask will depend on if you know the mentor or if you don’t. Here are two examples:
For a Mentor You Don’t Know:
I was thrilled to meet you at the Washington conference last month, and I learned so much from our brief conversation. I am writing to you with a proposal to consider mentoring me.
Like you, I am also transitioning from full-time employment to writing freelance and full-time. While I have made good progress on my career journey, I know that I can learn so much from you, and I would be really grateful if you would consider my proposal.
Perhaps you would like to see examples of my writing; I am happy to share these.
Looking forward to chatting about your experience and any potential to become my mentor.
For a Mentor You Do Know:
I am astonished by how your career has taken off, and you’ve shown such resilience and innovation in shaping your upward trajectory. Like you, I would also like to transition from a full-time job to a career as a writer.
You’ve inspired me, and I would love it if you'd consider mentoring me in the basics of entering the writing world. I believe you have a lot to teach, and I have a lot to learn.
Final Thoughts on How to Ask Someone to Be Your Mentor
Knowing how to ask someone to be your mentor is a valuable skill. Even if you can convince the person you admire to mentor you for a short while, you’ve already won. Mentorship is one of the best ways to learn about an industry or skill as you’ve got hands-on guidance and advice.
Best of luck on your mentorship journey, and to boost your chances of success, read our article on great daily habits of successful people. Even small things can make a HUGE difference.