5 Questions to Ask Before Hiring a Mentor

Illustration by Ramiro Roman.
Illustration by Ramiro Roman.

Books and blogs are great, but you can’t ask them questions…

So there you are: You’ve read all the books, you’ve skimmed all the blog posts, you’ve subscribed to all of the newsletters, and you’ve had long chats with your peers in the freelancing community. And yet, somehow, you’re still not “ready.”

You feel “stuck” and you fear messing up. You’re paralyzed and you have no one to turn to for answers to your most “stupid” questions. (The ones your peers would scoff at and make snide comments about without truly providing answers…).

Sounds like you need a mentor!

But there are a few key questions to ask before you hire one:

1. Do they practice what they preach?

Before signing any contracts, make sure your mentor knows what they’re doing. And, more importantly, that they’re still active in their field.

What worked in the past may not be what works today (especially in the fast-paced online business world!), so you’ll want to check to make sure your mentor’s skills are up-to-date. After all, what good would updating your skills do if the person teaching you is stuck in the past…?

Mentors who are actively working in their field get ongoing feedback that teachers don’t.Whereas mentors who solely mentor can end up losing some of the edge to their once-sharp skillset after a period of freelancing inactivity, those who are actively working can continue to hone their skills and pass on their knowledge to you!

2. What EXACTLY are you getting?

Most mentors who are on the up-and-up aren’t shy about stating exactly what their mentees will be getting out of a mentoring experience with them. On their sales page, you’ll likely find a ton of information on what you’ll be getting if you sign up.

Read what they wrote.

The quickest way to determine is a mentoring session is “right” for you is to thoroughly read — and understand — what you’re getting yourself into. And don’t be afraid to ask questions! You’re potentially going to be spending a lot of time with this person: There’s no harm in getting to know them first.

Just make sure you don’t ask so many questions that you leave them feeling like you conned a free session out of them!

3. How will you be communicating/do you need to install anything?

Will you be talking over the phone? In-person? Via an instant messaging system?

Before you pay, make sure you know how you’ll be communicating with your mentor — and if their preferred method of communication works for you. Do you feel uncomfortable speaking aloud? Then you should find someone who runs their sessions via writing. Is your current computer too shabby to run modern software? Then you’ll need to look for someone who uses more traditional means communication.

Also: Pay attention to timezone differences.

Having the right technology and knowing how you’ll be mentored won’t mean anything if your schedules don’t line up!

4. Do they know more than you do?

Your potential mentor doesn’t need to know everything, but they should know more than you do. And that their knowledge is relevant.

You wouldn’t hire a proctologist to perform a wisdom tooth extraction, right? Nor would you hire your dentist to teach you how to paint with watercolors. It’s not that those people aren’t skilled professionals, it’s just that the knowledge they have isn’t relevant to the skills you’re trying to learn.

Tip: Don’t get hung up on testimonials. It can be hard for mentors to gather a nice hefty stack of testimonials from their mentees because so few people like to publicly admit that they needed help.

Instead, look at the testimonials from your mentor’s business clients. Why? Because the skills they’re going to be teaching you are likely the skills they utilize in their own business (again, this is why it’s important to nab an actively practicing mentor!), so if they have happy clients then you probably will too!

5. Do you like them…?

It’s unlikely you’ll sign up for mentoring from someone you don’t already know. Or at least “know” in the online acquaintance/I’m-a-huge-fan-of-your-work sense.

In general, the persona your potential mentor presents through their business is going to be the same as what you’ll be dealing with behind the scenes.

So, in the case of Sophie Lizard of Be A Freelance Blogger, the same “I’ll kick your butt if I have to if it means you’ll succeed!” personality she has in her blog posts is what she brings to the table when mentoring. (I know this for a fact as she’s mentored me in the past!).

Whereas if you sign up for mentoring from me, you’ll get something a little more gentle and a bit silly — much like my blog posts!

But do you prefer tough love or a gentle touch? That’s something only you know for sure!

Whoever you end up choosing as a mentor, keep an open mind and do your best to utilize the information that’s most relevant to you and your business. You’ll be un-stuck in no time!

What about you? Have you ever been mentored? How did it go? Leave me a comment below!

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