What to ask yourself before hiring a writing mentor

You know you want to write, but you’re stuck and frustrated. A writing mentor might be the answer to getting unstuck, but only if you set clear expectations before you begin.

I’ve worked with writers for almost two decades. I’ve also had plenty of mentors of my own, so I’ve seen what works and what doesn’t first hand.  

For starters, there’s no rule you have to work with a writing mentor. You could find someone who will mentor you in smaller, less concentrated ways. Or work on your own. Or find a peer writing group.

If you want someone to work with you one-on-one for an extended period of time or on a specific project, then you’re better off paying someone to spend the time and attention you need to help you focus and reach your goals.

Your mentor keeps you accountable, learn skills and keep organized. Your writing mentor encourages you to dance with fear and stretch yourself to do more. Here are a few questions you should ask yourself when looking for a writing mentor.

What are your goals?

You’ll always want to chat with someone before you hire them, and make sure you discuss your goals. You want to know what you want to accomplish and know if their expertise coincides.  That way you both enter the mentoring relationship with a clear direction and set of tasks you want to accomplish.

Do you have the same working philosophy?

Each writing mentor will have a philosophy behind the work you do together. It might be to lead you through specific tasks based on their expertise that you then apply to the rest of your writing life on your own. Or you they may give you input on one project, such as developmental edits on a book or a query to an agent without looking at the bigger picture of your work. Some writing mentors work only with advanced writers who are looking to take the next step in their careers.

I work primarily with newer writers helping them shape their writing goals and improve their writing skills. So whether you’re writing a book or creating your writing roadmap, my goal is to help you learn and develop your abilities so you’re more prepared to take your next steps on your own.

Your writing mentor encourages you to do more.

What if you don’t know what you want?

Let your potential writing mentor know up front. They should be able to tell you immediately if it’s a good fit with the way they mentor or not.

There are times when someone comes my way who doesn’t even know if they want to write. That’s a decision I can’t help you make.

I do often work with people who dream of writing but aren’t yet sure what kind of writing they want to do. It’s one of my favorite ways of working with writers because there’s such potential for growth. Together, we create a writing roadmap that allows you to test different areas of writing and create your ideal writing life.

This is so central to what I do, I even wrote a book about it.

What’s your writing mentor’s working process?

(Do they have processes?)

From the time you contact a potential writing mentor through working together, you want to know they have a well-established method of working with people. Do they have a clear intake process? Will they meet with you for questions before you agree to work together? Do they communicate next steps?

Before you start working together, your potential writing mentor should be able to explain how you’ll work together, how long, how often you’ll meet and what you can expect to accomplish.

How quickly does your writing mentor respond to questions?

If you find your potential mentor doesn’t reply in a timely way to messages, run fast and far. If they can’t respond in decent time at the beginning of the process, it’s likely to be worse when you’ve already paid.

What does “a timely way” mean? I’ll give examples.

I wrote someone to work with them on PR for my book. It took a couple days for her to reply to set up a meeting. No problem. Her current clients’ needs took precedence to a potential client. That’s a good sign. When we spoke, she told me she would e-mail me her rates and specifics about the kind of work we’d do together. I didn’t hear from her for another two weeks. Imagine you’re working on a deadline and need your writing mentor’s input. Two weeks would push you past deadline. Hard pass.

How much does it cost to work with a writing mentor, and what’s the payment process?

Ask upfront about how much it will cost you to work with this writing mentor and know before you agree to work together how the payments will be made and how often. Do they offer installments? Packages? One-off sessions if you need a quick pep talk? Access to them via email or texting?

Any fudging in this area is a big red flag.

Will your writing mentor tell you things you don’t want to hear?

One woman who came to a retreat of mine wrote the beginning of a gorgeous book. I loved the characters and the themes. The writing was wonderful, but there was no clear story arc. I had to tell her so.

If your potential mentor can’t be honest and tell you the things you need to know, you will not grow. They must be able to give tough love when necessary.

Do you get along?

While your writing mentor will sometimes tell you things you don’t want to hear, their input must be constructive and kind. Sometimes people’s communication styles simply don’t work well together. It’s not personal, but if you find your personalities clashing, it’s probably best to find someone else.

Do you trust the person?

It’s hard to know who to trust when you first begin working with someone. Even when you do your due diligence, things can go wrong. If you notice red flags during your initial conversations, trust your instinct. Do not work with that person.

Other ways to know if you can trust a potential mentor?

Do you feel your writing mentor is knowledgeable in the areas of their stated expertise? Do you feel they can help you solve the problems you want to solve? Do you feel comfortable talking to them? Do they take the time to listen and respond to your questions in a timely way with information that makes sense?

All of this engenders trust.

One more thing: Ask for references, too!

It’s crucial to be able to talk to previous or current clients before working with a writing mentor. Obviously, your potential mentor will refer you to people who loved working with them, but you’ll have the opportunity to hear how the mentoring relationship works from the mentee’s point of view.

Getting your writing out into the world can feel like a daunting task, and sometimes hiring someone to help you focus and stay on track can be a valuable investment… if you find a good writing mentor. Don’t rush your decision. Take your time, consider the questions above, and trust yourself. It will be worth it when you find the right person.

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