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11 Urgent Questions to Ask Before You Hire a Writing Coach

Carol Tice

Earn More: How to Choose a Writing Coach. Makealivingwriting.comHave you ever wondered whether you could achieve your freelance dreams a lot faster if you hired a writing coach to teach you how to become a freelance writer?

Spoiler: You definitely could. I know because I’ve been coaching freelance writers for about 5 years now.


There are a ton of people on the interwebs today, offering to coach you to freelance success. How do you know if a particular coach could help you, or if you’d be wasting your money?

Remember, there is no official freelance-writing coach school. Anybody can hang out a shingle.

Since a key part of my mission is helping writers avoid ripoffs and scams, I offer this guide to vetting a writing coach. It’s derived from my experiences on both sides of the table, as I’m not just a coach myself but have also productively invested about $20,000+ hiring coaches during my career.

Yes, I know this list means you may ask me tougher questions before you hire me as a coach. I say: Bring it on.

What do you need to know before you hire a writing coach? Here are 11 key question to ask:

1. Are you someone I know?

You’ve probably heard about building authority online, and the importance of becoming someone your readers know, like, and trust. Your coach should be someone you have those feelings for.

Don’t sign up for a coaching program with someone you just met, or who perhaps a friend recommended, but you don’t really know.

Look at people you’ve been hearing about or reading for years, someone whose reputation is solid. Remember, anybody can put together a long sales page and create fake testimonials.

Coaching should be the next step in a relationship you already have with an expert, from listening to online or chatting with in blog comments, on email, or perhaps LinkedIn.

You should already have a strong sense of their personality, and whether they’re about gentle encouragement, tough love (me!), checklist-based systems, or what.

2. How long have you written for pay?

You might assume that freelancewriting coaches only offer to share tips after a long, successful career.

If only.

In this era of the ‘instant expert,’ the internet fairly bursts with people offering to be your writing coach.

Many of them have barely earned their first freelance check.

At this point, I’m no longer shocked when I find writing coaches whose About pages brag of having quit their job to freelance last year. Or last month.

Obviously, instant experts have a heck of a lot less expertise to share. You may be comfortable with a ‘coach’ who’s really more of a peer than an expert. But if you want someone who’s been through the wars and has a giant bag of tips and tricks they can share, be sure to ask how long they’ve been around.

3. How successful is your career?

You might think anyone with the gall to call themselves a freelance-writing coach is at the peak of a highly successful, award-winning career.

And if you thought that, you would often be wrong.

I’ve reviewed coaching sites where the coach only seems to have written for a small handful of low-level publications or smaller business clients. They’ve won no awards, not even local ones. Nonetheless, they’ve anointed themselves an expert and they’re ready to coach you.

4. Have you freelanced in a recession?

With #recession2020 a growing worry, one of the biggest questions to ask is whether your coach has freelanced during a major economic slowdown. Freelance writing in a downturn is a whole different ballgame than doing it in boom times.

If you want recession-beating tips, find a coach who’s been freelance writing since 2008. That eliminates probably 80% of the coaches targeting freelance writers today (but not me — freelancing this go-round since 2005.)

5. Does your career resemble mine?

It’s a weird thing, but some writers seem to think that if a coach has done any type of professional writing, they can coach you successfully on… whatever you need.

Not true.

I routinely hear from novelists, screenwriters, and poets who want to know if I could coach them.

Sorry — that’s out of my wheelhouse!

At the risk of stating the obvious, your writing coach should be successful in the type of writing you want to do. Don’t hire a journalist to help you get direct-response copywriting work, or vice versa.

This rule is why hiring a general ‘business coach’ to guide you is usually a total waste of money. Someone whose business success came from operating retail stores or being a management consultant has no idea what we do.

It’s like asking a giraffe to teach you how to hunt like a cougar.

I’ve watched too many writers throw money down this hole. Be sure you know exactly what types of writing your coach has done before you sign up.

6. Are you still actively writing for clients?

Here’s something many writers seeking a coach may not know: Most coaches are no longer doing the thing they’re coaching on.

It’s fairly rare to find a top writing coach who still has freelance clients, or is actively writing novels. Usually, they’re just coaching now.

Whether that’s a good or bad thing is a matter of personal opinion.

I may be an odd duck here, but I think when it comes to freelance writing coaching, having fresh marketplace knowledge is important. That’s one reason I’ve never stopped freelancing.

A story: Once, I was considering hiring a freelance-biz coach who I knew well, and thought would be terrific. Until I heard her on a podcast, saying this:

“Back when I was doing client work, here’s what I used to say in that situation…”

Honestly, my heat sank. I realized it had probably been years since this coach had writing clients! In a fast-changing marketplace, that meant her tips might well be out of date. I passed.

7. What, exactly, will you coach me on?

Every coach structures their coaching program differently. There’s no standard format or template. It’s important to ask what your focus will be, and what topics you’ll cover.

Is there a proven, step-by-step program you’ll be following? Or will you define a set of goals together, at your first session? Is it more like a weekly therapy check-in on whatever’s bugging you that week, but with a business focus?

You don’t want surprises here. For instance, I find many writers approach me hoping I will teach them writing craft — that I’ll review their article drafts and such.

But after 20 years of reporting on business and talking to entrepreneurs, I excel at coaching writers on growing their freelance writing business. Few coaches have my particular background, and I think it’s where I can bring the most value for my students.

P.S. If you’ve found clients and earned some, assume you write just fine.

8. What ongoing support is provided?

Here’s the coaching industry’s dirty secret: When it’s over, your coach usually disappears.

This is why hiring a coach to work with you one-on-one often fails to produce positive change. There is no ongoing support in the execution phase of this transformation plan!

The top factor that determines coaching success is having a peer group go through the coaching program with you. You get accountability from your group on an ongoing basis, and have the option to stay connected.

With my coaching, we call this the Den 2X Grads group (and I have students still using it, 4 years later). My experience is that success rates skyrocket when coaching is done in the context of ongoing peer support — so that’s the only way I offer coaching.

9. How many students have you coached?

With new instant experts hanging out their shingle every week, it’s important to know your proposed coach’s experience level.

Ideally, many, many writers have already worked with this coach and seen success. Hundreds, maybe even 1000+.

Just like in any other career, coaches learn as they go. I’m certainly a better coach today than I was in 2012.

If your coach is new, fees should be quite low. You’re basically a guinea pig in their experiment of learning how to be a coach.

10. Do you guarantee your coaching?

This is sort of a trick question, because about 99% of the time, the answer is going to be ‘no.’

Almost nobody guarantees coaching. Because coaches have no way of making you follow their advice. Coaching contracts routinely bristle with “cannot guarantee results” verbiage.

I’m sort of an odd duck here, because I guarantee my coaching. (And have never had to refund anyone.)

How can I do that? Because my students follow a six month, step-by-step system together that’s reliably worked for years now, for hundreds of writers. So I’m confident that if you follow it, it’ll work for you, too. #nobrainer

If you want a coach who guarantees results, the pool may be small. But ask yourself why so many coaches don’t offer a guarantee. Maybe they’re not getting consistent results?

10. Can I talk to your happy grads?

Successful coaches who get great results should be eager and happy to connect you with former students.

But weirdly, many coaches are not. I’ve heard from many writers who’ve asked big-name coaches if they’d provide a few names to contact. Too often, they’ve been ignored, or flat-out told ‘no.’

Consider that a big red flag.

My grads come to live coaching events for prospective students (here’s an example), and have handed out their emails for private chats. I think the single best way to make an informed coaching decision is to hear from at least one former student.

11. What is my investment?

Let’s talk about the top reason writers don’t hire a coach: It costs real money.

This isn’t taking a $9 class on Udemy here.

Recently, there’s been a trend of coaches in the writing world charging a serious ton. I’ve been invited to $20,000 coaching masterminds. I know a good copywriting coach who charges $12,000, and another who charges $5,000.

Obviously, when you can end up earning tens of thousands more, any of these price tags could be a good investment that would easily return in value to you, many times over. That is, IF you’re able to invest that much. My experience is that for many struggling freelance writers, paying mid-four figures and up for coaching just won’t be doable.

Why I made my coaching affordable

If other coaches are charging five figures for their programs, why is my coaching program just $1,300-$1,800, for six entire months of support with me?

Mainly because booking high-ticket coaching takes a lot of selling. A. LOT. I’ve tried that road, and I’ve concluded it’s just not for me.

Recently, I had an insight: I’d rather spend less time selling, and more time coaching. Because my mission is to help as many writers as I can earn more, fast as I can.

I can either pay my team a ton to help me promote-promote-promote the usual 90-minute sales Webinars, multiple daily emails, and so on. (Blecch!)

OR…by pricing coaching affordably, I can quickly connect with more writers who know and trust me, and we can get down to coaching. I’d rather invest less of my time and money in selling coaching, and be able to offer more affordable coaching.

So that’s what I’m doing.

Yes, I run the risk that some writers will see my services as lower value because I’ve priced them far below market. But I think if you read my students’ success stories, you’ll still understand how value-packed I’ve made my Freelance Writers Den 2X Income Accelerator.

Other coaches may price high for their own reasons — they want to book $1 million in coaching, or the high price tag flatters their ego, or they love sell-sell-selling. Maybe their program is longer than mine or more in-depth. More power to that.

As a student looking for coaching, be sure to ask the coach about their pricing, read your contract carefully, and be sure you know what you’re getting for your money.

Hire a writing coach to level up your biz

I wish more freelance writers understood what a powerful shortcut investing in coaching can be (assuming that coach is a fit for your situation, based on the questions above).

When people tell me they can’t afford coaching, I always think they’re asking the wrong question. The right question is:

“Really, can I afford NOT to do this coaching?”

How much additional income can a good coach bring into your life? Let’s use my own experience and do a little quick math.

I had 12 years of award-winning staff journalism under my belt when I got back into freelancing in 2005. I built my freelance writing income fairly quickly to $50,000 per year, replacing my staff-job salary.

But it took 6 years to slowly build from there to $100,000, on my own. How much more would I have earned, if I’d hired a coach and hit 6 figures in 2 years instead?

Answer: $140,000 more.

Just reading that figure causes me physical pain. Ow!

Hiring a qualified coach with a proven track record of helping writers like you is always a good investment. It’s just simple math.

Looking for a coach? The only 2019 class of my Freelance Writers Den 2X Income Accelerator small-group mastermind for mid-career writers begins June 1.

Double your writing income: Coaching for working freelance writers. Freelance Writers Den 2X Income Accelerator. Freelance Writers Den - A Writing Community