To Coach or Not to Coach

Coaching - Golden Key on White Background. 3D Render. Business Concept.

Five coaches weigh in on how to make an informed choice

If you see yourself as a business owner and you are committed to success, you might benefit from working with a coach. With the right coach, you can grow your business and income faster than you can on your own.

But hiring a coach is a serious investment in time and money.

Steve Slaunwhite, Nick Usborne, Ed Gandia, Steve Roller, and Cyndi Fine are coaches who offered advice on how to decide whether coaching is the best decision for you and how to choose a coach that will be the best fit.

There are several ways a coach can help you as a web writer …

And each of the coaches I interviewed provided unique insights into how coaching can work best for you as a writer. But first, let me introduce the coaches and share a few of their qualifications. I think you’ll agree, they are a group worth listening to:

  • Steve Slaunwhite, co-author of The Wealthy Freelancer and author of several other business and copywriting books, has a private coaching program geared to help writers find more ideal clients and find ways to package their services so they make more money.
  • Nick Usborne is the author of Writing Kick-Ass Website Sales Copy, Popcorn Content, and four AWAI programs including How to Write Your Own Money-Making Websites. His coaching clients experience “big breakout moments” of positive change and growth. He encourages his coaching clients to overcome the fear of failure to reach their true potential.
  • Ed Gandia helps writers transform their freelance businesses by teaching them how to make more money for every hour they put into their businesses.
  • Steve Roller, founder of Copywriter Cafe, offers one-on-one and group training for copywriters, and The Ultimate Writing Retreat. His coaching program includes professional writing critiques.
  • Cyndi Fine focuses on helping her clients spark creativity, discover their own gifts, and express their own vision.

Each coach has a distinct style and, since it’s important that the coaching relationship is a good fit, they are selective about who they take on as clients.

When choosing a coach, you should be selective, too. Explore the websites of at least 10 coaches. Your initial list of potential coaches will be long. Then, ask questions to narrow the list down to one ideal match.

But first, there are a few questions you should ask yourself:

Why do you want to hire a coach?

Some people seek out a coach for the wrong reasons. Are you one of them?

“If you think that the coach will have the keys to the kingdom, or the coach will make you be successful, that is a big red flag,” said Slaunwhite, who prefers to work with people whose businesses are more established. “If someone contacts me and says something like, ‘You’ve been my guru,’ I might not work with them, because that’s just not my style. I’d much rather hear, ‘I’m a copywriter, and a business owner and I think you can help me.’”

Use a pen and paper to brainstorm why you want a coach in the first place. Where are you now and where do you want to be? What type of help do you need?

Cyndi Fine’s clients are people who are ready to make a change or a shift. “One good time to use a coach is when you finish a program and you’re with a lot of people who are also doing it. Times when you feel motivated, but nevertheless feel like you’ve been left at the starting gate. Each time you find that your learning curve is going up.”

“You should have a clear idea of what success looks like,” said Gandia. If you can’t describe what success looks like, getting a coach may not be the right decision. If you don’t know what you want to achieve, how will you be able to tell if the coach helped you?

Writing down what you need ahead of time will make it easier to choose which coach best fits your needs.

For example, if you want to improve your relationships, you can look for a coach that takes a holistic approach and is willing to discuss your personal life. If your goal is to grow your business as quickly as possible, you should concentrate on finding a business coach who has a deep understanding of your industry and a track record of helping people make more money.

What is holding you back?

Here’s an example:

In 2003, Gandia was confident that his writing skills were ready, but his prospecting efforts were still failing. “I was sending direct mail to companies I found in a book and networking,” explained Gandia. “It was like throwing spaghetti at the wall.”

“A good coach can help you see things that you don’t see. Helps you see your strengths and how to leverage your strengths,” he said. Gandia worked with Chris Marlowe, who helped him focus on his area of expertise and leverage his strengths.  “After three months of prospecting, I landed my first client. After that, I got very busy very quickly.”

Gandia made a good investment in coaching because he knew he wanted to create a more effective prospecting plan, and so he hired a coach who could help him achieve that particular goal.

Can you afford to make this investment?

First, let’s define “afford.”

“You need to be ready, financially,” said Slaunwhite. “Don’t max out your credit card. Preferably, you should be spending your business income. Ask yourself, ‘Is this a wise way to spend my business money?’”

“If the fee is more than they can afford to lose, I discourage them,” said Usborne.

Even the best coach in the world can’t guarantee that you’ll make the money back, and if you are in a stressed or desperate place, financially, you won’t be able to have the optimistic and positive outlook that you’ll need to make coaching worth it.

Coaches have different packages, group training sessions, full-day or half day intensives, retreats, and pre-packaged products. Choose an option that fits your budget and time frame.

And remember, if you can’t afford coaching now, you can make it a business goal for the next year.

Can you get the same result with a less expensive strategy?

Your list of needs might point you in another direction.

“Some people want a coach to gain accountability,” said Roller. “It can be an expensive way to be accountable. You can get an Accountability Partner.”

Most coaches offer a wealth of free content on their websites like webinars, articles, books, and courses. Taking full advantage of these resources and implementing the strategies can bring you a long way.

You might realize that you need a different form of help: If personal problems prevent you from reaching your professional goals, or if your emotions sabotage your best efforts, a counselor might be able to help you more than a coach. If time management or organization seems to be a problem, a Virtual Assistant might be a better solution than a coach.

What if you need to improve your writing skills?

Some coaches will help you with your writing, others will not.

Coaches focus on building your business; it’s best to approach them when you’re ready to provide writing at a professional level.

“I want people who can already write,” said Gandia. “I focus on the business side of launching and growing a writing business. That’s where I can help the most.”

Take classes, buy books, practice, and complete real-world assignments to improve your writing.

“I don’t work with someone who cannot offer copywriting services at a professional level. You have to be a fairly good copywriter to get the clients that I will show you how to get,” said Slaunwhite. Slaunwhite has workshops and courses to help people improve their writing skills, and prefers to work in a workshop environment. See his website (

Steve Roller does include a 1-2 page copy critique each month with his coaching sessions. “Some pretty experienced writers come to me because they like to get feedback before handing the copy in to their clients,” said Roller. “My coaching services are more hands-on and time-intensive because I’m still in the beginning stages of building a coaching business and am willing to do that.”

Choose the right coach for you

When you’re narrowing down your list, absorb the free content that is posted on the coach’s website, take advantage of their free half-hour coaching session, and above all, choose the coach you feel a connection with.

“I often tell clients to talk to other coaches,” said Slaunwhite. “It’s the first piece of advice I give, as a coach. That way you can make an informed business decision.”

“If you have to choose between two coaches, find out which one you trust the most,” said Usborne. “You have to trust that they’re going to deliver value and you have to trust them as a person, because during the coaching process, you have to open up.”


Mandy Marksteiner

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