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How freelance writers can get the most out of a coaching session

By August 29, 2018 June 29th, 2019 No Comments

In the last eight months, I have coached over 30 different freelance writers. I’ve worked with writers in person, over Skype, and from all over the world including Australia, the USA, Canada, France, the Philippines and Mexico. I wasn’t 100 per cent sure about becoming a freelance writing coach, but it’s become one of my favourite parts of the job. Many writers I coach aren’t making the income they want, so I think it’s imperative that if you are going to pay for professional support, that you get the most out of it. 

How freelance writers can get the most out of a coaching session

While each writer’s situation is different, there are certain things you can do to ensure you maximise your coaching session. 

Be clear about what you want from the session (and your coach)

Before you decide to engage a writing coach online or in person, ask about their intake process. 

Does the coach have a form where they ask for details about your background and writing experience, your goals for the session and the goals you have for your career? 

I’m a really big believer in the need for freelancers to invest in themselves and their businesses. 

I’ve engaged writing coaches before and each time I loved (and needed) the opportunity to put all my thoughts down on paper before we met. 

Doing this helped me articulate exactly what I was struggling with and why I had asked for a coaching session. 

I underwent coaching initially because I felt stuck with my writing and how to diversify my income streams.

Having an hour to speak in depth with another writer who successfully managed multiple income streams and who was entrepreneurial was exactly the boost I needed. 

Sometimes its been helpful to get advice about simple things – one of my coaches suggested that I start and outsource my transcription as a way of saving time. I had been using Fiverr but I really didn’t like the system so at her recommendation I switched to Rev (oh and this is an affiliate link where you can get $10 off your first order).

That simple advice revolutionised my productivity and business. Now I outsource the transcription of all my interviews. 

Other times the coaching I’ve had has been more general – early on, I struggled with not having a niche and really valued speaking with Illse Benun about my quandary. 

But a key to the success of my external coaching sessions was me identifying what I was struggling with.  

There are many reasons why freelance writers get in touch with me to request coaching. 

The most common reason freelance writers come to me are:

– Not making the income they want

Feeling disheartened, demotivated or lost about freelancing and their future

– Wanting to break into content marketing writing but aren’t sure how or where to begin

– Needing help with their pitches, story ideas or where to pitch

– Wanting a ‘tune up’ or to refresh their freelancing business

– Wanting to become more efficient and establish a routine 

But it’s not enough to know what your challenges are.

You need to think about what you want the outcome to be.

Do you want to walk away with clear steps to undertake in order to reach a particular goal?

Do you want to brainstorm different angles and outlets for a particular story you have?

Do you want to finish the session with a ‘to do’ list? 

Do you want to work out which potential clients to send letters of introduction to?

Do you want to edit and polish an article during your time with the coach?

Knowing what your challenges are and also what you want the result to be means your coach can tailor their session to fit your exact needs, and hopefully, when you finish you’ll be in a stronger position than when you started. 

Are they the right fit for you?

You’re not going to get along with everyone, and when I started looking for an online writing coach, I must admit I was scared off by a few writers offering their services.

I’m a fairly sensitive soul and while I welcome feedback, I’m definitely someone who prefers criticism delivered tactfully.

Have a look at your prospective coach’s blog posts, social media feed, their testimonials and how they interact with others.

Do you like (and respect) the way they conduct themselves? Do they seem like they are the right fit for you?

You may be someone who thrives when people are blunt and forthright or your wuss-o-metre may be more like mine, and prefer someone a little softer. 

I had heard wonderful things about a particular coach and was very close to signing up to an expensive multi-session package with her, but over a few emails I felt like I was just one of a number of writers in her massive marketing machine and I decided I wanted something more personalised.   

So whatever you choose, remember you have to choose the person who is right for you.

Not the one who is right for the masses.

Can you afford it? Or rather, can you afford not to?

Rates for writing coaches can vary dramatically.  

I’ve paid up to $200 an hour for a writing coach, and usually it has paid off almost immediately. 

I’ve either got a commission off the back of talking through a pitch, or made a strategic business decision that has paid for the coaching session. 

It can seem like a big investment when you are paying someone more than you might earn per hour, but you are paying them because they can offer you (in most cases) results that you want, but don’t have, or they have help solve a problem that you have, but don’t want. 

Many of us pay to see an accountant, have a yearly checkup at the dentist, to have our car serviced, to be a member of a gym, or even to see a therapist.

I see coaches as offering writers a valuable professional service and I plan to make my external coaching sessions a regular occurrence.

They are a wonderful opportunity to set goals, be accountable and talk through issues with someone who has been through it all before. 

And for me, that’s where the growth is. 

Ask questions

One of my favourite things is when the writers I coach come prepared with questions. Lots of questions. 

Bringing questions means writers are invested in the process and to getting the most out of it as they can. 

In my coaching sessions, I waste very little time at the beginning with general chit chat because I know it’s important to get down to business.

I really think it’s worth writing down all your questions, and if you are organised enough send it to your coach beforehand, do so, so they have time to think about their responses. 

These are some questions that I’ve found (as a writer) are important to ask a writing coach:

– Can I record the session?

– Have you seen or heard anything that you think I’ve missed or need to know about?

– Could you check in on me via email in a week/fortnight/months time just to see how I’m going?

– If we only need half the session, can I use the other half session at another time? 

– Are there any resources, groups, publications that you think I need to know about or be part of?

– Have you coached people with similar issues to me? What have their outcomes been? Could you put me in touch with them?

– Can I send you questions, a pitch, an article before our session together?  

Coaching is a conversation and if you find the right coach, it may just be a game-changer.

From a writer’s perspective, coaching has been one of the most valuable things I have done.

Now that I have become a writing coach, I can’t tell you what a joy it is to get feedback from writers like this:

Yes, I’m a writing coach, but there are lots of fantastic coaches out there. 

I recommend looking around until you find the right fit for you. 

Some great writing coaches that I have either used or have had recommended to me:

Ginger Gorman –

Sue White –

Rebecca L. Weber –

And the amazing and incredibly generous Jennifer Gregory offers short, free calls to writers who have questions about content marketing. 

Have you engaged a freelance writing coach? What was your experience like? 

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