Wanna start a coaching business? Here’s some beginner tips

I’ve been coaching full time since 2013. It’s a hell of a mission. In my first year, I only made $25k. It wasn’t for about 5 years until I had clients coming to me without me needing to go find them. I’ve had some hard times for sure.

The upside is that I’ve learned what works and what doesn’t. Very few coaches make it to 10+ years in this business because they crash and burn early. Either because they never should have tried to be a coach in the first place (e.g. motivated by money rather than helping people), or because they didn’t do the right things to build the business and had to find another job.

These days, it looks like 1000s of new wannabe coaches are emerging every day, flooding social media with their inspirational quotes and spamming everyone with their template marketing emails that they got taught from some scam artist.

Based on a conversation I had with a client of mine who’s keen to become a coach himself, I wanted to put together a guide for your first year of coaching. What to expect; what works; what you should focus on; and what you should avoid.

What is coaching? (and what it isn’t)

It’s critical that you first understand what “coaching” is, so that you start on the right foot.

Coaching is not teaching, mentoring, or therapy, though there are elements of all these in coaching.

You do not need to be “better” than someone else to coach them, and this is important to remember when you first start out. You can coach people more successful than you by any measure, so long as you remember that coaching is about eliciting their own strengths, not about impressing them with yours.

Coaching starts from the assumption that the client knows what is best for them – indeed, they’ve known on some level their whole lives what they should be doing differently. Your job is to provoke that knowledge and help it emerge into their conscious awareness.

While you might be able to provide expert tips or relevant stories of your own journey, expertise is not actually needed to help someone. Just help them find the answers they already have inside.

Why you need to start coaching for free

The thing that fucks up the mindset of most new coaches is neediness for money, or pressure to turn coaching into a successful career. This neediness is poison to a new coaching business.

To get started, it’s best you take all this pressure and stress off the table. If you’ve been coaching for less than a year, or done less than 50 coaching sessions, then you can’t even be sure that this is the right path for you.

So don’t charge anything at first. Or barter with non-financial rewards such as honest testimonials or referrals.

Make it so you aren’t thinking about money during your sessions, and that when you’re inviting people to coaching you see it as a gift and as training for yourself, and nothing more. Make it clear to them that they’re actually helping you, and that you aren’t sure of yourself yet so you appreciate them letting you practice.

When you’re sure of yourself as a coach, then you’ll be more confident in exploring how to make this your source of income as well.

I coached for 6 months completely for free, part time on the side of my day job, before I first charged someone.

ABC’s of Coaching

Always Be Coaching.

Whatever questions, doubts, or concerns you have about being a coach, usually the answer is to simply do more coaching.

Most of your education will take place in coaching sessions. Every session will be unique, and every person has surprises. But after a lot of coaching, you’ll naturally start to see patterns and become better at helping people have insights.

If you’re reading books, doing courses, or watching videos about how to coach, make sure that your putting in many more hours actually coaching. I’d suggest that for every 1 hour of information you absorb from videos and books etc. you should be doing 10 hours of coaching sessions.

Plus, when it comes to building a business in coaching, nothing is more important than getting people in front of you for a session. Coaching sells itself; free sessions are the most effective form of marketing. 10 years on I’m still giving people the first session for free. I don’t try to sell coaching, I just try to get people into a session.

So when you’re always just constantly filling your calendar with coaching sessions, you’re not only learning to master coaching but also the art of getting people into a session, which is fundamentally the entire business side of this thing.

Finding people to coach

The business side of coaching is simply about getting people into a session with you. Coach-marketing is actually pretty simple at first. You bring people in, and the coaching sells itself.

At first, don’t have any rules about who you coach. A good friend. Your cousin. Members of your hiking group. An ex-work colleague. Your dance partner. The nice old lady who always sits next to you on the bus.

Don’t impose restrictions about who you’re “allowed” to coach, especially when it’s free. These are just people helping you practice.

Once you’ve scraped that barrel clean – i.e. everyone you know has said Yes or No to a coaching session invitation – then you can move onto learning the art of finding new people to coach.

From there it’s simple but courageous.

You identify someone that you like or admire for some reason, such as they posted something interesting on Facebook, or they impressed you at your local BJJ class.

Then you approach them, online or in person, and compliment them on what you liked about them.

Follow that up with explaining that you’re currently training to be a coach, and that they’re the kind of person you might like to work with as a client someday.

Then ask if they’d mind letting you practice your coaching on them in a session. Make it clear that it’s totally OK to say No, and that you’re not going to try sell them anything. You just need the practice.

If they say Yes, book in a session. If they say No (or look really uncomfortable), thank them anyway and move on.

After you’ve had a session with someone, and you enjoyed it enough to want to do another one, tell them that. If they seem keen, book in another session. Keep doing this until one of you has had enough!

(If people fail to show up for sessions without warning or unexpectedly ghost you, which happens a lot in the early years, don’t chase them. Just move on to someone else.)

The 50 session rule

Don’t even bother considering whether you’re a good coach or whether this is the right career path for you until AFTER you’ve completed 50 coaching sessions at least.

I know that sounds like a big number, but considering a full time coach does hundreds of sessions per year, this is really just a small sample size.

A few sessions won’t give you enough data to measure anything meaningful. But by the time you’ve gotten to 50 sessions, you’ll automatically become very sure about those fundamental questions, and from there you’ll just be fine-tuning your style, methodology, favourite clients, and marketing methods.

And the quality of who you coach will improve over time, meaning that the worst ones come first! Better coaches get better clients, so get through the first 50 asap, safe in the knowledge that if you enjoy these ones, it’s only going to get even more rewarding from here.

Incremental learning

Don’t try to become a master coach right away. Instead, focus on one small element you wish to improve on, and repeat that until you’ve got it.

Maybe at first you just want to get through some sessions from beginning to end. So you just have 3 basic questions that you ask everyone: What one thing in your life do you want to improve? What’s stopping you from improving this? What do you need to do to overcome those barriers?

From there, you’ll notice things you want to practice or improve on.

If you learn a new coaching tool, then do 5 sessions in a row just practicing that tool.

You might find a cool question you want to try on people, so for the whole week you only focus on asking that one question.

Maybe you want to try some basic reflective listening techniques, so for a whole month you coach by only doing reflective listening and nothing more.

It might feel repetitive and simple, but THIS is the path to mastery. This is why your first 50 sessions should be free of charge. You’re doing basic training; just running drills to build up a foundation of basic skills. These people are your willing lab-rats.

First session structure

Your first time with someone is usually the most nerve-wracking session. It feels like starting with a blank slate. Once you build a longer term relationship with someone, coaching will fall into natural patterns.

But there’s a simple template I can share with you that works well as a first session structure (and actually could be used for any coaching session).

Start with a basic “Hello, how are you?” warm up.

Then ask them if they’ve had any prior experience being coached before, and if so, what they want you to know about that (e.g. things they didn’t like about how a coach talked to them etc.)

Then set expectations: tell them what you plan to do in this session, and what’s expected of them. I’d generally go with, “We’ll just have an honest conversation about what’s important in your life, and I’ll ask some questions to try help you make progress in that area”. At this point you might want to confirm that this session is free and that there’s no obligation to continue with more coaching afterwards.

Then comes your first proper coaching question: “WHAT is the one specific thing that we need to talk about today to have a positive impact in your life?”

Get them to clearly identify what the problem is, and what it would look like to have this problem solved.

Then explore WHY this is the issue they chose to bring up today. Why is it important to them? Why does this happen to them? What kind of pain does it cause? Why are they stuck on this issue? How would their life be better if they improved it? Challenge any answers that don’t make sense to you, and keep getting them to clarify this issue until it’s crystal clear for both of you.

Then it’s time to explore solutions, the HOW of problem-solving. So you ask: “Is this an awareness problem or a courage problem? In other words, either you don’t know what you need to do differently (awareness), or you do know but you’re too scared to act (courage).”

If the problem is awareness, then the next question is, “How could you find out what you’re supposed to do?”

If it’s a courage problem, the next question is, “What could you do to make moving forward on this less scary, to the point where you’ll actually do something different, even if it’s only a small step?”

End with them clearly committing to the next action they need to take, with measurement units so you can both be sure whether it happened.



If you’d like to get mentoring from me, check out my coaching training program


Avoid the coaching pyramid scheme

As a new coach, you’ll be exceptionally vulnerable to the huge predatory coach-training industry. Your social media feeds and email inbox will inevitably start to fill up with hyped-up offers that promise to make starting a coaching business comfortable, easy, and guaranteed to make ridiculous profits.

Steer clear!!!

Most of it is complete bullshit. Sure, there’s some good stuff in there, but at your level of experience you won’t know the difference.

There’s a common pyramid scheme style training, where people claim to be successful coaches, and promise to coach you on how to be a successful coach like them. You’ll then pay an exorbitant, non-refundable amount to join a faceless community with very little personal time with any coach. There, they will teach you simply how they managed to manipulate you into joining their program, so that you can do it to others.

In other words, they’re coaches training new coaches on how to sell coach-training to new coaches on how to sell coach-training to new coaches!

I hate to break it to you, but a healthy, authentic, sustainable coaching practice doesn’t come from quick-hack marketing manipulation.

You need to provide real value to people through building a good-will audience who sees you as the most helpful person in their life. This takes time, effort, and determination. You can’t just throw $1,997 at the problem and hope it goes away.

Dealing with Imposter Syndrome

As a new coach, you will hopefully experience Imposter Syndrome, meaning you’ll doubt yourself, wonder why anyone should ever listen to you, and fear that you’ll be revealed as a wannabe bullshit artist who can’t coach people for shit.

I say “hopefully” because if you don’t have this fear then you’re probably suffering from delusions of grandiosity. You will suck at the start (compared to what you’ll become).

Coaching is a hell of a profession. You will become literally the most important person in someone’s life, and have a huge impact on their future. You should be nervous!

But we can’t let this stop you, especially if it’s irrational. Just know that you will feel this way even when the evidence shows that things are actually OK.

Rather than trying to avoid feeling this way or pretending you don’t, use it as your motivation to remain humble. Let it push you to look for real evidence of your effectiveness as a coach. Let it worry you into asking for direct feedback, and listening to critiques from reliable sources, and constantly upskilling yourself.

How to measure if you’re a good coach

To avoid becoming psychotic from Imposter Syndrome, you need to measure how well you’re actually doing.

Strangely enough, it’s not your call! It’s your clients who decide how good you are as a coach. And they don’t decide how good you are generally, but just how effective you were with each of them individually.

Often, a session will feel difficult and confusing, and yet the client had a great breakthrough that completely redirects their life. Other times, you’ll feel that it was a really good session, only to discover the next week that your client basically hasn’t changed at all.

Here are the 3 measurements you can use after each session to track your progress (AFTER you’ve done your first 50 sessions of course):

  1. Ask the client what they found helpful, and what they didn’t like, about each session.
  2. Measure the intended behavioural changes in the client – did they happen or not?
  3. Does the client come back for more when invited, or do they go elsewhere instead?

No matter how you feel, if the client liked the session and had an insight that positively improved their behaviour, even just a little, then the coaching was good. If the client says it was worth their time and better than not talking to you, then the coaching was good.

But if they give you all sorts of compliments without improving their behaviour, then it really didn’t do anything to them.

One thing to keep in mind is that some people are uncoachable. Their feedback and results do not apply to your measurement of your coaching ability. Even after 10 years I sometimes accidentally end up in a session with an uncoachable person.

No matter how “bad” your coaching is, a responsible and dedicated self-development enthusiast will turn it into some form of positive impact on their life. So if your client was difficult to talk to, resistant to change, has a history of avoiding challenging things, has a history of not investing in their self-development, and didn’t try to make anything good come from the session, consider it a non-event that doesn’t even get measured.

Naive Inquirer basic methodology

If you’re unsure what to do in a coaching session, there is a simple conversation style that can be used any time, known as the Naive Inquirer. Here it is:

Moving to paid coaching

After you’ve done your 50 first sessions, it’s time to consider whether you want to make this into a career, a business that provides income.

To figure out if you’re “ready” yet, I recommend you first tick off these requirements:

  • You can fill your calendar with 5-10 coaching sessions every week (or you can consistently fill whatever time you have available).
  • You’re loving it, and feel certain that this would be a great long-term job to have if you could just figure out the money side of things.
  • Your clients consistently report having good results from your coaching, as measured by improvements in their behaviour.
  • You are currently coaching 3+ people in a long-term arrangement (i.e. they see you regularly for coaching every week or two).
  • You no longer feel the need to tell people that you’re “just practicing” when you invite them to a session (i.e. instead of asking to practice on them, you just tell them you’d love to coach them).
  • You’ve had people show interest in working further with you without being prompted, and even better, have offered to pay for coaching because it was so beneficial.

If you meet these criteria, I’d say things are looking very promising for you. It’s about this point in time you might want to consider getting coaching or mentoring yourself from a successful coach (not just someone who sells coach-training courses online).

I recommend you start by charging $1 per session.

It’s just a mental thing, to break the money barrier and start getting used to talking with someone about paying for your services. You can start with your current clients and then introduce it to new people.

From there, simply double the price every time you get a new client. Or you can increase it by whatever amount you feel comfortable.

And you keep doing this indefinitely!



If you’d like to get mentoring from me, check out my coaching training program




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