The Art Of Transitioning From Serving To Selling

By Toku

After reflecting on my own experience of enrollment, talking to a myriad of coaches about their challenges, and spending hours thinking and studying the process of enrollment itself. I’ve found there are 3 places coaches typically lose clients. While these places are subtle and at the edges of where we often put our attention, mastery of these 3 weak points can lead a coach to vastly improve their chances in creating clients in a skillful and honorable way.  

Weak Point 1 – The Invitation: If you’re struggling to get people into coaching conversations with you, it’s usually for two simple reasons.

  • You’re inviting in a way that doesn’t feel authentic and comes off as either pushy or needy, usually because you’re asking too soon, too late, or in a forced way.
  • You’re inviting in a way that garners a yes but fails to create a powerful context for what you’re offering which can lead to problems later on.

Point 2 – The Create/Propose Transition: As you practice connecting with more people, inviting them into coaching, and serving them powerfully you’ll often end up talking to more prospects, but you might still struggle to get into proposals or struggle to sign clients because the transition into your proposal wasn’t powerful enough. As a result your prospects either thank you for the session and disappear, you wait so long they end up losing interest, or you end up proposing something but so much power and leadership is lost in the transition that you continue to struggle sign clients even though you’re coaching is powerful.

Point 3 – Coaching Beyond Yes and No: For new and experienced coaches alike this is perhaps the richest area of growth. This is where most prospects are lost and not just because your prices are too high, or you failed to serve them powerfully enough.  

The reason so many coaches struggle with this is that it’s the failure point for all other stages of the enrollment process. It’s like knees on a runner. While many runners suffer knee injuries, the problem is rarely the knees. Usually it’s the way their foot strikes the ground, the tightness in their hips or hamstrings, or the imbalances in their form. But since your knees are the point of greatest impact when you run this is where the failure occur.

When you lose clients at the Yes/No phase of enrollment it’s either because they’ve leaked power/leadership at some point earlier on OR they have stepped out of service and into self absorbed doubt concern or victim mindsets. Which is why I want in this post I want to focus on the transition from Serving to Proposing, because it’s a place we often overlook and also because it’s the easiest way place to make improvements.

The Art and Illusion Of Transitioning From Serving To Selling

PART 1 – The first 75% (AKA  Shift Happens . . . or Does It?)  

The biggest mistake I’ve seen coaches make as they transition between serving and selling is imagining there’s anything different between these two stages. So much so that all of the other problems that arise are in direct relationship to this illusion.

As a coach you love to serve people and to nurture their growth. And in general as coaches we feel some aversion to selling or monetization of what we do. There’s lot’s of reasons for this.

  • We understand that money is a poor analogy for what we do
  • We have a negative view of sales or sales people habituated by our usually very negative experiences of being sold to
  • We don’t want to sully the sacredness of our work
  • We feel guilty that we have to ask them to pay
  • We feel guilty about getting paid for something that we love to do
  • We feel some shame around needing or have money

The list goes on and on. You show me a coach and I’ll show you someone with a money story. It’s one reason why the scarcity mindset is so prevalent in an industry of people who work so hard at helping others escape their scarcity mindsets.

And it’s why this illusion is so important. If you think about the process of enrollment as Serving and then Selling you’re screwed. Because you’ll always have this ethereal gate in your mind of NOW I’M COACHING and NOW I’M SELLING. This gate will trigger shame, fear, doubt, resistance, awkwardness and make transitioning hard. It of course will be made even worse by the fact that almost ALL of our clients will have a similar reaction to this illusory transition. And it’s why it’s so important to overcome.

There are two ways to disrupt this illusion –

  1. Stop Thinking of Selling As Different From Coaching – I like to think about it like a one versus a two armed hug. You don’t need to step away to add an extra arm. You just add the arm. It’s still the same hug. Sure you might not give everyone a two armed hug.
  • Maybe you don’t want to hug them and maybe they don’t want to hug you.
  • Maybe they have a bad memory of getting hugged.
  • Maybe they’re claustrophobic.  
  • Maybe their father was killed by a boa constrictor.


But whatever the case it’s no big deal if it’s one arm or two it’s still the same hug. AND if you’re selling with honor it can still be masterful coaching, it’s still of service. You don’t serve them powerfully so you can sell them. It’s not serve them first, sell to them next. It’s ALL SERVICE . . . if you do it artfully and with honor. And the way to do that is to remember to always be serving, to always be coaching, even as you sell, to always hold the intention of drawing out of them the most powerful YES or the most powerful NO they’ve ever said in their lives.

This takes time and practice, but it all begins with letting go of the way we separate selling and coaching.

  1. Feel the Guilt of Getting What You Want – No matter what you do to let go of this illusion it’s likely you’ll still feel the shift. Even if you clean your own stuff up around money, sales, or whatever. You’ll still sense a shift in your prospect. As soon as they get a notice they might be getting sold to either their well defined enrollment defenses or excitement arise and your guilt will likely get triggered.

You can spend years trying not to feel guilty about this but in my opinion this is a waste of time. Enrollment always has two faces.

One of pure service where everything you do from the connecting with a prospect to the price of your service, to the way you process their payment is in powerful service of the client. From this place there is no coach and client, the money is just a symbol, and there’s nothing to feel guilty about. And if you read most coaching books/blogs/whatever they’ll try to get you to focus on this. Which is true.

But the other side is also true. There’s a side where you need to pay rent and this will help you do that. There’s a side where the client works for money and then gives you the thing that represents their time and effort. It’s transactional and in some ways zero sum.

You don’t both win. You have the money and they no longer do. YES of course you can help them make more money, but in the moment of the transaction. You’ve ‘won’ and they’ve ‘lost’. They gave and we took. There’s an imbalance and we all feel this.  

We can do a lot of fancy dancing around this, but this side is always true. It’s a truth that sits at the center of our capitalistic society and is what drives commerce. It’s cold and sometimes dark, but it’s also drive incredible creativity and advancement. It’s a balancing act that serves our well being but it also produces guilt.

Because this side will always exist some element of guilt will usually exist in enrollment. It may be very small and we may be able to move it aside with a simple letting go and stepping into the first perspective. But until we become fully enlightened, we must deal with the guilt that arises as a natural and normal part of who we are.

If we don’t we either:

  • Sabotage ourselves so we don’t have to feel it.
  • Try to create innocence by over explaining, talking in circles, over justifying, or setting ourselves up as superior to cancel out the effects of the guilt.

Some of these lead to bad enrollment and creaky transitions. Others of these lead to arrogant coaches who are total ass hats. But it doesn’t have to be this way. You can always choose to just feel the guilt of getting what you want, and here’s how:

Getting Good With The Guilt Of Selling

Every time you feel guilt during the enrollment process. Take a deep breath and choose it. Feel it in your body. Accept the guilt. Realize that it’s there to keep you honest and humble and in belonging with the world. Don’t try to make it go away or destroy it. Simply be with it.

Take a deep breath and say ok to it. That’s it. Rinse and repeat. If you do this you can stop running from it and you can stop having it run your enrollment conversations as well.

If re willing to feel the guilt of getting what you want and you can learn to stop thinking about the transition as a transition at all. You’ll  be 75% of the way to making more artful transitions and enrolling with great honor. Of course then there’s the other 25% which is all about the mechanics and techniques of the transition but we’ll get to that in Part 2.

For now just go and try this out and see how it feels. See what changes when you practice not feeling the gap between coaching and selling. See what happens when you notice the guilt of wanting to sell your coaching and choose to feel it.

These steps may seem incredibly simple but it’s often the simplest things that lead to the most powerful results.

In my last post I talked about improving your transitions from serving to selling by letting go of the illusion between these two phases in enrollment and by choosing the guilt of getting what you want.

In this post I’m going to break down some of the mechanics and techniques of transitioning between serving and selling so that you can move more easily between coaching prospective clients powerfully and proposing to them with excellence.

Great coaches enroll amazing clients. Download my free masterclass on how to enroll clients with skill and honor.

Apply Now

To start the application process, fill in your full name and email and you’ll be taken to the application page.

Free Masterclass

Great coaches enroll amazing clients.

Download my free masterclass on how to enroll clients with skill and honor.