15. How to sell like a human: Authentic sales strategies with Caryn Gillen

EPISODE 15 OF WHAT WOULD THEY DO? THE CUSTOMER EXPERIENCE PODCAST FOR SMALL BUSINESS OWNERS

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In this milestone first-ever guest episode, I welcome business coach for coaches, Caryn Gillen, to answer a question many business owners wrestle with:

“What do you do when you love what you do, but you don’t want to sell your work?”

Caryn shares her human-first, non-extractive approach to selling: one that’s authentic, empowering, and centered around helping rather than “extracting” money from your audience.

If the thought of selling makes you cringe or you want to create a more relational (rather than transactional) sales process, this conversation will leave you inspired and ready to reframe how you sell.

What we cover:

Why So Many Business Owners Struggle with Selling – And how to reframe selling from extraction to helping.
What It Means to “Sell Like a Human” – Caryn’s step-by-step approach to making sales feel natural and relational.
Creating a Trust-First Sales Journey – Why setting clear expectations before, during, and after sales calls builds buyer confidence.
How to Serve First & Invite Later – Caryn’s practical strategy for warming up her audience through value-packed events before making any offers.
Why It’s Okay to Have “Groupies” on Your List – And how to release the pressure for everyone to become a buyer.

Soundbites:

Caryn Gillen: “Most of us have been taught that salespeople are bad. They’re going to come after you. They’re going to make you do something you’re uncomfortable with. They’re going to take your money. And I think what we have to note is selling done in that way is extractive. So rather than calling that selling, why don’t we call it extracting? I don’t teach people how to extract money from others. I teach people how to help them. And at the true heart of a great sale, the kind of sale where when we come together, you feel seen, I feel seen, and we make more good in the world because we did. That’s selling. And if you’re not doing it that way, then just stop. Stop what you’re doing. Something’s not working right.”

Caryn Gillen: “I think something that doesn’t come up often in sales, so I want to bring it up on this one in particular, is it’s okay to love people. I think oftentimes we can be afraid of clients or we can be trying to keep people at bay. It’s okay just to let yourself love them. I think one of the things that a sales call process does is the client has to prove to you that they really want to do it.”

More about my guest, Caryn Gillen:

Caryn Gillen helps life coaches build sustainable businesses, businesses that feel like home to them. She lives in Eugene Oregon with her family but Alaska will always be “home” to her.

Download the FREE 5 Ways to Make Coaching Your Marketing Guide here.
Connect with Caryn on Instagram here.

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Episode Transcript:

Nadine Nethery (00:00)

Welcome to this first ever guest episode of What Would They Do? Exciting. This is where I invite an expert in their field to answer your burning customer experience questions. And today’s question goes a little like this. What do you do when you love what you do, but you don’t want to sell your work, which is something I’m sure most of you have struggled with at some point on your business journey.

So to answer today’s question, I’ve invited the amazing Caryn Gillen. Welcome to the show.

Caryn Gillen (00:36)

Thank you, it’s good to be here.

Nadine Nethery (00:38)

So good to finally meet you too. I’ve followed you for a while. We’re in the mix of mind together. So always nice to actually have a conversation and dive deeper into your expertise. Yes. So before we dive in, why don’t you tell us a little bit about what you do, who you serve and how you got here.

Caryn Gillen (00:52)

Yes, so fun.

long and windy road. So I’m a coach at heart and a business owner at heart. grew up in a lot of family businesses. And so for me, it was always like, well, what will the business be? Not would I or would I not be in business? So.

⁓ yeah, I work with a lot of coaches. help coaches get their businesses off the ground and get them sustainable. I also help a lot of coaches recover from doing a lot of wild and crazy online business things that didn’t end up being sustainable for them and help them find their way to something that does feel really good. And I’ve been doing it for about 15 years.

Nadine Nethery (01:44)

Wow, it feels like a little lifetime, I’m sure. But you know what, experience, right? You would have seen so many trends and inverted commas come and go. And as you said, so many, you know, fads that people jumped on thinking it’s going to solve all their problems.

Caryn Gillen (01:46)

Yeah, coach grandma over here.

Yeah, absolutely. know, everything is a shiny object. ⁓ But I think what’s so fun is like what makes you inevitable? That’s always my question for folks.

Nadine Nethery (02:08)

Yeah, right. needs to be sustainable. Totally believe in that. And, know, as a mom, there’s only so many hats you can add to your plate. So you need to find what lights you up and what works for your customers, obviously. So selling, as we said before, you know, really feels so icky and often, you know, cultures don’t get into coaching for the marketing and sales side of things. They really want to, you know, support their customers with, yeah.

Nadine Nethery (02:42)

making progress, but unfortunately selling goes with the territory. So do you have some insights for us, your secret sauce for making selling feel more aligned with, you know, what works for you, as you said, and also, you know, how the customer potentially can organically work out that you’re the right coach for them.

Caryn Gillen (03:00)

So I think the first thing we want to start with is the language around selling, right? Like most of us have been taught that salespeople are bad. They’re going to come after you. They’re going to make you do something you’re uncomfortable with. They’re going to take your money. And I think what we have to note is selling done in that way is extractive. And so rather than calling that selling, why don’t we call it extracting?

I don’t want, I don’t teach people how to extract money from others. I teach people how to help them. And at the, at the true heart of a great sale, the kind of sale where when we come together, you feel seen, I feel seen, and we make more good in the world because we did. That’s selling. And if you’re not doing it that way, then just stop. stop what you’re doing. Something’s not working right.

Nadine Nethery (03:38)

Love that.

Caryn Gillen (04:01)

And we have to open the door to it getting to be that way so that we can be okay doing it. Because none of the people that we work with are looking at other human beings and thinking, how can I get the most money out of them? I can’t. That’s just not what my clients aren’t saying that. Are your clients saying that?

Caryn Gillen (04:24)

Never, I’ve never heard it, right? So, and that would

be that extractive, like I’m gonna, there’s a person, there’s my target, and I’m gonna just suck the life out of them, get as much money as I can. None of us wanna do that. What we wanna do is like, if I can help you, I wanna offer to help you in a way that you can receive it. And I think that’s what selling is, at its best.

Nadine Nethery (04:46)

Love, love the terminology as well, you know, like helping people rather than extracting the most money. And ultimately, I think if you are coming at it from that helping perspective, it really puts your customer front and center of everything as well. So rather than, ⁓ you know, getting that quick sale and pushing your sales agenda onto people, it really lets your customer, your audience decide when they’re ready to work with you, right?

Caryn Gillen (05:18)

Right, and it really lets you just lean back. Like, if you actually want what I have, if you need it, I’ve got it. If you don’t, it’s okay. I can like, tell you where to go. Like, if you’re actually looking for this other thing, I can actually probably introduce you to that person, because we all know so many of each other out here doing great work, right?

Nadine Nethery (05:26)

Love it. It’s that perspective shift from, you know, taking to giving really giving and serving and, ⁓ yeah, just being off help. I think if we all shifted to that mindset a little bit more and, yeah, stopped following the ⁓ gurus if you want to call them that way, you know, where funnel leads into funnel and heart cell. And, you know, if you are on someone’s email list and you’re not actually dropping

Nadine Nethery (06:05)

dollars, you’re not of value. I think ⁓ we all really need to step away from that and treat people like human beings and, ⁓ you know, realize that not everyone is in a position to invest right now. And exactly right. And, you know, some people just love to follow along and be in your orbit as well for a while to suss out whether you’re right for them.

Caryn Gillen (06:07)

Yeah, and that’s like how it’s supposed to work.

Isn’t that fun? Like you can have groupies on your email list. That’s okay.

Nadine Nethery (06:32)

I love a good conversation with people who have never bought from me. I’m not sure they’re ever going to buy from me but just that one-on-one conversation and actually knowing that people are reading my emails and engaging with my content is you know really lights me up as well.

Caryn Gillen (06:42)

Yeah, I think the thing that can get in the way is like, if we’re looking at our email list, like these people need to buy from me, again, that’s extractive. It’s transactional versus relational. And it can be like, I’m going to write this email for the people who do want to buy from me. Everyone else can just follow along. And if it’s

more than they can handle, can leave and that’s okay. Like if they’re done being in this relationship in that way, I’m okay with it. But you still have to, even when those people are there not buying, we still have to sell, relate to the people who are buyers, who we do want to work with and who do want what we have to offer.

Nadine Nethery (07:17)

Yeah. And you know what, people who walked into your list and hang around, um, clearly resonate with what you have to say. So, um, talking about having to sell to your list at some point, how, um, do you approach this in your business? I’m sure, you know, coming from a helping perspective and a helping angle, you have some, some strategies in some way that you like to sell to your audience. Can you share a little bit about that with our listeners?

Caryn Gillen (08:01)

I like the serve first approach.

So the second you get on my email list, I don’t want it to be about me selling you something. ⁓ I like to host events where I teach people things or like right now I’m doing how to sell like a human and it’s really like my entire sales process and I teach people because I want them to know how to sell on a sales call. I teach them how I think about it. I give them the format for how to run a sales call and I answer all the questions that I possibly can about it. And then after that, I say, if you like.

this kind of teaching and you like this kind of support, you’re welcome to join me inside of my membership. So I think about it as invitations, like let’s get to know each other. How can I help you? If you want more of that, come over here. But there is no, I’m not writing a sales letter every single time. At least I don’t try to. Yeah.

Nadine Nethery (08:51)

Yeah. Yeah. Now love the, ⁓

invitation process and really just getting people to put their hand up, ⁓ and show their interest. Do you, how do you approach emailing your list about those open invitations, the events, do you exclude people after a while if they haven’t shown any interest as such in the event? So you keep extending the invite.

Caryn Gillen (09:17)

You know, there are people on my list who were there 10 years ago when I was an intuitive eating coach. And I just keep treating everyone the same, whether they are there for, who even knows why they came on there? Cause I’ve made a bunch of shifts in 15 years, right?

But I always invite everyone. It’s the same way I think about other people’s wallets. Like, I’m not going to decide whether you can afford this or not. That’s your job. I’m also not going to decide whether or not you should come to this or not. That’s also your job. So I’m going to put the invitation out to everybody. Sometimes that means people unsubscribe. I’ll do an opt out of a sales process. So if you’re on my main list and I want to run an entire sales process to something going on, I’ll say, if you don’t want to hear about this anymore, click here on those emails. But I give everyone the chance. And sometimes even the people who are in the program don’t get opted out. And I tell them, I’m leaving you all on so you can see all these emails and see how this process goes, because so many of my clients are doing exactly what I do. Yeah.

Nadine Nethery (10:17)

Yeah, absolutely. And

it would help your, your coaches to see how, you know, your approach works in action. So sometimes it’s that show, don’t tell approach, right? Taking them behind the scenes, taking them along for the journey and yeah, showing what you’re doing in your business. Can you tell me a little bit more about your, sell like a human approach? Because I’m really intrigued, obviously fits really well with the ⁓ concept of this podcast and yeah, making your customer and your audience the center of everything you do.

Caryn Gillen (10:54)

Yeah, so it’s really about how do we focus on the individual who’s showing up for the call? Because if you think about a consultation call, how many times does a grown human show up for one of those in their life? As coaches who hire coaches, we probably do the most out of anybody. But the general population might hire one maybe three coaches in their whole life might have a consultation call with a doctor sometime about something or might go see a car salesman. But I think it’s this really unique opportunity that we get to host and lead this experience for someone who doesn’t do things like this very often.

And we ask really ⁓ intimate questions about their life. We ask them all about their problems. We expect them to share vulnerably with us and tell us all about how their life sucks in these certain areas. We ask them to tell us about like their greatest dreams, hopes, and aspirations, which they don’t probably share with even their partner fully most of the time.

So we’re having this incredibly ⁓ privileged conversation. And a lot of what I’m talking about is like, how do we honor it in that way? How do we hold space for them? How do we make sure that we don’t accidentally do something silly that makes them leave when they’ve just poured their heart out to you when you actually could have helped them?

So it’s really a lot about honoring the human where they are, making sure that you’ve taken care of yourself so that you’re not distracted. Things like never, ever, ever negotiate about the price of your offer in your mind when you’re on a sales call, because all that does is take all the energy away from them and put it on yourself.

You always just say, I’m going to send you a proposal tomorrow, right? You got to have these lines in your back pocket that support you to really stay with them. Because sometimes someone gets on these calls and you’re like, I can help them, but it’s going to be completely different than how I’ve done it before. And that’s okay. But we’re going to need a little time to put together a package, right? Yeah.

Nadine Nethery (12:56)

Yeah. Yeah.

Love that. It’s so true in a coaching capacity. There’s so much trust that comes with opening yourself up to someone, whether it’s, know, life coaching, even business coaching, you know, working out what you’ve been doing wrong the whole time and what those mindset blocks are that have been holding you back. It’s quite confrontational. ⁓ yeah, I love that you teach these strategies that support your cultures to build that trust and give people confidence in ⁓ processes. How do you, do you have any processes around the trust building component? Again, obviously you’re holding space for ⁓ people on those calls. Is there anything around the call that potentially comes after or before even to build that element of trust to even jump on those calls? Yeah.

Caryn Gillen (13:47)

Yeah, the whole journey, like what you do. I

always, I always just think about if somebody pops into my world, I need to grab their hand and I need to lead them where they need to go. Because when we’re new places, we feel unsafe. Even if we don’t realize it, we don’t know what’s going on. We don’t know what we’re supposed to wear. We don’t know what time lunch is. Right. So all of the things like, like I liked your email reminders for this podcast. Like it’s time to get excited. In four hours we have our interview, right? Like things like sending a reminder email that the call is coming.

up at the start of a call. like to say like, like, here’s how this call is going to work. I’m going to ask you a whole bunch of questions. And at the end, you’ll have time to ask questions too. And then together, we’re going to decide if now is the right time. And if I’m the right person for you, like, and really create the space, like they know what’s going to happen and lead them through it. And when you end the call, the same thing I’m going to, I usually end up asking people if they want to think about it, like, well, how, like,

when are you thinking you’re going to have your answer by? And they might say, I need the weekend. I’m like, great. If I haven’t heard from you by Monday at five, I’m going to reach out just to make sure we follow up and circle back and get your answer. Whatever it is, I’m here for it. Yeah.

Nadine Nethery (14:58)

Yeah, I love,

love that love how you’re not only holding space, building trust, also set expectations around every step of the customer journey. Because so often I feel, you know, as business owners, we obviously know our process. know what’s involved, but as he said, so many times you make this appointment and you’re not quite sure what to expect. Even who’s on the other end, you might’ve followed someone along, you know, someone on Instagram for a while been on their email list, but it’s a whole different thing to be on a one-on-one call. So yes, super clever to set the expectations before, during, and after the call as well. And that buy in to get permission to follow up. think that’s important as well.

Caryn Gillen (15:39)

Yeah.

Yeah, because otherwise I found I was like negotiating with my own self about like, God, is it too early? Is it too late? Should I let them contact me? Like anywhere where you’re going to get into your own anxiety about how things should work, you should decide those things ahead of time. And I think one of the greatest tools for me is just thinking through what would I want done for myself and create your journey in a way that it is at least as good as you would want for yourself in that first round. And then think through like,

Well, what if I were someone who was a little more excited or a little more anxious or if I’m someone who has a lot of questions like does this work for the different kinds of decision makers and thinkers that are going to be coming through?

Nadine Nethery (16:24)

Yeah, so clever. Again, anticipating what might come up as an objection or as a hesitation is so, so clever. And also people really expect cultures or business owners to step up and take charge of the project. If I come out to hire you and put you in charge of, you know, my business journey or, you know, my customer experience, your dreams, your life journey, big, it’s a big deal. Like I want to feel like you can take control of the process and you know exactly, I need to know that you have a plan and it’s not just this, you know, piece together ad hoc ⁓ approach. So yeah, love, love, love that. Yeah. You’re so strategic with it and really holding your whole people’s hands at every step of the journey. Yeah. Do you ⁓ have.

Caryn Gillen (16:54)

I need you to know that you have your stuff together. Yeah.

Nadine Nethery (17:20)

before we wrap up because we like our episodes bite-sized. ⁓ Do you have any action steps, some practical things that people who are listening and who are curious to incorporate this human first approach in their sales calls, in their selling strategies that they can implement after this episode?

Caryn Gillen (17:41)

I think something that doesn’t come up often in sales, so I want to bring it up on this one in particular, is it’s okay to love people. I think oftentimes we like, can be afraid of clients or we can be trying to keep people at bay or I don’t know, like it’s okay just to let yourself love them and…

make really sure like, I think one of the things that a sales call process does is the client has to prove to you that they really want to do it. That now is the right time and that they’re the right client for you and you’re the right practitioner for them and whatever you’re doing. Right? So I think like, let yourself love this human being and see them and witness them and whatever’s going on. And then

make sure, like really hold kind of hold them off until you know I can wholeheartedly serve you and by doing that you will have asked enough questions and given them enough opportunity to feel the emotions that they actually need to feel in order to buy and buy without remorse. But we have to have all that curiosity about like

is it the right time, but let me check. Can they really do it right now? Are you sure you want to work with me? Because I hear you say this or this, but maybe some other fit would be better for you. You do want to figure out that they’re going to come in and be successful and that they’re going to feel that, no, I really want this by you going through all those kinds of questions.

Nadine Nethery (19:10)

Yeah, lovely. So it’s such a approach again, just sort of not only vetting that you’re the right fit, but making sure they actually committed enough to get the results, which obviously works in their favor, but also your favor because, you know, there’s no point you and them wasting your time. So yeah, really leading with curiosity, asking enough questions to make sure you’re the right fit is some.

Nadine Nethery (19:39)

Such a good starting point. Awesome. One question I ask all my guests in line with the theme of this podcast. What’s a burning question that you have when it comes to the customer experience and who would you love to answer that question for you?

Caryn Gillen (19:59)

Hmm. I mean, can I have you answer the question?

Nadine Nethery (20:03)

Yeah, I can come up with a future episode and answer your question. Go for it.

Caryn Gillen (20:05)

You’re an expert, right?

So one of the things I’m thinking about all the time, because I started a membership last year, is that, like, how do we keep people tuned in and using the stuff that’s always there for them? Right? So it’s like, OK, this stuff is evergreen. It’s always sitting there. You could get it any day of the week. But how do we help them get to what will really help them in the moment?

Nadine Nethery (20:16)

⁓ yes!

Mmm, so good.

good. Love it. It’s on my list for future episodes and I will ⁓ let you know when it’s out there. I’ve got so many ideas but have to wait for the episodes. Awesome, great question. I love it. ⁓ Before we wrap up, as per usual, I would love to invite listeners. If you are going, my god, I need Nadine or her guest expert like Caryn.

Caryn Gillen (20:39)

Okay, good, I’ll listen.

Perfect.

Nadine Nethery (21:01)

To answer my burning question, you can submit the question in the show notes anonymously, or if you feel like a little shout out on the episode, you can totally drop your business name there. And if you enjoyed this episode, I’d love you to follow, subscribe, share with your besties, anyone who might be remotely interested. ⁓ thanks so much for joining me on the show, Caryn. So lovely to chat and yeah, thanks for tuning in.

Caryn Gillen (21:24)

Thank you for having me.