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Using Humor to Transform Sales and Create Authentic Connections with Ray Engan
Episode 14225th November 2025 • Collaborators UNITE Podcast • Chuck Anderson
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In this episode of the Collaborators Unite podcast, host Chuck Anderson speaks with sales expert Ray Engan about the importance of connection in sales, the misconceptions surrounding the sales process, and how to effectively communicate with potential clients. Ray shares his unique background in stand-up comedy and how it has influenced his approach to sales, emphasizing the need for warmth, humor, and authenticity in conversations. The discussion also covers practical strategies for overcoming sales challenges and building meaningful relationships with clients.

GUEST BIO:

Ray Engan is a former stand-up comedian turned top-performing sales leader who blends humor, human psychology, and communication mastery to help entrepreneurs sell with confidence and authenticity. After writing for The Tonight Show and becoming the #1 salesperson in his company in just his second month, Ray reverse-engineered the hidden people-skills behind his success and now teaches coaches, speakers, and transformational leaders how to create engaging conversations that convert. His signature approach makes selling fun, natural, and deeply connected—proving that charisma, humor, and trust are learnable skills anyone can use to grow their business.


CHAPTERS:

00:00 Introduction to Impactful Sales

01:51 Ray Engan's Unique Journey

03:36 The Importance of Connection in Sales

06:16 Common Sales Challenges and Misconceptions

08:59 Transforming Conversations into Clients

11:51 The Role of Humor and Body Language

15:19 Building Trust and Authenticity

17:56 Removing Roadblocks in Sales

20:25 Final Thoughts and Advice


LINKS:

Ray offers access to his Friday Mastermind, a weekly live coaching experience where you bring your real-world challenges—copy, outreach, sales conversations, follow-ups, roadblocks—and Ray helps you quickly remove the barriers between you and more clients. Members get Ray’s hands-on support, creative outreach strategies, humor-infused communication tools, and real-time feedback.

Normally $2,000 for a year, but listeners of Chuck Anderson’s podcast receive three full months free.

Connect with Ray and claim your 3-month complimentary access here: https://www.linkedin.com/in/rayengan  (via Ray’s LinkedIn—look for his newsletter Making Selling Fun and the mastermind link directly below his profile content)

Was this episode helpful?

Please leave us a review and subscribe to the show to be notified of future episodes.

Until next time, keep moving forward!

Chuck Anderson,

Affiliate Management Expert + Investor + Mentor

https://AffiliateManagementExpert.com/


Transcripts

Speaker:

Hello everybody and welcome back.

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This is the Collaborators Unite podcast.

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Chuck Anderson here, your host.

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And this is the show where we help you make a bigger positive impact in the lives of your

clients and in your communities and even the world with the work that you do while also

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being profitable.

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And so when we talk to people, we know that they wanna make a big impact.

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They also need to be profitable so that can be sustainable.

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So I like to bring on guests who can help you with that on that mission.

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And this topic of sales comes up a lot.

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And especially for those of us in the transformational industry or coaches, there's

various attitudes towards sales.

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I don't like to sell.

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if you've ever felt like that,

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This is a really good conversation to uh lean into, because we're gonna give you some

ideas that maybe you haven't heard before, or give you kind of some ideas of what you can

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do differently.

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So today my guest is Ray Engen.

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uh Ray, welcome to the show.

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Thanks, Chuck.

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It's great to be here.

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I'm so excited to talk about this.

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This is a lot of fun.

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Yeah, exactly.

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Well, we're just barely scratching the surface so far and I'm excited to dive into this

with you.

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you've got really, I'm excited for you to share this with our audience, because you have

such an interesting background and a mix of skills that really lend itself to this.

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And this whole idea of helping people with their sales.

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but you actually have a really interesting background as well.

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So tell everybody your story uh and a little bit more about you, who you are, and the work

that you do, and we'll go from there.

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I did stand-up comedy for 15 years and wrote for The Tonight Show a little bit.

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I left that and I went into sales.

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I started out and I joined this one company and the second month I was there I was the

number one salesperson in the country.

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I became a manager, did that whole thing and everywhere I went sales went up.

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I thought, wow, I must be the luckiest guy on the planet to go to the right places where

have these great salespeople.

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And I thought, wait a second, this is different companies, different products, different

things.

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What do I do that makes this happen?

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So I reverse engineered it.

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And I realized that what I was doing was the part of stand up that you don't think about

and you don't see.

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I was teaching that to my staff.

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And what that is, like I could walk into Rock Springs, Wyoming with have five big old

bikers playing pool for a couple hundred bucks a game and.

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Five minutes the show starts, I have to get him to stop playing pool and turn around and

watch my show and enjoy that process.

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And I could do that like that was Tuesday.

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And I thought, what is that process?

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And I figured it out.

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And then I said, well, who would buy this?

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I don't know where to try this.

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So I went to a seminar company, sold my soul to a seminar company to try it out.

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I taught their leadership classes with my content.

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And I learned a lot that way and I should have stopped after about a year because I proved

it worked.

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I proved people wanted to hear it.

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uh I didn't.

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It took COVID to shut me down because I couldn't go across the country anymore.

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And I started working with entrepreneurs and I created these things that they were doing

so well.

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They were in my eyes, my God, they're so smart.

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But the same thing happened all the time.

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They'd come up and they said, well, I have

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uh I have a great product, a genius idea, and I build great rapport.

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What's the problem?

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Well, no one calls me, nobody returns my emails.

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And what we have here, I think with COVID and the emergence of AI, we've lost as a

society, five years of people skills.

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And if you look at it, what every business has been trying to do since the dawn of time, I

call it the action framework, they attract.

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then they connect, then they transform, and they do that with individuals, organizations,

and networks, right?

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Well, in order to transform, and you can attract, that connection is the missing piece.

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And that's where it goes wrong.

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And we can get people to look at us, but if they don't feel like it's connected.

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And there's so many little things we do to put the wall of stranger in front of you.

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ah The first simplest thing that you can do with people you meet,

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When we go into a business meeting, you want to stay at a level playing field.

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You don't want to be up or down, looking up or down at these people.

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But we'll always say things like, oh, thank you so much for having me here.

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What an honor it is to present my company to yours.

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Well, the two things that build charisma, the two things charisma is built on, is warmth

and competence.

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And if you can show you're warm right away and that you're competent, they will...

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I'm listening to this guy.

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But if I'm sucking up to you right off the bat, who wants to hire that?

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You hire people that are good, right?

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uh But the key thing with strangers, if you don't know somebody, do not start a

conversation with a question.

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Start with a statement.

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You know why?

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Because that's what your friends do.

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Your friends always come up and they'll say, yeah, hey, I love that, yes, you can, or the

background, you know.

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Love the color of the walls back there.

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Your friends never said, good morning, how are you today?

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And I learned that in my first job, because it was in retail.

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And in retail, during Christmas season especially, you go in, can I help you?

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No, no, I'm just looking.

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Two seconds later, they're, where is that person?

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have questions now.

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And I noticed that, and I walked up to somebody, I just said, I'll let you buy that.

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And what they did is they laughed, go, oh, I bet you will.

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But while you're here, let me ask you this.

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Nothing good happens outside of a conversation.

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So what we're trying to do when we sell is show what we can do, not tell what we can do,

but show what we can do.

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And you have to have a conversation to do that to connect.

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You can't do it through email.

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You can't do it through anything else.

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But somewhere a conversation has.

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And I work with coaches and speakers.

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So uh they are people that have to have conversations.

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You don't sell your coaching program.

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through an email unless somebody trusts you so much and they won't trust you until they've

talked to you.

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Amazing.

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I want to dive deeper into some of this stuff, but before we do, I just really want to

anchor a little bit for our audience in terms of what you're hearing from the people that

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you work with.

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So when they come to you and they have questions or they're describing their challenges,

like, Ray, I'm struggling to sell or, you know, you know, I'm not getting enough clients

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or whatever it is.

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What are you hearing from them?

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What are the words?

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that they're using to describe their experience.

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A couple ones that come up all the time.

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I don't want to bother people too much.

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I don't want to be salesy.

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I don't want to feel icky.

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It doesn't feel authentic to me.

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And so they have this view of a salesperson as if they're walking onto a used car lot.

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What's it going to take to put you in the car today?

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If you're really going to the car today, I'll you really good deal.

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Every other day of year, I'm going to screw you.

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But today, you get to screw me.

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Come on.

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I've always wanted to be a...

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car salesman for one day so I can say all the things that they say.

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Yeah.

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And what we try and do is like, well, no, I don't know where to find these sales.

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don't know.

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And they're everywhere and we don't see them.

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um One of the things that comedians do is they see the logic of every word instead of the

logic of the big idea.

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And so where are the people who are going to buy my product?

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Well,

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You have them already.

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And if you take things like, uh if you go through your uh CRM that has your calendar in

it, it keeps a record of everybody you've ever scheduled a Zoom call with.

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Well, you're going to find 20 people in there that, my God, that fell through the cracks.

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my God, that fell through the cracks.

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uh Your LinkedIn comments, all these people that they know who you are, that's a warm

conversation.

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We overthink it.

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We'll send this long email letter uh to rekindling your old relationships with people.

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ah Who did you used to work with that you loved working with that you smiled when you

thought you talked to them?

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Well, guess what?

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Send them this one email.

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Take off all the logos.

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Take off everything official and just put Chuck.

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It's been too long.

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Let's catch up.

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Ray.

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PS, your Zoom or mine?

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That's what a friend sends.

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Because if you act as if you're a friend, they treat you as if you are.

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And what I do is I'm always thinking of ideas.

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oh I want to have, the people that you love the most as clients, you love to talk to.

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And they'd like to help you.

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And you say, I'm trying this thing out.

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ah What do you think of this?

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And just present what you have and let them talk about what it is.

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And you say, well, great.

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If you know anybody that needs this,

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Send them to me.

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Well, I want that.

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That's what happens.

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That's where 90 % of my sales come from is that simple conversation.

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Hey, I'm doing this.

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What do you think of it?

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And I either get information that changes it, makes it better, or I get uh a client out of

it.

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And it's that conversation where they go, we celebrate getting clients around here.

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And for those of you listening, there were balloons going up around my screen.

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uh

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And those kind of things, they're so simple, so easy.

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uh All these things that we have sitting there, you can create things where you find out

who's interested in you and who you've talked to before.

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uh You can use AI to scrub your Zoom chats if you're giving a webinar.

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And you say, well, who here is having problems doing this?

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Oh, I see Chuck Anderson's having problems doing that.

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And then

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You could forget that Chuck said he had problems doing that.

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And then you find who the people are that really resonated with what you're saying.

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And you just send them an email.

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Whoops, forgot to tell you something yesterday.

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And give them a chance to remove a roadblock.

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uh We think about selling as if it's this horrible game we play.

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And what you have to look at, you have to reframe it.

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You have to reframe it to tame it.

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uh

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What coaches do, what speakers do is we transform people.

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And if you are a true transformer and you know that what you do makes your clients lives

better and easier, you're changing the world for them.

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we look at, my, I don't want to force them to buy something from me.

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Well, if you change the world and you don't give them the opportunity to do that, you're

being selfish.

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That, because I had that same, I had those very same thoughts.

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And the second I realized that, my God, everybody I hang around since I've been 12 years

old, their sales have gone up.

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Little League candy sales.

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I was actually one of the first people that I know of, because I heard it a year later,

but I did it for, I told my friends, uh two daughters that were selling Girl Scout cookies

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to go, I'm in California, so.

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We have these cannabis stores, right?

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I said, sell it right outside the store.

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And they led their whole region in sales by doing that.

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it's the way in, finding the way in.

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And there's always a way you can get somebody interested in a program you're doing.

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One of my mentors is a guy named David Newman from Do It Marketing.

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The best thing he ever said about me is that Ray could stand in line at the grocery store

and make a $5,000 sale.

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And I haven't done that yet, but I have made $3,500 at karaoke night.

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And a guy came to fix one of my appliances, and I wound up giving him a friends and family

laser coaching package.

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So I made about $2,500 by having him clean my dryer lint.

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Yeah

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It's starting the conversation and trust plus congruent, irresistible offer equals a sale.

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And curiosity creates conversation and connection creates clients.

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And these little things you do to make people smile when they talk to you.

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uh And that's another thing about if you're not using humor in your conversations with

potential clients,

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you're missing out because it is instant rapport, likeability, and trust.

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And you can see that uh physiologically.

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And here's another thing to back up that questions versus statement.

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If I walked up to you on the street, and we didn't know each other, and I said, uh can I

ask you a question?

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You would pull back, drop your chin a little bit, go, OK.

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Because there's instant resistance.

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If I reframe that question as a statement, it's an, have the craziest question.

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What is it?

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And the things that make people lean in, curiosity, relevance, and specificity.

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And uh if you can do that, people will listen to you.

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Now, humor, there's a book called Humor Seriously.

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And if you want to have the business facts about what humor does for you,

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They took the same person giving the same presentation to a bunch of different people.

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And they added one line at the end.

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So here's how low the bar is.

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At the end of his presentation, he just said one thing, and I'll throw in my pet frog.

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That sold 30 % more dollars.

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I believe it's 30 % more dollars.

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That is a simple little statement that created a smile.

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What happens when you laugh?

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So when a stranger creeps you out, you pull back.

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When you laugh, this is the most vulnerable area of your body, your neck is.

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And we hide it from strangers.

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That's hardwired us from caveman days.

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We do this because we trust you.

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So it's built in.

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everything that's good in life happens after the laughter.

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So if you can control the laughter, you can control what's good in life.

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And you don't even have to be

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funny to do that.

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You just have to have a sense of humor.

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You can let uh cartoons do it for you and emails.

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You can do funny little cat videos.

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That's what they were invented for.

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uh It's such a comfort building thing.

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uh Another simple thing that I learned from Zoom, there's not a lot of people, there's not

great presenters live are not necessarily great presenters on Zoom.

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And one of the things that people forget about on podcasts, your hands show trust and

confidence.

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And if we keep them down here, which a lot of people do on Zoom, I've learned to talk with

my hands higher.

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But if you see nothing in my hands, open palms, that's trust, subconsciously that's trust.

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Your thumbs are confidence.

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And there's a reason that politicians do this, not because they have that in their DNA.

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but because some handlers told them that your thumbs are a show of truth.

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If you put your hands in your pocket when you speak, it's totally, uh it shows lack of

confidence.

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And the key thing when you speak, your body language is like the inner, uh it's your inner

thoughts, it's the closed captioning for your inner thoughts.

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And you can't turn that closed captioning off.

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So your inner thoughts have to match your outer words.

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And if they don't, there's something off between what you're saying and how you're acting

that you don't know that they're picking up on.

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And it's that congruence between that.

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That's what authenticity is.

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If you can show that your enthusiasm, if you can't tell, I like this stuff.

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So I get enthusiastic talking about it.

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And a lot of times there's no way for anybody to get another breath in.

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But it's these things come across to people and it's fabulous.

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It makes people lean into you.

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uh They're little things, little simple things to work on.

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And that's the real core of making connection, talking to people that you love to talk to,

finding those people you already know that really trust you and going back to them and

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find out where they'd send you.

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Sometimes it's right to them.

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Other times it's to other people.

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And that's something we don't do.

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We feel like we're bothering people and uh emails,

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We send a lot of those.

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Guess what?

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The numbers on those are amazing.

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80 % are never opened.

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80%.

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And think about all the stuff you get.

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There's a lot of stuff in my inbox just sitting there that's been sitting there for too

long.

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um And then when we do send an email, and I have a thing I give out called the 26-second

email.

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That's how long people that love you read your email.

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And even if they don't,

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Even if they love you, they still will skim.

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That's about a hundred words.

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Yet we send these long sales emails to strangers.

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Click gone.

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Click gone.

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ah It's a fast, quick thing that just hits home and it resonates.

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Your subject line should be no more than six words because that's what fits on a phone.

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And it should have curiosity, relevance, or specificity.

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uh

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One of the simplest ways to notice what's going to work is what worked on you.

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I got an email from Target, I believe.

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And it said, whoops, sent you the wrong email.

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I said, they did?

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Maybe they sent me coupons I wasn't supposed to get, right?

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And I opened it up.

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It was just their ad.

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So the email itself was very, it let me down.

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uh But that one moment where I got excited, go, OK, why did I do that?

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And how can I use that?

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And so when I do a speaking engagement, what I do is I do the speaking engagement and the

next day I send out to the list, whoops, forgot to tell you something last night.

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And that gets opened like 85 % of the time, because it creates that curiosity.

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ah The more specific you are, the better.

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These things.

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And talk to people as if they're your friends.

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They'll consider you as a friend right away.

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It's such a simple concept.

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ah Nothing is easy in life, you know, but it's all teachable.

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Humor is teachable.

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Charisma is teachable.

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Sales is teachable.

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Just like accounting.

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It's a process.

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It's a step-by-step process.

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And there's ways.

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What we really want to do is remove the roadblock that are stopping people from buying us.

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And that's what I try and do.

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try to, everything that somebody brings me,

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And I do this Friday mastermind with a group of people.

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They'll bring me the problems and I remove the roadblocks that are getting in the way from

people buying from them.

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uh What's an example for that?

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uh If you have the place to click for what you're trying to sell on the third page of your

website versus right there where you can see it.

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uh Take these things out of the way.

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You have to let people know what you do as a

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When we present to people, it's not important what you do, it's important what they get,

right?

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That's a basic sales premise.

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Show them, don't sell them the product, sell them the result.

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And when you do that, uh I always ask my customers, what did I do for you?

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Because what I think I'm doing versus what they say they're getting are two different

thoughts.

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And guess which one isn't important?

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My thought of what I'm doing.

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uh One of the things that became a mantra for me, I went to a client and said, so what do

I do for you?

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She said, that's easy.

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Everything I give you, you clarify it, simplify it, and amplify it.

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I'm like, that describes everything I do, but I've never used those words.

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Well, what you want as a client to look at you, especially as a coach, uh you want to

look.

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at a client and say something and have them go, oh my goodness, this person gets me.

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And you do that by using their language, their exact language.

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So those are great conversation to have.

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It sparks.

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The more you have a conversation with people, the more things happen.

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Nothing good happens outside of a conversation.

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ah Those are key things.

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And how do you start those?

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Ask questions?

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No.

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Make statements?

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Yes.

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I almost screwed up and backed it up there.

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you

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I know you teach this every week in your group and it's kind of the work that you do.

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First of all, great, great content and I know we're just scratching the surface and all of

the ideas and ways to connect.

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uh Tell everybody um how they can connect with you and learn more from you.

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And so what are the ways that we can do that?

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One of the fastest, easiest way to connect with me is on LinkedIn, or Ray Engin uh on

LinkedIn.

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I've got a newsletter called Making Selling Fun, which is absolutely free, and it's got

all these tips here in different ways I've used it.

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uh I always have a section in there on things you can steal and use today.

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uh So I've got a lot of these tips in there.

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The other thing is I do a mastermind every Friday, and...

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What it is is exactly what I say.

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You bring me problems.

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You bring me something you're working on.

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It could be, it could be copy.

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It could be a way to get a hold of somebody.

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It could be the situation.

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uh And, and uh like I have one guy come in and he's trying to reach soap manufacturers.

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And I said, well, do you have kids?

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He goes, yeah, I'm great.

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How old are they?

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Four, five and seven, I think.

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He goes, great.

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What I want you to do is get postcards with crayons and have them draw on the crayon, draw

soap bubbles, and then just put a message on the back.

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uh Will you please contact my daddy?

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He loves your soap.

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And he sent him out and he sent him out to 10 people.

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Nine of them contacted him back.

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One didn't.

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It was the one he wanted.

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And I said, he said, well, how do I get that one person to do it?

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Well, take your kid again, make a video that said, why won't you write back to my daddy

and send it to him?

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And if that person doesn't contact you back, you don't want him as a client because he's

not human, right?

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So.

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It's finding unusual ways, becoming an acceptable usual notice in this area.

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And it's something for a year, the mastermind is $2,000.

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But anybody that comes there from Chuck, you get three free months in it.

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So that's like, I don't even know how many there are weeks and three months, but let's

call it 12.

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So you got 12 weeks of the mastermind.

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It's Fridays, 11 o'clock Pacific.

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And if you go to the link, which will be down below here,

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hop on in and we'll get you started in there.

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Bring me a roadblock, bring me a problem, bring me something there.

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The other people in there will be chatting about it.

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I have had weeks where it winds up being me and you.

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And that's great because then we sit there for an hour and we talk and solve as many

problems as we can in an hour and work on these things.

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And if can't tell, I can talk without taking a breath.

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oh bring your own oxygen because I'll need it.

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Love it.

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Well, to make it really easy for you to connect with Ray, we've put all of Ray's links

just beneath this video.

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So just look beneath the video.

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All of the links are there.

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First of all, Ray, very, very generous.

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I love that.

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And I highly recommend that you listening in right now takes Ray up on that offer.

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That's super generous.

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:

And by the way, if you're not watching this on video, if you're listening on a podcast,

just open up your phone.

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and the software that you're on right now, all the links are there as well.

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um Ray, this is great.

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And I know that we've just scratched the surface.

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Sales is a big topic.

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There's lots of things that people are concerned about.

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At the end of the day, it is about connection.

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It is about building relationships.

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And it's really about communicating.

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um So as we wrap up here,

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Any final words of wisdom or piece of advice?

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Well, I think what hurts entrepreneurs, there's three, I call it the entrepreneurial

conundrum.

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There's three things you need to have to be able to sell yourself to other people.

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uh The first is belief in your native genius.

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And you have to believe that what you do is great.

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You have to believe that what you do makes other people's lives better and easier by using

it.

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And you also have to believe that your skill,

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is something that's so unique that you can charge unique pricing for.

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So that's something I had problems with when I started.

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I just talk.

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Who would buy that?

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So that's one.

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The second is you have to have uh communication skills.

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And you have to have multiple types of communication skills.

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You have to be good virtually, good one-on-one, good one-to-many.

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You have to be good written, uh good email, good on video.

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All these things, you have to have them all.

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You have to understand how to use them all.

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And the third thing you need are people skills.

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And if you have uh confidence, humor, you can influence, and you have charisma, that's the

whole package in people skills.

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You can survive with two out of those three.

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But if you have all three, that's the sweet spot where you're working with people that you

wanna work with, not people that you hope come to you.

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uh

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And the key, like I didn't have the belief in my native genius at first.

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And if you have somebody that has good people skills and good communication skills, what

happens to those people is you're the best salesperson for someone else's company.

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And that's what I was.

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I failed twice on my own uh until I figured that out.

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What I realized is that I was a great sales manager for other people.

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I was a horrible sales manager for myself.

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I wasn't doing the simple little things I needed to do and I failed twice on the way to

where I am today.

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yeah, me make, learn from my mistakes.

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That's what I wanna do.

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:

Yeah, so to sum up your advice to people in 30 seconds in a sound bite, what would you say

to

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create comfortable conversations, you'll create clients.

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uh Curiosity plus connection equals clients.

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Number one thing to do if you're going to change anything and walk away with anything,

when you go to a stranger, do not ask a question or take the question and transform it

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into a statement.

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And you will have a cleaner, softer way in.

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They'll start with a smile.

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They'll lean in and talk to you.

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Those are the simplest things that you can do that probably have a huge impact on your

next conversation.

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Great, great advice and awesome words to end this episode by.

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uh Ray, thank you.

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uh So much knowledge, so much information, so much experience.

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I think anyone who is listening in, who could use a boost of bringing new energy and new

life to their sales conversations can learn a lot from you.

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And uh so I highly encourage you all.

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:

Go and click the links beneath this video.

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:

Connect with Ray.

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:

Take Ray uh up on his offer to have you uh complimentary access to his program for three

months, and you will have that connection that you can use to learn more and to improve

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:

your skills.

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:

And so I want you to remember that as you go out today, I want you...

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:

to take an action that you heard us here talk about today.

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Maybe it's something we reminded you of.

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Maybe it's a follow-up that you've forgotten to do, that sales is in the follow-up, and

also go and connect with Ray as well.

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:

And remember that your big mission is possible and worth it, and you might just be one

collaboration away from a big breakthrough that will help you to make the big impact that

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:

you wanna make.

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:

Maybe Ray is that person to collaborate with.

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:

And whatever it is, there's no obstacle too big to be overcome.

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:

uh Keep moving forward everybody, and we will see you on the next one.

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:

Thank you.

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