Sales Hustle is now Sales Transformation
Sept. 3, 2021

#143 S2 Episode 12 - Social Worker to Helping Sistas Get Close to the Juice with Cherilynn Castleman

On this episode of the Sales Transformation Podcast with Collin Mitchell she's joined with Cherilynn Castleman, executive coach and chief learning officer at Sistas in Sales, managing partner and executive coach for CGI Executive Coaching.

Cherilynn will talk about the importance of building professional relationships to get to the core of one's problem and how to fix it. Not only that, she talks about just why sales can make such an impact with one's life and mindset.

Deep dive with Collin and Cherilynn as they dish out the why, the how, and the opportunity being good in sales brings to the table.

Get your FREE Vidyard account and bonus Video Sales Process Playbook here!


01:14 Cherilynn's start in sales and why she went into the business

03:14 The importance of getting good in sales and why you should be excited about it

07:14 Asking the right questions to get things done and how it improves everything

10:07 How the pandemic has equaled the playing field

17:37 How to support and connect with Cherilynn has invested her time and resources in


02:45 "If you have to had to sell a 16-year-old on why to get in bed and go to school in the morning, you can sell anything to anybody."

08:01 "You know what I'd like to know? I said, what is your wish for your team when it comes to this? What is your wild wish? And what is your fantasy?"

09:10 "The huge learning lesson there is that people are just people, and if you become, you know, a lot of people struggle with going into conversations like that. Or with people at that level where they don't consider themselves as equal. Which is a lack of confidence."

11:39 "The key thing there is, you know, a lot of people in sales tend to think oh I can help everybody or everybody is my client and that's not true. Being able to have those types of conversations to say hey is this a relationship where I can add some value or maybe it's not." 

20:17 "If you criticize people you raise their defensiveness, but if you challenge people you raise their game."

Learn more about Cherilynn in the link below: 

If you enjoy the Sales Transformation Podcast, please subscribe, share, and send us your feedback. Please make sure to rate us and leave a review on Apple. 

Learn more about Collin in the link below: 

Also, you can join our community by checking out If you're a sales professional looking to take your career to greater heights, please visit us at and set a call with Collin and Chris.

Looking to start your own Podcats? Book a FREE strategy call. 🚀


[00:00:00] In the world of sales, you either sink or swim or breakthrough to the next level. My name's Colin Mitchell, and this is sales transformation, a new kind of sales show designed to bring you through the epic life-changing moments of elite sellers. So you can experience your own sales transformation.

[00:00:24] All right. Welcome to another episode of sales transformation, and today's going to be a solo episode with me. What are we going to cover? We're going to talk about how I ran an experiment and how you can book three to five meetings per day on LinkedIn using video. All right. So let's jump right in. I ran a bit of an experiment and I did this for eight weeks across sending 1600.

[00:00:48] Connection request. Okay. And I averaged three to five meetings per day on LinkedIn. Uh, I did this right after vid yard [00:00:59] had released their integration with LinkedIn. I was really excited. I'd been using video card for quite some time. Uh, and once they released the LinkedIn integration, I was super pumped.

[00:01:10] It kind of motivated me into wanting to run this experiment. Uh, and so what I did, and this was right around the time, right after LinkedIn had made a lot of changes with their connection requests and it was trying to figure out. How to really maximize building new relationships on the platform. I also really wanted to debunk the myth that you should never send a video on the first touch.

[00:01:33] I know you've heard it. I've heard it. Many people will say this. I will let you know what happened when I ran this experiment. So, uh, what I did is I broke it into, uh, across eight weeks for four weeks. I sent a connection request with out. Any message. Okay. And once people accepted my connection request, then I would send them a custom video that was around 30 seconds adding something of [00:01:58] value and ask them that they would be open to hopping on a call to discuss that.

[00:02:03] I also like to let folks know about mine. Sales pitch guarantee. You want them to feel safe, to hop on the call and say, yes, you want them to know that you're not going to just pitch, slap them as soon as they get on your zoom. So this is a really important piece. Now you need to find something. How you can add value to people that you're working with, that you're building relationships with me.

[00:02:26] Uh, we're helping folks get booked on podcasts. We're also managing podcasts. So I live, breathe in the podcast world. So I had to find something of value in the podcast world that these people would be interested in talking to me. Uh, like maybe guesting on shows, something like that. Okay. Uh, so find something that works for you in your industry and how you can add value in, please, please, please.

[00:02:49] Not an ebook, not a blog, not something your marketing department created. Think outside the box, be creative. How can you add value to them? [00:02:57] What information can you share with them? Maybe it's you know how SAS companies are growing by X. By doing these couple of things and you have some insights around that that you want to share with them.

[00:03:08] I don't know. I coached somebody through a, that was doing some sort of, I don't remember exactly, but, uh, their business had something to do with compliance, uh, for on networks. And they had a way of showing them where they had vulnerabilities. So he would offer that free assessment. And that's how he booked a ton of meetings following this same sort of philosophy.

[00:03:31] All right, so let's dig in. All right. So after four weeks of sending message, sending connection requests, without a message, I got a 55% acceptance. Okay. So out of sending a hundred connection requests, 55 people accepted that. Now from there, I had a 32% meeting booking rate, meaning 18 people booked a meeting.

[00:03:55] [00:03:56] Okay. Now the following four weeks, I sent a hundred connection requests a day. I got 65% who accepted, so I got 65 new connections. So 10% more excepted by me sending a personalized message. However, here's where it gets. Interesting. Only 18% booked a meeting so far less meetings. With more connections now, 14% less meetings booked is a pretty significant number when you only have a hundred connection requests you can send per week.

[00:04:31] Now, I think here what happened is when the first hut. Is a video. People get a lot more excited to talk to you. If you send a video after you sent text, it's not as significant. So when that first impression is a video, people are much more likely to watch it. They're much more likely to reply. [00:04:55] They're much more likely to raise their hand, to book a meeting.

[00:04:58] Okay. This is what worked for me. Okay. And there's people who sit on different sides of the fence on this. You need to run your own test. There's just too many variables with what you do, who you are, your profile, who you're connecting with, what you're offering them. So run your own experiment. You don't have to do four weeks, maybe it's two weeks each, uh, and figure out what recipe works best for you.

[00:05:24] I'm just sharing the results that I got here. Um, you know, and so with the videos you want to keep them around 30 seconds and make sure you're adding back. Offer up that no sales pitch guarantee. Uh you'll you'll get some great results with that. So get out there, test this, uh, hit me up. Let me know what results you get.

[00:05:45] Uh, happy to share any of my videos or anything with anybody who wants to learn more around how to book three to five meetings per day on LinkedIn. [00:05:54] And if you enjoyed today's episode, please write us a review, share the show with your friends, and then always we are listening for your feedback. Hey, you stuck around that tells me you're serious about your own sales transformation.

[00:06:06] If you're tired of doing things the old way and want to get started in your journey with other people on the same path, head over to sales, cast. community, and crush your numbers on your list. Yeah, it's free sales cast, doc communities send me a DM with your best pitch and mention this ad. And I might even give you free access to our best templates.