The Do’s and Don’ts of Video Prospecting with Katherine Caldwell

Foreign. Welcome to the live Better Sell Better podcast with your host, Kevin Dorsey of Inside Sales Excellence, the number one Patreon group and YouTube channel for tech sellers and tech sales leaders, where we dive in deep for tactical advice on how to book more meetings, close more deals faster, and lead sales teams to success. But we don't stop there. We also focus on the person in salesperson. We talk about mindset goals, time management, and so much more. So thank you for listening and if you're interested, head on over to patreon.com InsideSalesExCexcellence now with that, grab a notepad, get ready, and let's dive into the good stuff. What up everybody? Welcome to another episode of the live Better Sell Better podcast. This is your host, Kevin Dorsey, AKA kd. And we get to talk about one of my favorite topics today, which is video. I am a firm believer that video is the way, that video is the future. And actually there's more and more data coming out to support this, especially around Gen Z on how they are actually using search engines for video. TikTok, Instagram, YouTube, they actually prefer to learn information via video. But I still don't think as salespeople we leverage it enough. Which is why I'm so excited to have Katherine Caldwell on the show with me today because. Because not only is she a video prospecting coach, but she's also the founder of Cash Consulting where she helps people build out high performing video prospecting and sales processes. So we're gonna dive into video best practices today. Katherine, welcome to the show.

Hey Kevin. Thank you. I'm excited to be here and get tactical.

Let's get into this here. So let's like why video for you? Why video? Let's start there. Like what started you kind of on this, this journey and really diving into video as a sales tool?

Yeah, good question. So I was in the SDR seat for about a year when I got out of college and I didn't have too much guidance in that role. And I had been kind of getting into LinkedIn and hearing that maybe video was a really good option. I didn't have good connect rates on the phone or very good open rates on email. So I started just building my brand and literally sending videos to CROs and VPs of sales all day, every day. And, and the return was instantly there. I was seeing how quickly people would reply. I think it really just came down to the fact that my face was right in front of them and they could hear my voice and quickly get to know me. In 45 seconds.

And so, like, I think what's so interesting about videos? Like, I think everyone can hear what you just said and go, yeah, that makes sense. But yet still, most sales reps don't do it. What. What do you think holds reps back from. From doing this? More like, what do you think that roadblock is for a lot of people?

Yeah, I know exactly what it is. People care way too much about what other people think of them. And every time I do a coaching session with people, I'm shocked at the very minuscule questions I receive about, you know, what should I wear? And is this background okay? And was this two seconds too long? And. And it blows my mind because I'm like, you really think anyone cares about you that much? And so I've always had that attitude of, I don't care what people think about me. Not in a mean way. I'm. I'm a really nice person and I. I care how I'm perceived to a degree, but I don't care about the way people think of me in a judgmental way. I don't have that crippling anxiety about how I'm perceived from the judgmental aspect. So I really think people just have to get out of their head about how they look or how they'll be perceived and just start sending them.

Yeah, we had. We had the phrase end it and send it on our team. End it and send it.

Yeah, stop. Stop rewatching it 10 times and fixing one word. Just send it.

Yeah, no, re. Recording like you. And if you, if you mumble and stumble, then you mumbled and stumbled, and that's what's going to happen. But to send it. So have you always been that way or have there been exercises or things that you've done to help get you to that place? Because I'm sure a lot of people listening would be like, well, yeah, I mean, I wish I felt that way. But like, how do you. Trying to think how to phrase the question? Like, how do you work through that? Or how do you get yourself to a place mentally where you're not worried about what the other person's thinking, or you are more willing to kind of put yourself out there? Like, has that always been a part of you? Or there's been kind of growth in your career in this area?

Yeah, so unfortunately, I think I'm inherently like that. I've just always had that piece of me. But I think a good way to get over it is to start talking to people. And the more people I talk to in the space and in my network, we're all feeling that imposter syndrome or fear of judgment to some degree. And so the more that you hear other people are feeling that way and they're still doing the things. If you have that competitive side to you, it can really motivate you to just get yourself out there.

For sure. For sure. So then let's keep going though, because I actually do want to unpack a little bit about how you present yourself in video. Because I do agree. Right. Like, we don't want to overthink it. We don't whatever. But we also do need to present ourselves in a certain way. So, like, how do you recommend people show up for video? Right. Does lighting matter? Does clothing matter? Like, talk about kind of some video appearance best practices. Because I do think this is important because I don't know if people watch this video, but if I show up, I got my hat on backwards, then I got my hood up and I'm slouched down in a dark room. Probably not the best for video. So what are some of your. Call it, like, appearance best practices for video messages?

Yeah, I think you hit on something important. It's not so much about what you're wearing or how you up here, but it's about your body language. So if you are pulling up a video and you're in a dark room and you're slouching over and you sound like this, like kind of scared, then, yeah, you. You aren't going to get someone to watch more than five seconds. That being said, I don't think it matters if you're wearing a hoodie, if you're in your kitchen or your bedroom. I just think in general, you, you know, look somewhat professional. I mean, I guess you could say, you could look at it and say, would I watch this video type of thing. But I've gotten so many videos from people in studios to basements, to hats on half, hats off, you know, no makeup. Makeup, whatever. But it really comes down to the way the person spoke that kept me watching. Because if I could tell they were nervous or maybe their manager's down their throat, I'm like, I think I'm going to move on. But if I open a video and I'm seeing the body language and I don't know if people watch this, but I'm using my hands, I'm leaning in, I'm smiling, all of that is going to play into how long someone will watch your video.

And that goes into the next two topics I want to talk about, which is how to get the video watched and then how long it should be. Right. So you kind of said the words like, you know, once I open that video. What are things you should be doing though to get the video watched? So, because that is one area that, you know, I've been sending videos for a while now and the click through rate on videos is lower now than it was two years ago. Like 40, 50% click through rates when you first started doing video. And it's come down a bit. But I also think people think just sending a video is enough to get it watched. So what are your tips? I'm like, well, how do I get that video watched? Right? It's like, well, you know, Catherine, like I took the time, I did the things, I recorded it, but no one's watching. What can you do to improve your watch rate on your videos?

Yeah, so if you think of TikTok, the maximum TikTok I think is three minutes. And I don't think anyone watches that full thing either. I think 45 seconds is the sweet spot. I think everyone's pretty familiar with that. No one's gonna watch more than 45 seconds. And when you send a clip, they can instantly see how long it is. So they'll already determine if they're gonna watch it from that. I think my secret sauce to the opener that I hate sharing my secrets, but I also love, it's like love. But the way I think what gets people to watch my whole video is when I open, I say, hey, Kevin, no idea how often you get videos like this, but. And then I go into my, you know, 32 second spiel at that point. And I think when you say, I'm not sure how often you get videos like this, it's already turning wheels for your prospect because they're, they're already thinking about themselves. You've kind of asked them a question without asking one and it's going to get them to start typing. So at that point when you said, I have no idea how often you get videos like this, they're already typing in, hey, Katherine, I never get videos like this. Love the outreach. And they may not even really pay attention to what you say in the last 30 seconds, but it's because you've kind of opened the dialogue. I think that they're going to start responding.

No, I like that because it's also, it's them focused right out the gate. I don't know how often you get messages like this. And putting it backwards, hey, I'm Katherine over at and it's about us. I Like that opener being about them. And then one thing I'll just call out on, like how to get them watched, right. That I have to give a lot of people feedback on is the email has to sell the click. You can't just say, hey, I recorded a video for you. You have to, why should I watch it? What's in there? Right? Like, how do you hook. My curiosity to get me to watch the video is very important in that email of like, hey, like, you know, wanted to share some thoughts with you, thought you might think they were interesting. I learned something from someone in your space that I wanted to share. I saw something on your website that I thought maybe I could give some feedback on. But you have to give them a reason to watch that video. Right. And so now if we get into the video frameworks, you talked about a good opener, right? Being about them, right. Kind of a little bit of a hook, little bit curiosity, what then? Right. So I have a good opener. You said about a 45 second like video. What's the framework then for a good 45 second prospecting video?

Yeah. So like any good message, you have to have a beginning, middle and end and people really overthink the middle portion. So you've opened. Not sure how often you get videos like this, but I'm reaching out because. And then you're going to make an observation, state why what you observed is a problem or could become a problem, and then provide a really quick solution, those three things. And then you can close out and just say, you know, is this worth the conversation or does this sound interesting? But it's that middle piece that people get really confused on. And so what I suggest is actually having it written down somewhere. So when you're going to send a video to a prospect, you can quickly do your research and plug it in there without having to recreate the wheel. So whatever product you're selling, you may have three different problem sets that you solve for. So when you're researching the prospect, you want to find one of those three problems. Like it could be hiring, promotion or a new product launch, something like that. So three triggers to reach out to someone and then easily plug those in. So you'll already know in your head, okay, when they're hiring usually means they're looking to solve this problem. And here's the solution that I have and then close out. So like you said, there's no, you know, my name's Catherine and I work at this company and we do this and we've solved this problem for so many other People, it's really, really concise and to the point. Hey, I'm not sure how often you get videos like this. I noticed this about you. Here's the problem that usually comes with this observation. Here's a way to solve it. Does this sound interesting to you? The end.

It's that simple, right? It's that simple. Right. And I love that. It's just the concise. I do think a lot of messages. It's so funny because still most people don't send video. Right. As a VP of sales, right. I had 150person sales.org. i'm very easy to find on LinkedIn and I would maybe get two video messages a month maybe. But oftentimes too they'd be like two, three minutes long. And I see that I'm like, I don't want to watch this. I don't have time for this. Right. They're way too in depth. So I love the short, concise and to the point. Now let's flip it the other way though. What if they don't watch? Because I think that's where a lot of people get stuck too. It's like, oh, I made this video, I sent it to Katherine, she didn't watch it. Video doesn't work. And that's where their mindset goes. What do you do if someone doesn't watch your video?

Yeah, good question. It worked really well for me to cold call people after I send the video maybe two or three days later and reference the video. So I'm not really a master cold caller, but I would say, you know, hey, this is Catherine, I sent you a video the other day. Does that sound familiar? And then instantly their interest was sparked. And I recall many times where people would say, well, hold on, hold on, let me go to LinkedIn, let me find this video and watch it literally with me on the phone. So just referencing the video really sparks interest. And a lot of the time the reason people aren't responding or watching it is just because they haven't gotten around to it yet.

Yeah.

So yeah, don't let your video go to waste. Definitely leverage it and. And bring it up multiple times.

Yeah. And that's where something that I had my team do after really about the first like six, seven months of our really getting heavy into video was resending the video if they didn't watch. Also, people with videos tend to one and done it. They send it once and they hope that it gets watched and then they never send it again. Versus if I know my open rate is 30%, I need to make sure I'm sending it at least three times to give it the optimal opportunity to get watched. Because the one thing about video that I think people forget all the time is you have to be in the right place to watch it. That's the only drawback with video is I can't watch your video when I'm in a meeting, I can't watch your video if I'm sitting at a stoplight or I'm in like, you know, the coffee shop and it's loud, I have to be somewhere, right, to watch it. And so what will happen? People will get the email, they'll open it like, I can't watch this now. And then it's gone, they forget all about it. Whereas you send it again. And that's the key. Now you were hinting at something too that I think is important and is multi channel. So you said they'll go to LinkedIn to watch it. Where were you sending most of your videos? Was it email? Was it LinkedIn? Like, what, what channels did you use for it?

Yeah, so most of my prospects were on LinkedIn and I prefer to send videos on LinkedIn because then you don't have to even mess with a link. They can just instantly hear the notification and see your face and watch it quickly. That being said, not everyone's Prospects are on LinkedIn. Not all of my prospects are on LinkedIn. So email is a good. But you will want something like Vidyard or Loom to make sure you're not going to spam, making sure that the email still looks cohesive. Because like you said, if you're sending an email, you're probably not just going to send a blank video, you're going to include some kind of text with it. So if you can, LinkedIn is like prime real estate for video. But if you need to move over to email, the number one thing is making sure you're not getting going straight.

To spam and keep going on that. How do I make sure I'm not going straight to spam? Are there any things that. Because that's always the question that people always bring up is like, well, won't videos like, make it worse for deliverability or won't I get caught up in spam? Did you see that on your end at all?

I don't think, I don't think my videos had a tendency to go to spam. I used Vidyard, so guess I'm plugging them right now. But I always use Vidyard because it just gives you that URL Quickly you can screen share and all that. And then people can just click into the URL after kind of seeing that GIF or that clip of you. So I believe it has built in whatever you call it as something built in that helps you not go to spam. But I do think if you were to like record a video straight from your phone or your webcam and try to send it on email and attach a huge file, you are not going to have luck with that.

Yeah, yeah, definitely don't attach y'. All, Please, please, please do not attack the video. That will go south real, real quick. And so let's talk about that thumbnail though, right? So what are things you did in the thumbnail to get more clicks and views? I've heard a whole bunch of different ideas on what to put there. What did you like to have in that thumbnail? Did you make it a GIF or an image? Was it you or their website? Like what was your setup there?

Yeah, so I've never done any, you know, people do the whiteboards and those kind of things with the person's name on it. I've never tried that. I think a simple hand wave and making sure you can add a title in as well. So making sure they understand the video is just for them. So your title could be hey Kevin, thought of you and then it's kind of a GIF of you waving. The other one I have tried is being on their LinkedIn profile. So sharing that on the front page and then you're kind of down in that little bubble. I think that one works pretty well too because they can tell that it's very much so just for them. But I think that's the key is, especially if you're sending a video over email, is making sure the person understands this is not a mass sent email, this is just for you.

Yeah, I love having their LinkedIn. Another one I used to love, especially if I was targeting, you know, some of the director level or below, is having their bosses LinkedIn. Right. So having their VP or having their CEOs LinkedIn pulled up behind me as like, oh wait, like that's my boss. Why? Why do you have my boss in the background? And that pulled people in as well from a curiosity standpoint. So okay, I like it. So so far we have covered why you should be doing video. We've covered how to get it watched, we've covered some of the frameworks, some of the channels. What are some of the other video best practices that you teach or you help people with to get More results from them.

Yeah, that's a huge question. I'm trying to think of questions that people ask me a lot. And like I said, I think people are just overthinking it and just thinking people care more than they do. So I think the best practice though when you're first starting out with video prospecting is don't over commit yourself. So I think a lot of sales managers would be inclined to say, okay, let's start doing 20 videos a day. Each rep needs to do 20, that's 100 a week. And I really think it should start more at 3 to 5. Like let's send 3 to 5. Let's not spend more than an hour on this per day and see what kind of return we're getting. Because the mistake you can make at the beginning is you spend four hours or half of your day making 20 videos and you get zero responses because your script still isn't good. So it's just like, you know, working out. It's a muscle that gets stronger. You know, just like anything in sales, you, you need to practice and repeat to get good at it. So same with cold calling, same with video. If you want to be good at it, just do a little bit every day until you gradually improve and feel confident. Now it takes me 45 minutes to send five videos every day and I try to be really consistent with that. So five a day, 45 minutes and I usually get two responses. So when you've really kind of honed in on your message and you're not spending way too much time and you're being efficient with it, it really pays off. So I would say if you're a sales manager, do not over commit sales reps to sending 20, 30 videos in their first week of video prospecting because it's going to turn out to be a huge waste of time for sure.

So break down that time for me though in terms of efficiency, right? So early on we said, hey, keep them at like 45 seconds, right? But then four 45 second videos in an hour. Where's the rest of the time going? Right? Because the video itself actually isn't that long. Is it like the research, is it figuring out what you're going to send? Like where do you spend that time to make it efficient? Right? Because I think that's where for my team's it would be almost like the other way. It's like they were taking 45 minutes to get three done because they kept re recording or the videos were too long versus what we did try for just like, hey, these are 45, 60 seconds. Like, knock them out. Like, just get these bad boys done over an hour. So, like, where else are you spending that time when you're getting these videos done?

Yeah, good question. Time flies by when you're having fun. That's really what the first thing I think of is. Like, you somehow the time does pass by. So going from. So your enablement tool, so the trigger that it's time to send a video to someone, to going to their LinkedIn, to getting your camera set up, you may do more than one take. I would say out of the five videos I do, I maybe do more than one take for one or two of them. And that's because I will just suddenly become stupid. Like, words aren't coming out. But I do think it's important to send on the first take if you can, even if you do mess up a little bit or forget something. But, yeah, the time can definitely fly by when you're trying to send videos, especially in the beginning. And I actually think 45 minutes for five videos is pretty good. It's less than 10 minutes per video. But it depends, I guess, how much you're personalizing them as well. But I am personally spending time going to their profile, reading through their posts. I might even listen to a clip of a podcast they were featured on, just so I can kind of reference it in the beginning. But, yeah, it just depends how much time you're really taking. And it can really fly by when it comes to video.

Yeah, yeah. And you started to get to it there at the end, right? Obviously, if you're doing, like, super in depth, like, research. So I think that would be my tip, actually, to people listening is I prefer to separate them. Do your research during one hour, do your videos in the other hour. So you can kind of stay in the same flow. Because it is like that task switching of like, hey, finally do my research. I'm listening, I'm finding a clip, then I record a video, and then I go do it again versus I did all my research. Now when I'm sitting down, I'm going, okay, I got Catherine's research pulled up and go, hey, Katherine, it's kd. I was actually just listening to your podcast episode. Da, da da da da Save. Okay, next one. All right, it's Jenny. And then just. That was what worked well for my teams was getting into a video flow of once the. Because you know this, right? A lot of people, too, once they get off of one video, you get distracted with something. Maybe you talk yourself out of that next video, you start to think about, ooh, should I redo it? Versus your research is done, work through it and go. So no, I love this. This is amazing. So, like, whereas we start to wrap on this Kathryn, right? Because it actually flips to the other side of this, right? Because the name of the podcast is Live Better Sell Better. Because I also have this weird idea that if we took better care of ourselves, if we have more energy, if we had more joy and happiness and confidence in life, that the sales would also improve. What would your live better advice be for people listening?

Yeah, I think it's twofold for me. The first one I touched on earlier, stop caring so much what people think about you. Your life will improve when you put yourself out there and you're not worried and you don't have that crippling fear of judgment. And the second thing, and one of my favorite things now, is learning how to spend time alone and enjoy it. So I know that sounds maybe a little bit random on this podcast, but I think the more you can learn to enjoy time with yourself and find ways to fill your time with hobbies or things that fill you up, it's going to be a really important life skill because a lot of people are afraid of that. And yeah, I just think when you enjoy yourself and your own time, you learn new things about yourself and you'll pick up new hobbies and you'll just be better for it.

No, I agree so much. There's like one being okay being alone, but filling that time like with things that bring us joy. There was a post, this was going viral I think now a couple years ago. But the tweet was basically, it's like our generation has forgot about hobbies. Like it's either work side hustle or nothing versus like what happened to like learning how to cook or learning how to knit, learning how to play the guitar. This like. So we've just gotten away from hobbies that give us bit of joy and stimulate our minds in, in a better way. So Catherine, this was phenomenal. Where can people get more of what you're putting out there? Where can they engage with you? Where do you have content like give. Give the people a way to find you here because clearly you know what you're talking about when it comes to video and I want to make sure people can find you.

I appreciate that. I'm all over LinkedIn every day, constantly active. So, Katherine Caldwell on LinkedIn, you can also sign up for a one on one or one of my training sessions. @catchsolutions.com It's K A T C H Solutions dot com.

Awesome. Well, Katherine, I appreciate you. I appreciate the energy and the insights that you brought today. Hopefully we can get more people on the video train because it works. And so I'm sure we'll be in touch again. Thank you so much.

Sounds good. See ya.