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Episode 1: Human or AI?

Can you tell if a sales email or phone call is AI-generated? It may be trickier than you think. Join Will Aitken and Jen Allen-Knuth as they face off in the first challenge of the season. Who will walk away with the first win?

Will Aitken
Jen Allen-Knuth

 Will. It's so good to see you again, buddy. You've ruined my entire week. It's only Monday. I truly, truly have missed you, and since we haven't spoken as much as we did when we worked together, the way I keep up with how you're doing is by going on LinkedIn lunatics and looking for your name. Finding all the great contributions you've made to the sales profession since we last wrapped filming.

So it's like a day hasn't even passed. I actually saw your face on LinkedIn Lin more recently, Jen, for justified reason because, um, and I mean half the hate comments were from me, but I, Jen, I have not missed you. You, but I have missed absolutely decimating you.

Are you guys excited? Cool. Yeah, we are. I'm excited to be with you. Yeah. I have no idea why they thought bringing us back together was a great idea, but we're here. And are you guys ready for your first challenge? Oh, I've been waiting for this. All right. All right. Today's competition is the classic human or ai.

We're gonna show you several sales, emails, calls and text messages, and you have to guess whether it was generated by a human or artificial intelligence. At the end of the six episodes, whoever wins the most of those episodes we're either gonna be donating to Will's charity. Rework Training or Jen's charity.

Many Pause Global Rescue, which he posts about every single weekend. And the loser is gonna be subject to a punishment chosen by you, the viewer. Let's get into it. We're gonna start with the emails. Oh, my first email. Hi, will. I've been following your engaging sales content and notice your emphasis on modern practical coaching methods.

Considering your approach, I believe integrating a streamlined video platform could further amplify your team's effectiveness. Our tool simplifies the creation of personalized video messages, making it easier to connect with prospects and deliver impactful coaching. Would you be open to a brief chat to explore this further?

Best regards your name? 3, 2, 1. Ai, ai, it's not the vibe adds a lot of, uh, what's the word? Adjectives in there. Also, it loves the word streamlined, doesn't it? Email number two. No more Kyle. Jen. There's nothing worse than getting a notification. Kyle is say, tagged you in a post. Imagine preventing his rude but accurate attacks before they happen.

No more online brand damage. No more notification trauma. When can we find time to discuss an affordable retainer model that guarantees no more than three digital attacks per month? Hoping this email finds you right after stepping on a Lego 3, 2, 1. Human. Human. I love pretty much almost all of it. I'll tell you what I don't like no more.

Kyle, as a subject line is just so obviously human. Jen, every week you post these pups that are up for adoption and every week I engage with your posts and I try not to get into the car to adopt them all. I can't thank you enough for the time you take to use this platform to impact something which you're clearly passionate about.

The real reason for my outreach is to see if you might be up for a chat about doing some sponsored work with my firm Smith in an effort to not be the next unicorn. As you suggested this week, replacing big bets on just a few influencers who live and breathe their values. No sponsored posts, no LinkedIn takeovers, but rather a few events where we'd love to give you a platform to educate our contacts and bring in some new eyes.

What do you think? Or the chat. Let me know if you have time in the next week or two and I'll get us connected. 3, 2, 1. Ai. Ai. Wow, we agreed on all three. First one, the answer is ai. First of all, someone saying that you have engaging sales content tells me right off the bat they've never seen your content.

So that is fake personalization and it is overly generic. I will say you have enough. Funny, unique, quirky things that if someone actually looked at your content, they could have had a killer first line. Keep going. This modern, practical coaching methods, I don't even really, yeah, I don't think any, any, any human being would look at what I've done.

That's why I was like, this could have been written by someone who's just never seen my support. Or is it, alright, let's go to the next one. This one was human. I'm gonna go ahead and get Kyle wrote it because he spelled my name wrong in with two Ns, and that guy is such a bad friend that of course he doesn't know how to spell my first name.

The only part I don't like is the parentheses of but accurate. That's how I knew Kyle wrote it. I like. Yeah. And the, and the hope I this email find you after step on Lego or fucking seem a bit personal. Yeah. The third email, this one was human, so, oh, see, I was on the fence because of that subject line.

This I felt was like, good ai, like someone kinda like pre prompting, like maybe some of your content, some of your language, what you talk about, they thought, oh good, AI could pull this off. The real, the thing that made me think this was AI is that. Fricking long ass hyphen on the second last. I felt like they put that in there for you.

I, yeah. That's bait. That's bait. We've been, we've been tricked. All right. I, I will say that even though I thought this was ai, I didn't think it was a bad email. Do you have a guess as to what human or which human wrote this? Oh gosh. Chelsea, it is the, show me, you know me, queen. Oh, no, wait. Now that you said it, now that you said it, it's 'cause that's totally her style of subject line.

Mm-hmm. And that is like, that would've caught my attention 'cause Lady Gva was the name of a dog that I had posted about shit. Sam, I'm sorry.

So end of this first round, you guys are tied. You got the same amount, right in the same amount. Wrong. You guess the same answers on all of them. We're gonna be moving into the call section. Of this something that one of you may be a little bit stronger at, one, a little bit weaker, but you guys are guessing AI or human.

I'll let you listen to both first and then you can make your, uh, guesses at the end. Hey, this is, uh, bill bla, Dino. Uh, may I speak to Greg, please? Uh, can I tell him what the call is regarding? Oh, absolutely. Yeah. Me and Greg have business to discuss. Yeah. I'm confident that I can solve his business needs as it relates to, um, data tools.

Data tools, you say? Yeah, that's right. Um, listen, this is a really important call that could save Dave in your company up to. Five figures in, uh, your data tool costs. So I really appreciate it. If you could just patch me through, can I ask if Greg is expecting this call? Yes. Uh, I sent Greg an email and I see that, uh, he just opened it right before this call, so he's expecting me.

Yeah, Greg is actually going into a meeting right now. Uh, can I take a message? Oh, and when is his meeting over? I don't know. Uh, it's eight 30 now. It, it could be an hour, it could be an hour and a half. I'm not sure. No problem. I just sent him a calendar invite for 10:00 AM when he gets out of his meeting, and I will, uh, see him on that too.

Uh, it's thanks for all your help. Oh my gosh. I need a minute to go take another shower today. That was so gross. Ew. 3, 2, 1. Human. Human.

Alright. And this second call that you're gonna hear is actually a voicemail, so it's a little different. Hi there. This is Rachel from close.com, the CRM platform. Your free trial of close is set to expire in the next few days. Do you have everything you need to come on board with close? If you have questions or need help, call our sales team at plus 1 5 7 3 2 5 0 8 7 3 0 or email us@salesatclose.com.

If you're ready to come on board, all you have to do is choose a plan and add your credit card to keep access to close. Thanks again for trying close. We'd love to keep working with you. By the way, we have a 30 day money back guarantee. So your first month is a low risk way to continue to see value from the product.

3, 2, 1. Ai. Ai. The first call they were talking to ai, right? That, that's, that's, I wanna make sure we're clear on that. Um, so there was a mock call with an AI bot, right? We're just answering whether the per the salesperson is human or AI at this point, simplify it for him. For the first one is human. Who was it?

It was your boy, Todd Klauser. Oh, he marketing. Because that's exactly how someone from marketing perceived sales to be fucking bull. I get it. I get it. Yeah. Why did you guys think that? The voicemail is going to be an ai, I think, 'cause it's, it could, right? Like that is if you are gonna use ai, it was a static one way thing.

It was like just sharing information. It wasn't having a conversation. It was just very, very perfect. Okay. Well I hate to break it to you both, but that was a human no. Fuck no. Were they reading off a script? Maybe that's why it sounded like an ai. Let's move on to the SMS part. I just wanna remind you guys, you guys are tied, you have both gotten only two wrong and all the rest, correct.

So it's, it's really down for all the marbles on this first episode here. Mm-hmm. So, uh, let's get into it. Sales rep p. Hi emoji. You said you'd be finalizing budgets this week. Sounds like the slide deck I shared has what's unique, but if I can add info slides, case studies, just ask 3, 2, 1, AI and then finally, oh, different.

This might be the game changer. Second one, sales rep Sally. Hey Will. Good chatting earlier. Sounds like this could really help your team. Want me to send over that quick demo? Vid we talked about? Might be easier to get the green light. 3, 2, 1. Ai. Oh my god. Wow. Wow. Hey, Jen just pulled a quick example of how another team cut replies down from four days to four hours.

Figured it might help. Want me to shoot it over? Three. Two, one. Human. Human. I just guessed. Three humans. There's no way you did. Three. Humans will do not be fooled by the M Dutch. All three of them are m dutches now. Now. Yeah. People, it's not an for context. That's what I now use my AI biggest clue. And then when you start seeing them, you see them everywhere.

You're so angry. Maybe consider using hyphen like a normal person, right? You're angry every marker. You have to hold down a key on a phone. You have to hold down a key for like two seconds and then select the M dash. Why would someone do that instead of just using a hyphen or a comm? You know, because it's on keyboard.

I don't even know what the shortcut is. I wouldn't know how to make one of those with them. Can we get off the soapbox? How do There's no button. But the hand waving, the waving is what I kind of thought was a bit off the answer to this one. Will you guest AI genu guest human? This was written by a human who wrote it.

Do you know Leslie Nettes? Hey, Leslie. Hey. Why did you guys think the way you thought? I think Will said AI and Jen, you said human on this. I said it because they said vid instead of video, and it sounded like a casual, oh, casual. That's a good pickup that it might make it easier to get the gray green light, not a complete sentence.

So it kind of felt more like a human. The answer to this one is human dam. It. This was written by the one, the only Chelsea Castle. Yes. I'm sorry, what? What? I didn't realize there was more than two people on the planet who used end dashes every bloody way. Did you, did you use AI to start this and then cut it down?

No, I wrote it. You wrote this from scratch. You are telling me you wrote this tat little key to get the m and you, you held down the minus key in the, in the, let me just, you just tell, you are telling me people do this. Am I? Am I am. I feel crazy. And the answer to this one is ai. No. This was the one I was like almost most confident about.

Confidently wrong. Surprising. But you know what's not surprising? You won winning, but all familiar feeling. So you in the audience, I'm gonna speak to you right now, do you, do you feel as M dashes, maybe were inserted because they knew how I feel about M dashes? Perhaps. Maybe the showrunners knew that I don't believe in that key.

Thank you guys for watching another episode of Will versus Jen. We're so happy to be back for season two. We are, and we're just getting started, so can't wait to hang with you guys every week for the next six weeks. You love a comeback story, folks. Now I'm coming back. Hey, no, you're not.

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