Give us 10 minutes and we'll tell you why Storytelling's broken

25 Sep 2025 · 11 min · 4 chapters

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In short

The episode argues that “storytelling” in sales/marketing is broken because it’s usually about the seller’s story, not the prospect’s.

Guests

Jack Frimson (sales trainer/coach; runs role-play and emphasizes “depth” and therapy-style discovery) and Zach Thompson (co-host; discusses heuristics and how to elicit examples).

Key claims

sales teams often chase meetings and logic (“tech stack,” “value prop”) instead of understanding the prospect’s world via emotion; shallow questioning leads to poor-fit meetings.

Notable examples

a cold-call role play where the prospect says they’re “fine” but admits one-in-three leads are poor fit; the host pushes for a “recent pain” example, noting availability/heuristics bias—if someone can’t recall examples, it reveals gaps and deeper issues.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Understanding Sales Through Storytelling

0:45 to 3:08

Discussion on the importance of storytelling in sales and understanding the prospect's perspective.

Role Play: Cold Call Scenario

3:08 to 6:14

A role play demonstration of how to effectively engage a prospect through storytelling.

“Oh, Jack, I've got a proposition for you if you're not against hearing me out.”

The Art of Depth in Conversations

6:14 to 9:23

Exploration of the significance of depth in sales conversations and understanding client pain points.

“So if you ask me to think of a recent time and I can't, and you really pushed me on it and I can't, the chances are it might not exist.”

Bizarre YouTube Challenge

9:23 to 10:44

Hosts invite listeners to leave quirky comments on their YouTube video with a chance to win prizes.

“And if you see one that you think's funny, like up it.”
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Transcript

Automatic transcript. May contain errors.

0:01Jack Frimston:If it isn't, my little guy who always looks a little bit under the weather, even though he's not.

0:06Zac Thompson:Do you know what I'm feeling? I don't know if it's this haircut or the style, but...

0:10Jack Frimston:Do you know what I'm feeling?

0:10Zac Thompson:Do you know what I'm feeling? Go on, then. I'm feeling like an 80s sitcom dad. If you're just listening to this, you won't get it, but when I looked in the camera there, I was like, ooh, 80s sitcom dad, do you know what I mean?

0:24Jack Frimston:You're like Jonathan Depp.

0:27Zac Thompson:is that the understudy for johnny depp i imagine right come on with you no mate you do what have

0:34Jack Frimston:you got what have you got for me no you look good man you look good right so i've been thinking about stories right you see a lot of this on linkedin don't you like it's all about the story story sell get your story across i think famously stephen bartlett was a believer in no outbound sales function just tell your story over and over again now if we took our school of selling like a therapist suddenly this falls apart doesn't it because it's not about you so to the majority yes i agree if you're out there marketing get your story out that should all be about your story what's unique and different blah blah blah about you but to the other person when you're selling like a therapist it suddenly becomes how do i understand their story and people might be like well yeah i do that i do that already don't they but when i say that to you and you think about most sales people that you speak with or most sales teams that you help do you think that really getting to understand the prospect story no no absolutely not and i love what you've done

1:42Zac Thompson:there with the inversion of like it's it's the other way around flip the mirror because that's what it is marketing is how do i make people come to me and then sales is people are here with me i'm gonna listen to you it's all about you it's all about your world and i think that so many sales people some people call it crab walking we call it like not going deep enough with the pneumatic drill but but i think it's that path you have two paths in sales of logic and emotion and i think a lot of people go down the logic wealth what are you using what's your current tech stack what does this look like what do you it's like why do they need to solve this problem let me truly understand your world for anybody that's ever been in therapy the therapist pretty much knows your world inside out they know your family friends names it's not just a case of call them contender b do you know what i mean they know they know he's called danny whatever

2:40Jack Frimston:so i think if we think of like traditional selling right i'm gonna move my notepad over here nice because we're gonna do a role play in a minute um if i think about traditional selling it would be i get over my value prop my my pitch if you will here's how i can help you do you want that help should we schedule some time right and that's a problem that's happened in sales that the trend has been just get meetings in the diary and now the counter trend is becoming how do i get quality meetings in the diary so i thought if we're thinking about how to get people to sell their story, I thought we could do a little role play of a cold call if we take it for Wham, and I'm really going to focus on trying to get to understand your story.

3:24Jack Frimston:Okay.

3:25Zac Thompson:I'm ready to tell my story.

3:27Jack Frimston:Okay.

3:29Zac Thompson:That's not Jack, is it? Yeah, Jack speaking. Who's this?

3:33Jack Frimston:Oh, Jack, I've got a proposition for you if you're not against hearing me out.

3:37Zac Thompson:Yeah, go on then.

3:39Jack Frimston:well i get brought in by ambitious business owners who are struggling when it comes to the new business side of things so often what they're noticing is there's not enough meetings in the diary so the pipeline's looking a little bit bleak or they are meeting people but it's the wrong types of people and they're trapped in these never-ending deal cycles that they don't seem to come to anything now i've got a feeling you're going to tell me neither of those problems apply and you couldn't possibly take on another new client uh i wouldn't say that i think there's a

4:07Zac Thompson:I think every business probably faces those at some point, but I think we're all right for now.

4:16Jack Frimston:Okay, you're all right. Well, can I push my luck and keep going? I've got a couple more things I'd want to ask.

4:21Zac Thompson:Yeah, yeah, go on.

4:23Jack Frimston:Okay, so you said you're okay. You recognize both of those two things. I suppose if you had to pick if it was a volume issue, not enough meetings in the diary, or actually we're just not meeting the right type of person, what would you say it is?

4:36Zac Thompson:it's probably it is probably the quality piece like sitting with the right kinds of people because there's no point if you've got 10 meetings but none of them are the right people they don't have the budget or they don't have a need for you then then it's completely pointless so i'd probably say like yeah it is more on that that quality side of things okay so let's stick on

4:58Jack Frimston:that there so that quality side of things when's the the last time you noticed that as an issue

5:05Zac Thompson:um the last time i'd probably say that there was a there was a point probably two weeks ago where one of my team sat with somebody and when they came in through the website they were presenting the form they filled out presenting all the symptoms but actually when we got in there they they weren't a fit they were they they didn't really have an understanding of what they needed and I think that's probably like where it fell down.

5:35Jack Frimston:What do you think it is that made you think of that one straight away?

5:38Zac Thompson:That was quite like an easy through line of they came to the website, they looked promising on paper, and actually the feeling afterwards was quite disappointing.

5:48Jack Frimston:Okay. So it sounds like that doesn't happen a lot.

5:53Zac Thompson:What one in – I mean, you get stuff that you don't even sit with, gmails uh disqualify straight away but but i'd probably say like one in three like if i could just sit with the ones every time you save time and money every day okay okay um okay pause right

6:14Jack Frimston:so you see how there what what i did was what jack crimson you were going deeper baby now this is the ultimate feedback that we give i think to our own sales team and other people's team is it's a complete lack of depth so it's not that you're i mean there's obviously an argument to make like always try and do more where possible and people like boast about like i have a fucking million conversations today and got two meetings and whatever but this idea of depth is a total lost art in sales because if you notice the way that call went and jack was being very kind to me it was it kind of started it we're all right like i wouldn't say those things apply i was and then and then i got him on to if you had to pick one out of the two which one would it be and he picks one give me an example of of that then becomes me actually trying to get to a recent story now why is it important jack that i get you on a real live time when you felt the pain of the

7:17Zac Thompson:problem i'm glad that you asked that thompson because if you didn't ask i was actually going to explain it anyway so this has made the conversation flow really really nicely um flowed um so it's all to do with the heuristics bias okay so we think about heuristics is when we have information readily available to us and that that's what what kind of confirms what what what we're feeling. So if you ask me to think of a recent time and I can't, and you really pushed me on it and I can't, the chances are it might not exist. Okay. So if I said to you, you know what, Zach, we've been friends for four years now.

7:55Zac Thompson:You're really, really doing my head in. Okay. You've been doing my head in recently. The last two weeks you've been awful and you go, okay, can you give me an example of what I've done in the last two weeks? That's been awful. I go, yeah. I pause and I think I go I can't think of something for me it doesn't necessarily mean it's the truth because you are an awful human being but for me it would showcase well actually there might be something deeper going on here and actually you're not being awful if I can't think of readily available examples so it's the same in the prospect story the more examples the more stories you can think of the more likely it is to cement the information that they're thinking exactly exactly so that's one example

8:41Jack Frimston:there's lots of other ways of getting there but it's really important to not just diagnose but get the other person to paint a picture of when this shows up how are you noticing it if you i mean it's the old analogy isn't it but the doctor scenario of what are the symptoms what happens when you spot them like the doctor is sat there getting you to tell a bit of a story of when does this come up so they can spot sometimes the holes in the story or spot like oh that's triggered by that that's really interesting so if you think about this like we're talking about it from a therapy angle but doctors do it lawyers probably do it to try and find holes in a case you solicit probably does it with also so it's happening all over the place people are always trying to get you to tell the story behind the pain so salespeople at home that's what we're gonna employ you to do find the story behind the pain wow this week's task jack frimston this week's

9:33Zac Thompson:task jack frimson yes it is what i'm asking people to do this week you know what really really makes me smile okay go on youtube comments right when i wake up in the morning i'll look and i say oh you've got a new you've got a new comment and some of them are the most bizarre comments so all i'm asking you to do is if you've watched this video leave the most bizarre comment that you can it can be weird it can say something about my shirt it can say something about zach's hair be weird be

10:06Jack Frimston:wonderful be witty what's wrong with my hair nothing's wrong with it what's wrong with my shirt

10:12Zac Thompson:but oh give us give us something weird and wonderful the three funniest ones we'll we'll get together we'll have a vote in session the three funniest ones we're going to give gift card tax-free, V-A-T-E-3 of£350 each. And if you see one that you think's funny, like up it. Vote it. Do an upper. Upper's not down. Do an upper. I've been Jack Frimson.

10:42Jack Frimston:I've been Zach Thompson.

10:43Zac Thompson:I've been Green Screen. Thank you guys. See you soon.

From the publisher

Everyone in sales and marketing is shouting “tell your story” — but what if that advice is completely backwards?

In this video, Jack Frimston and Zac Thompson break down why the storytelling hype has gone too far, and why the real power in sales comes from understanding the prospect’s story — not forcing yours.

Here’s what you’ll learn in the next 10 minutes:
✅ Why the “just tell your story” trend is broken
✅ The difference between marketing stories vs. sales conversations
✅ How to flip the mirror and uncover your prospect’s story
✅ A live cold-call role play showing depth over surface pitches
✅ The psychology behind why recent examples matter (heuristics bias)
✅ How to use story-driven questioning to find the real pain

If you’re tired of surface-level pitches and want to learn how to sell like a therapist — this is for you.

📖 Want to go deeper? Grab our book Sales Is Therapy here: https://amzn.to/3L0mD2h

And don’t forget: drop the weirdest YouTube comment you can think of. The funniest three get a £50 gift card each.

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