How can lessons from improv comedy transform video selling in 2025?
And when does humor help or hurt your sales scripts?
Let’s find out.
In this episode of Closing Time.
Thanks for tuning in to Closing Time, the show for go to market Leaders.
I’m Val Riley, head of marketing at Unbounce and Insightly.
Today. I’m joined by Chris Bogue, a sales coach
and author of The Complete Guide to Selling on Video.
Chris, thanks for joining us.
Thanks for having me. Awesome.
So listeners of our show know
that we’ve talked about ways to use video in the sales process.
So let’s use our time to dig a little bit deeper with some actionable tips.
I want to start with why you believe video should be a part of your arsenal.
As a sales person.
Great question.
So why should video be a part of every seller’s arsenal?
Well, because it gives you storytelling gifts that you don’t have access to
in other forms of communication.
So in an ideal world,
we would do all our sales face to face,
right?
An actual human connection, looking someone in the eyes, talking to them.
That’s the best way to do sales, and that’s just not something
most of us have access to.
So video is the next best thing.
And I say that because, you get all these wonderful
storytelling tools that you don’t have in other forms.
So your eye contact,
your tone of voice, visuals on the screen,
these are all different ways you can make yourself understood.
These are different ways to make your message more concise, more, efficient.
You can show people directly what you want.
It’s not like email or text based messages
where sometimes your tone can be misread.
You have 100% control over everything in video.
And I think that’s why sellers are intimidated by it.
It’s a lot to think about.
So instead of trying to understand it, they just kind of revert to
what works, which is the email and the phone.
But there’s so much that’s out of your control there.
And video is the ultimate in sales.
We say control what you can control in video, you can control everything.
So, Chris, you have a side gig,
a side hustle, and an alt alternate ego.
An alter ego?
I’m not sure what it would be called, but, where you do a lot in comedy.
And so I see a lot of comedic aspects in your LinkedIn feed,
but you don’t necessarily bring that into your video selling.
Can you talk about why that is?
Right.
So this is very important.
And this is actually a thing that people misunderstand about me.
The comedy that I do is for the newsfeed.
So, we could do a whole episode about LinkedIn video content,
but my philosophy is basically like when you go into your news
feed, you want to be taken somewhere you’ve never been before.
So go nuts with the creativity.
You want to be funny?. You want to be interesting.
You want to be surprising.
You want to be shocking.
That’s what the newsfeed is for.
People want to be taken to someplace they’ve never seen before.
They want to be surprised.. They want to laugh.
That’s the newsfeed.
When you’re doing sales, you are in someone’s work inbox.
You’re in their Gmail.
And the rules are different there.
Especially because, let’s be honest, you probably weren’t invited to their inbox.
Right?
So, I don’t instruct people to lead with jokes
in their outreach
because your job is not to tell jokes like it is out in the newsfeed
when you’re doing sales, when you are sending an email unsolicited
to a very important person at a very big company that can get you
a large chunk of the way to your quota.
Your job is to talk to them straight.
You’ve got a very limited amount of time to build trust.
So your job is to be relevant, to be professional, to be, direct.
To be clear with what you want.
And, opening up with
your standup routine can get in the way of that.
So I’m going to venture a guess and say you’re the first guest
on Closing Time that ever has received training at Second City.
So let’s keep on this path and let me ask you, are there
other lessons from improv that people can bring into the sales profession?
Yeah.
Here’s one that you’re not going to like.
If you’re a sales trainer, don’t ask questions.
Whoa.
Mind blown. Right.
How do you do sales without asking questions?
Well, you do ask questions, but you have to remember
that questions can be a selfish thing.
if you and I start an improv scene
and I’m like, hey, mom, what are we doing today?
I’ve just put the entire onus of the scene on you,
as opposed to what we teach in improv is we teach to give gifts.
All right.
So, if I come up and I say, mom,. I got you a cake.
German chocolate, your favorite.
I’ve already given you all these wonderful gifts.
I’ve set the scene.. We know what day it is.
We know what relationship we have. It’s not even just a cake.
It’s a German chocolate cake. There’s so many gifts
in that scene.
And so often sellers
go into, like, the first thing they do is they’re like, this is a cold call.
Can I have 30s?
And then it’s like, you get your 30s and then they just start interrogating you
and they wonder why buyers are just like, all right, hey,
let’s not let’s not just just email me and whatever.
And if you start with a couple of gifts,
I mean, I don’t mean gifts, like send a bottle of wine to them.
I mean, come with a strong point of view,
come with a strong statement.
You know, if I call someone,
I probably done a little bit of homework on them.
And remember, we all do.
We all sell different things.
I am training people on video.
So one of the useful tools for me
is do I understand what this person’s tech stack is?
You can look that up.
There are places you can look that up. LinkedIn Sales Navigator and other ones.
But if I go in there and the person has the right job
title and I’m like, Val,. I wanted to reach out to you.
I know you adopted Sendspark recently.
I see your team has been starting to put the videos out.
I wanted to run one thing by you because I’m serving my network.
You got a second?
I gave you gifts.
I know who you are.. You know what your team does?
I know what tool you’re using.
I’ve established why it’s relevant.
I’ve given you five different gifts to understand.
Who is this conversation?. What are we talking about?
Why should I care?
I’ve given you all those things.
And again, this is context building.
Now I can drop the question.
I do feel like sometimes a discovery call can feel like an interrogation.
So I’m picking up on what you’re saying. There.
So in video, though, so you don’t have the benefit
of having that other person that you’re doing the scene with, right?
So if you’re preparing a video that you’re going to send,
are there any lessons from improv there where you,
where really the camera is the other person, so to speak?
Yeah.
So this is a great question.
So there’s another golden rule of improv
which is don’t talk about people that aren’t in the scene.
If you and I start a scene and I’m like, well mom’s really mad at us
because you did this and that and blah, blah, blah, we got to go apologize to mom.
That’s a weak scene.
It’s a stronger scene.
If I come up to you and I go, mom,
I know I disappointed you. I’m sorry.
Please forgive me.
Now, we’re not talking about something that’s not on screen.
We are talking about our relationship.
And instantly the audience can look at us and go, I recognize this.
I know what’s going on in this scene.. I know who these people are.
I recognize this, so I tell people, maybe you’re the only one on camera.
This is not a one person scene.
This is a two person scene,
and you are not the main character.
You are the supporting character.
That camera is the main character.
You got to treat this
like a video about them, not a video about you.
And it starts with writing the word down: you.
I literally take a post-it note.
I write the word you, you, you, you and I reach out.
I send the video.. Hey Val, I’ve been reaching out.
I’ve been listening to your podcast.
I’ve been hearing what you say on LinkedIn.
I know one of your goals is this I know
one of your goals is that I know you value this.
And that’s why. I want to ask you a question.
It’s like I’ve said you seven times,
you know, so, if you’re watching it,
you’re not thinking, wow, look at this man’s funny jokes.
I’m going to continue to be entertained by him.
You’re thinking, what’s this guy going to say about me?
Okay, you know who I am.
You know, my podcast is what do you have to say?
And we forget that.
We think because it’s just us here, we got to put on a show.
We got to make it about us. It’s not you are.
You know, this this device that we all have
when you are on somebody’s phone, you are closer to them than 99.9%
of people in their life will ever be you are inches away from their face
and they are the main character of their story.
Everybody is the main character
in their own story, so you have to treat them like that.
And again, this goes back to why we don’t open with jokes.
We’re the support player. I agree.
the intimacy of the phone is really something I hadn’t thought of.
And so I think that’s a cool, interesting perspective.
So let’s switch gears.
Tell me what you see in video sales that you think is a big miss.
A big
miss that I see in video selling is too much.
Focus on the screen share.
So there’s a reason why
every video technology has screen share technology.
I’m a Sendspark guy.
I’m an advisor for Sendspark.
Sendspark has wonderful abilities for you to showcase what’s on your screen.
But think about the mindset of the person who’s watching your video.
As someone I get, I probably get more videos than the average person
because I’m like the video guy and nobody sends me videos, you know?
But when I see when I when it opens up and it’s 95% my website
and it’s a tiny little person in the screen, I’m like,
okay, this person is just going to tell me that my website is bad
and that, you know,. I got to pay $15,000 for a new one.
I’ll check that out when I feel like it, you know?
Whereas, like, again, you got to remember, like,
this is a video about them.
So if I’m talking about you and what you value
and what I notice about you and the things you said, that’s much more attention
grabbing than me, you know, showing you your website, which, you know what
that looks like, you know, it’s not to say don’t ever use screenshot.
I use screenshots all the time. I use it my code outreach.
I use it, for mid pipeline stuff, but,
I, you know, I know. I keep going back to improv analogies.
Forgive me, but it’s it’s, you know, me, but
it’s this idea of, like, in improv, there’s nothing.
You start with nothing.
You get a word from the audience, and you can always
tell a beginner improviser because the second the scene starts,
they start talking, they start going, blabbermouth, blabbermouth, blabbermouth,
and then they cling to the chair.
There’s a chair on stage.
They gotta use the chair,
and they got to sit on the chair, and they got to move the chair around.
It’s because the chair is something real.
And in a
situation where there’s nothing real yet you cling to the only thing that’s real.
And I find that, people will use it as a crutch
sometimes where it’s like they’re afraid of starting that connection.
They’re afraid of actually talking to the prospect directly.
So they’re like, I’m
just gonna turn on the screen, share and talk about the screen share.
It’s too long. It’s not personal enough.
It’s not filmed with that you kind of mindset.
And then they’re totally baffled.
Once the other person doesn’t watch it, they’re like, well, I,
I haven’t made my background, their website.
Why wouldn’t they watch it?
And it’s like they’re missing that part where you’re building that context
and you’re creating that human connection and you’re saying,
hey, I see you as a human being. Care about this.
I as a human being notice that.
Here’s why I noticed you, and here’s something I’m wondering about you,
and here’s the simple framework you can follow if you want to respond to this.
So if you’re making a video and you’re including
perhaps a point of view that you might have on this company,
maybe it’s a cold call Where would you establish that point of view?
What resources would you use?
Or are you just taking shots in the dark?
Oh, I never take shots in the dark.
If you want to find a company’s point of view, it is incredibly easy.
It’s never been easier to find a company’s point of view.
So I’ll start by saying marketing.
You know that department that salespeople love making fun of?
That’s where their point of view is.
Yeah, I make fun of them too.
But if you’re doing sales, marketing is a goldmine.
Press releases, social media posts,
LinkedIn posts, earnings statements,
company mission statements and values
like these are very easy to find.
You know, there are AI tools that will curate this stuff for you,
but honestly, you don’t have to dig that deep to find it.
And again,. I always try to think about like,
they’re not watching this video because they are so enamored by me.
They’re watching this video because of what their boss said
in this week’s all hands meeting.
So what was that?
You know, these value statements and these mission statements
that may seem corny if you’re, you know, at the bottom rung of the ladder.
Well, there’s a reason why you’re founder talks
about that in literally every single call.
There’s a reason why they go back to that mission.
There’s a reason why they put out all these marketing materials about that.
That’s how they want people to perceive their organization.
So I start there, maybe they’re like, hey, we’re really focused on diversity
and we’re really focused on, you know, creating a diverse workforce.
I can lead with that.
I’ll say, hey, I know that right now, diversity is a priority for you.
I can see you’re working really hard to make sure
that you’re creating a diverse workforce that’s prepared for the future. So
the question I had is,
how are you sharing those voices and what role is video playing on that?
Is video being used to share everybody’s voices?
Because I find even organizations that want to do that have trouble.
It’s hard to get started with video.
You’re wondering about how long should it be?
Where should I put the lights, what should I do for the thumbnail?
And and that’s why. I wanted to speak with you, you know,
and then and then I segue to my here’s what I want from you here.
Here’s why I think we should talk.
But it’s never for my reasons.
It’s always for their reasons.
There might be differing opinions on this, Chris.
But if you are producing a video for a prospect,
should you be striving for perfection?
Or is it quantity that’s most important?
Like how many takes, is it just one and done,
or do you do multiple takes like what’s your opinion there?
The first take is usually the best,
however
I am.
I differ from some video trainers in that
I actually think you should be striving for perfection.
And by that I mean like,
are you actually looking at your videos with a critical eye
and wondering to yourself, could I do this better?
Could I present this message in a way
that is more welcoming to my prospect?
And, there’s a lot of different ways to do that.
I will say, here’s one thing. I never hear video trainers
talk about that. I am very about coaching with my clients,
pay attention to your ending.
Pay attention to what your face is doing at the end of the video.
There’s so many prospecting, you know, sales
people on video who are like, they got their cheesy,
whiteboard and they’re like, hey, Val,. I want to talk to you about da da da da
da da da da da.
And then they get to the call to action at the end, and all the confidence
drains out of their face and they get tongue tied.
And it’s like, this is the moment where you’re telling the person
what you want them to do.
And all that confidence just disappeared from your voice.
And now you’re speaking in up tones, which, if anybody doesn’t know
what an up tone is, an up tone is when you’re not asking a question.
But it sounds like a question.
So if you’re not too busy, maybe you could think about
maybe I could send over a calendar and make for five minutes,
if that’s okay with you.
And that doesn’t work as well as being like, let me know if you want a chat.
I would love to chat with you on zoom next week.
If you’re open to it, send me a thumbs up.
I’ll send you a calendar invite if you want to choose a time
or if you’re not interested, that’s fine to let me know either way in
no matter what. Thanks for watching.
Thanks for watching.
There’s a down note that ends on a period.
That is something I’m confident in.
If you are a sales person who is doing video prospecting
and you think you’re doing, you think you’re pretty good,
but you’re not getting the results you want to see, go watch your last
5 or 10 videos and check to see how that ending went.
And I find this all the time.
Usually when I am reshooting a video, it’s because the ending
was not nearly as strong as the beginning, Well,
in the spirit of having a strong ending, we’re going to wrap up.
Chris, thanks so much for joining us and closing time today.
Where can folks find you if they want to engage more with your content?
if people want to find me,
the easiest thing they can do is go to LinkedIn and ring the bell.
So, if you look up. Chris Bogue on LinkedIn, you will find me.
I do lots of content about selling on video.
I also do funny sketch comedy, not in your inbox, but in your news feed.
So go look up Chris Bogue on LinkedIn.
If you go to ChrisBogue.io, you can find my course,
The Complete Guide to Selling on Video.
That’s 2.5 hours of in-depth
training on video prospecting on camera performance, script
writing, outbound for LinkedIn, outbound for Gmail, editing follow ups.
We cover all of that.
Or you can find me on Spotify.
Listen to Chris Sells His Soul.. That’s my show.
You can subscribe on there conversations
about selling and, doing video
in this modern world where everybody’s got to be able to sell themselves.
So, yeah, lots of places to find me.
Sounds good. Chris.
Thanks to all of you for tuning in to Closing Time.
Remember, you can sign up for the Closing Time
newsletter and get the show delivered right to your inbox.
We’ll see you next week. Take care.
