jefe

🍁

Do you/would you wear a hat on a video call with a prospect?

So I was on the other side of a prospect call getting pitched, which is still a bit of a strange feeling.

The AE on the other end was wearing a baseball hat. I know WFH is casual, and it really didn't bother me at all, but it got me thinking.

This is something I'd never do - it just wouldn't feel right, and I've got a glorious mane - but given how much can be defined as 'acceptable work attire' has changed over the last 18 months or so, I'm curious what everyone else thinks!

Thoughts on hats during external meetings?

Do you/would you wear a hat on a video call with a prospect?

Attached poll

Yea - why not?! Nope - unprofessional I'm bald, gimme a break Other - adding a comment

*Voting in this poll no longer yields commission.

☑️ Qualification Calls

🏡 WFH

🦠 COVID-19

100 comments

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hh456

Celebrated Contributor

sales

Hell yeah. A vest, a bow tie, and a fedora. Give it a lil tip of the cap as we enter the call and I open by telling the prospect how men don't know how to treat ladies anymore and then I show them my tattoo that says VENI VEDI VICI on my forearm and how it's a great conversation piece when I approach tables with my IPA. Throw some random card tricks at them and then laugh when they ask for my help when they spent their nights & weekends drinking and chasing tail while I studied the blade.

No, probably wouldn't wear a hat on a sales call.

jefe

Arsonist

🍁

Rarely do you disappoint, Grizzle.

hh456

Celebrated Contributor

sales

that's bc we haven't fucked yet. ask mi esposa

CuriousFox

WR Officer

🦊

I appreciate the honesty.

hh456

Celebrated Contributor

sales

#StrongerTogether

jefe

Arsonist

🍁

Not sure if she would though..

Incognito

WR Officer

Master of Disaster

Well idk about your lady, but I can make anything work.

For me.

justatopproducer

Politicker

VP OF SALES -US

Hahahahah what about the black pine tree tat on the other arm because you went hiking in your city park once and now you “love the outdoors”?

Kinonez

Celebrated Contributor

War Room Enthusiast

Unless that that has something to do with the prospect's background like their favorite sport or university, I would stay away from it.

InQ5WeTrust

Arsonist

No marketing, mayo isn't an MQL

Really depends on the market segment.

When I was selling to the design team, they were all stoners anyway so they couldn't give a flying f what I was wearing.

Outside of that though should definitely match the expectations of the audience.

Sounds like the AE was a little out of touch.

jefe

Arsonist

🍁

I had similar a similar thought. It was a good hat at least

InQ5WeTrust

Arsonist

No marketing, mayo isn't an MQL

If someone turns up wearing a Diamondbacks or Giants hat on a call I'm hanging up.

jefe

Arsonist

🍁

He was smart enough to make sure it was Team Canada.... Less likely to piss anyone off.

Might need to add some options to the CRM's Closed Lost list...

InQ5WeTrust

Arsonist

No marketing, mayo isn't an MQL

That's why you have to do that pre-call research.

jefe

Arsonist

🍁

Q5 where did you go?! :(

Tapped into this thread again and I see so many names that I just don't see anymore...

paddy

WR Officer

Director of Business Development

I think it makes u look like a fucking dork

jefe

Arsonist

🍁

No argument there

Incognito

WR Officer

Master of Disaster

If my prospect is a “insert sport team of choice” fan, then sure. But as an obvious warming tactic. Or something to get a laugh when I think it will be well received.

Otherwise, why?

jefe

Arsonist

🍁

I could see it as a rapport building tactic like you laid out, but this was obviously just a dude wearing a hat in his house.

First thing I thought of was Tony in the restaurant scene in Sopranos ep 1.

Incognito

WR Officer

Master of Disaster

Did it influence your buying decision?

jefe

Arsonist

🍁

Wasn't a good fit, but I was not influenced by the hat...

Incognito

WR Officer

Master of Disaster

But it WAS memorable, or you wouldn’t have posted about it 🤷‍♀️

jefe

Arsonist

🍁

Ugh can't believe you're gone incognito...

jefe

Arsonist

🍁

Such a shame :(

CaneWolf

Politicker

Call me what you want, just sign the damn contract

I’m bald and don’t wear a hat.

MoonDog349

Valued Contributor

Sales Manager

I did this morning. Fuck it. Got my peloton and golf clubs chilling in the back of my “office” as well.

jefe

Arsonist

🍁

Sounds like a good setup, not going to lie.

alecabral

Arsonist

Director - Digital Sales Transformation

I guess it'll depend mainly on how well you know your customers and how you think they'll react. It could be a big fail or a big win. On both my jobs I stay away from accessories as my buyer personas are simply not into them.

jefe

Arsonist

🍁

I definitely opt for less is more. Ring and a watch and that's about it.

Telehealth_2the_Moon

Notable Contributor

Director of Business Development

I usually don't wear hats, I have pretty long hair and putting a hat on either makes it poof out over my ears or make it look like I have a mullet (no judgement, just not my thing). I do have one of the Sales Hats next to my desk that I use to break the ice and say something along the lines of "let me put my sales hat on real quick" before putting a literal sales hat on. Then I take it off for the above reasons.

jefe

Arsonist

🍁

Heh, I hear you on that. My hair is growing out and I do not like the impressions/dents made - reduces that all-important flow.

Nice use of the sales hat! I'm sure that goes over well with a bunch of people.

Side note: I did have a mullet for a bit in the '90s, but I was a Canadian hockey kid so it wasn't the worst.

(Although it was pretty bad)

Telehealth_2the_Moon

Notable Contributor

Director of Business Development

So if it was "pretty bad" but "wasn't the worst" then was it just only "pretty bad" because you were one of many 90's Canadian hockey kids rocking the flow?

jefe

Arsonist

🍁

You got it.

Looked epic under a helmet. Picture day? Not so much.

Jewcan_Sam81

Politicker

Account Executive

People need to chill the hell out, the world is a different place than it used to be and we're all either freaked out, overworked, over-Zoomed, sick with the plague, or dealing with being locked in a prison with a bunch of small children. It's a freakin hat...unless it's red and has some politically charged and touchy white words written on the front, that's probably a bad call

jefe

Arsonist

🍁

Agree with you on the red hat part, and while people DEFINITELY need to chill the hell out, there's a large population of DM's that do think this way.

Especially if you're selling into certain verticals that are full of the old guard.

I've encountered, and worked for, these types. Not the most fun, but if you can treat that kind of prospect with respect while also commanding respect yourself, it can go a long way.

Sunbunny31

Arsonist

Sr Sales Executive 🐰

I wouldn't, but I'm not male, and I also sell into the C-suite, sooooo

jefe

Arsonist

🍁

True women are less likely to have a cap on... I think the C-suite is the key here though!

Diablo

Politicker

Sr. AE

Not relevant to the product we sell but I am thinking of trying once 😬

jefe

Arsonist

🍁

Just make sure it's a younger person, I know a lot of older people would not take well to it.

jefe

Arsonist

🍁

@Diabloyou still around? And did you ever end up trying?

Cornholio

Opinionated

Account Executive

Depends, if it’s a ball team, especially local or alma mater it could play. Wouldn’t wear my PING hat and mention my evening tee time.

ultraman

Tycoon

Shepherd

I don’t rock them IRL.

jefe

Arsonist

🍁

Me neither, except a toque on the coldest of winter days.

MoonDog349

Valued Contributor

Sales Manager

Also, what if you have a company branded hat? What if it’s Friday? Would YOU judge someone wearing a hat?

jefe

Arsonist

🍁

I guess I'm kind of old school despite being pretty young, and just think it's not a respectful move.

Didn't bother me, but it surprised and threw me a bit.

sellingsellssold

Politicker

SDR

It truly depends what you are selling and who the client is

Balltricks

Contributor

SDR

I work in an office that has a completely casual dress code (hats, athletic shorts, tank top, whatever you want) and wear hats in office often because of that. But I ALWAYS take it off when I’m on a call with prospects/customers. When in doubt, play it safe. First impressions are incredibly sticky, and you don’t want yours to be “I remember he wore a hat and I thought that was kind of odd”.

jefe

Arsonist

🍁

Totally agree. And, as they say, you only get one chance.

Mobi85

Politicker

Regional Sales Manager

Depends to me on the market segment that you are meeting with. I can’t say that I have worn a hat to a first meeting but have had to wear hardhats and hats to a job site more than a few times after that first meeting. Also really bucked the norm because I was wearing sunglasses as well, so it felt awkward but just had to run with it and it was better than squinting into the sun the whole meeting.

TheOverTaker

Politicker

Senior Account Executive

Really just depends on the person and your comfort level with them. If it was a first time call, no chance. But a secondary call or something where I know that's not gonna raise any flags....why not?

jefe

Arsonist

🍁

Totally different when you know the person or have a relationship. But a few emails/LI messages and a first time meeting?

Looked 40 in his LI profile pic and 22 on Zoom lol

Mjollnir

Politicker

Unemployed Account Executive

I don't wear hats indoors lol

jefe

Arsonist

🍁

I think that's most people

FormerStartupJobHopper

Tycoon

Yeah, fuck em. If they care about you wearing a hat on a call, they weren't gonna buy

jefe

Arsonist

🍁

You ever deal with the C-suite? There's still some people that would absolutely be quite turned off by that and that alone.

Not everyone is selling to young execs at tech companies...

Don't agree with the mentality but it's naïve to think it's not out there.

FormerStartupJobHopper

Tycoon

I'm sure it's out there. I'm hesitant to give into it lol. But tbh yeah, if I was working a larger deal and felt I needed to turn my camera on, I may take the hat off.

jefe

Arsonist

🍁

It’s all about understanding your audience. Like mirroring language

tonysoprano

Tycoon

Sr. AE

I never would just for my preference, but after wearing it on an internal call my VP said something about not doing it on prospect calls. basically, a lot of us are experts in our specific product, ICP and all that and need to establish that credibility with a prospect who has likely been in the biz since we were in college and maybe before. They know we're wfh and it seems like it shows a bit of laziness because at the end of the day its not hard to clean up and throw on a collar for 30-60 min, especially when you're wearing a hat and your prospect is not

jefe

Arsonist

🍁

100% agree with all of this!

That modicum of effort means something to me, both personally and being on the other side of the call.

jefe

Arsonist

🍁

Also, great user name!!

This scene came to mind when I saw him lol

https://www.youtube.com/watch?v=Hqp1bGuiHHs

JECU

Opinionated

Account Manager / Co-Founder

I have only worn a hat while talking to certain clients I sell to. My prospects are mainly wearing hats of some kind repping their brand etc. I’ll wear one to come off as more relatable and even had a partner tell me I “looked the part”. Sometimes it more comforting as I feel a bit of a “shelter” too lol. Can you guess the industry I’m referring to?

jefe

Arsonist

🍁

That sounds legit. And I'm drawing a blank, though guessing you work with B2C brands...

JECU

Opinionated

Account Manager / Co-Founder

Close, since the customers are very B2C retail centric. We’ve been working with Cannabis companies lately and all DMs we work with a very lax.

jefe

Arsonist

🍁

You'd hope they'd be pretty chill! Is that in the US or Canada?

JECU

Opinionated

Account Manager / Co-Founder

They are here in US. Mostly new ones becoming operational in Missouri. Lots of pain points but hit or miss with budgets. I’m based in NC so when it does happen here, we hope to be market leader

jefe

Arsonist

🍁

Very cool! Thanks for sharing!

Just noticed your title tag - did you start the company up yourself?

JECU

Opinionated

Account Manager / Co-Founder

I did start it with one other founder. I run the majority of sales, projects and finances. I’ve been tossing the idea of selling my ownership stake and getting back into sales for someone else.

jefe

Arsonist

🍁

Great to see savages starting their own thing. Even if it's not the meant to be in the long term, love the initiative.

JECU

Opinionated

Account Manager / Co-Founder

Yea it’s been a ride for sure. Especially combining software with services, then some things being out of your control. It just seems like it would be so easy to go into another org and “only sell”. I know that’s exaggerating but it honestly feels that way sometimes. Also gained a lot of experience in dealing with executives looking at them eye to eye and how they want to be sold to etc

countingmyinterest

Politicker

Account Executive

oh yeah, all the fucking time. I have long hair and will sometimes throw a hat on. It might be a conversation starter and let's me show a bit of my personality.

My manager also said not to worry about it so I don't.

jefe

Arsonist

🍁

Good to have your manager's blessing. And the personality aspect can be very true.

What industry are you in?

emkayxx

Opinionated

Enterprise Account Executive

I've worn hats in tons of sales cycles. There are also a ton of sales cycles where I've steered away from it. Make adjustments according to the persona type you are selling into.

jefe

Arsonist

🍁

Definitely agree with this

harebrained

Politicker

Enterprise Account Executive

I'd wear hats more if I were a guy... a ponytail is my hat substitute.

jefe

Arsonist

🍁

Ponytail is fair game. Mine's almost long enough to do that, but usually just use a headset to push it back instead and will probably continue with that.

Fletch

Opinionated

Full-Time AE/Side-Hustle Owner

For my full-time job, likely not. I already dress fairly casually, and I’d prefer not to push it. For my side hustle, I do but I’ll wear my pancake hat (It says pancake, it’s not shaped like one) as a quick rapport build.

jefe

Arsonist

🍁

Makes sense, I don't like going TOO casual myself, just doesn't seem right.

Side hustle sounds like fair game though.

closesomething

Executive

Account Executive

I do this all the time - it's never seems to be a problem.

jefe

Arsonist

🍁

It definitely seems a little more commonplace than I expected!

I think things are a-changing quicker than I thought. Admittedly, I'm quite old school for a millennial.

Undefined

Valued Contributor

SDR

Depends, if the prospect identifies with it in someway. Like I have IU hat, I might wear it if I'm chatting to an IU alum, nice way to spark a conversation gets us talking about family ultimately.

But if I'm reaching out to most I'd forgo the SALES HAT. But I also don't have a sales hat so it's a moo point.

jefe

Arsonist

🍁

I always wore some purple when presenting near K-State, so absolutely get that.

Agreed on all counts.

pretengineer

Politicker

Head of the crumpets

It depends. Sometimes for dramatic effect, I like to bust out my "Sales hat" in a demo. It's quite fun to do this: "And I'll put on my sales hat for a bit ... (and pulls out the sales hat)"

jefe

Arsonist

🍁

I like this approach - it's intentional.