The (Dreadful) Coffee Meeting

This is me making sense of a “coffee meeting” gone awry.

A few weeks ago, I met a very interesting couple at a UX industry event I spoke at. It was an evening of stories where speakers share their career paths, how they got into design, and what they’re up to today.

There was a couple in the event, Jack and Rose (not their real name), and I am still floored at what happened when I met them especially in that “coffee meeting” they invited me in.

They were a very friendly couple. Rose, in particular, seemed to just gravitate towards me before I headed on stage and was incredibly chatty before and after the event. Jack too was friendly (although he was a bit subdued than Rose). As I always do on design events, I kept a friendly and open face because you just never know who you’ll be meeting today, tomorrow, whenever.

So I was really shocked to see Rose ask for my number. She said she really wanted to connect with me and get to know more about my background and what I do. Like the docile and meek guy that I am, I gave my number because you never know who you will meet in this industry.

(I’m skipping a LOT of details to protect the innocent. 😉 )

The following day, I got a text from Rose asking if I’m available for coffee “next week”. We settled for Tuesday afternoon and this is where the fun begins.

Going Commando

As soon as the pleasantries ended, Jack offered to buy me coffee while Rose warmed me up for the conversation ahead. As a freelancer at that time, I wondered if this was going to be a ‘test-the-waters’ meeting where my brain gets picked a lot, asked about pain points, designing for digital, what would I do in X, Y, Z, among others.

That didn’t happen.

Instead, I was treated to a meandering conversation about e-commerce, digital marketing, landing pages, eyeballs, and other marketing stuff.

Me (mentally): Okay, carry on. “Purchase funnel” was in my talk anyway. Maybe she hung on to that. Maybe she wants a custom e-commerce site?

Finally, we arrived at the “product” they were talking about – an e-commerce platform that lets you earn while you shop (just like Ebates, although it’s NOT Ebates). I had this tiny flicker of hope now. “Finally, we’re talking about something UX can be of assistance with! Yay!” 


Turns out I was being introduced to a second “stream of income” rather than an opportunity to use my UX skills for an actual company/client. It wasn’t a freelance opportunity in the strictest sense of the term, but a sales meeting (that happened to have coffee in it).

(It wasn’t even a “pick my brain” meeting which, though dreadful to some, can at least be productive and pass as my good deed of the day).

I want to be clear: I’m not against other streams of income. Having a few extra “bowstrings”, as Rose puts it, is a smart move in today’s economy and a lot of us UX practitioners supplement our income either as design teachers/coaches or moonlighters for those who need design help. But there’s something to be said about valuable opportunity – opportunities that fit what you’re doing right now and can enhance your skills ten or even hundredfold.

So I came home feeling ambivalent, wondering if I wasted my time meeting with Jack and Rose. I soon felt guilt rising up my spine and said, “No no no! It’s always worth meeting other people! They’re a nice couple. Maybe their ask is not for me.”

Coffee Meeting Etiquette

That evening, former Facebook Design Executive Nick Finck retweeted Felicia Sullivan’s blog on professionalism and the things we do to screw up first interactions. High up on her list was the coffee meeting and the ways people botch that chance to really make a connection.

Nick Finck on Twitter

One of my students pointed out this excellent article by @felsull on how to approach professionals for advise/critique/mentorship/etc. This is what many professionals struggle with every hour of every day:

If you’re looking to get schooled on how NOT to invite someone for a coffee meeting, Felicia’s your lady.

Frankly, I hate articles that scold you. But as a possible victim of a botched coffee meeting, I read it to see if I was right.

Turns out, I was.

The agenda-less nature of my coffee “meeting” did me in. It really wasn’t clear what this meeting was about until Jack and Rose said that it was about finding if I have an “open mind” and whether I’d like “business opportunities” other than what I’m doing right now.

Eventually, I wondered what would I have done had I not been with Jack and Rose. Maybe I’d be sending another application or preparing a conference talk. Maybe I’d be sending LinkedIn invites to my fellow speakers in the event or business emails to folks doing fine work in UX and design education.

The opportunity cost discussion became real. And I thought I wasn’t supposed to think like this because freelancers have ‘time’ in their hands.

Hint hint: Not always.

The Morning After

So I put two and two together and concluded that they wanted me to sign on to their e-commerce platform and become a customer (or a seller). 


It wasn’t a freelance opportunity but more of a sales pitch. 

I understand. 

It’s not for me.

That’s the reality of going into these coffee meetings. Sometimes they work, often they don’t. That’s okay.

I looked at the parent company, however, and… man alive, it wasn’t good.

I’ll spare you the details but let’s just say the inner workings of the parent co’s business is super sketchy. Like way shady and raises red flags. 2017 federal racketeering lawsuit and many other shady stuff.

Those “business presentations” should have been my dead giveaway.

R: “Where’s North York, Jem?

J: “Well, we’re down south right now. But North York is north of Sheppard Avenue… pretty sure it is,”

R: *nudges tablet* “If you want to learn more about the business, there’s a business presentation happening this evening!”

Wow. Just wow.

It is tempting to get mad at Jack and Rose for, well, advancing their business. Yes, they had an “e-commerce platform”; but the success (and profitability) of that platform depends on how many people will sign on to become customers and/or sellers. And you know what happens when a referral becomes a converted customer, right?

Go on. It starts with a C… 😉

Still guessing? Here’s a longer description of that “business” (I’ve redacted the business name to protect the guilty – which I’m sure you can find anyway 😉 ):

I know someone who is very deep into the [redacted] stuff.

It’s not a scam, in that its not illegal or immoral or anything, but it certainly is a pyramid scheme and he probably won’t make any money from it.

They give you a website (and charge you $20/month to maintain it or something) and you are supposed to get people to buy products through that website (it’s like [redacted].com/{yourusername}) and when they do, you get a small cut of each sale I believe. I’ve found things to be very overpriced (when compared so I’ve never used her website to buy anything.

I do know that the money is mostly made through recruiting people below you, so that you get a cut of people shopping through their website as well. It’s pretty cut-and-paste [Multi-Level Marketing], but with a “we’re an amazon competitor” twist to it. It’s funny, because no-one but [redacted] considers them competitors in any way.

A Redditor who is familiar with the
“e-commerce” company I ran into. Go figure.

I hope that explains why there was all sorts of wrong flashing and that trusting your gut could be your saving grace.

I don’t regret meeting Jack and Rose. But it’s also a lesson in being discerning and thinking things through. It’s still a good idea to assume the goodness of others. But it’s also not a guarantee that everybody can be very good. 

Always be discerning. 

Published by Jem

Jem is a UX practitioner who builds insightful, creative and usable digital experiences. A journalist by trade, he transitioned to digital media upon discovering its power to create compelling (longform) stories that captivate and motivate. Today, he combines both UX research and strategy to design digital experiences that people love.