New Swag: Pocket Squares / Handkerchief / Head Scarf / Hair Tie / Cravat / Dog Scarf
Falling for swag after socks. Finding a new partner. Fooling myself into options.
So I said to myself: those Slack socks worked out pretty well so many years ago. Maybe it’s time for another swag option for the discerning software sales person?
Maybe!
Truthfully, I’d had a Slack pocket square on my mind for a few months before I started to do anything about it.
One first caught my eye in a shop in Heathrow Airport. I unfolded it from a display table and looked closer. It wasn’t quite right — the colours echoed Slack’s colours and fell in the right cross-hatched pattern, but the shades were off. It wasn’t the right number of colours. The fabric texture was too coarse. As a model of what I’d been noodling on, it worked. But only as a model.
I bought that pocket square and tried it in my suit jacket the next chance I had. People noticed: Oh cool. Is that a Slack pocket square? It was not, but it was close and its exactness wasn’t the point. The point was the noticing and the association and the question of whether it was a Slack pocket square.
Pocket squares had some style. We aspired to have some style too. This could work.
Finding New Partners
I did a bit of research and got in touch with a few suppliers. I met Jaspal from Monsoon Corporate Gifts in Montreal. They had lovely scarves, ties, pashminas, bow ties and (yes!) pocket squares on their website to demonstrate their capabilities.
Through email, Jaspal and I worked on our order — materials, dimensions, quantity, production considerations. The design felt solved with our existing cross-hatched tartanish pattern. Yet we still needed to find a border colour, a blend for the silk and a finish to the material (how matte or glossy it would show).
We got to an agreement on the details. On January 23, 2018, I called Jaspal and read him my credit card number. A few weeks later a box arrived to our Vancouver office filled with 250 Slack pocket squares. At least, that’s what I thought they were.
I showed some teammates. They had some different ideas as they unfolded the silk.
Oh, a scarf! A headband! A hairband! A handkerchief for my dog!
The immediate feedback was all definitely positive and it was also definitely in many different directions. Giving folks a 14” x 14” piece of silk with the now retired corporate colours invited many interpretations. Did I mention that the corporate colours were now retired? Yes, right.
And, confession time: the whole pocket squares project was off the books and unsanctioned. Grey market because I wanted to give it a try.
Slack’s marketing had matured and moved on, and rightfully so. We had hundreds of millions in annual recurring revenues, close to 2,000 employees and customers in 120+ countries. Experts were in charge and doing a great job and I was not one of them.
But I still felt like I could get away with a niche project like the pocket squares and run a covert mini marketing operation in Executive Programs. But it would only ever be small and niche and under the radar. Unless it wasn’t.
I started giving away some of my stock of 250 pocket squares, one by one, to folks who asked about them. I’d leave one on a teammate’s desk. I carried a stash of them with me when I visited different Slack offices. I handed them to co-presenters. I started getting some requests for them, or some requests for restocks from folks I’d already shared one with and who had passed theirs on. Unbelievably, dogs managed to lose their handkerchiefs. Woof!
And playing the role of the Slack Man, I of course wore my own pocket square. That prompted questions. People often wanted to know how they could get one.
My favourite thing to do when prompted for a pocket square was to pull my own from my jacket (unfolded with a flourish) and give it to them. This required me to have a few backups at all times, but was well worth it for the reaction it provided. The flourish made the sale and left an impression, a nod towards a magician’s conjuring.
Fooling Myself Into Options
The pocket square felt like a very small prop in the small performances I engaged in. Sales presentations, Executive Briefings, Innovation Tours, lunch and learns — all the ways we went about hosting and coordinating small groups of important people and helping them have effective discussions towards specific objectives.
Speaking felt like stage work, and, truthfully, it was. People made decisions of perception all the time with very little information. They sought out the signals they could find. They wanted to be introduced to Slack because our PR game continued to be strong. They’d heard of Slack. They wanted to learn and have a frame of reference to fit Slack into in their minds. They especially didn’t want to miss out on something cool like Slack.
In addition to pocket squares we had other executive programs swag made. Fancy umbrellas that went up and down from a spring-loaded handle, whose segments unfolded in an elliptical shape that made it easy to pass someone else holding an umbrella on the sidewalk, and slipped through the air so gusts of wind couldn’t flip it inside out. These were amazing and cost $30 each, way too much for a giveaway except in limited quantities.
For swag, we tried to keep a playful and professional and useful approach to everything we did. We tried to play to our strengths and avoid just having more random plastic crap people didn’t want. We wanted even our giveaway items to reflect our company values — craftsmanship, courtesy, playfulness.
In shooting for high standards in all the parts of our work I’d also like to think we made Slack a better place to work for everyone. No one wanted to aspire to mediocrity, yet it seemed so many companies’ swag outputs reflected mediocrity. Aiming high meant that even if we fell short we still ended up striking a good spot.
I don’t want to give you the impression we were perfect. We weren’t. We failed at things. We compromised. Reality consistently tamped down our aspirations, and sometimes we fell back to earth with some scorch marks. If socks were a 500,000 hit, pocket squares were more like 500.
But trying to hit high standards meant we chose our own challenges and then had to marshall our own gumption to reach them. We investigated space pens that could write in zero gravity and decided that nah, $100 for a giveaway item was too much. That kind of autonomy felt like rocket fuel to me and the folks I worked with, even if it was just in our own very small EBC corner of the organization.
It made the idea of leaving Slack nearly unfathomable too. We had momentum and money and amazing people to work with on hard problems. Why would anyone want to go elsewhere? We had our problems and we loved them, in the way that work can be love made tangible. We didn’t want to trade them for any other problems. Each day was mortal combat against our own limitations.
Did this Slack Man start to feel a bit like a Slack mascot with branded socks and laptop sleeve and pocket square? With my purple jacket and changing my accent so I pronounced process as prah-sess instead of pro-sess? Yes, maybe a bit.
But overall, that feeling felt pretty small. The larger feeling I carried was how lucky I was to have such a sense of play in my work with teammates, to be able to explore rich territories, to be able to fail or succeed, and to be able to try again with a flourish.
Up next: WORK on NYSE — Going public from Yellowstone. Finding the unreality of it all. Acknowledging the change.