8 Ways We’re Helping Our Remote Team Feel More Connected

Here’s a hot take: for remote workers, gone are the days of watercooler talk and after-hours drinks at the dive down the street. And the world is a better place for it.

I’ll tell you why. It’s straight up lazy to call unstructured, distracting, and impromptu conversation or after-hours drinks “connection.” Beyond that, it simply doesn’t account for the wide spectrum of personality types that make up your team. Dreaming up an array of ways to connect—and making nearly all of them optional and/or low-commitment—can make a huge difference when it comes to building better, more grounded relationships among your team while also honoring the introverts, the people who don’t like booze, the people who like to keep work and life separated, and everyone in between. 

As a remote-from-day-one growth marketing agency, it took us a long time to figure out a baseline mix of things that help us connect in ways that feel “Tuff.” I’d highly recommend that your takeaway from this is less “let me go install HeyTaco” and more “who on our team might have a good idea to contribute to a conversation about ways to connect?”

And, ultimately, this is NEVER just a box to check. As your team evolves, so should your culture and ways to connect. We make sure to always keep up the zest and excitement for things to update, introduce, and even ditch as time goes on.

But, for now, here’s our (not exhaustive) lineup! 

Full Team Annual Retreats

THIS. This is the thing we constantly find ourselves talking about all year round. Once a year, a small group of volunteers get together to plan our all-company retreat. Although this year it will look much different with 30+ attendees vs. the 12 we had last year, all of the same fun things will be baked in.

First, we always leave space for a full company IRL meeting. In it, we’ll hear from each service team lead about things they’re excited about, areas of opportunity, and goals for the quarter ahead. We’ll hear from Ellen, the founder and CEO of Tuff about Tuff’s quarterly performance and strategy for our growth into the future. We also always do superlatives! Who will win “Best Hair” this year? Time will tell!

A few considerations we maintain for this retreat is doing our best to accommodate the multitide of people on the team. For example, partners are always welcome and we’ll do a full dinner together with the entire crew. We’ll also have several different optional events so that the people that want extra social time can show up and connect, and the people that might have a drained social tank after a big dinner can recoup the way they need.

donut! #virtual-coffee

The donut app Slack integration is one of our newest and most successful ways to connect at Tuff! Shout out to Rebecca for the idea! Our team (mostly Raj and Megan) were noticing that as our team started to grow, there was less opportunity for organically “bumping into” friends throughout the workday. To combat this, Raj started sending out invites to “tea time” to members on the team he didn’t see as frequently. 

Ultimately, we all caught on to how much we enjoyed meeting with Raj and decided to implement “Tea Time” on a larger scale. That’s where donut became our perfect solution. Every other Tuesday—for anyone that opted into the Slack channel, #virtual-coffee—donut randomly pairs you with someone else in the channel and invites you to connect. It even scrapes your calendars and recommends times to meet. Easy!


On the flip side, the HeyTaco Slack integration is one of our oldest and most loved ways to keep communication pathways open. Admittedly, at first, the loud recognition/public praise aspects of HeyTaco felt a bit contrived. This was especially for team members coming from toxic workplaces wherein praise was few and far between. 

But, we’ll happily report that it’s a staple of our everyday and a great way to encourage we each shout about our teammates’ accomplishments and wins throughout the day. It’s a tiny addition to our Slack process that’s done so much for our positive outlook and culture of feedback. We’d highly recommend.

Book Club

Before we shopped around the idea of a Tuff book club, we had NO idea Tuff was so full of bookworms! We’re currently reading our second book together and meet twice a month to discuss agreed-upon chapters or sections. 

About a quarter of the team participates and shows up with their book and sometimes a cold beverage to talk about ideas, big and small. It’s been a great way to get face time with people around the organization that share interests and want to talk about big ideas. 

Dedicated Weekly Time with Your Manager

As our team continues to grow, investing time and resources into setting our people managers up for success is at the absolute tippy top of our to-do list. But beyond simply making sure they’ve got the training they need, it’s consistency that really makes a significant difference.

Cultivating real relationships in consistent weekly 1:1s with all managers and direct reports is oftentimes one of the most anchoring connections within our company. Having an advocate, a confidante, and someone to nudge you in the right direction is to feel seen, supported, and connected. We’ll never stop investing heavily into our management.

Show & Tell

Back to Slack! Show & Tell is a highly anticipated, always fun, always casual weekly occurrence in Slack pioneered by Richard. Each week, Richard will drop a fun prompt into the #general channel and it always has the ability to fire up conversations. Here are some of our recent favorites!

  • If you weren’t working in advertising, what would you be doing? What’s your alter ego’s career?
  • What is one artist / musician / band that you consider to be a “guilty pleasure”, and aren’t afraid of people judging you for it?
  • What is one piece of memorabilia (from sports, music, movies, culture, etc.) that you own that you treasure?
  • What’s your lock screen wallpaper and does it have a good story?
  • What’s your all-time favorite “classic” Youtube video? Links required.

Tuff Times

What started as a fun idea soon careened into a full-blown weekly internal newsletter replete with (some) pertinent company information but most frequently hotly contested surveys on the best popsicle flavors, weird TikTok trends, book recommendations, employee spotlights, and so, so much more. 

Virtual Happy Hours

And, of course, the ol’ reliable. We do continue to hold monthly all-company happy hours. Because our team has grown significantly since we first started them, we’ll typically devise a game or activity that splits us up randomly into breakout rooms of 4-6 people so that actual conversations can happen.

Although it took a little legwork, one of our all-time favorite happy hours was when we collected two random facts from each team member and had the opposing team pair each random fact with the human it belonged to. The weirder the facts, the better the game. Here were some standouts:

  • I once had to have my dad come to pay for a bar tab I ran up underage drinking in Mexico because the bar refused to take my credit card (while on family vacation)
  • I’ve been in a commercial before (lol)
  • One time when I was camping, someone dared me to catch, cook, and eat a lizard. I did it. It was gross.
  • When I was young I crashed a golf cart into a rock and then ran away

Ultimately, it’s up to you to decide what’s right for your team! The caveat is that if you work to create a work environment where people feel called to contribute and get excited about developing company culture, it will naturally evolve and take on a life of its own. 

And, if you’re still calling watercooler talk and boozy happy hours “culture,” here’s your sign that your team wants more.