Tips for Creating an Epic Annual Team Meeting (Lessons from our commonsku HQ Gathering)

Like many of you, we’re still learning how to best blend the virtual world we love (with all its efficiencies and benefits) with the need for in-person connections that create a strong culture. So, in the spirit of sharing, we thought we’d give you a glimpse behind the scenes of our annual HQ gathering and share with you our lessons learned on how to create an epic annual meeting for your team. 

Over 30 commonsku-ers gathered together last week at the beautiful Evergreen Brickworks in Toronto for our year-end celebration and 2023 strategy kick-off meeting. It was two full days of solid planning plus plenty of fun and laughs over dinner and drinks, and most importantly, it was a time to connect in-person with our team.

Here are a few lessons we learned from our experience that you might be able to use for your own epic planning session:

(1) Treat your annual team meeting like the epic experience it should be 

We had an epiphany: We always roll out the red carpet for our client events like skucon and skucamp, and thought: Why would we do any less with the team that powers the platform our clients love? 

Since we’re an all-remote team, our gatherings are few and far between (generally, every quarter or every six months). So we knew it was important to bring everyone together to connect and learn but also, to do it in a way that made it special.

Creating a unique experience around an in-person event takes a l-i-t-t-l-e more energy than a simple virtual session and maybe a little more (merch) magic. 

Moreover, for those new to the company, an in-person experience might be the first time they’ve ever met their colleagues IRL. At our gathering last week ten of our 30+ employees were new to the company this year, that’s ⅓ of our workforce! 

So, we treated our team like we treat our clients: When everyone arrived at the Brickworks, waiting for them at their desk was a merch welcome kit (we practice what we preach!), a special fleece from our good friends at PCNA, and a journal and pen from our good friends at PCNA, plus a personal note from the founders.

Note that every little detail is intentional: Even where we placed the merch kits was strategic: We wanted people from different departments to sit next to each other and not congregate in their usual pods, so the notecard provided both a welcome touch but also a tactical purpose.

(2) Power in a little pre-planning 

Weeks prior to the event, during our weekly VP meeting each Mon morning, we started chatting about our upcoming HQ visit. We’d bring up the year-end meeting each week as an agenda item but only briefly. However, for one full meeting, we spent the majority of our time pre-planning our experience.

It might feel like overkill for some, but the pre-planning is where some of the smartest work is done. Think of it like sculpture: In pre-planning, we consider every possible idea that would maximize our time together and slowly chip away the rough edges until a strong vision of what we want begins to form. 

It’s in pre-planning where we talk about the schedule, how to welcome newcomers, which voices are the most important to bring out from behind the curtain (more on that below), how to structure our meetings (and even dinners) to optimize our time to connect. 

But if pre-planning a planning meeting sounds a bit meta, remember this: Since we rarely meet in person anymore, it’s critical we make the most of every minute. And if you know Team commonsku, you know we’re all about efficiency, so we kept the convo around pre-planning tight and succinct but like we’ve learned at our events: caring about the details makes the entire experience feel spontaneous and special.

(3) Create a public schedule and FAQ for everyone

Seems like a simple and ridiculous step you’d like to avoid, right? 

But we’ve learned this from our events: Creating a special branding experience is the first impression. Our HQ visit included a landing page and a formal schedule for our gathering and this step accomplished a few things: 

• It sparked anticipation and set expectations for a unique experience 

• It emphasized the fact that this was no normal get-together: it was strategic and purposeful but also, on-brand in the sense that it felt both fun and serious, formal and informal! 

• Most importantly: For our new team members, it was critical we didn’t take it for granted that everyone knows common details like where our HQ is located, where the Brickworks meeting place is, or even how long our event would last, our landing page included a schedule and a map listing each location that we would be at (for dinners, HQ, and all meetings) and even a FAQ page. 

And TBH, this little step saved our planners (aka, Mark) and our managers a ton of messages back and forth with everyone on the team. 

It’s a little touch but it adds a lot of texture and color to the bold fact that our time together is important and we —-actually, our amazing designer Lucia—- did it in a way that kept it serious, but fun!

(4) Invite Clients to Your Gathering 

The most important voice that might be missing in your planning and strategy sessions? Client voices. 

During Day 1 of our HQ meeting, we invited two clients to join us via Zoom to share their reflections on how the platform has shaped their business. Alicia Matthai, Owner at Haymaker Promotions in Baltimore, Maryland; and Tom Rector, CEO of  Screenbroidery, generously gave of their time to each talk about how they use the platform, how it has changed the way they work, and how it has affected their growth.

Our clients are the heart and soul of our community. And hearing their unique perspective is invaluable to us, particularly for those on our team (like in IT) who might not have much client contact. It’s one thing to talk about listening to the customer, but a real-life experience shared with the whole company that talks about the stresses and strains, wins and losses, is an experience best felt directly from their voices, after all, 80% of our communication is non-verbal! 

(Thanks, again, to Tom and Alicia for tearing yourselves away from your busy day in the middle of Q4 to share a glimpse of how commonsku has shaped your business and how we can serve you better in the future).

(5) Bring out the quiet voices

About our meeting structure: Each quarter, our VPs share a “look back” presentation (5 min each) of highlights from the previous quarter and also a glimpse into priorities for the next quarter. But the stars of our in-person gatherings (next to our clients!) are the quiet voices, those who rarely share center stage.

I’ll explain. 

Like you, we have an incredibly diverse team from all walks of life and literally from all over the globe. In fact, Dave Shultz, our VP of Supplier Partnerships commented to me once, “I have never seen such a diverse team as this.” Some of our team hails (originally)  from China, Russia, Dubai (and more), and these voices represent a unique perspective on the world. Plus, the work they do is fascinating. What we learned through our customer events like skucon and skucamp was to ask those who don’t normally share the spotlight to join us on stage and share their story.

For example, this year, Ilya Yakubovich, our Director of Design shared some sneak peeks at the UI design he has been working on for future platform development. Our Manager of People & Culture, Martha Carscadden, demystified the role of HR by sharing what the new role of HR looks like in today’s fast-paced world and hybrid work environment. Ksenia Denisova, Content and Marketing Coordinator, shared the work she has been doing around trends, the podcast, and some of our most popular posts. Colin Uren from Sales Development shared his expertise around landing clients. Shannon Donnelly explored a Sales Op review through Hubspot, Marcella De Ocampo provided glimpses of her work as a customer success specialist, and Aly Brunton, Product Marketing Manager, provided an overview of the platform marketing that has generated amazing results, as well as customer testimonials.

During our HQ visit, breakouts were devoted to big topics that required cross-departmental concentration (such as security protocols, event team details, success and sales coordination) but our solo sessions featured our quiet voices, the place where the heart of our enterprise lives!  

(6) Create (unscheduled) time to connect 

For two full days, we strategized around the table and in breakout rooms but our evenings were devoted to dinner. On Day 1, we had departmental dine-arounds at various restaurants across Toronto’s legendary food scene (example: the marketing and content departments spoiled ourselves at Henry’s). 

It was also important that we create an opportunity for unscheduled hang time as well so, in order to create space for more spontaneous gatherings, we booked everyone in the Anndore hotel to allow those who wanted to, close proximity to gather informally and get to know one another. Rumor has it a few developers on our team have an incredible knack for karaoke - who knew?!

Ultimately, we learned that the closer in proximity we can gather our team (rather than allowing everyone to scatter to a dozen AirBnBs) helped build community and spark spontaneous connections. 

(7) Take advantage of Shoulder Days

Our official meeting days were Tues and Wed, but some departments chose to meet a day before or after to take advantage of having everyone together. We call them shoulder days, these are the days right before and after the official HQ meeting. 

For example, our marketing and content department met on Monday preceding our HQ visit, which helped get everyone on the same page before we walked into our company meeting. 

Plus, shoulder days might give those who are new to your company, an easier entré into the business and their department before they meet the entire company. 

Yes, it can make for a long week, but the shoulder days have become a great way to allow smaller groups to spend more time together so that by the time we meet as a company, we are ready to create more cross-departmental connections. 

(8) Kudos are Critical

We live such fast-paced lives and work in such intense businesses that the one thing we should do more often is simply pauses and give thanks.

It sounds like the simplest thing to do, but we built a moment in our meeting where we stopped to give kudos to our fellow colleagues. 

Martha Cascadden, our Manager of People & Culture, led us in the exercise: Everyone was handed a pad of sticky notes and we were given 5 minutes to write a kudos to someone else on the team. We stuck these on the wall and read many of them out loud. They included kudos from our success team to development. Kudos from a VP to their team. Individual shout-outs for a job well done. 

What can seem like a forced expression of gratitude actually created a moment where we realized that what we do here is vital – to everyone. Stopping to express our appreciation for each other, in-person, was one of our most important lessons learned.

(And, BTW, if it’s important –and it’s always important to pause and note good work– it goes in the schedule). 

To end our epic HQ visit, we gathered for dinner at Oretta restaurant and even here, we were intentional, placing name cards at each seat so that each person would be sitting beside someone new on the team.

It was a fitting finale to our epic HQ experience because today, many of us in hybrid or virtual workforces meet so often with our teams virtually that we can unintentionally take our shared humanity for granted. 

That sounds grandiose but because the virtual experience has proven to be such a strong and efficient way to work from anywhere, the most important lesson we learned was that our in-person visits now require us to be more prescient and intentional and above all, to make them important by making them special, celebratory, and communal. 

Thanks for letting us share a glimpse behind the scenes and lessons learned from our HQ gathering, bring on 2023!