How I planned an event for the toughest audience – a team of event planners

It might have been the toughest task of my event career. In spite of the fact I’ve been planning events for over twenty-five years for senior audiences, when it came time to planning an event for my own team of event planners, I have to admit, I was intimidated.

One of the most important decisions early on was to involve some of the team in the steering committee. As owner, it was important  to me that we celebrate the team at year end; but I quickly realized planning the offsite is also an opportunity for some of the team to get involved.  The results were an event that felt collaborative.

Here is a breakdown of the typical event components and how we tackled them:


This might have been the greatest challenge. We decided to focus on the fact that we are a rapidly growing team. Four new people in the last twelve months alone. In the last four years – we’ve gone from five to fifteen.

And so it was . . . the name Fearless Fifteen was born. Our graphic artist used photos of each team member and developed a superhero persona. The theme was unveiled upon arrival with the superheroes featured in a welcome postcard at each employee’s place setting when they arrived for lunch. This provided an immediate ice breaker with everyone trying to identify who each person was from the caricatures.



We’re pretty spoiled in the event industry; we get the VIP treatment when we’re hosted by venues for site visits, staying in luxurious, five star properties. It was important to lock on a venue that would create excitement and offer the team a chance to feel spoiled. We decided on the Marriott Rosseau in Muskoka. The views, the outdoor fire pits, the lounge and dining, together added up to all of us feeling incredibly pampered.



We are the most judgmental of judgers when it comes to selecting giveaways for our clients. How on earth would we find something that our seasoned team of planners would appreciate? We have a mix of young, urban, city-dwellers and those with families living in the ‘burbs, so finding something that might appeal to everyone’s tastes is a challenge.

Our planning team focused on ‘need’ and ‘whimsy’.


What event planner couldn’t use a compact passport holder? We paired it with YYZ luggage tags from the Drake General Store.



We often visit The Drake General Store for inspiration for our client events, so, it’s no surprise that we turned to them for something fun to gift.

We decided on the Lump of Coal – yes we have a rather dark sense of humor. A gift package that included black shot glasses, because what event planner doesn’t need a drink once the doors have closed on the final guest?  And a box of incense. We paired it with a TK logo’d black beanie cap.



Create some mystery

We told employees what to wear/bring. We let them know they’d be working in teams and who would be on their team. But we didn’t let on what the activity would be.

Announcing the teams ahead of time created instant competition. Teams caught wind that others were coming up with names and costumes. By the time we all convened in the lobby for the surprise scavenger hunt, there was lots of laughter as team names and costumes were revealed along with good-natured taunting right away.

Some team bonding highlights:

  • Our new intern being held up as Simba in the ‘create a scene from a Disney movie’ challenge.
  • Some original stunts for ‘I can’t believe you fit in there’.



Once again, the pressure of planning menus for a team that regularly manages high end catering was intimidating. We experienced the resort’s restaurants, but also added some customized components.

A craft beer and wine tasting paired with appetizers provided a taste of the region.  A specially crafted smoothie and unique pairings at a juice bar provided a healthy and natural alternative to breakfast and breaks. S’mores over the fire après dinner were a big hit.



While celebration is a key component of the agenda, learning is also something we wanted to focus on, particularly as we grow. We engaged Cutting Edjj Consulting to focus on communication – an important session to help us manage both clients, as well as our own teammates, through a project.

It might have been the toughest event task, but it was one that was full of reward as we all settled into enjoying some R&R and camaraderie.