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It might have been the toughest task of my event career. In spite of the fact that I’ve been planning events for over 25 years for corporate audiences, when it came to creating a memorable occasion for my own team of talented pros, I have to admit, I was intimidated.

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

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


fearless 15This 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 12 months alone. In the last four years, we’ve gone from five to 15.

And so it was . . . the name Fearless Fifteen was born. Our graphic artist used photos of each team member to develop superhero personas. 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 in a venue that would create excitement and offer the team a chance to feel truly celebrated. We decided on the JW Marriott The Rosseau Muskoka Resort & Spa. 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 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 was 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 Tyvek 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 gift package – yes we have a rather dark sense of humor. The package included black shot glasses, because what event planner doesn’t need a drink once the doors close on the final guest? And a box of incense. We paired it with a TK-logoed black beanie cap.


Create some mystery. We told everyone what to wear and 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 a surprise scavenger hunt, there was lots of laughter as team names and costumes were revealed along with immediate good-natured taunting.

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. Specially crafted smoothies 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 was a key component of the agenda, learning was also something we wanted to focus on, particularly as we continue to 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.

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

Trish Knox

Trish has been turning her clients' event vision into reality for 18 years. Known for continually pushing the envelope both strategically and creatively, she has set the bar for helping clients effectively engage with audiences. With more than 25 years in marketing, Trish's career includes a combination of both agency and client experience that proves invaluable when operating in the corporate environment. She has guided clients through some of their most sensitive and high profile programs. Trish applies a thoughtful, unique approach, while embracing new ideas and blending the latest industry trends to all event programs. She has developed event programs for leading corporations such as Avaya, Facebook, Canadian Tire, Dell, D2L, Microsoft, Salesforce and Softchoice. Her event experience crosses the corporate spectrum including the management of large scale conferences, national roadshows, trade show booth design, award galas and C-level customer engagement events. Trish works in conjunction with the client to position the company as forward thinkers and leaders in innovation.

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