While Dragon’s Den will always be our favourite show on television, we do have a soft spot for Undercover Boss Canada.

The show follows CEOs of some of Canada’s biggest companies as they surreptitiously join their employees on the job, posing as new hires. They get the full experience of what day-to-day activity is like on the ground floor of their companies. Cool concept, right?

Turns out one of our real estate industry industry chums, Michael Sneyd of Skyline participated in one of this season’s episodes working at Horseshoe Resort near Barrie and Deerhurst Resort in Muskoka. 

For those unfamiliar with Skyline, the company is a leading Toronto-based developer of hospitality properties and destination communities. Horseshoe Resort and Deerhurst Resort are two of their hottest destinations in the summer, winter and everything in between.

On the show, which will air Thursday, March 29 on the W Network, Michael waits tables, makes snow for ski hills and hauls hay for horses.

“The staff I worked with shared valuable information which I would likely not have learned if they knew they were shepherding the boss around for a day,” he said, describing how valuable the experience was.

In fact, he thought it was so valuable that he implemented an annual “Undercover Jobs Day” at Skyline. Corporate executives, general managers and hotel leadership committee members will all spend a shift filling line-level jobs. Sounds like a managerial move worthy of Jack Donaghy himself.

Here’s a couple of pics of Michael on the job!


Not your typical day as the CEO of a huge development company.


She doesn't suspect a thing...


"Hey Michael!" "Hay is for horses."

Tune in to the W Network on Thursday, March 29 at 9pm (Eastern and Pacific) to see Michael in action.

In the meantime, check out two of our favourite Skyline developments, Horseshoe Copeland House and Deerhurst Golf Cottages.

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