I’m in bed, lying on my back, when the hotel room door opens. I close my eyes and pretend to be asleep. Door closes, a shuffling of feet. A moment passes and then the footsteps get closer. I feel a man standing over me. I make my body still.
This is at a work offsite in 2014 or so. The man standing over me is my assigned roommate who I don’t know very well. I do know that even though he decided to leave the company, he still went on the offsite. He saw it as a reward.
And for the first chunk of my 20 years of company all org offsites, I mostly saw it through that lens. As a reward China based companies were expected to give employees. The bigger the company, the more extravagant the offsite. And we were Microsoft. We went to awesome locations. Hong Kong (twice), Sanya, Shanghai, Changbai Mountain, Huangshan, Xiamen, Xian and many more. The structure of the offsite was fairly standard. Travel day with a team dinner. An all-hands meeting where each team gave a presentation. A gala dinner with team performances. A sightseeing day. Travel day home. Often groups in the org would extend the offsite by taking an extra couple of days before or after the main offsite. To the frustration of the directors and with support of some others, small groups would skip out on the organized events and explore on their own.
My first day at Microsoft was in fact one of these offsites. At the gala dinner the next night I watched my future boss and three other men dance in tutus. A young PM was standing next to me and whispered these offsites have performances “like it’s in a men’s jail”. At the time, I laughed out of curiosity. And in future offsites, I would wait the “men’s jail” moment. There was always at least one.
But I had my own secret about the offsites. I couldn’t stand them. Travelling in a large group, having to mingle, sharing a room, sharing meals. Always exposed. I felt I was an outlier and tried to fit in. I would self-talk myself to enjoy the experience and be curious. A couple of times that worked. The HK offsite for MSRA’s 10th anniversary stands out. It was a magical time with some special colleagues. But on most offsites, I was looking for an escape hatch by the time we reached the hotel. I shouldn’t admit this, but I used to mark time by counting down the meals of the trip. Six to go..five to go..and so on. My reward was the sense of relief when I made it back to the refuge of home.
I was by far in the minority of those who didn’t enjoy the offsites. But I was not alone. As a manager, almost every year someone on my team would ask not to go. There was a lot of pressure to go, basically you needed director level approval to skip out. The more clever people who didn’t want to go, wouldn’t ask directly. They’d have an unavoidable conflict - like a college tour for their child or an urgent business trip. I felt a sense of duty to go, so I went until my final two years when paternity leave and a sabbatical were my excuses. In later years, we could get our own room (paying half the cost) which I found a lot more comfortable and I no longer needed to explain why I showered in the morning.
Some of the offsites involved a lot of drinking. This I could do. You would go from table to table and toast. With beer it was manageable. With baijiu it was dangerous. Then there were the after parties. Yes, alcohol was a lubricant that helped bring people together. It also could be slippery. I once pushed back on the drinking culture and was told I could choose not to drink.
I came to see the offsites not just as a reward but as a bonding time. Truly. Many colleagues told me they didn’t feel part of the team until the offsite. I would see individual confidence grow and team collaboration improve as a result.
The organization also grew. We went from maybe 300 people at my first offsite to over 3000 in later years. In the early years, I presented for my team and was incredibly nervous to face those 300 people. In the middle years, I studied how leaders presented to over a thousand, and in the later years I got to present to a large audience. My secret? Writing and endless practice repetition.
Back to that 2014 hotel room. I slow my breath. The roommate is standing over me for what feels like an eternity. I feel him bend over. Reach down. And then pull up the sheets to tuck me in.
I seldom enjoyed the offsites but came to appreciate their value. Here are some photos from the last offsite that really mattered to me - in Xian before Covid.
