Five Company Offsites Later, I Finally Understand What They’re Really For

I still remember it like it was yesterday. The first time I got to travel for a company offsite was in Bali.

For the uninitiated, a company offsite is when you and your colleagues are “invited” (forced, really) to a multi-day retreat involving presentations and team-bonding activities. In theory, it gives everyone a chance to step away from daily work and get to know one another better.

In practice, it feels more like a school camp organised by HR.

Having attended more than five offsites across several companies, I have experienced everything from all-day hotel ballroom briefing and resort stays, to catered late dinners and “fun” games that somehow required me to sweat in a dri-fit company T-shirt.

Over the years, I stopped viewing offsites as something to survive with a perfect strategy. Instead, I see them as condensed versions of corporate life itself: occasionally awkward, sometimes exhausting, but unexpectedly revealing.

The roommate decision that taught me about boundaries

If you’re lucky, you get to choose who to room with at an offsite (some companies assign it at random, gasp).

Before my maiden offsite experience, I thought that choosing your roomie for a “vacation” was straightforward - just pick your work bestie!

I soon found out that enjoying someone’s company for a day is very different from sharing a small room with them for several nights. She was talking on the phone with her family constantly, even asking me to participate in her video calls. In the morning, we agreed on who would wake up first, but she snoozed her alarm too many times and our bath times ended up clashing. Safe to say, I had to complete the fastest shower and makeup routine in my life ever.

After my first mismatched roommate experience, I became more thoughtful about whom I shared a room with. At a later offsite, I picked a colleague who I knew was quite chill. We even discussed what our routines would be like.

With her, I could take my time to wake up and get ready as she was an early bird who would go out for morning walks. Her routine meant we didn't have to fight for the bathroom. I even got a little me-time before the day’s events began.

A compatible roommate understands that silence isn't hostility. It may simply be two tired adults allowing their social batteries to recharge.

If you’re allowed to choose your roommates, I'd pay less attention to who makes you laugh the most at work and more to whether your habits are likely to coexist peacefully. After all, we still have to see each other in the office when the trip is over.

IMAGE: UNSPLASH

Let loose, but remember that at a company offsite, your boss is still watching

I’ll never forget last year’s offsite at Kuala Lumpur, starting with a random karaoke session at 9pm. I swear I saw something I can never unsee: my boss showing up to dinner in a Hawaiian shirt so loud it looked personally offended by neutral colours. All while someone from senior management belted "I Want It That Way," eyes closed, all in.

This was just hours after a major serious group discussion about company strategy. For a while, I genuinely forgot these people approved my leave applications or made million-dollar decisions.

But here's the thing: I kept catching myself and going, “Okay, match the energy, don't outrun it.” There was a colleague going around all night trying to get everyone to drink with him, and while I partook in every enthusiastic round of “cheers", I was mindful to sip, not to down drinks with the same vigour. When our CEO got all nostalgic about his first job, I just listened. What I didn't do was use that as my window to complain about being understaffed, because it wasn’t the right time and place for it.

That's what these offsites do to people. Everyone's defenses drop and it starts feeling like you're all just friends. Just don't forget that offsite-you becomes office-you when Monday arrives, and office-you would still like to be taken seriously.

Learning how to stand out without becoming the main character

This reminds me of Marcus (not his real name). Every group photo (including ones for teams he wasn't even on) somehow had Marcus in it, usually doing an elaborate pose.

But the real masterstroke came during dinner. Someone innocently asked how his team was doing, and Marcus treated it as an opening statement. Less than half an hour later, we knew everything about his coworker's alleged incompetence and how his boss never seemed to be around when he needed him. Someone tried to change the subject to dessert. Marcus brought it back to his coworker.

As I watched this unfold, I remember thinking this was a masterclass in exactly what not to do. Nobody left that dinner thinking Marcus was easy to work with.

Being visible isn't about making sure everyone knows your name. It's about being present and engaged so people remember you as someone friendly and easy to work with. Sometimes, being remembered as pleasant to sit beside at dinner is enough.

The best offsite version of yourself is just your usual professional self, with about 20% more enthusiasm and a sprinkle of humour.

Surviving team-bonding activities with a good attitude and decent footwear

No company offsite is complete without at least one activity designed to "build trust." It could be a quiz, a scavenger hunt, or an obstacle course.

I've done one where you're blindfolded and your teammates have to verbally guide you through a maze of cones, where someone just kept yelling "LEFT, no, OTHER left" until I gave up. I've done an "Amazing Race" style competition across a hotel property in Singapore heat that nearly ended me. I've seen them all.

I am, for the record, not a big fan of these activities. But unless you're genuinely unwell, go in with an open mind. Show up, contribute where you can, and have fun - but not to the extreme (see point above about not becoming the main character).

Tip: always wear comfortable shoes, even if the itinerary insists it's "casual."

I once trusted that word and turned up to what I thought was a chill outdoor session in sandals, only to find out "casual" meant a forty-minute uphill scavenger hunt through gravel and grass. My feet were destroyed by 11am and I still had a full day ahead of me. The next offsite, I made it a point to bring sunscreen, a water bottle, and a pack of wet wipes. These are the little things that separate the survivors from the offsite casualties.

Also, be mentally prepared for icebreakers. At some point, you may be asked to share a “fun fact” about yourself. Keep one ready, so you don’t panic and end up oversharing. Think of something harmless. Save the real stories for people you actually know.

The fine line between making memories and becoming one

Every company has an offsite legend. You don't want to be that story.

Take the middle manager in another department who once slept through his alarm on the last day and missed the bus to the airport entirely. We tried everything. Calling him endlessly, knocking on his door, even getting the front desk to ring his room phone. Nothing worked. He missed his flight, and to this day, someone brings it up whenever offsites come up in conversation.

Or there's my colleague who, in her very first year, got so drunk at the company offsite that she cemented her reputation as the "office alcoholic" for years afterward. Some people have even told her story to outsiders. Yikes.

These are the legends. You don't want to be one of them.

That said, I'm not saying you should be boring. Some of the best offsite moments happen when people let their guard down a little. I discovered that my quietest HR colleague does rock climbing and that the guy from Finance does a mean impression of the boss. Those are the good stories.

But when the drinks are flowing and the mood gets extra cheerful, ask yourself one question: “Will I be comfortable if this becomes a group chat sticker?”

If the answer is no, maybe it's time to switch to water and call it a night.


IMAGE: UNSPLASH

After five company offsites, have I finally learnt to enjoy them?

I still wonder whether we can achieve the same thing with a nice lunch and an afternoon off, rather than a weekend offsite. Yet I cannot say offsites are completely useless either.

They've shown me that workplace relationships are often built in the little things - not while discussing company values, but while helping a colleague find a misplaced room key. Not necessarily during the team game, but while laughing about it.

After more than five offsites, I still hope for my own room. But I've started to care less about the awkwardness of it all.

I return to the office knowing which colleague needs coffee before conversation, who becomes ultracompetitive during games, and who has a surprisingly good singing voice. More importantly, I return knowing a little more about myself.

If I can do that without becoming a WhatsApp group chat sticker, I consider the offsite a success.

For the latest updates on Wonderwall.sg, be sure to follow us on TikTok, Telegram, Instagram, and Facebook. If you have a story idea for us, email us at [email protected].