Shopping with the boss

Shopping with the boss

Last week, my colleague Sumiko Tan wrote about a harrowing near-death experience.

I was with her when she nearly got hit by a tram in Berlin. Little did I know that hours later, a very different sort of potential train wreck loomed over me.

It all started the night before at dinner with some German business contacts. We were talking about places to shop in Berlin after our daytime work meetings and one of them was raving about this little store on Alte Schonhausenstrasse that made the most exquisite, yet inexpensive, suits.

The next day, our meetings ended early. It was not even 4pm and we had a good three or four hours to kill before dinner. Standing on the sidewalk and wondering what to do, The Boss suddenly piped up.

"Why don't we go and check out that suit place?" he suggested.

I was naturally enthusiastic, never having turned down a shopping expedition even once in my life. But suddenly as we turned to the business of getting a cab, everyone else announced they were tired and wanted to go back to the hotel.

So it was just The Boss and Me heading to a store called Herr von Eden, in the middle of one of Berlin's vibrant shopping belts. We were two grown men who have probably never discussed anything outside of work - save for a line or two once about "the new Coldplay album".

As the taxi raced towards its destination, all sorts of questions raced through my mind.

What are the politics of shopping with the boss and was there a rulebook I should have downloaded before the trip? Am I allowed to try clothes? What do I say if he tries something on and asks me for my opinion?

Can I buy things? If they are expensive, does it signal that I'm overpaid? If they are cheap, will I look like a cheapskate? If I buy a tight T-shirt at age 42, will he ever take me seriously again? So I wondered if I was doing the right thing by heading straight for the sale section when we finally got there. I quelled my nervousness by chatting with the owner of the shop about "his good friend in Singapore who works for Chanel".

But it was just the beginning of the afternoon's challenge, for when we left the shop, it grew infinitely in complexity. Down the road, for as far as the eye could see, was an almost random mix of local and international stores. Some higher-end stores, such as Wood Wood that stocked the Japanese label Comme des Garcons, commingled with high-street names such as Zara and H&M.

As we starting walking, it felt like a scene straight out of the reality TV show The Apprentice. You know, where dramatic music is building up to a crescendo and the voice-over comes on. "For this week's challenge, we are leaving our contestants on a busy shopping street with their bosses for two hours. The stores they choose to walk into and items of merchandise they pick up and comment on will put their powers of deduction and sense of intuition to the ultimate test!

"Will they prioritise bonding over branding? And will they be able to keep their focus on the ultimate prize or give in to their baser shopaholic instincts?"

I will leave you, dear reader, to assess how I performed. I think we had a reasonably good time, but based on the feedback I got from friends and other business contacts, I would have received quite a few demerit points.

Apparently, I recklessly dismissed the cult jeans brand True Religion as being "so nineties!" without checking my blind spot and being absolutely sure that The Boss wasn't himself a fan. Then, at one store, I made The Boss wait unreasonably long as I waited for shop assistants in the middle of a major stock take to rummage through the backroom for my size. He got so bored he started checking his e-mail.

I also made him appraise a suit I was trying and, in the end, I had so many big shopping bags, I couldn't reach for my wallet in the taxi to pay for the fare back to the hotel. The Boss, who didn't buy anything, had to pick up the tab.

He later told one of my colleagues that he thought some of the sales assistants were very chatty and almost flirting with me.

"O-M-G... that means he felt you upstaged him!" exclaimed one business contact when I told her the story, her eyes widening in mock horror.

She proceeded to tell me her own story about shopping with the boss. She was trying on lipstick at the duty-free store at the airport one morning when she was startled by the famously gruff voice of her CEO behind her.

"Don't you know there's a rule: No shopping before 7am?" he said.

Another contact had the ultimate experience: shopping alone with a politician's wife, and one of the most powerful women in Singapore, in a store in Beijing.

I wanted juicy details, but there was none to be had. She said she cannot remember what they did or said, except for the overwhelming sense of the surreal situation she was in.

I guess such feelings are natural because shopping is such an intensely personal experience.

What we buy and how we buy it speak so much about the people we truly are. And unlike two colleagues playing golf or going on a cycling trip, skill and rapport between two shoppers is such a subjective and hit-or-miss affair.

People have told me that if two colleagues who go shopping for the first time together hit it off, they will form such a strong unspoken bond between them that it will often overcome the worst petty divisional divides and e-mail squabbles.

And some people say that their strongest friendships in the office are with colleagues who are their favourite shopping kakis.

People who have gone shopping with the boss may feel "traumatised", but the experience would also give them a glimpse of their boss in a more relaxed mode.

This may sound unorthodox but if shopping be the food of better working relationships, shop on.

This article was first published on September 21, 2014.
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