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Every Wannabe Entrepreneur Should First Wait Tables

Skip your next sales conference and go to the best restaurant instead

Photo by Troy Guo from Pexels

There is a diplomacy to entrepreneurship that I find refreshing. Entrepreneurs come in all different shapes and sizes. The last time I looked around a restaurant, I noticed the exact same thing. The more I watched our server the more I recognized the skills on display. This guy could be a prototype for today’s leading salespeople.

He came to our table to introduce himself at exactly the right time. Our party of four had just reached that first break after a few pleasantries and getting comfortable, menus still faced down. We all felt his presence as soon as he arrived at the table side.

“Good evening everyone. It looks like we’re just getting settled in. Would anyone care for a cocktail before dinner?

The speed and volume which we all said, “yes,” provided a quick comic relief for the entire table, including our server. I decided to crack open the wine list. We all decided on having some champagne to kickstart the evening. After all, we were celebrating my wife’s new business venture.

Our server was there again at just the right time.

“Are we ready for cocktails or are we thinking about a bottle of wine for the table?

He smoothly came over to my side of the table, noticing that I had the wine list.

I quickly said, “Bubbles. We are thinking we would like to start with a bottle of champagne. What do you think of this one,” pointing at a bottle I recognized.

“Lovely. Are we celebrating something?”

I nodded in my wife’s direction.

“It’s a popular producer. We sell a ton of it. But I would recommend this one,” as he slid his finger down the list. It’s a smaller producer, it’s owned by the daughter of a famous gentleman that worked for Dom Perignon for ages. Plus I think it’s a better value at a lower price point.”

I closed the wine list as I simply said, “Sold! “

As our server walked away, I marveled at how this guy had used so many tactics that seem to be missing from most people in sales. It was effortless and we hadn’t even ordered yet. As someone that waited tables in NYC throughout my twenties and has since become an entrepreneur, I couldn’t help but continue to connect the work of our server with the most successful entrepreneurs.

Timing is everything — This is true whether you are setting up an email campaign or calling a potential investor. Everyone has been at a restaurant and a server is at the table too early or even worse, leaves everyone rubber-necking, trying to find the server. Understanding the importance of other people’s time and schedule is a key factor in the fate of your message. I am extremely thoughtful about the timing of my emails. Never send a first email that requires a lot of time or original thought on Monday morning. The chances are that the recipient is trying to get through the inbox and digging through the carryover from the previous week.

Read the room — “If your mouth is moving, you’re not learning anything.” I don’t know who said that first, but I love it. The server did not barge into our conversation. He clearly watched us, observed that we had reached a break and he took action. He picked up that we were celebrating something just because we ordered champagne. Most importantly, he identified me as the unofficial table leader.

This same skill can be found in successful salespeople across every industry. While it is definitely more difficult to do this over a zoom meeting, it’s still important to remember. Whether it’s a pitch meeting with potential investors or your weekly staff meeting, read the room and act accordingly.

After we enjoyed the first sips of the champagne, everyone at the table started to look over the menu. Our server executed the wine service perfectly. He poured me a taste and then the women at the table in a clockwise direction. Perhaps equally as impressive, he gave us the run down on the menu as he poured.

“A quick note about this evening’s menu. The top section are smaller apps, whereas the section below are larger items that are definitely meant to be shared. We are known for our homemade pastas and will try to keep our list of purveyors local.”

We all followed him around the table, nodding like school children.

“One item not listed on the menu is a whole black bass. Oven roasted with potatoes, lemon and fresh rosemary. It is meant for two people and is a great choice”

When it was time to order. My wife had a few questions about the menu and portion sizes. All of which, our server handled like a pro.

“I think that might be a little too much food. You never could actually, probably do a side of the gnocchi of the table and eliminate the Winter salad. Oh, we do only have three black bass left. “

As the table leader, I ordered some apps and thankfully convinced my friend’s wife to split the black bass. It was early, but it was a perfect night so far.

Know your stuff — There’s nothing worse than the deer in the headlights stare of a stumped salesperson. If you’re selling insurance or software, you better be able to answer questions about your products. The level of confidence that comes from nailing a complex question is always beneficial in the end. Not only did our server know the menu, he did so with style.

Trust goes a long way — When it comes down to pulling the trigger on a big decision, people tend to go with their gut. That same gut feeling is also where we tend to store our trust. The most successful salespeople are able to build trust quickly and efficiently. There will always be challenges to this process. For example, your business or product is new or your industry (see car dealer) doesn’t exude a positive history.

The most successful salespeople are able to overcome obstacles and close the deal. Our server instantly built trust when he recommended a less expensive bottle of champagne and again when he told us that we didn’t need to order so much food. In theory, hose suggestions negatively affected his tip, but he did it anyway.

Our entire experience was absolutely wonderful. That doesn’t mean it was perfect. My friend’s steak was a little overcooked, but even that speed bump wasn’t enough to rattle our server.

“How good is the black bass? How is your steak, sir?”

“Actually, it’s just a little too well done, but it’s good though.” I could tell that my friend hated to say something.

Before I even had a chance to swallow the massive bite of fish, the server had slid into action. He apologized, even though he didn’t overcook it. He quickly removed it from the table as someone else put down a smaller plate in its place so we could share with him.

When it came time for dessert, we waved the white flag. We opted for after dinner drinks and coffee. I told him that everything was perfect and he could bring the check whenever. But just as I said that someone appeared from the kitchen and placed a chocolate tart that said “Congratulations Shania!” in front of my wife.

It was perfect, except my wife’s name is Shaina. Our server winked and over emphasized the Sha-nia! Our entire table laughed so hard that the table next to us turned around. I was left shaking my head because our server had obviously overheard how often my wife’s name gets butchered. It drives her crazy, normally, but she was smiling ear to ear. It truly was a wonderful experience!

Accountability is a beautiful thing — It’s not sexy but it sure is attractive . Today’s customer service is automated phone systems and online bots. To hear another human being apologize and fix the problem in a timely manner is so refreshing. Our server didn’t blame the kitchen for overlooking the steak. He just fixed the problem. The apology was sincere. That made what could have been a train wreck, into a forgettable moment.

Everything will not go according to plan — Every entrepreneur knows how difficult operating a business can be even when things are going well. Problems will happen no matter how strong your plans are. The question and most valuable lessons tend to come from these times. Trucks will break down, apps will crash, and some customers will be unhappy. The biggest question is how well and how fast will you adapt? I watched our server dodge little mishaps all night throughout the dining room. But he never let it show.

No risk it, no biscuit — Take chances to be memorable. The pandemic has forced every business to adapt to ever-changing environments. Things are tough and the future is unknown. This is the time to do something special. Show up to a Zoom meeting in costume. Send your best customers a thoughtful home office gift. The point is to do something unexpected like a free dessert with a misspelled name on it!

Published inEntrepreneur's Handbook