Why I Left Gary an 84% Tip

JeffBlog, Entrepreneurship, LeadershipLeave a Comment

So I just had an awesome date night with my wife. Yes, a date night. We do these typically on Mondays because our son spends the night with my parents. However, that will change very soon, as we’re expecting our second child any day now. So tonight was a special one (well, more special than normal), because we’re not sure how many we’ll get to have over the next few months.

Anyway, my wife and I went for dinner at one of our favorite restaurant chains, Olive Garden. I just can’t get enough of those breadsticks!

To make a long story short, our waiter did this one thing and we left an 84% tip. Yea, you read that right… 84%. His tip was only $7 less than our total bill.

Why such a big tip? Let me explain.

I think I should start by explaining that I typically leave pretty nice tips; possibly too nice. I’ve been this way for a while because I have spent the majority of my life working in or running restaurants and I have a great deal of respect for those in the service industry.

Anyway, the dish that my wife always gets has recently been removed from the menu. Add that to her already indecisive mind, now clouded with a billion pregnancy hormones gone crazy, and you’ve got the cutest pregnant girl in the world… who cannot make up her mind to save the world.

What did our waiter do? He figured out exactly how her favorite meal was made and offered to go back with the chef and make sure it came out precisely how it had always been for her.

Is that good enough to warrant such a massive tip? Not really, but there’s more.

So I’m not a super adventurous guy when it comes to food. I’m a pretty picky eater, but also fairly easily pleased. What I mean by that is; I don’t necessarily like everything, but you can feed me pretty much the same thing everyday and I’ll be just fine. Anyway, my typical choice at the Garden is the simple spaghetti and meatballs. I know, I know, wild man here! Look, its nothing special but I love their sauce and I love the spices they use in their meatballs. Not the point here. The point is that I was looking to try something new. I was back and forth on a new “Chef’s Choice” dish on the menu but was torn between the risk of not liking the new dish and sticking with the guaranteed spaghetti and meatballs. My mind was eased when our waiter not only guaranteed I would love this new dish, but gave me his word that if I didn’t, he’d have spaghetti and meatballs out for me in seconds and pay for my meal.

Now that could just be a great sales technique (as used by many other waiters) or maybe it was just a guy making sure his customers are taken care of. But is that enough to warrant the gratuity? Possibly. But it was something else that really earned him my respect.

First, I need to also mention that I love it when a waiter or waitress is all over the drink refills. This dude was so on top of it, I didn’t even notice him slipping new iced teas next to my half finished glasses. Our breadsticks were replenished anytime we were down to one and he was always in sight and making eye contact to ensure we knew we could get him if we needed anything. Superb service!

So lets add that all up; took care of my wife + got me to try a new dish (which I loved) + was all over the drink and breadstick refills + readily available and checking in.

That all adds up to one heck of a waiter. But I’ve had a lot of great experiences where our waiter or waitress took great care of us. So why such a big tip for this guy?

He was real.

He didn’t try to be super peppy, cause he was a calm, collected, and cool guy. He didn’t try to act like he knew everything, because he didn’t. Instead, he answered what he could and went and found out what he didn’t know. He didn’t try to crack jokes (which usually leads to awkward silence moments), he waited for the right time to joke and nailed it. He didn’t pretend he loves his job more than anything; or that this was his dream job or what he was meant to do. He simply did his best. He was positive, friendly, respectful, and good at it. He was true to himself and takes pride in what he does, and it shows. This waiter, Gary, made us feel like we were being served by a friend or family member. Remember Olive Garden’s old slogan, “When you’re here, you’re family”? Well, this guy delivered that experience. So I tipped the heck out of him.

But there’s another side to this story. My wife and I are always very friendly, very respectful, and very understanding when dealing with waiters and waitresses. In fact, we often bus our own table; stacking all our plates, putting the silverware all together, and usually wiping down the table as best we can. This is probably a large part due to my experience in the service industry, but we also just love to be nice and to see people smile. So we joked with Gary, we thanked him sincerely throughout the meal, and we built a solid rapport with a person who is typically nothing more than a food delivery machine to most people.

What did we get in return? He bought our desserts.


Here’s my favorite part: I left the tip before I knew he covered our desserts and he bought our desserts before he knew what kind of tip he was getting. Just a couple of people trying to brighten each other’s day and earning each other’s respect in the process.


So what does all this have to do with you and your business?

A few things.
1. Find yourself a Gary (or two) and treat them well. You need this type of person as the face of your business.
2. Take care of your customers. Go above and beyond. Do those little things others won’t. You’ll find that people respect it, they appreciate it, and you will be rewarded for it.
3. Be yourself. Be real. If you’re a leader, lead the way that best suites you. If you’re not the super peppy, over-the-top type, don’t try and lead that way. If you’re not a brash New Yorker, don’t try and deliver your content like Derek Halpern. If you’re not a goofball who’s not afraid to make fun of himself, don’t add a podcast intro like Pat Flynn. Find your own style. Be your own self. Do whatever it is you do, to the best of your ability, and take pride in everything you do.


Be yourself. Be Real.

Do that, and you’ll see an endless flow of 84%+ tips.



Gary also hooked us up with a bunch of those awesome Andes mints. And tomorrow I will be calling his managers to inform them of our experience.

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