The Unexpected Benefits of Doing the Unexpected

Surprise the people around you, in business and relationships. You might end up surprised yourself.

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By Steve Tobak

Opinions expressed by Entrepreneur contributors are their own.

Returning home from an international business trip I struck up a conversation with the guy seated next to me. Turns out we were both executives in the tech industry and had a lot in common, except he was older, more experienced, and quite a bit wiser than I was.

Toward the end of the flight we somehow got onto the topic of relationships. This guy had been married forever, and I wasn't sure my wife and I would get through the year. He gave me a brilliant piece of advice that I've never forgotten: Do the unexpected.

That's so true. It's funny how the big things – expensive gifts and grandiose gestures – never seem to make our spouses as happy as we think they will. It's the little things, the unexpected things, that matter most.

Bringing home chocolates when it isn't even Valentine's Day. Giving her a single rose from the garden. Doing the dishes. Saying, "Let's go out" when you know she's tired and it's her night to cook. Saving her a trip into town by picking up groceries on the way home from work.

Do I actually do any of that stuff? Wouldn't you like to know? All I know is that trip was probably 15 or 20 years ago and I'm still married. Yes, to the same woman. Don't be a smartass.

Related: 10 Behaviors of Genuine People

In any case, the guy was right, and about more things than just personal relationships. As it turns out, doing the unexpected is key to success in business, too. After all, the next big thing is never what anyone expects.

Dozens of VCs and Internet companies passed on Google until one guy, Andy Bechtolsheim, finally cut Larry Page and Sergey Brin a measly $100,000 check … an investment that would come to be worth over $2 billion.

Besides, it wasn't the search engine that made the company. The search market was highly fragmented with Google's share at about 8 percent when it launched AdWords in late 2000. It was the advertising component that made Google a household word. And that surprised everyone.

The media unanimously thought Apple was crazy to get into the hyper-competitive cell-phone business. Likewise with opening retail stores. And one pundit called Apple's iPad "good for nothing" and "just a gigantic iPod Touch." Look how all that turned out.

When Evan Williams bought out Odeo's investors for a few million bucks, a side project was discussed but nobody paid much attention, including some very smart and accomplished VCs and investors. That side project was Twitter.

Doing the unexpected benefits businesses in lots of other ways besides product innovation.

Related: Want to Be Successful? Quit Wasting Your Brain.

When it comes to customer service, tell me what makes you walk away feeling great about a brand: when they finally give in and cut you a break after you spend hours and days complaining to tone-deaf service reps, or when they treat you with respect and do the right thing without hesitation right off the bat?

Likewise, the key to motivating employees is never what you'd expect. It's not a big paycheck that rocks their world but being empowered to do their best work and make a real difference. They want to be recognized and rewarded for their performance. And an unexpected promotion, raise, or bonus goes a long way.

Come to think of it, a piece of the action doesn't hurt either. I'm pretty sure Intel was the first company to give employees stock options. Hard to believe nobody had ever thought of that before then-CEO Andy Grove came up with that novel idea.

Look, I'm not saying you should suddenly pull the plug on projects, back out of commitments at the last minute, or change strategy at the drop of a hat. I used to have a CEO that was a chronic flip-flopper. It drove employees and customers nuts and didn't work out too well for him or the company, for that matter.

There's a clear distinction. You want to do the unexpected in ways that might benefit employees, customers, and the company, not behave like an alcoholic parent that has everyone on edge wondering what crazy antic your going to pull next. Now that I think about it, I guess the same goes for relationships, as well.

Related: The Truth About 'Fake It 'Til You Make It'

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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