Why 'Maybe' Is Your Enemy in Business

Why the M-word isn't good enough for things that really matter.

While I'm not really one for banning words, an exception would be "maybe." (Well, that and "dude," which made an appearance in a recent New York Times article about me. I'll be avoiding that word in future interviews...) But back to "maybe."

I've learned that when entered into the dialogue of a decision-making process, "maybe" is a really bad thing. "Maybe" is weak. "Maybe" is a cop out. "Maybe" is distracting.

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Oftentimes, "maybe" is employed in an effort to be nice. You want to help someone. You're dedicated to supporting someone as they learn and grow, and so you go along when they ask for more than you originally signed up for. "Can you get me a job?" "Maybe." "Can you introduce me to some big player you used to work with?" "Maybe." "Will you take this meeting with my wife's friend's boyfriend?" "Maybe."

But "maybe" can lead you in the wrong direction. It can lead you away from what you want to do and what's really important in the bigger scheme of things. Not only is it suboptimal for you, but even more often, it's suboptimal for many of the people you loop into the process. I've realized that I waste a lot of other people's time when I open the door and introduce a problem to their inbox.

At WIN, the investment company that I founded and help run, we used to have a high tolerance for "maybes." We introduced "soft yeses." The problem? As pure and good as our intentions were, this mechanism kicked off a lot of bad decision making. With "soft yeses" in the way, decisions got waylaid, they took too long, and we got confused when we should have been totally focused. That didn't work well when so many decisions to to be made.

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We see hundreds of companies a year. And we need to say "no" a lot more than we say "yes." In 2014, we invested in 10 new companies. That means we got to "yes" 10 times -- and we believe in each of these 10 companies with absolute conviction -- but we had too many "soft yeses" ("maybes," really) along the way that eventually became definite "nos."

Our goal this year is to do away entirely with the "soft yeses." That means that I've had to stop feeling bad if the team was enthused and I wasn't. For the most important decisions, you need to know you're making the right call -- even if others aren't in agreement.

Listen to the "maybes" you say aloud or in your head. Don't ever let that lead you to a "yes" you don't mean. "Maybe" is your instinct telling you that you don't want to do something, or you're not enthusiastic because you don't yet have enough information. Figure out which one it is, and proceed accordingly. "Maybe" isn't good enough for things that really matter.

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