Tue. Sep 18th, 2018

Winning and Losing

Do you love to win or do you hate to lose?

I remember being asked this question in an interview once when I was younger. I thought the right answer was to say that I loved to win, so I said it emphatically, “Nobody loves to win more than I do!” After the interviewer wiped the spit off his face, he followed it up with, “but DO you hate to lose?” Again, I was thinking I shouldn’t even address losing so I blabbed on that I just loved to win so much and I never really thought about losses, or something along those lines.

The truth was, I was in my 20’s at the time, and I didn’t really know what I loved or what I hated. I just did what I was supposed to do and took everything as it came.

I like winning. There’s no doubt about that. I not only like to win, but I like to celebrate wins. As a Market Manager for Townsquare Media and for Cumulus I had a bell that I would put up for sellers to ring when a sale was made. What we do is very hard. So, when we’re able to overcome all of the obstacles and make a sale – ring that bell, baby! Celebrate it with everyone in earshot.

But, as I’ve grown in my career, the actual answer to the question, has become much clearer for me – I hate to lose. I despise losing. As I’m typing this, I’m thinking of recent proposals that were turned down and getting more and more angry about them every second. “You can’t take it personally,” they say. Hogwash, I take it personally. It was my idea, presentation and product and you didn’t want it. To me, that’s personal, and secretly, I walk away wishing for a small amount of harm to happen to you.

We work too hard to lose. Losing hurts. I remember hearing a college basketball coach talk once about how when his team won a game, he would enjoy it for minutes, but if they lost, it stayed with him for days. Yes, coach, I know what you mean.

So, the question becomes, if you are like me and you hate to lose – how do you make sure it happens less? Three things come to mind:

  • Be prepared. If you are headed out to meet with a client for the first time, take time to do a little research. Read about the company, their competition or even their industry. Look at their website and where they show up on Google for their category (you’ll discuss their digital strategy with them, too, won’t you?). If nothing else, this shows that you cared enough to try and learn about their business before meeting with them.
  • Pitch the client based on what you learned in the first meeting. If you asked the right questions, you have all the answers you need for the presentation. If you really asked the right questions, you have everything you need to write good copy. If they mentioned a certain show or host, have a spec spot made using one of those voices or pitch a feature inside that show. Relate everything back to what they told you. Here is the problem, and here is the solution.
  • Sell it like you mean it! Your enthusiasm, your body language and your tone will make all the difference in the world. You are asking a businessperson to spend money and invest in you, so don’t make them wonder if this is something you truly believe in or not. When pitching business, be more Jon Gruden and less Bill Belichick.

Unfortunately, we all know that no matter how good we are at what we do, the awful truth is that we are still going to lose plenty. So, we also need a plan for what to do when we do lose.

I remember reading “Man’s Search for Meaning,” a book by Viktor Frankl chronicling his experiences as a concentration camp inmate during World War II. My favorite quote from the book was: “Forces beyond your control can take away everything you possess except one thing, your freedom to choose how you will respond to the situation.”

It’s not about what happens to you, it’s about how you respond to what happens.

I still hate to lose and get angry when I do. The difference now is that I use it as a motivator. In fact, losing may be my second biggest motivator after money. I hate the feeling of losing, so I am willing to do more beforehand, to try and avoid it coming back.

Take that extra energy and turn it in to a positive. Get back out and close the next one – preferably to the competitor of the business that turned you down. Now that would be something to ring the bell about.

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