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A lot can be learned from Emma Peel in The Avengers or Jane Smith in Mr. & Mrs. Smith. And it isn’t just how to dress. Several times a year, in New York City and Las Vegas, groups of women gather to learn spy skills. They learn hand-to-hand combat, fencing, interrogation techniques, poker, martini mixology, fire arms training and more. But the women who attend Stiletto Spy School are not training for the CIA or Department of Homeland Security. Most of them are training for a different type of combat zone – the business world.
Stiletto Spy School was created by entrepreneur Alana Winter. As a child, Winter was captivated by Bond girls and other female spies who were impossibly glamorous. As an adult, her career was quite a bit less glamorous than international espionage – she owned a video distribution businesses. While running her company, Winter continued to crave action and took a hand-to hand combat course.
“Hand-to-hand combat is about learning to assess which situations are truly a threat and which situations you can still talk your way through,” says Winter. Learning when it’s time to stop talking and take action became a metaphor she soon adopted for running her business.
“I had a funny feeling about a partner I took on in my last business,” says Winter. “I spent a weekend pouring over accounting records and discovered a clear trail of embezzlement. In my mind, I heard what I learned in the hand-to-hand combat lessons. ‘It’s time to stop talking. It is clear that someone means you harm, there is nothing to talk about. What is my desired outcome and what targets can I hit to achieve that desired outcome?’ My business partner had no idea that I knew what was going on until there were court papers in his hands and I had already straightened things out with the bank.”
In May of 2008, Winter founded Stiletto Spy School to help other women benefit from the lessons she learned. One of the goals of Stiletto Spy School is to get participants out of their comfort zone and practice something that most women were not raised to do – embrace confrontation. To really shed their inhibitions, all participants use an alias spy name during the program.
Stiletto Spy School graduate Judy Briggs owns a 1-800-Got-Junk franchise in Framingham, MA. She was able to implement lessons she learned from a Stiletto Spy School poker lesson. “Playing poker taught me about negotiating and reading people’s faces,” says Briggs. “We had to assess the situation and consider, ‘What do I have in my hand? Should I just walk away from this deal, or should I continue?’ The same holds true in negotiating a business deal.”
For many business owners, Stiletto Spy School is a much more personal way to enjoy a shared experience with employees or clients than just going out for drinks or to a ballgame. “I’ve had people at these events with their clients, in hand-to-hand combat, out there on the mat, rolling around on top of each other, and punching each other,” says Winter. “I think things are changing, and people are becoming much more open on so many levels. Just look at Facebook; people are sharing so much more and becoming much more authentic.”
Christine Dimmick, founder and owner of New York City-based The Good Home Company, brought two employees to Stiletto Spy School this past August. “I thought it would be a great way for us to bond, empower ourselves and learn something new,” says Dimmick. “It’s been a hard time; everyone has been working so hard through this recession and it’s been depressing. Alana sent me that email about Stiletto Spy School and it was something that everyone here seemed excited about.”
From a business owner’s perspective, Dimmick felt that having employees participate in Stiletto Spy School encouraged creativity. “Any time you look outside the box you can translate what you learn to the work world. Anytime you grow personally, it benefits work because your personality directly affects the work you do and the quality of your work.”
For men who want to get their James Bond on, Winter also recently launched M16, a similar program for men and co-ed groups.
Stiletto Spy School attendees also learn “the art of seduction;” but reporting on that training would be a breach of security – skills are classified.
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Daria Meoli is the Executive Editor at The New York Enterprise Report. She can be reached at dmeoli@nyreport.com



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