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Art of the ask: How to get to yes – and past no

This column is part of Globe Careers' Leadership Lab series, where executives and experts share their views and advice about leadership and management. Follow us at @Globe_Careers. Find all Leadership Lab stories at

I've been talking my way out of "no" since I was 18. Never the best student, I dropped out of high school just one course short of graduation (thanks for nothing, algebra!). Officially, I shouldn't have been able to get into college, but I went straight to the admissions office and pleaded my case. The school made an exception, and I turned a dead-end into a new beginning.

This willingness to "make the ask" serves me well running four companies today. Successful entrepreneurs have to make requests in almost every context, whether it's getting advice from a mentor, asking investors for funding, or pushing for a little more from employees. The ability to ask using humour, persuasion, and occasionally pressure, is the difference between success and failure in most business settings.

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Although being able to make requests is key, it's even more important to learn how to turn "no" into something that pushes you forward instead of keeping you down. Here's how to master the art of the ask and make the most of rejection.

Have some guts!

There's powerful truth in the saying, you never know what you'll get until you ask. By nature, most of us don't like the feeling of imposing on others, but this fear can hold you back from new opportunities or relationships.

I started WOW 1 DAY PAINTING after asking the guy who painted my house if he'd like to have a beer after work to tell me more about his business. He had such a unique model – using a big crew to paint a home or business in a single day – that I wondered if he'd be interested in franchising it. Turns out he was, and today there are dozens of locations across North America.

Some of the best-known entrepreneurs got their start with a simple ask. At 12, Steve Jobs called up founder of Hewlett-Packard Bill Hewlett to ask for spare computer parts. The tech titan agreed to help the aspiring computer whiz, and even offered young Steve a summer job at his company.

So work up the courage, and ask for what you want. You'll be amazed how often people will just say yes.

Get to the point – politely

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When I bumped into Subway founder Fred DeLuca at a convention years ago, I knew I had only one shot to make an impression on a business legend. Instead of posing a generic question like, "What's your secret to success?", I asked him about franchising – one of his passions and certainly an area of expertise. He was a great help and even encouraged me to follow up with an e-mail. From there, we began a long professional relationship that was hugely valuable to me.

This may be obvious, but good manners go a long way, too. Jodi Glickman, author of Great on the Job, recommends saying that you're about to ask for a favour at the start of the conversation. The other person will be put in the right mindset and become more prepared to help. Providing a reason for your request gives it added weight. If you can do these things and also convey motivation and passion, your odds of success skyrocket.

Expect – but don't accept – no for an answer

Of course, you should always prepare for "no" and go into the situation with a contingency plan. Often, I'll have backup requests ready or think of alternate ways to pose the same question – the best salespeople are Jedi Masters when it comes to this. Or I'll plan to approach the same issue later through a different person or channel. Insider tip: Executive assistants are the gatekeepers in any organization. Get on friendly terms with them.

Even when "no" really means "no," there's almost always something you can salvage. When I'm pitching a story about one of my companies to a media outlet like The New York Times, for instance, and get rejected, I ask the expert journalist what I could do to improve my delivery or story. The advice almost always results in improvements – and sometimes, a bite when I take it somewhere else.

In short, when you hear "no", your next question should always be, "Why not"?

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Learn to love rejection

Full disclosure: I still get turned down most of the time, but I never look at it as a failure. At least when a door slams in my face, I know it's one less option to explore – and that I'm another step closer to finding the way forward. The key is not letting it get you down.

Perseverance is an important trait in the business landscape: 78 per cent of entrepreneurs believe lessons from previous failures play an important role in their present successes. J.K. Rowling's Harry Potter draft was rejected by 12 different publishers who are now kicking themselves. Bill Gates' demos for his first project, the Traf-O-Data, didn't impress investors, but they became the starting point for Microsoft.

When I first decided to franchise 1-800-GOT-JUNK?, I took my plan to a dozen experts. Every single one said the idea was doomed. Instead of giving up, I reinvented myself and the business after each discussion. By ditching the parts of my plan that didn't work and refining my vision, I was able to create the world's largest junk removal service.

No matter where you are in your career – at the helm of a multinational conglomerate or grinding it out in a basement startup – asking has the potential to change your trajectory. Whether you get a yes or a no, you're on your way to success, one question at a time.

Brian Scudamore (@brianscudamore) is the founder and CEO of O2E (Ordinary to Exceptional) Brands, which includes companies like 1-800-GOT-JUNK?, WOW 1 DAY PAINTING, You Move Me and Shack Shine. He helps others grow small to medium businesses and corporate culture.

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