Make the Impossible Ask | Get Out of Your Comfort Zone

I want you to make this the year of the impossible ask. What’s the impossible ask? Well, I’m glad you asked. Because it might change your life and make this your best year ever.

Make the impossible ask

Make 2014 your best year ever. Make the Impossible Ask. A lesson in stretching yourself from @ferrazzi. (Tweet That) | Share this Graphic on Pinterest | Share on Facebook

The impossible ask defined

The impossible ask is the question that scares you the most. In fact, just thinking of asking it terrifies you. It’s the question that has never been asked before. It’s the question that seems…well impossible to ask. It’s crazy. It’s potentially embarrassing. It leads to unknown places.

It’s different for everyone. And asking it will change your life.

The impossible ask might be when you ask your boss for that huge raise. It might be when you ask a publisher to publish your book. Or asking to play piano with Billy Joel. It could be any number of things.

But most people never ask.

Lunch with the CEO

Keith Ferrazzi, author of the legendary networking book Never Eat Alone (you would do well to read it), was twenty-four years old. He was a recent graduate of Harvard Business School with two job offers, both from prestigious companies. Most HBS grads were lucky to get one offer and pounced on it, but Keith had two.

So how did he decide which one to take?

Money? Location? Prestige? Title?

No. None of the above. Keith had a condition to choosing.

Never Eat Alone by Keith Ferrazzi

Want to be more like Keith? Read his book and start networking like you never have before.


Twenty-four year olds don’t have conditions on job selection. They don’t get to be choosy. But Keith was and his one condition was that he must have dinner with the CEO of the company. How else could he make an informed decision?

Both companies in the running hire thousands of new recruits every year, many of whom were vastly more experienced and qualified than Keith. But none of them…not one…ever asked to have dinner with the CEO. And the CEO said yes.

One more condition

When they finished dinner, Keith agreed to come work for the CEO at Deloitte. On one more condition.

The new condition was that each year, the CEO and he would eat dinner at the same restaurant. He made the impossible ask. He asked the question that no one, not one single person in the tens of thousands of previous applicants, had dared to ask.

And the CEO said yes.

So who of the thousands of people hired that year and even in the years before had a direct pipeline to the CEO?

One. Keith.

Who do you think was promoted most rapidly in his class?


Not the most qualified. Not necessarily the hardest “worker” (in the traditional sense). Not the smartest. Not the best-looking.

Keith was. And he quickly became CMO, passing over literally tens of thousands of others who started at the same time or much earlier than he did.

Others say:

“It’s not fair.”

“He got special treatment.”

“He’s just lucky.”

“It’s because of his daddy.”

“If I knew the CEO, I would get promoted like that, too.”



Afraid to make the impossible ask.

Why did he know the CEO? Because he busted it. Because he dared to ask. Because he got out of his comfort zone.

Because he made the impossible ask.

When the answer is no

What if the CEO at Deloitte had said no?

Then the next time Keith asked the same question, it would have been easier.

Each time you make the impossible ask, you grow. Each time you step out of your comfort zone and dare to ask, it gets easier to ask again. And soon…you will hear yes.

And it will be oh so sweet.

Question: What’s your impossible ask this year? What will asking it do for you? Are you committed to making the impossible ask this year? You can leave a comment by clicking here.

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