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.

What’s your impossible ask this year? What will asking it do for you? Are you committed to making the impossible ask this year?

18 thoughts on “Make the Impossible Ask | Get Out of Your Comfort Zone

  1. Mark Sieverkropp says:

    First off, I LOVE this post! This is what I needed to start 2014!
    My impossible ask is to substantially increase my income…I’m talking more than double it. I’m talking a complete life change! And it completely fits your criteria, because it seems almost impossible and scares me to death! But I’ll accomplish it or spend every last second of 2014 trying!

    1. Jon Stolpe says:

      You can do it, Mark! I was thinking about you this morning as I listened to your interview on Joshua Rivers’ podcast (Quality Living Made Simple). I have a great friend of mine who recently lost his job and is going through job search and career analysis. I was thinking how you might be a great resource for him.

      1. Matt McWilliams says:

        Both Mark and Scott Barlow can definitely help him. Mark, give Jon your email and he can intro. the two of you.

      2. Mark Sieverkropp says:

        Jon, I’m honored that you’d think of us at HTYC. Thanks! Even before Matt mentioned it below, I had planned to give you my email. If you want to introduce me to your friend he and I can visit and see where we might be able to assist him!

        mark [at] happentoyourcareer.com

      3. Jon Stolpe says:

        Thanks Mark! I just copied you on an e-mail to my friend.

  2. One of my goals is to be more assertive. Basically asking for what I want. You will never get a yes if you don’t ask.

  3. Jon Stolpe says:

    Great post, Matt! I think one of my big asks for 2014 involves asking to guest post on some “bigger” blogs this year and asking people to guest post on my blog.

    1. Matt McWilliams says:

      Ask big!

      The great thing is if you ask ten and nine say no, you still get to publish the one. 🙂

      1. Jon Stolpe says:

        Great point!

      2. Jana Botkin says:

        Let us know what happens! Hey Matt, maybe Jon will even ask to post on yours about the process of asking ten Big Bloggers.

    2. Mark Sieverkropp says:

      Go for it Jon! You certainly have the content to make it happen!

  4. Paige Gordon II says:

    Awesome post Matt! I haven’t ever heard this concept before but I love it! I don’t really have any clue what my impossible ask for this year is, but I am committed to figuring it out and then going and actually DOING it. Thanks for the encouragement!

    1. Matt McWilliams says:

      Think about it, then make it happen…

      And report back to us on how it goes!

      Then do another one.

  5. Jody Maberry says:

    What I liked here was you did not stick only to the inspirational side of this message, including the story about Keith is something I can put my hands on. I can consider it and see how I can apply the Impossible Ask to my life. Thanks you.

    1. Matt McWilliams says:

      It’s a powerful story and one that every single one of us can copy on some level.

  6. Dan Black says:

    Great post, Matt! The key is to have courage in making the big asks.

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