How to A-S-K for What You Want and Get It


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A Story about ASKing for what you want, and getting it

Let me paint a picture for you. I am in a NYC bagel shop. There’s a line out the door. After about 15 mins, I make it to the counter and order my bacon, egg, and cheddar breakfast sandwich on a jalapeno cheddar bagel. I can’t wait to bite into this thing. I wait, as patiently as possible, for my food to come. I see it come off the griddle, go into it’s aluminum sandwich pouch and the guy yells out “Stef!!!” I basically jump him, as he hands me my food.

Now, I turn to find a table to sit at. This place is overflowing with people. I scan the room looking for a table: taken, taken, taken, taken. Toward the back of the room, I see an 10 person table, and two old men sitting at one end of the table. I walk up to them and politely ask “Would either of you mind if I snag this seat to enjoy my breakfast?”

“Sure!” they respond, almost happy to see me and delighted that I asked, so they could help me with a place to sit and enjoy.

I sit down, dig into my breakfast and delight in the fact that we are all sharing this wonderful table, and instead of eating my sandwich on a curb, I get to enjoy every morsel from this table and comfortable chair.

About five minutes later, while I am still eating, these older fellas stand up, grab their canes (yes, they had canes!) and teeter out of the place, leaving me alone, at one end of my long, ten person table.

As I sit here, continuing to delight in my breakfast, I begin to observe: First, a family walks by, inspects the table, then turns, walks away, and exits the restaurant. Next, a couple walks by, inspects the table, then turns and walks away, and exits the restaurant. After that, a lone businessman walks by, inspects the table, pausing as if he intended or needed to say something, then turns and walks away, and exits the restaurant. Finally, another family, walks by, inspects the table, then turns to walk away — I’d had it at this point, and I stop the family and say “Hey, I am about to take off, would you guys like this table?” They are thrilled, and take seats at the table as I get up.

I feel good that I was able to offer this family my table, I hope that their trip to this NYC bagel shop was slightly better as a result of my offering it up. I walk out of the bagel shop, basically skipping back to my hotel, fully belly, full heart.

My trip concludes. I head back home.

With the spaciousness and clarity only brought to me by a sunny weekend and a long walk pushing my daughter in a stroller, I recall this experience with wonder.

Why didn’t anyone ask to share the table with me?

For the cost of a few words and a smile, and at no inconvenience to me whatsoever, any one of those groups of people could have enjoyed their breakfast sitting in a comfy chair with the help of this big, long table, instead of wherever else they had to go to do the same… huh?…

As I am thinking, I am reminded of my college professor, the guy who taught my Sales 101 class, he used to ask:

“What does it mean to ‘Assume?’” We didn’t know. “Make an ASS out of U and ME” he’d say.

Now, I don’t think that any of these groups made an ASS of themselves, let me be clear. I do suspect that they made some wrong assumptions about the situation though. Here are a few assumptions I came up with:

  • “She must be waiting on a group of friends to join her, I don’t want to impose.”

  • “She must not want to sit with anyone else, I don’t want to impose.”

  • “She’s probably turned others away already, I don’t want to be rude and ask again.”

  • “She’s probably smelly, I don’t think I want to sit with a smelly person.”

^ Okay that last one I hope nobody thought, but it’s possible!

In each of these instances, the people searching for a table ASSUMED something about me, the situation, and their ability to get what they wanted from me, to help their situation.

And in every case, they got a less than desirable outcome… for themselves! They ended up without.

For the cost of just a few words, ASKing me if they could sit, instead of ASSuming they couldn’t, any of them could have had a much different start to their day.

I’ve been thinking about ASKs since. What kind of ASKs are there in this world? Why don’t people ASK? How can I help them?

As someone who’s been an entrepreneur bootstrapping a startup, as someone who’s been in sales for the majority of my career, and as someone who’s been hosting a podcast for the last four years, there’s one thing I’m damn good at doing: ASKing questions, ASKing for the business, ASKing for help, ASKing really for anything I need to go from where I am to where I want to go.

So I thought I’d write about it.

Here’s some rough draft thoughts, notes, and ideas to inspire you to ASK for what you need.

ASKs come on a scale of one (simple asks) to three (life-changing asks):

  1. Simple ASKs — “Can I sit here?”

  2. Complex ASKs — “Are you ready for me to send you a contract for XYZ?”

  3. Life-Changing ASKs — “Will you marry me?”

Anytime you ASK anything, you need the same three components to the formula:

A - Find Your Angle

  • Understand your goals and incentives;

  • Project what you believe to be true about their goals and incentives;

  • Use this information to find the potential for mutual benefit… this is your Angle.

S - Say It Outloud

  • Go over the ask in your head… What are the words you will use to be clear about the ask, intentional about how you frame it to the person you are asking, and set yourself up (as much as possible) to be successful?

  • Think about the ask from their perspective: They will be on the receiving end of your words, how do you want them to feel when you are done asking? Practice and revise until you get to something that feels suitable for the situation at hand.

  • Say the words out loud to the person who holds the answer. You won’t know the answer unless you ask.

K - Know The Answer

  • Yes, gets you what you want.

  • No, means “not now,” “not yet,” “you’re talking to the wrong person,” “you haven’t positioned this in a way where I care about it enough to say yes,” “try harder,” and in some instances, can even be “god’s re-direction.”

  • In either case, you’re further along now than before you asked, as you have the answer you need for now to keep it moving.

Mastering the skill of ASKing is key to a life well-lived

ASKing is a compression algorithm for getting what you want out of life, whether it’s as simple as asking for a seat at the table so you can enjoy your breakfast, as complex as asking for a contract that helps your company keep the lights on, or as existential as committing to your soulmate that you’re in it for the long haul, if you don’t A-S-K, you won’t know the answer.

Getting to “Yes” or “No” is helpful. These answers as they propel you forward, unlocking new challenges, obstacles, opportunities and ASKs.

It’s only wondering “How would things be different if...?” that keeps you stuck, ruminating, and wondering what the answer could have been if only you’d ASKed.

Now there are other, more complex, elements to this that I won’t get into as part of this writing — things like having the courage to ask, believing that you are worthy of asking, even the timing of the ASK, to set yourself up for the best result. but I’ll save that for ASK 102 :)

Next Steps

Inspired? Want to put some of this into practice? Here’s my challenge to you:

  • Step 1 — Start seeing moments in your life in terms of opportunities to ASK

  • Step 2 — Figure out the scale of the ASK (simple, complex or life-changing) and give it the appropriate amount of forethought for the situation at hand

  • Step 3 — Use the ASK framework to:

    • Find your Angle

    • Say it Aloud

    • Know the Answer

  • Step 7 — Reflect on the answer, the process, and how you felt about the outcome. Consider how you might approach a similar ASK in the future using the lessons learned from this one.

  • Step 8 — Repeat this every time you have an ASK on your heart, in your mind, or in your gut. Watch as doors open, or close, and you make progress regardless.

Author’s Note

The picture for this blog post is a picture of Theo Von, one of my favorite standup comics, whom I saw on a trip to LA. I did not have tickets to this show, yet I found my way to:

  1. The VIP lounge where celebs like Theo and their VIPs hang out before and after the show

  2. A front row seat for me and my friend, at no cost to either of us, laughing along with Theo during his set

  3. The memory of a lifetime

This is the power of ASKing. Maybe I’ll tell you the story about how this ASK another time :)

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