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How to make an ask so they say yes

We're always trying to get someone to say yes to us. We often ask others for help with this. But there's a step a lot of us skip that's hurting our odds of getting that yes we want.

This week I’ve had more than the usual people asking for help with making an ask. And in the process, I’ve found that there’s a concept, one I call “It isn’t about you, it’s about the other person,” that stumps most people. So voila. Ya’ll get a write-up.

Here’s what version 1.0 of most people’s asks look like:

“Can I have x?” (Or some variation of that.)

  • Can you connect me with…?
  • Can I have a raise?
  • I want a job doing X, do you know someone who’s hiring for x?
  • I have this idea. Can you approve it?

Now don’t get me wrong; version 1.0 does have some things going for it. Like a strong “close” that includes a specific request at the end.

Asking at all is a great first step. We should do it more. There’s nothing to lose. What’s missing, though, is the context. Or the “why” that makes it easier for the other person to say yes. 

So often, people skip this step when “Yes!” is precisely what they want to get from the other person. 

Case in point: A super interesting person in my network (let’s call him Steve) wanted me to connect him with a very famous CEO. I, of course, said yes. Now, I could have just forwarded the email from Steve to the CEO in question. Sure, I’m connected to Fancy CEO but I know I’m no Oprah—an email from little ole me would probably get routed to someone on his team. 

So I wrote Steve back and said:

“Hey, happy to help. But can you put some language together on why Fancy CEO should say yes to the introduction? I’m connected, but I want to make sure Fancy CEO is excited about your ask.” 

Steve’s response was to send me a relatively generic batch of marketing materials about his organization and what they were doing.

No. Just no.

Let’s break down why.

  1. Fancy CEO probably gets thousands of emails like this every day. Would he open and read them all with glee? I think not. 
  2. So now, let’s assume Fancy CEO doesn’t have time to read the email but knows I wouldn’t send him spam and forwards the email to an EA or someone in another department. Note – this is HIGHLY likely. Would this person make an effort? Maybe. And, assuming they did, what language do you think they’re going to use to explain to Fancy CEO what this ask is all about? You guessed it; it’s their own.
  3. By just sending me marketing materials, Steve made it more difficult than before for me to connect him to Fancy CEO. Because I never make an ask without considering the recipient I’m going to have to craft a whole new email. Like all of us, this inevitably means the “send” part of the process gets delayed. If you’re asking someone for a favor shouldn’t you make it easy for them to help you?

Fortunately, Steve was open to feedback. He did the work of putting language around the “why.” He thought about the result he was after, and the people involved in saying yes: the Fancy CEO, me, and all the people in between.  

He’s got a better version now, It still might not work, but my guess is the odds are significantly more in his favor.

SO WHAT DOES THIS MEAN FOR YOU AND HOW YOU ASK? 

Let me back up a second and lay the groundwork. We’ve talked about my friend Cinderella and the Fairy Godmother before. Cinderella wanted to go to the ball. The Fairy Godmother understood that her job was to help Cinderella get to the Ballroom floor. And to get her there, Fairy Godmother needed to think about how to make it easy for everyone between the front gate to the dance floor to say yes to Cinderella. 

The dress and shoes were never just about winning the Prince. They were about making it easy for all the literal gatekeepers to say, “Yes, you should be here,” so Cinderella could gain entry to the ball.

Now, I want you to take your “Can I have x?” and make it about the other person.

Why should they care?
What’s the context?
What do the people they care about, care about?
Who else is involved in the decision?
How can I make it easy for all of them to say yes?
What do they care about?
How do they measure success?
What happens for them if the answer is yes?
Do they need to explain my ask to someone else?
Are there any gatekeepers in their way?
Do they need to follow any process or procedure that might slow them down?

This is just the start of a list of questions I ask when I’m helping someone with an ask. If you have an ask you need to make in the next 24 hours take a moment and think about the answers to the questions. I have NO doubt you’re more likely to get a “yes.” So my last question is “what will you do when they do say yes?.” I’m that confident.

Ask for a raise, an introduction, a promotion, a job, for someone to say yes to your idea—whatever the ask is, “why” matters. A lot. 

So to all my Cinderellas and Cinderfellas do you know what ball you want to get to? Great. I promise you’ll have much better luck getting in if you make it easy for everyone else to say yes.

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