How to ask for what you want

I’m traveling in Mexico with my family this week. It is really special: the first time in decades that my family has traveled internationally together and the first time we’re doing so with my two nephews. And operating in such close proximity reveals some habits that I don’t love.

We don’t use the word please, for example. Growing up, please was mostly used as a demand in moments of peak frustration. “Will you please do what I asked!” More generally, we (and I am very much included in this assessment) are not very good at asking directly for what we want.

Except for pushy telemarketers, most of us don’t ask for things directly. And almost nobody asks without some amount of demand or expectation.

But asking is really important – whether in closing a sale or voicing an opinion. Without a clear expression of what you want, it’s hard to get anywhere quickly.

Here are some habits that I’m practicing with my family – and will be exploring in more depth in a workshop on selling I’m planning for the New Year.

Recognize what you want

It is pretty hard to ask clearly for something that you aren’t clear about wanting, yourself.

Identify what you want. If you don’t know, write a list of things you might want and pick the ones that seem the best.

Know why

After you’ve recognized what you wantconsider why. For a primer on finding your why, check out last week’s article on the topic.

Brainstorm a list of reasons why. Choose several! The more reasons, the stronger your desire will be.

Let fear be a guide

Fear is an excellent guide. When you’re afraid of selling your idea, your product, or voicing your opinion, that’s a great reason to move towards that fear, not away from it.

Start small

Starting small is a secret to unlocking any sort of behavior change.

Don’t compare yourself to anyone else’s ability to persuade, ask or close a deal. Just take the next small step from where you are currently.

Practice in advance

Asking for what you want requires rehearsal, just like athletic performance and everything else in life.

If you aren’t good at selling your idea, that’s probably because you haven’t practiced!

Start by writing out your pitch. I suggest writing out a pitch in three formats – one sentence, one paragraph, and one page.

Iterate as you go

Great salespeople – greats in any domain – don’t just get good at their thing and then stop progressing. They continue to iterate.

Learn from every pitch, notice what works and iterate as you go.

Ask for what you want

Ask for what you want!

When you are talking to someone, writing to someone, speaking to them on the phone, or promoting your thing on social media, end with a clear ask.

“Would you like to buy?”
“Would you like to go to dinner?”
“Do you agree with my opinion?”

Get feedback

A day or a week after you’ve tried to sell someone or pitch your idea, ask them about their experience. How was it received? Is there anything they think you could have done better?

There’s a lot about my family that I’m grateful for. And we come with quirks and challenges.

I’m not proud of the extent to which I don’t comfortably use the word “please” and hesitate to make my opinion known. But when I see those dynamics within the broader context of my family, I have a bit more empathy and understanding.

The only way to get better at asking for what you want is by observing where you are now and taking the next steps from there.

Enjoy your holidays and see you next week,


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