It Never Hurts to Ask

shiny new (used) cowboy boots
The Boots

While shopping at a trendy second-hand store last month I spied a nifty pair of burgundy cowboy boots that looked about my size.

I wasn’t in the market for boots that day, but these were pretty and I couldn’t resist trying them on.

They fit perfectly!

There was a price tag inside each boot. It was a little yellow one like you might see at a grocery store. Or maybe the Salvation Army? It said $25.

What a steal for genuine leather made-in-the-USA cowboy boots! How could I NOT buy them at that price?

However, there was a piece of tape on each sole on which someone had written “$58” with a marker.

This seemed like a more realistic price, and I suspected the store hadn’t noticed the price tags inside the boots when they priced them.

I wasn’t going to buy them for $58, because I didn’t have an urgent need for cowboy boots. But if I could get them for $25, it was a no-brainer.

I took the boots to the cash register where two young women were manning (womanning?) the counter.

“Excuse me, are these boots twenty-five dollars?” I asked, holding the boots so that they could see the price tag inside.

They examined them inside and out.

“No, they’re fifty-eight,” said one of them uncertainly.

“Oh,” I said. I started to mentally kiss the boots good-bye…

And then I thought, ‘What the hey? I’m allowed to ask, and they can always say no.’

So I asked.

“Um … Can I have them for twenty-five?”

The young women looked at each other, and after the briefest of pauses, they agreed.

“Yes, it says twenty-five on the inside, so we have to let you have them for twenty-five.”


Anatomy of the Ask

It’s true what they say: It never hurts to ask. But how one asks can mean the difference between a successful interaction and an unsuccessful one.

These are the “ask” rules I live by:

1. I always have a right to ask, but I don’t necessarily have a right to get.

Remembering this basic rule ensures that my attitude as I’m asking is one of humility and gratitude, rather than entitlement.

Asking in this spirit leaves room for the other party to decide how they really feel about giving me what I’m asking for.

In the example of the cowboy boots, the women themselves seemed to feel it was fair to charge the lower price inside the boots, after being asked to consider honoring it.

2. Ask someone who has the power to say Yes.

If you ask someone who has to go ask the boss, it’s easy for the boss to say no to the employee, leaving the employee no option but to pass the “No” on to you.

3. Trust the other person to say No if they need to.

I don’t have to be responsible for the financial well-being of a store that offers me a discount. The store takes care of its own finances by adding a healthy markup to its prices.

Similarly, if I ask Mike to give me the last bite of his taco, I trust him to say No if he doesn’t want to give it up. If he gives it to me and resents doing so, it’s not my fault.

4. Asking is a good way to practice healthy entitlement

You can ask for absolutely anything. Just because you’re not necessarily entitled to receive what you’re asking for, doesn’t mean it’s stupid, wrong or mean to ask.

  • You can ask the bus driver to let you off in front of your house.
  • You can ask a stranger for ten dollars.
  • You can ask your doctor, dentist or hairdresser for free samples (or a foot massage).
  • You can ask your gym to reduce the cost of your training sessions.
  • You can ask your city council to declare your birthday a municipal holiday.

Asking is free and, done politely, does no harm.

You’ll be surprised how often you get what you ask for — even if you think there’s no way you should!

Have you ever been surprised to get something you asked for?

12 thoughts on “It Never Hurts to Ask”

  1. Growing up in NYC, we were weaned on negotiation, since it took this skill just to navigate the streets! I agree, respectful asking does no harm and you okay get a bargain to boot (pun intended!) By the way, I bought an authentic pair of cowboy boots for $25 too from the Bargain News – just my size, in black and I love them! We should go line dancing!

  2. I agree: if you don’t ask, the answer is always no. I admire your concept of phrasing it in such a way that you receive your desired result A.K.A. tact, not always my strong suit lol; I too grew up in New York City where directness was the norm. I’ve been learning other ways since living in the South these past 21 years.

  3. Just Googled to see who wrote one of my favorite quotes, “if you don’t ask, the answer is always no.” The author is Nora Roberts, who wrote this: “If you don’t go after what you want, you’ll never have it. If you don’t ask, the answer is always no. If you don’t step forward, you’re always in the same place.”

    • Good advice, Multnoma. Now that we’re adults, we can freely exercise our rights, both to ask, and to say No.

      I taught an assertiveness class yesterday and during a role play, someone simply and quietly said, “No.” We all took a moment to marvel at the sheer power of that word, all by itself — no posturing, shouting, attitude, or explanation. Just “No.”

      Actually, let’s not tell Mike about that. 😉


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