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Might As Well Ask

Posted on July 1, 2024July 3, 2024 by Steve Ainslie

When I was a younger man I was a terrible negotiator. I rarely returned anything I ever bought – even if it didn’t fit or function well. I accepted whatever salary, terms and conditions were placed in front of me when I made a purchase or signed a contract.

I would hear other people brag about how they negotiated for a phenomenal discount on a new car, a higher salary, better benefits or a lower retail price and I wondered how they had the nerve to do this.

You might think that working in sales for decades would have made me a better negotiator. Nope. It didn’t.

What helped me get better was negotiating for a higher salary when I was interviewing for jobs.

At first, all I did when presented with an offer was repeat the offer out loud. For example, if the offer was $35K base salary plus $35K commission at plan I would say:

“$35K commission plus $35K at plan?”

Then I’d be silent and wait.

Sometimes, the person across the table would sweeten the deal just from me saying that. If they didn’t’t and I wanted more I would say, “That’s lower than I expected.”

Nine times out of ten, they would reply, “What were you expecting?”

As I moved up the career ladder and knew my worth, I would challenge offers by saying, “I really want to join your company. I think I would be a great fit and we would be a great team, but if you cannot offer a package that gets me to $XYZ, I cannot accept the position.”

You’d be surprised how many times I’d get a significantly better package the next day. Or, at least, I was.

Whenever I got a “final” offer, I’d also ask, “Can you do any better?”

That worked well too.


“Can you do any better?” has become my go to negotiating phrase for anything I buy today. It’s remarkably easy to ask. Often, just asking will get me a discount of 10% or better. Sometimes, the seller will throw in something extra to sweeten the deal. Sometimes their price is firm and they won’t negotiate.

I don’t think I ever get the “best price”. But I get one I can live with.


A few days ago, I ordered another hat from Conner Hats. They’ve become my new go to hat maker. Unfortunately, when I received the hat it was too small so I returned it to exchange for a larger size.

When I did this it got me thinking about my leather Conner Hat I had purchased back in April. I referred a large, which was too small and exchange it for an XL. The XL is still pretty tight but I figured it would “loosen up” over time. I haven’t worn it much because it’s too warm for summer but I intend to wear it a lot in the fall, winter and spring.

I’ve been stretching it over my knee, as instructed to loosen it up.

It’s still too tight. It looks great but gives me a headache when I wear it for more than 5 minutes.

So I sent an email to Conner Hats, asking them to make an exception and allow me to exchange this hat for a XXL – even though I am well past the 30 day exchange window. After all, I recently purchased 3 expensive hats from them and will likely purchase more going forward.

Will they do the exchange? I don’t know yet.

What’s the worst that can happen? They can tell me no and I’m stuck with a hat that’s too small. Well, I already am in the situation.

What’s the best that can happen? They let me exchange this for an XXL and it fits great.

Or they might offer me a partial exchange credit.

I figured I might as well ask.

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