Hi, my company is considering getting our CEO a Rolex for her 35th anniversary with the company.
I went into an AD store today and found one that I thought was nice (a 2020 Datejust 28mm for $9,250 USD).

Went down the street to another AD and found another one that I also like (a Datejust 31mm for $10,300 USD). The owner of that shop knows one of the guys on our board of directors, and offered me a discount down to $8,700.

It doesn't seem like the supply problem is as bad for ladies watches, as it is for mens watches, so will I look like an a**hole if I ask the sales person at the first store if they work with me on the price? I would be asking for a similar, 15% markdown on the price of the 28mm Datejust, as what salesperson #2 offered on the Datejust 31mm.

 

I don’t think you would look like an a-hole and frankly, who cares! Asking for dealers to compete to get your money is not rude- it’s savvy shopping. That said, they are very different watches and depending on the style of your CEO (do you see her wearing dainty watches or chunkier ones), one may be more desirable than the other.
In terms of modern women’s esthetic- the 31mm seems more appropriate. But if she prefers smaller accessories- then the 28.

 

Why not buy the 31mm watch from the store that voluntarily offered you the discount and has a connection with your company?

 

Why not buy from the AD you got the best price from? If you prefer the other dealer then ask for a discount, the worst he can say is 'no'.

Who is actually paying for this watch? Employees or company funds? Is gifting your CEO a watch worth $10k going to cause issues? It's income to her, is it going to be reported as such? Many CEOs wouldn't feel comfortable accepting a gift that expensive, it tends to send the wrong signals. Would she want a $10k Rolex? There are reasons companies don't give out expensive gifts anymore, it causes headaches with taxes and image. There are lots of questions that need to be sorted out.

 

Without getting too far into the weeds....there is a board of directors, 7 of us to be exact + a very well heeled investor that owns the other 49% of the company. It's not not entirely my money to spend (I will only be picking up about 7% of the cost) and I want to bring the board members choices, vs. just saying "hey here is the best one, do we want it or not". FWIW: I do like his 31mm ladies DJ better than the other one.

 

Well, I'd like to see what watch the board thinks is the nicest, and then go from there. If there is a $2K spread on price, then that might affect which watch gets the nod.
I don't really have a preference on either dealer, just want to get her something nice that's not going to break our budget.

The 7 board members are in for half the cost and the other rich dude that owns the other 49% of the company is in for half the cost.
The watch will be paid for out of our (employee owners) own money, not company funds.
No, it's a small, privately held company so I don't forsee any issues. We would not be reporting it as income.
She puts up with alot of sh!t from some of the other board members so at the very least I think this would be a nice gesture to show her that her hard work and patience with some our less level headed board members is appreciated.
Not sure, on that. She wears an Apple watch now so...
Due to the small nature of the company, I really don't forsee any issues regarding taxes and image

 

you can always get the reference number of the watch you like and give it to the second store that offered you the discount. They may be able to source it for you. Best of three worlds. Keep the relationship, get the discount, get the watch.

 

If she has been ceo for 35 years, she should be buying you guys all datejusts lol. But to answer your question, no harm in asking.

 

...and don't forget to negotiate being added on the waiting list for a prof. SS model!!

 

The 7 board members are all commission based. Last year 5 out of the 7 board members earned income 2x-3x her salary, so I don't think the Rolexes will be flowing that direction anytime soon.
Sadly I was not one of those 7. (thx covid!)

Does it make me a terrible person that maybe ~5% of my motivation to spearhead the in person visit, picture taking, and explanation to the rest of the board, was that in the event we end up getting her one, that I'll be the guy associated with the purchase and can get added to AD's recent buyer list.

 

Only 5%!?!?

But the answer is, naaaaa, you are knowledgeable at this stuff, and if along the way, you get a little reward, why not?

Just make sure that your “own interests” do not conflict with the task at hand.

 

The choice of metal, dial , bezel and bracelet is up you. I would just lean towards the the 31 because that slight increase in size makes the dial more legible. At $10300 it seems you are looking at two tone smooth bezel. The fluted dial is only$100 dollars more and that fluted bezel really lifts the watch. Two tone yellow gold and steel, fluted bezel, jubilee bracelet, champagne dial, sort of a true classic. But price goes up to $10400. Two tone rose gold, fluted, jubulee, has a lovely rose dial $10750. You can always ask for discounts but most Rolex AD are at the no discounting on anything these day.

 

31mm seems more standard for a ladies Rolex these days, but if she likes an Apple watch it seems she’s more casual than someone who would wear a gold or two tone fluted bezel DJ.

It may however be a dressy alternative to her Apple watch but are you sure she would even wear it?
If she’s an understated practical person are you even sure she would appreciate that you guys blew 10K on something she might not even want or need?
When maybe she’s dreaming of a 10K Hermes handbag or a 10K budget to go on a trip with a significant other (virus permitting)?

I would try and probe her before pulling the trigger.
You can finance a rural school in Kenya with 300 kids for 3 years for that kind of money, maybe it’s worth ensuring she’s really blown away by the present.

I think you gents might want to consider doing what’s recommended for a present to a loved one:
Set the budget and let her decide what she wants.

Sorry for your standing with your AD and your future Rolex purchases.

 

^very sound advice from @Syrte making sure you can't go wrong with the recipient.

 

Women aren't buying the ladies sizes for themselves anymore; I understand 36mm is now popular.

You should ask for a huge discount on a ladies size that's in the case. If the AD can offer you 15% off that pig in the case, he'll probably let it go for 30% off.

 

Not all ladies are alike.

 

Fair enough.

In general, women aren't buying the ladies sizes for themselves anymore; I understand, in general, 36mm is now popular.

 

Speaking for my wife, who collects nice jewellery and likes good watches, she would definitely prefer 36mm - in fact she has had her eye on my Datejust and keeps dropping hints...

 

I’m gonna 2nd (rather 3rd or 4th?), the folks above. 36mm DJs are very much on display on women’s wrists as of late. Perhaps due to Apple’s larger wrist presence. Or maybe that the status symbol is easier to see in larger print. I lean towards the later. Regardless, if you’re shopping for something smaller then by all means negotiate the price!

 

To give a counter, I'd lean on the 28mm. Everyone is different so generalisations are tricky.

As @Syrte says so well, make sure the recipient would like a watch compared to a Hermes handbag, or flights etc. As watch nerds it's easy to get carried away and think "of course she would love a Rolex, that must be a grail for her!".