Sometimes brides and grooms get hung up on politeness as they start the process of selecting their wedding resources. They may think it's rude to ask some of the below or even awkward trying to negotiate something into their package but in the end, it's better to know the good and the bad before selecting some of your most important resources. Just remember, a little charm and humor go a long way.
Event Designer
"What's the worst thing that's ever happened at a wedding you designed?" I'm not talking about a groom being stood up or a bride running away with the best man. I mean what went wrong with the design, coordination, anything that falls in the event designers realm of pulling off an amazing wedding event. This is kind of like the interview question we all dread when a recruiter asks us "to talk about our weaknesses." There is a reason this is asked -- because you can learn so much from the answer. Of course we are looking for a real example. If someone tells you that all of their weddings have been perfect without a detail out of place, most likely they are lying. There is only so much an event designer has control over especially because they are dependent on other resources -- what you want to hear is how they overcame the issue despite of it happening. This actually can be used with all of your wedding resources. And don't be afraid to dig deeper and ask follow up questions or for more examples.
Photographer
"Can I see ALL the photos from one or two weddings?" As most photographers tend to showcase their best images, you will be able to better gauge their skills once you see the whole package.
Florist
"Do I get a mock up of what the centerpiece will look like?" I think this is a must no matter how big or small the order. Though some florists may have a minimum number of centerpieces you must order before they do a mock up, you may consider having them including this in your package to seal the deal. I think most florists would prefer to book the wedding vs. lose one over a mock up.
Cake Baker
"Can you coordinate with the florist?" "Huh, I just bake cakes?" Wrong answer. Well, it is if you want to use fresh flowers on your cake. Yes this happened to me -- and a guest actually helped me add the flowers and it was not at all how I had envisioned the cake, not to mention it felt weird having my guest help when she should be enjoying the party. So make sure if you do want fresh flowers on the cake that you know how they will get there and what it will look like.
Custom Wedding Dress Maker
"What if I gain weight?" Yes it happens -- the stress of planning a wedding may have you tipping the scale in the wrong direction. Especially you DIY brides to be, who sometimes take on more than you can chew! Make sure dress seams can be let OUT or in. I write from experience -- when I was pouring over details of my big day and planning everything from ceremony to reception, I tended to visit the sugar shack a little too much. At our last fitting I found out that my dress could not be let out and my strapless silk mikado sheath dress may spontaneously pop during the ceremony. It didn't!
Videographer
"Can I see a CUT and UNCUT version of your most recent wedding?" Just like your photographer you should see the good, bad and the ugly. By seeing before and after you can assess his cinematography skills -- or lack thereof.