The 3 Best Questions You've Never Asked a Prospect

Rachel Sheerin, She Sells

How are you? How’d you get engaged? Were you surprised? Are you bored yet?

That’s right, we’ve all asked these questions and we’ve all known deep down that brides & clients have heard these same questions from every other vendor since getting engaged. While we’re coming from a curious, sincere interest in their happiness, their story & their big day, these questions are equivalent to a big-old-yawn when it comes to the great questions you could be asking instead. I mean, you’re unique, your business is one-of-a-kind, so why aren’t you asking questions that reflect that?

Ask these 3 questions and never have a dull, average conversation with a prospect again:

How did you get started?

Yes, this could be similar to “How did you meet?” or “How did he propose” but this question is my favorite at ALL events because it brings people back to the beginning and sparks a story. As we know, the beginning of all stories is almost always full of joy, hope and excitement and that’s exactly the emotions you’ll evoke from your prospect when asking them how they got started. Whether t bridal shows or a professional networking event, ask this question and gain insight into someone’s life, motives, story and values instantly. Use this interesting & deep connection to assess if this client or partner is a good fit for you and your business.

How do you prefer I follow up with you?

This is a double-edged question with a dual purpose: Find out if this prospect is a good personality fit with you and know how they respond best. In the world of email, text, Facebook Messenger, and a good old fashioned phone call, asking prospects how they prefer to be communicated with can open you up to communicating in ways that make them happy, valued, heard and understood. Have a client that loves to text? Understand the challenge ahead (aka they may be hard to get a signed contract) so be sure to have an online contract they can fill out (no printing required!). All your clients Facebook-aholics? Shouting them out on your page may lead to more referrals. Remember: We’re here to serve clients and make it easy for them to say YES to us, so asking their preferred method and adjusting your pitch accordingly can spell out big returns!

What is your biggest fear about booking a (insert what you do here)?

Yes, fears are scary but we all have! If you’re an expert in DISC behavior profiling like me, you may know how to tell what people’s biggest fears by watching their behaviors, but if you’ve not yet been trained, asking your prospect can yield some very illuminating fears that can help you soothe their concerns. Some folks may be concerned about being ripped off (used car salesmen, style!) while others may be concerned about what their friends will think of their choice, or perhaps that they are not smart enough to make this decision and will suffer decision peralysis. Whatever their fears, asking them can provide your prospects with a sigh of relief by sharing them and having you massage their fears away. Sometimes people’s fears will be invalid or seem ridiculous to you, but it’s important to remember they’re real to your prospect and need to be relieved in order to get them to sign up for your great biz!

A final note about questions: Somewhere along in our life, we were scolded for asking too many questions. As a child, asking questions was so endearing, until asking too many questions (some of which our parents didn’t have answers to) was deterred and as adults, many of us never let go of the shyness that comes with asking questions.

I am here to adamantly share with you:


Asking questions is literally just attempts at having a relationship that is honest & meaningful. That’s right: IF YOU ASK QUESTIONS OF SOMEONE, YOU CARE ABOUT THEM! And when you think about questions like that, well then, who wouldn’t want to get to know and care about someone? So get out there, start asking, & enjoy the rewards!

rachel sheerin

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