I’ve been working on some version of this list of questions to ask new prospects over the years. I’m recommitting to asking these questions and getting good answers–even if they challenge people–during our first interview, which is why I’m sharing them here.

If you can use these questions in your own sales process, or some variation of them, please do.

• What’s your elevator pitch/what do you do? Although this is often gets them to answer further questions, it’s a quick way for them to frame what they do. It also has the benefit of showing me when they’re not exactly clear what they do, why they do it, and who they do it for. It’s always great when it’s precise:
  
  • “We run an organic landscaping business in Greater Portland.”
  • “We shred private documents for businesses and government agencies on the east coast.”
  • “We help people with disabilities in Texas get paying jobs and get them set up with housing as needed.
• What are your top 3 business goals? There doesn’t always have to be three; sometimes there’s more and sometimes there’s less, but I found that three, well, it’s a magic number. It reminds people that they may have more than one business goal, but also helps others focus so they’re not trying to manage 20 business goals.
• Who is/are your top 3 audience(s)? Again, 3 is somewhere between random and arbitrary, but it gives us a target. I’ve found that some people are extremely specific, i.e., “women in their 30′s and 40′s making $100K or more who don’t have kids but love being the “cool aunt,” and some obviously haven’t thought about it, i.e, “um…women?”
• What do your prospects/web site visitors want to accomplish at your site? People get this question wrong more often than you’d think. And by “wrong” I mean that they give me their answer in the form of “what do I want my visitors to accomplish at my site.” So answers like “learn more about my capabilities” or “sign up for my email newsletters” may be outcomes, but they are probably not the driving force for people to visit your site. “Get design ideas for their kitchen,” or “make a reservation,” or “schedule a massage” are probably more accurate.
• If you choose to work with flyte, what will make this project feel like a success/money well spent in six months? In a year? This is my favorite new question. This is really the target/goal setting question. Does success look like a well designed web site? Does it look like a high ranking at Google? Does it look like increased conversions at the website? Does it look like better communications with their customers? This also helps us keep our eye on the prize through the development process.

I also ask what’s your budget for this project (they never have one) and what’s the timeline (invariably yesterday.) Depending on the conversation I might ask about what they’ve been doing so far (especially if they’re frustrated with the current state of affairs) and what other marketing/advertising/sales they’re doing (to help determine if I need to manage expectations.) I try not to ask too many technical questions (who’s your registrar, do you have pop boxes or a mailserver) as that’s better saved for a later conversation if we decide to move forward.

What questions do you ask your prospects? Which ones do you think I should be asking that I don’t?

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