The Worst RFP Questions We’ve Ever Seen

One of our favorite use cases at 1up is helping sales teams automate RFP responses.

We’ve had the rare privilege of analyzing more than 45,000 RFP questions, and let us tell you…there is no shortage of creativity. Most Request-for-Proposal questions are tame and mundane. But, occasionally, you get some real gems. We’ve seen queries so bizarre, confusing, and outright offensive that one must wonder how they made it into a sales process in the first place.

Here are the WORST questions we’ve seen in RFPs over the past year:

The Australian Deal-Winning Tarantula, of course. Its venomous fangs can close even the hardest enterprise deals. The best part about questions like this is they’re reminiscent of a lame job interview – only we can’t just get up and leave when we get them.

HR has informed us that a violent rampage is out of the question, so we’ll settle for wishing you well in working with our competitor.

Seriously, this question had us wondering if the whole vendor selection process isn’t just some cruel joke.

Responding to an RFP is hard enough…now you’re asking us to write it for you?!

Uhh…OK? This probably rules out most private corporations, as a security breach is almost an inevitability at this point in time. It sounds like the folks writing this RFP were looking for a unicorn. Not the billion-dollar-company type, but the literal mythical creature that doesn’t exist.

There’s only one way to respond to this:

Nope. We plan on going through several more rounds of negotiation in a vicious race to the bottom before you inform us that our competitor already won this deal 6 months ago over dinner with your CEO.

Obviously, we’re not a real company. Spending hours filling out this spreadsheet just so a customer can consider buying our product is all part of an elaborate con.

This one sounds ridiculous until you find out this RFP was for a company in the personal grooming space, so maybe this one is ok?

Context is everything.

Questions like these remind us why we need to normalize embedding blank stare GIFs into vendor questionnaires.

Err…we’re not entirely sure how anyone would answer this. We’ve actually seen this type of question in more than one RFP. The best way would probably be some inverse of your value proposition. For example:

This question appears in a document with hundreds of questions across multiple tabs, so it sounds like the requestor got lazy. Again, being asked to write the RFP while filling it out is truly something. Are we getting paid for this? Probably not.

Me and my new partner at the project kickoff call:

Of course it’s you guys! The thing about this query is it’s probably a roundabout way to ask for a customer reference. If you’re out there writing RFPs – please keep your asks direct.

You already know how we’re going to respond to this:

A highly inappropriate question, probably illegal, and it left us speechless. The interesting thing was that this questionnaire had nothing to do with the healthcare industry and was part of a website design project for a single-person agency.