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:

If your company were an animal, what would it be?

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.

How will you react if you don’t win this RFP?

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.

If you were us, what would you ask of you?

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

Worst RFP questions we've seen this year

Have you ever been breached?
(later in the same RFP: We can’t work with vendors who have been breached)

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.

r/dalle2 - "synthwave fat unicorn watching tv and eating snacks in a comfortable couch"

Your competitor says they can give us everything you do at half the price. How would you respond to this?

There’s only one way to respond to this:

Is this the absolute lowest possible price you can give us?

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.

Your company address is an empty plot of land on Google Maps. Please explain.

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.

Do any of your executives have a beard?

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.

What is your sales rep’s LinkedIn?

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

Why shouldn’t we work with you?

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:

Here’s a reason…

If you’re looking to spend twice as much on half the features while taking 3x longer to deploy, we suggest working with our competitor.

Please provide all responses in this RFP in one tab.

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.

Are you willing to work with competitor X to win this account?

Me and my new partner at the project kickoff call:

Who is the best customer you’ve ever had?

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.

Who’s the #2 in your company? Please provide contact information so we may contact them.

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

And the #1 worst RFP question of 2023…

How many times have you had Covid?

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.

Tired of filling out RFPs by hand?

Try 1up for free and you’ll never manually complete out a questionnaire again.