Mini quiz time. Which of these have you encountered?
- A detailed clarification question answered with “Please refer to the RFP”
- A 1000-character limit for a “comprehensive and technically sound” response
- A 10-day deadline for a “strategic procurement that will shape our organisation for the next decade”
- All of the above
I bet you picked D. These classics of the bidding world are no longer just war stories we share over coffee; they’re now daily posts on our feeds. The rise of professional social media has made it impossible to ignore just how widespread (and absurd) these situations are.
And while it’s easy to laugh (or cry) at these contradictions, they reveal a deeper truth: our profession often operates under a bizarre blend of formality and dysfunction. Some of it comes from internal processes but a big chunk originates in the procurement process itself.
Let’s break this down. There are two kinds of Catch-22s we deal with.
Structural contradictions
These are the true Kafkaesque moments: conflicting instructions, broken scoring logic, or requirements that undermine the stated goals of the RFP.
Arbitrary constraints
Think: 2,000-word limits for entire solution sections, impossible turnaround times, or formatting rules that prioritise uniformity over clarity.
For the first type, there’s not much we can do. We should keep providing feedback, but real change depends on procurement teams embracing modern tools and practices. The good news is that it’s already starting to happen. As more buyers use AI to draft RFPs, we’re seeing better structure, more consistency, and fewer contradictions. That trend is promising.
But the second type, the arbitrary limitations? That’s where we can take back control. Because here’s the thing: AI won’t stop silly deadlines or word counts from being imposed. But it will help you deal with them.
If you’ve got to squeeze a brilliant answer into a tiny box or produce a winning response in days instead of weeks, AI gives you the speed and flexibility to pull it off without compromising quality. For Catch-22 situations, this is gold.
But I want to go further because the higher quality and faster proposals that AI gives you are not the real advantage. Everybody is using it (or is about to) so that’s the new bar. It’s what you do with the time that AI gives you that really matters.
Imagine using those freed-up hours not to wrangle layouts or cut words but to deep-dive into your client’s business. To map out competitor strategies. To hold a real conversation with your SMEs. To think creatively about your solution. To run a proper red team review instead of a rushed proofread.
That’s where bids are won.
Javier Escartin
Javier is an aerospace engineer who has climbed the corporate ladder from engineering to business development. He is a full-time freelance Proposal Manager and has recently launched a business to make our work easier with artificial intelligence. He is the founder of DeepRFP.com, runs the proposals newsletter jescartin.com, and manages proposals for worldwide technology companies as a consultant.
