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Writing Good RFP Questions

Crafting an RFP doesn’t have to feel like wrestling an octopus—especially in our post-2020 world of remote work, AI demos, and supply-chain surprises. Here’s your friendly, chatty guide to getting the right info from vendors, fast.

Summary:

  1. Your “best” vendor is the one that fits you—not necessarily the flashiest name in town.
  2. Nobody knows your needs better than you do.
  3. Let vendors wow you with live demos, AI prototypes, or virtual walkthroughs—but keep it relevant.
  4. Be respectful: don’t fire off essay-length questions they’ll just ghost.
  5. Closed questions (think multiple-choice) give you apples-to-apples answers.
  6. A handful of killer questions beats a mile-long questionnaire every time.

1. Why Simple Bid Comparison Works

Back in the day you could email “We want X—send a proposal” and call it a day. But after the 2021 supply-chain crunch and the rush to cloud during COVID-19, those one-size-fits-all replies just don’t cut it. You need a format that lets you stack responses side by side and score them without agonizing over follow-up emails.

2. You’re the Expert (Really!)

With vendors rolling out fancy AI features in 2023 and beefing up remote-support offerings, it’s tempting to ask tons of technical questions to “stump” sales teams. Spoiler: it backfires. They’ll assume

  1. you’re not sure what you want,
  2. you’ll drown in data, and
  3. it’s safer for you to pick the brand that feels “tried and true.”

Instead, zero in on your own goals. Ask how their solution solves your problem—whether it’s keeping clients updated via Slack integrations or ensuring 99.9% uptime for your global team.

3. Finding the Right Granularity

Breaking your RFP into clear sections helps with scoring—but go too broad and you lose detail; go too deep and you drown in minutiae. Here’s a quick example:

Question Weight
3. Describe your support offering 20%

That’s too general—one answer could span docs, phone, chatbot support, 24/7 SLAs, and more. A clearer approach splits it up:

Question Weight
3.1 In-app help features 3%
3.2 Printable documentation 5%
3.3 Training options 3%
3.4 Website support (forums, email) 7%
3.5 Phone support hours & fees 2%

And if you really need depth—say you care about community moderation—drill into sub-questions. But beware of getting lost:

Question   Weight
3.4 Website Support   7%
3.4.1 Do you have a support forum? Yes / No 1%
3.4.1.1 Are comments moderated? Yes / No 0.6%
3.4.1.2 Can anyone post anonymously? Yes / No 0.4%

4. Closed vs. Open Questions

Open-ended prompts let vendors tell their story (“Describe your company history”), but they’re a pain to rank. Transform them into crisp choices:

Instead of:
“Please describe your company history.”

Try:
“Which best describes your company’s age?”

Please indicate your company’s age:

  • 3 years or less
  • 3–7 years
  • More than 7 years

Then assign scores—maybe anything under 3 years needs extra scrutiny after those 2021 supply-chain lessons, while 3–7 is “solid,” and over 7 is “veteran.”

Worried about edge cases? Add a “Comments” box so bidders can explain, say, a new spin-off that inherits parent-company muscle:

Comments:

5. Wrapping It Up

RFPs are less about grilling sellers and more about understanding—and communicating—what you really need in today’s fast-paced market. Think remote-first support, AI-powered demos, ESG commitments, and supply-chain resilience. Draft, score, iterate, and come out the other side with a clear winner who’s ready for 2025 and beyond.

Further Reading

Effective RFP Development, by Bud Porter-Roth

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