5 Questions to Ask When a Prospect Says "Send Me a Proposal"

"Send me a proposal" sounds like progress - but it's usually where deals die. Here are 5 questions to ask before sending anything, ensuring your proposal gets read and actually moves deals forward.

"Send me a proposal" feels like winning. They're interested enough to ask for next steps, right?

Wrong.

Most proposals sent after this request die unread in inboxes. Prospects use "send a proposal" to end sales conversations politely without committing to anything.

The solution isn't refusing to send proposals - it's asking 5 critical questions BEFORE you send one.

Why "Send Me a Proposal" Kills Deals

It's a Polite Brush-Off: Prospects say "send a proposal" when they want to end the conversation without saying "not interested."

You Lose Control: Once you send a proposal, you're waiting for them to respond. They control timing and next steps.

Critical Information Is Missing: You don't know decision criteria, stakeholders, budget, or timeline. Your proposal is a guess.

No Champion: If they won't discuss details before proposal, they won't champion it internally after you send it.

Result: You spend hours crafting proposals that get ignored or used to validate decisions they've already made.

The 5 Questions to Ask

Question 1: "What specifically would you like to see in the proposal?"

What This Reveals:

• Whether they've thought through what they actually need
• If they're serious or just brushing you off
• What matters most to them

Red Flag Responses:

• "Just send me whatever you normally send"
• "Your standard proposal is fine"
• Vague or generic requests

Good Responses:

• Specific requests about pricing, timeline, scope
• Questions about how you'd address their situation
• Concern about particular aspects

If They're Vague: "I want to make sure I send something relevant rather than generic. Help me understand - what specific questions do you need answered to make a decision?"

Question 2: "Who else needs to review this proposal?"

What This Reveals:

• If you're talking to decision-maker or influencer
• How many stakeholders are involved
• Decision-making process

Red Flag Responses:

• "Just me"
• "I'll handle that internally"
• Won't reveal other stakeholders

Good Responses:

• Names specific people and their roles
• Explains what each person cares about
• Describes review/approval process

If They Won't Share: "I ask because different stakeholders usually have different priorities - finance cares about ROI, operations about implementation, IT about security. Who should I make sure this addresses?"

Question 3: "What's your timeline for making a decision?"

What This Reveals:

• Whether there's real urgency or this is exploration
• If timeline is realistic or they're delaying
• What's driving timing

Red Flag Responses:

• "No specific timeline"
• "Whenever we get around to it"
• "We're just exploring options"

Good Responses:

• Specific date or timeframe
• Reason for timeline (budget cycle, deadline, problem urgency)
• Consequences of missing timeline

If Timeline Is Vague: "I ask because if there's no timeline, proposals tend to get deprioritized. What would make this urgent enough to decide by [specific date]?"

Question 4: "What's your decision-making process after you receive the proposal?"

What This Reveals:

• Steps between proposal and decision
• How long process takes
• Where deals typically stall

Red Flag Responses:

• "I'll review and get back to you"
• "We'll discuss internally"
• Can't describe specific process

Good Responses:

• Clear steps (review → stakeholder meeting → legal → approval)
• Timeline for each step
• Criteria for moving forward

If Process Is Unclear: "Help me understand what happens after I send this. Do you review alone first, then bring to others? Is there a formal approval process? I want to set expectations for next steps."

Question 5: "Rather than sending a proposal blind, would it make sense to schedule a call to walk through it together?"

What This Reveals:

• If they're willing to invest time (signal of seriousness)
• Whether they just want to get you off the phone
• If there's real interest or polite brush-off

Red Flag Responses:

• "Just send it, I'll review"
• Won't commit to any follow-up
• Resistant to any additional conversation

Good Responses:

• Agrees to proposal review call
• Suggests specific time
• Wants to involve other stakeholders

Why This Question Matters: Serious buyers want to understand proposals thoroughly. Brush-offs just want you to go away.

Alternative Framing: "I've found proposals are most effective when we can discuss them together. That way I can address questions real-time rather than you wondering what I meant. Would [specific day/time] work for a 30-minute walkthrough?"

What to Do Based on Their Answers

Green Light (Send Proposal):

✅ They answer all 5 questions with specifics ✅ Multiple stakeholders identified ✅ Clear timeline and decision process ✅ Agree to proposal review meeting ✅ Engaged and asking good questions

Action: Send tailored proposal + schedule review call

Yellow Light (Qualify Further):

⚠️ Some vague answers but some specifics ⚠️ Timeline exists but process unclear ⚠️ Some stakeholders identified ⚠️ Hesitant about review call but not dismissive

Action: One more qualification conversation before proposal. "Before I invest time in detailed proposal, let's make sure I understand [specific gaps]. Would 15 minutes this week work?"

Red Light (Don't Send - Qualify Out):

🚫 All vague answers 🚫 "Just send whatever" 🚫 No timeline or decision process 🚫 Won't reveal stakeholders 🚫 Resistant to any further conversation

Action: "Based on our conversation, I'm not confident a proposal would be valuable right now. Here's why: [specific reasons]. Would it make more sense to reconnect when [timing is clearer/stakeholders are identified/you have budget allocated]?"

The Proposal Control Framework

Don't: ❌ Send proposals immediately when asked ❌ Accept "just send your standard proposal" ❌ Lose control of next steps ❌ Spend hours on proposals that won't be read

Do: ✅ Ask these 5 questions first ✅ Qualify whether proposal is worth sending ✅ Schedule proposal review meeting before sending ✅ Maintain control of process

Quick Reference Checklist

Before Sending ANY Proposal:

• Asked what specifically they want to see
• Identified all stakeholders who'll review it
• Confirmed timeline and urgency
• Understand decision process after proposal
• Scheduled proposal review meeting
• Confident they're serious, not brushing you off

If You Can't Check All Boxes: Don't send the proposal yet. Qualify further or qualify out.

Conclusion

"Send me a proposal" isn't progress - it's often where deals die. Protect your time by asking these 5 questions before sending anything.

Serious buyers will answer them. Time-wasters will reveal themselves through vague responses or resistance to conversation.

Send fewer proposals to better-qualified prospects. You'll spend less time writing and more time closing.

Ready to practice handling "send me a proposal" requests? Book a demo with the Sellible team and work with AI prospects who test your qualification skills.