Picture this: A promising prospect ends you sales call with those magic words every salesperson loves to hear: "Can you send me a proposal?" Your heart skips a beat. This is it: they're ready to buy! You clear your calendar, fire up your laptop, and spend the next few hours crafting what you believe is the perfect proposal.
Three weeks later, you're still waiting for a response. When you finally reach them, they give you the dreaded "we've decided to go in a different direction" or "it's just not in the budget right now."
Here's what really happened: You weren't competing against another vendor or losing on price. You were writing a proposal for a problem you didn't fully understand, to people you'd never met, based on assumptions rather than insight. After analyzing hundreds of proposals and working with sales teams across industries, I've discovered that most proposals fail not because of what's in them, but because they were written too soon.
That enthusiastic request for a proposal? Often it's a polite way to get you off their back.
Why we rush (and why it backfires)
When someone asks for a proposal, every instinct tells us to move fast. We interpret their request as buying intent, and it sometimes is. But here's the trap: we confuse their interest in solving a problem with readiness to evaluate our specific solution.
The excitement of a proposal request triggers what I call "execution mode." We start thinking about pricing, deliverables, and timelines instead of asking the harder questions:
- Do we really understand their situation?
- Have we met the people who will actually make this decision?
- Can we clearly explain why our approach creates value worth paying for?
Most of us address proposals to the person we've been talking with. Usually this is a functional manager like an IT director or head of marketing. But in reality, the bigger the deal, the more people get involved. We're often writing for an audience we've never met, trying to solve problems we haven't fully diagnosed.
Sound familiar? You get excited about a proposal request and suddenly you're in full execution mode, crafting what you think they want to hear instead of what they actually need to understand.
When assumptions kill your credibility
Every effective proposal needs to address four fundamental questions (I call this the Transformation framework):
- Where is the buyer now?
- Where do they want to be?
- What needs to change to get there?
- And why is that change worth the investment?
Rushing to propose usually means you're guessing at the answers.
When you don't have solid information, you end up writing in generalities. Your value propositions become vague and your promises get watered down by uncertainty. The difference shows up immediately in your language:
Weak: "Our platform helps reduce processing time"
Strong: "We reduce invoice processing time by 40% within 60 days"
The second version makes a specific promise. It puts your reputation on the line, which is exactly why it's more persuasive. When you're willing to stake your credibility on an outcome, and buyers take notice.
But you can only make promises like that when you understand their current processing time, why it matters to their business, and what the 40% improvement would mean to their bottom line. That level of insight doesn't come from a single discovery call. It comes from multiple conversations with different stakeholders.
Can you clearly articulate your prospect's current situation in their own words? If not, you probably need to go back and ask more questions.
Going back isn't weakness, it's wisdom
Here's where many salespeople hesitate. They worry that asking for another conversation before writing the proposal makes them look unprepared or unprofessional. The opposite is true.
Consider this: 81% of customers will share relevant details with a salesperson who offers genuine consultative help. That means deeper conversations aren't just acceptable; they're expected. Buyers want to work with someone who takes the time to understand their unique situation.
I've worked with sales professionals who consistently achieve high win rates on their proposals, sometime over 70%. What do they do differently? They refuse to write proposals until they have enough information to make them compelling. They'd rather risk losing a prospect by asking tough questions than waste time writing a document that misses the mark.
One of my favorite techniques comes from the book "Go for No!": try to uncover reasons why you should NOT write a proposal. Ask questions designed to disqualify the opportunity. This approach serves two purposes: it saves you from writing proposals that won't go anywhere, and it uncovers the real issues you need to address.
What's the worst that can happen when you say, "I want to make sure I understand your situation completely before putting together a proposal. Can we spend 20 minutes talking through a few more details?" Most buyers respect the thoroughness.
The information you have to have
Real discovery goes beyond surface-level pain points. You need to understand the full context of their decision. Here's the minimum information you should collect before writing any proposal:
Their current pain points: What's driving this conversation right now? What prompted them to reach out?
Desired outcomes: What does success actually look like to them? How will they measure it?
Budget parameters: Is there a defined budget? Who controls it? What's the approval process?
Decision timeline: Are they ready to move forward now, or gathering information for next quarter?
Key stakeholders: Who else will influence this decision? What matters most to each person?
When prospects are vague about priorities, try this framing question: "If we could only solve one thing for you, what would that be?" This forces them to clarify what matters most and gives you a clear target for your proposal.
The evaluation process often involves people you'll never meet: CFOs, board members, other department heads. Your proposal needs to speak to their concerns too, even if you're addressing it to your main contact. Use your champion to understand what different stakeholders care about and how to speak their language.
Sometimes the best proposal is no proposal
Not every request deserves a full proposal response. Learning to recognize when NOT to write a proposal saves time and keeps your pipeline realistic. Here are three scenarios where you should consider walking away or at least pausing:
Lack of clear information: If you can't define the prospect's current situation, desired future, required change, or expected value, you need more discovery. Period.
Unqualified decision maker: When the person you're talking to doesn't have authority or budget to move forward, be skeptical. Even if they're enthusiastic, there are probably other decision makers you need to meet first.
Competitive red flags: If you suspect you're a "column filler" (the third quote they need for their procurement process9, invest your time wisely. A quick, generic response might suffice while you focus energy on better opportunities.
There's a hidden cost to writing proposals beyond the obvious time investment. Outstanding proposals inflate your pipeline and create false confidence. They occupy mental space that could be better used prospecting for new opportunities or deepening relationships with existing prospects. Treating proposal writing as a strategic investment rather than an administrative task makes you more intentional about where you direct your efforts.
The path forward
The next time someone asks for a proposal, pause before you start typing. Ask yourself: Do I really understand their situation well enough to make a compelling case for change? Have I identified a core theme that will resonate throughout their organization? Can I make specific promises about the value we'll deliver?
If the answer to any of these questions is no, you know what to do. Go back to the prospect with a few more thoughtful questions. Frame it as ensuring you can put together the most relevant proposal possible. Most buyers will appreciate the diligence. Those who don't probably weren't serious prospects anyway.
Your proposal is the most important sales document you'll create for a deal. It needs to persuade people you've never met, address concerns you might not know exist, and compete against alternatives you can't anticipate. The only way to write something that powerful is to base it on deep understanding rather than hopeful assumptions.
Ready to transform how you approach proposal writing? The difference between proposals that get ignored and proposals that get signed often comes down to the quality of discovery that happens beforehand. If you'd like to learn more about systematic approaches to proposal writing that consistently deliver higher win rates, join my newsletter for practical frameworks you can use immediately.
The best proposals don't just describe your solution, they demonstrate your understanding of the customer's world. That understanding starts with being willing to ask one more question before you write the first word.