Winning Proposal Checklist
Writing a winning business proposal isn't about showing off your company…
It’s about proving you understand the buyer’s real problem and showing how you’ll fix it better than anyone else.
The secret?
Very simple: focus on the buyer, not yourself.
Winning proposals speak directly to what the client cares about:
- saving money
- speeding things up
- lowering risk, or
- getting a better result.
They’re clear, direct, and easy to skim.
Why?
Because buyers don’t read, they scan.
A really great proposal has:
- one strong idea
- repeats it in all the right places, and
- backs it up with proof.
Most B2B sales teams struggle because they make the proposal about their company.
So they list credentials, use too much jargon, and bury the buyer’s pain under buzzwords.
Too many proposals are written in committee language, with no clear voice or strategy.
They forget that buyers are human—they want to feel seen, not sold to.
Winning proposals don’t just inform; they persuade.
And that takes empathy, structure, and guts.
What's in a Winning Proposal?
Click each step to see what goes into a winning business proposal.
- Have you identified the buyer’s most urgent and costly problems?
- Can you state their pain better than they can?
- Are you aligning with what’s really driving the decision?
- Do you know what “Yes” looks like to this buyer?
- Have you mapped all influencers, approvers, and gatekeepers?
- Do you address their formal and informal decision process?
- Do you have a clear Win Theme tailored to this buyer?
- Is your offer uniquely positioned—different, better, faster, or safer?
- Are you taking a stand, or just listing features?
- Does every section lead with buyer needs, not your capabilities?
- Are benefits clear, measurable, and tied to their business outcomes?
- Is your language confident, clear, and conversational?
- Is the executive summary written to sell, not summarize?
- Are headings and visuals skimmable and persuasive?
- Do you repeat key points in high-visibility spots (like captions and callouts)?
- Do you preemptively address buyer doubts or fears?
- Are you offering proof—case studies, data, client quotes—to reduce risk?
- Is your pricing framed around ROI or total value?
- Has someone outside the deal read it for clarity and persuasion?
- Have you tested for “client-focus” (vs. “your-firm-focus”)?
- Would you buy this if you were in the buyer’s shoes?
Have a Proposal Team?
We make them look like rockstars.
Let’s Make Your Next Proposal a Winner
Get a free proposal evaluation—plus $400 off if you need help rewriting or building a new one. No pressure. Just honest, expert advice to help you win more deals.
👉 Book Your Free Review Now – Don’t send another weak proposal.