An RFP lands in your inbox. It's in your wheelhouse, the contract value looks interesting, and the due date is three weeks out. The instinct is to start writing.
Don't. Before a single word of proposal gets written, you need to evaluate whether this opportunity is actually worth pursuing. Here's a framework for doing that rigorously in under an hour.
Start With the Issuer, Not the Scope
Most teams open an RFP and go straight to the scope of work. That's the wrong place to start. Before you evaluate whether you can do the work, evaluate who's asking and why.
Do you have an existing relationship with this buyer? Have you done work for them before, or for adjacent agencies or departments in the same organization? Is there someone on your team who has met the decision-makers?
These questions matter because relationship is one of the strongest predictors of win probability — often more important than technical approach or price. An RFP issued by a buyer who already knows and trusts you is a very different opportunity than one where you're starting from cold.
Also ask: why is this RFP being issued now? Is this a re-compete of an existing contract? If so, who holds it, and are they likely to defend it? Is this a new requirement, or an old one that just got funded? Understanding the procurement history tells you a lot about your actual position in the competitive field.
Evaluate Strategic Fit Before Win Probability
Even if you could win this contract, should you pursue it? Strategic fit is about whether this opportunity builds the business you're trying to build — not just whether it generates revenue.
Market alignment. Is this in a sector, geography, or customer segment you're actively targeting? Winning contracts outside your target market can feel like progress while actually pulling resources away from where you want to grow.
Capability alignment. Does this contract let you deliver at your best? Work that stretches your capabilities too far creates delivery risk and reference-ability risk — a marginal win that goes poorly is worse than a no-bid.
Reference value. If you win and execute well, does this contract position you for better opportunities down the road? Some contracts are worth pursuing at lower margin because of where they take you next.
Assess Your Competitive Position Honestly
This is the section where most teams lie to themselves. Competitive assessment requires you to answer uncomfortable questions without letting optimism distort the answers.
Who else is likely bidding? If you know your main competitors, evaluate them honestly. Do they have a stronger relationship with this buyer? A better past performance record on similar contracts? Lower overhead rates?
Is there an incumbent? Incumbents win re-competes at a significantly higher rate than challengers. If you're challenging an entrenched incumbent, you need a compelling reason to believe the buyer is genuinely open to change — and evidence that you can make the transition low-risk.
Did you influence the requirements? If you had pre-RFP conversations with the buyer that shaped what's in the solicitation, your win probability goes up significantly. If you're seeing the requirements for the first time when the RFP dropped, someone else probably had those conversations.
Read the Risk Before You Read the Scope
Before you get excited about the scope of work, read the contract terms. Specifically, look for the things that turn a good contract into a bad one after you win.
Payment terms. Net 90 payment terms on a labor-intensive contract mean you're financing the government's operations for three months. That has real cash flow implications.
Termination for convenience. Standard in government contracts, but the presence of aggressive termination language in commercial contracts is worth flagging.
Staffing requirements. Does the RFP require specific named individuals, clearance levels, or certifications that create delivery risk if those people leave?
Scope creep risk. Is the scope well-defined, or does it contain language like "and other duties as assigned" that could expand your obligations without expanding your budget?
Run the Financial Reality Check
Contract value is a vanity metric. What actually matters is margin — and whether the work is profitable enough to be worth the opportunity cost of pursuing it.
Estimate your bid cost first. A realistic bid cost estimate for a competitive proposal includes proposal management, technical writing, SME time for content development, pricing, graphics, and review cycles. For a mid-size opportunity, that number is often $15,000 to $60,000 in internal labor cost before a single dollar of revenue comes in.
Then estimate your win probability honestly — not optimistically. If your realistic win probability is 15%, your expected return on that bid investment is $0.15 times whatever margin the contract generates. Does that math justify the pursuit?
This isn't a reason to only chase sure things. It's a reason to be honest about what you're investing and what you expect in return — so the decision to bid or not bid is a financial decision, not just an emotional one.
Put a Number on It
Once you've evaluated all four dimensions — strategic fit, competitive position, risk, and financial viability — the final step is to translate that evaluation into a score. Not because a number makes the decision for you, but because a number forces you to be explicit about what you actually think.
A score makes the conversation different. Instead of "I think we should bid on this," the conversation becomes "we scored this a 58 — here's what's dragging it down, and here's what we'd need to change to feel confident." That's a more useful conversation, and it produces better decisions.
The teams that evaluate RFPs this way — systematically, before they start writing — submit fewer proposals and win more of them. That's not a coincidence. It's what happens when you treat the bid decision with the same seriousness as the proposal itself.
Evaluate your next RFP in under 15 minutes
WinWorthy walks you through all 16 criteria and delivers a scored recommendation your team can act on.