For Compensation & Benefits Managers ·
What you'll accomplish
Three broker firms just sent back RFP responses running 30 to 50 pages each, and you are choosing a partner, not just a carrier. Reading all three closely and building a fair scorecard by hand usually eats several days. This walks you through getting a first-pass comparison in a few hours, leaving you time to verify the parts that matter before you present a recommendation.
What you'll need
Before uploading anything, write down the criteria you are actually scoring against. If your team already uses a scorecard template, pull it out now.
What you should see: A short list of criteria you can paste directly into Claude in the next step. Troubleshooting: If your organization has never used a formal scorecard before, ask Claude to help you draft one first, based on what typically matters in a broker selection, then adjust it to your organization's priorities.
What you should see: Confirmation that each document uploaded successfully, usually shown as a file name in the conversation. Troubleshooting: If a document is too large or in a scanned image format Claude cannot read, try exporting it as a text-based PDF instead of a scanned copy, or paste the relevant sections as text.
Give Claude your criteria from Step 1 and ask it to compare all three responses against each one, with direct quotes.
What you should see: A comparison organized by criterion, with each firm's relevant answer summarized and quoted, not just a generic paragraph per firm. Troubleshooting: If the first output reads too much like a summary of each document separately rather than a true side-by-side comparison, ask again explicitly: "Put this in a table with one row per criterion and one column per firm."
This is the step that turns a first draft into something you can present.
What you should see: Either confirmation that the quote is accurate and fairly represents the section, or a correction you need to make before using it. Troubleshooting: If you find a quote that does not match the source, do not assume the rest of the comparison is equally unreliable. Spot-check a few more sections, then correct what you found and move on.
Broker RFP responses sometimes say one thing in the executive summary and something narrower in the detailed answers further in.
What you should see: Specific callouts naming the page or section where the mismatch appears. Troubleshooting: Treat this as a lead to investigate yourself, not a final verdict on a firm's honesty. Executive summaries are marketing documents; some gap between summary and detail is normal.
What you should see: A scorecard and narrative ready to bring to your broker selection meeting. Troubleshooting: If two firms score close to evenly, that is useful information. Say so directly in your recommendation rather than forcing a tiebreaker score that does not reflect real uncertainty.