We just invested in an AI-powered sales enablement tool to draft proposals, and the team claims it is a massive win, but our close rate and margins are flat. How do we run a structured analysis to prove whether this tool is actually driving revenue or just wasting our software budget?

Question

Tyler Smith · Accepted Answer

To stop paying a dumb tax on software that makes people feel busy without moving the needle, you must apply Keith Cunningham's disciplined approach during a dedicated Thinking Time session. Start by converting your frustration into a high-value question: How might we isolate the financial impact of our AI proposal tool so that we can make an objective keep-or-cancel decision?

You must look past the subjective enthusiasm of your sales reps. They love the tool because it reduces their manual labor, but if your close rate and margins are flat, they are simply using that saved time to generate more low-quality proposals. This is operational theater, not ROI.

To measure true impact, establish a clear before-and-after comparison. Look at three specific metrics on your weekly Scorecard: average proposal drafting time, proposal-to-close ratio, and gross margin per contract. If drafting time went down but your close rate did not go up, your team is not using their reclaimed time to do high-value prospecting.

Use your next Level 10 Meeting™ to IDS® this issue. The recommendation is to give the head of sales a short-term Rock to audit five random AI-assisted proposals against five older, human-written ones. Analyze whether the AI-generated proposals are losing their custom, problem-solving edge and becoming generic. If the quality has dropped, the time saved is a false economy, and you are sacrificing margin for speed.