MEDDPICC Analysis Worksheet & Field Guide

Most MEDDPICC scoring happens the same way: an AE fills in a field after the call and calls the deal qualified. Nobody grades it independently, so nobody finds out where the AE and SE actually disagree, which is usually right where the real risk in the deal is hiding. This worksheet exists to force that disagreement into the open, on purpose, before a demo ever gets booked.

Use this in two steps

Grade the deal yourself before anyone grades it for you. Knowing what you can actually prove, and what you're only hoping, is the whole skill. Then let the coach check your work.

1. Grade solo with the worksheet. Score all eight letters 1 to 3 and write the evidence next to each one: names, dates, quotes, numbers. If you can't quote it, leave it blank.
2. Run it through the MEDDPICC Deal Coach. A free Claude skill built from how I review deals. It grades the evidence, compares its read to yours, ranks the gaps, and hands you this week's to-do list.

What's inside the worksheet

A scoring worksheet, a field guide written specifically for the SE seat, and a second worksheet built for the two of you to run together.

• The scoring worksheet: score all eight letters 1 to 3, with an evidence-or-gap column for each, plus a reading of what the total actually means for the deal
• The eight-letter field guide: a plain job description for each letter from the SE's seat, with what you own outright versus what you only influence called out separately
• The four deal-killers: named patterns worth watching for on your own pipeline, including the demo gate and the enthusiasm-only champion who loves the product and sells nothing
• A shared grading exercise: a second worksheet built for AE/SE pairs, graded solo first and reconciled out loud second, so the disagreement becomes the data instead of getting smoothed over
• Where it connects: how the worksheet ties into a qualifying workshop and a forecasting workshop, if you're running either with your team

How to use it

Grade solo first. No peeking at your partner's sheet. Then sit down together and reconcile out loud: the gaps between your two sheets aren't a problem to smooth over, they're the most useful part of the exercise. Re-score after every material touch on the deal, not just once at kickoff. A stale MEDDPICC is worse than no MEDDPICC at all, and a demo with three blanks in the map is a demo you're giving for free.

The MEDDPICC Deal Coach: an AI coach built from how I coach

The worksheet gives you the map. The skill gives you the coach. I turned the way I review deals into a skill Claude can run: evidence-cited grades on all eight letters, every letter you've actually earned called out, and the gaps ranked by deal impact, with the one that moves the deal most on top. Then it does the part most deal reviews skip. It turns the whole thing into this week's actions, each one tagged with whether you own it or only influence it.

It won't grade what it can't see. Enthusiasm is not evidence, and "probably" is not a plan. Scores that rest on hope come down. Scores that earned more than you gave yourself go up. Either way, the evidence gets quoted back to you. It also watches for the four deal-killers by name, so the stale sheet and the one-person deal get called out before they cost you a quarter.

Here's the power move. Have your AE or SE partner grade the same deal solo, no peeking, and submit both sheets together. The coach builds the whole review around the disagreement: a delta scorecard sorted by gap size, a read on who has better information letter by letter, and the one conversation you two need to have out loud this week. It never averages your scores. The gap is the data.

Getting pushed to demo a half-blank map? Say so. The coach will arm you with the push-back that uses the map itself as the argument, and the fallback that makes an immovable demo earn its keep.

Installing it takes about a minute:

1. Download the .skill file below.
2. Open Claude (web or desktop), go to Settings, find Skills under Capabilities, and upload the file. Claude Code users can unzip it into ~/.claude/skills instead.
3. Start a chat and say "grade this deal." Paste in your worksheet, plus any call notes or email threads you have. The coach takes it from there.

It runs in your Claude, on your data. Nothing comes back to me unless you send it. Works best on Claude Sonnet or better.

Want a second set of eyes on how your team is qualifying deals? Book an intro call and I'll walk through it with you.