How do I run win/loss properly, so that losing a deal actually teaches us something?

From a firm that does nothing but win/loss. It lays out the four steps end to end: mine the CRM data you already have, go get direct buyer feedback, isolate the real decision drivers, then push the findings into sales, product and marketing so they change something.

The Ultimate Guide to Win-Loss Analysis

From Clozd 30 min read

• Roughly 85 percent of loss reasons in your CRM are wrong, buyer and seller reasons agree only about 15 percent of the time.
• Use three channels by depth: 30 minute live interviews for high value deals, AI interviews for reach, surveys for scale.
• 63 percent of companies running win loss programs raised win rates, and 84 percent of programs older than two years sustained the gain.
• On a 10M dollar quarterly pipeline, two points of win rate is 1M dollars a quarter.

The actual interview guide, plus the one habit that decides whether your answers are worth anything: ask what was your interaction with the sales team like, never what did the sales team do poorly. Leading questions give you the answer you already had.

Win-Loss 101: What to ask buyers in your win-loss interviews

From Clozd by Nate Bagley 10 min read

• Ask what your interaction with the sales team was like, not what the sales team did poorly, so you do not plant the answer.
• Open wide, then narrow, and never spend a question on anything you could read on LinkedIn.
• Keep it to 30 minutes, a 20 page guide for a half hour call is overkill.
• Lead with the topic you actually came for rather than working through a fixed script.

Kellogg's point that a deal that died internally is a different animal from a deal you lost to a competitor, and that mixing them lets you report a 66 percent win rate while actually winning four opportunities in a hundred. Fix your categories before you trust any win/loss number.

Win Rates, Close Rates and Milestone vs. Cohort Analysis

From Kellblog by Dave Kellogg 18 min read

• Narrow win rate is wins over wins plus losses, broad win rate is wins over wins plus losses plus derails.
• Every sales accepted opportunity ends in one of three states: won, lost, or other (derailed, no decision).
• Milestone analysis counts what crossed a stage in a period, cohort analysis follows a generation of leads forward to resolution.
• With a nine month cycle, deals closing in quarter N were mostly created in quarter N minus 3, which is why milestone math misleads.

The single most common thing win/loss uncovers: you did not lose on product or price, you lost to the safe choice, higher up the org than you were selling. Read it for the counter moves, including his line that nobody ever got fired for buying the incumbent, but nobody ever got promoted either.

What To Do If You're Winning the Product Evaluation But Losing the Deal

From Kellblog by Dave Kellogg 12 min read

• If you win the evaluation and lose the deal, you are probably being killed higher up by a big vendor's safe choice message, not on price.
• Have marketing debrief several recent losses to test that hypothesis before you assume price sensitivity.
• Fight it with total cost of ownership over the lifetime, where the mega vendor often runs 2 to 3x more, plus peer proof.
• Answer nobody got fired for buying IBM with nobody got promoted either, and sell the career upside.

The interview itself is where win loss either works or produces polite nonsense. This walks through how to open, which questions surface the real reason, and why the person who ran the deal should not be the one asking.

How to Conduct an Effective Win Loss Interview

On Clozd by Clozd win loss research team 35 min