The reason most win/loss is useless is that the rep writes the reason, and the rep writes price. Buyers almost never say price when someone neutral asks them. So separate the two: the rep's CRM field is a hypothesis, and a real interview with the buyer is the evidence. Call within two weeks of the decision while memory is fresh, keep it to 30 minutes, and ask open questions that do not lead (what was your experience of our sales team, not what did we do badly). Interview your wins too, because the reasons you win are the ones you should be repeating. And fix your categories first: a competitive loss and a project that died internally are different diseases with different cures, so track derailed deals separately or your win rate will flatter you badly.
5 hand-picked resources, 5 link-checked. Pick how you want to dig in.
Why we picked it 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.
On Clozd by Clozd win loss research team 35 min
Why we picked it 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.
From Clozd 30 min read
Open clozd.com →Why we picked it 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.
From Clozd by Nate Bagley 10 min read
Open clozd.com →Why we picked it 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.
From Kellblog by Dave Kellogg 18 min read
Open kellblog.com →Why we picked it 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.
From Kellblog by Dave Kellogg 12 min read
Open kellblog.com →How running a sales process and closing reads from a different seat.
The same ground, over in Money, pricing & model, our Starting Up track.
The same ground, over in Money, pricing & unit economics, our D2C track.
