Last week’s piece left you with an open question: were you even there?
But before we get to the answer, a confession.
This work isn't easy; it isn't fast. You will get lots of resistance, and nobody will thank you for it today. You will carve out hours you don’t have. You will convene people who are already behind on their quotas, their roadmaps, and their MBOs. You will ask strangers painful questions and hear answers that bruise.
The reason to do it anyway: you are removing an insurmountable challenge in the future. A preference you don't form today becomes a revenue hole you cannot fill later, at any price, with any headcount. The extra work today is the cheapest version of this you will ever get.
You’re stress-testing it wrong
Most GTM leaders run win/loss analysis backward. They want to know why we won and why we lost.
Both questions point the lens at yourself. Both produce lists of your own qualities: features, pricing, relationships, effort. Those lists feel like learning. They aren’t. They are a catalog of what you already believed about yourself, confirmed by strangers being polite, or ignored by those who don’t care if you are wrong.
When you lose: Ask why the winner won. A loss analysis hunts for your defects. It will tell you what you did wrong, but it never shows you what good looks like. You can’t fix your way to a win if you’ve never seen one up close. A winner analysis hunts for what the winner built before the deal started, and that is the picture worth copying.
When you win: don’t ask why you won. Ask why the others were on the list at all. The questions:
Was I number one on the list, or just on it?
How did the others get on?
When did you first know we were on your list? What did we do to prove it?
Who did you consider but never even engaged, and why?
That last question is the sleeper. It asks the buyer to name the proof that actually registered (and where proof didn’t). Companies that never ask it keep shipping collateral into the dark, guessing at what works.
And notice what a win buys you: time, candor, and a buyer willing to talk about consequences and context. A loss gets you fifteen guarded minutes. A win gets you an hour and the truth about everyone else. Spend it on why they didn’t choose the other people — and on who was considered without ever being engaged. That is the mistake you don’t want to repeat, and the win is the only place you’ll hear it.
The stool
Here is where most companies stop: they decide to do this, then hand it to the sales team.
That’s the wrong owner. A rep who just closed a deal cannot get the correct level of candor from the buyer they sold to, and a rep who just lost cannot hear the answer without flinching. Worse: whoever runs the debrief cannot be graded on its answer. Put sales in charge, and every loss becomes a pricing story. Put marketing in charge, and every answer becomes a lead-gen story. Both parties have an interest in the answer.
The organization that does this well stands on three legs, and the CRO holds the question without holding the conversation.
The CRO owns the cadence. Not the interview. A CRO has a vested interest in the close — that’s the job. So their role is to institutionalize the debrief: convene it, read the findings, and weight them as heavily as the forecast. They must not conduct the conversations, because nobody tells the person who controls their comp plan the truth about why they almost didn’t buy.
Product marketing owns the conversations. Marketing is usually not incentivized on the close. That’s exactly why they're the right instrument here. They can hear your product was the third choice or your evidence was thin without a quota consequence. Product marketing's job is to learn what the buyer was trying to believe during the buying process, and which proof moved them toward believing it. The debrief is the primary research they should already be running. In my experience, many companies run the flow backward: sales commits to product marketing on how many units they could sell, instead of doing the TAM/SAM/TSM research.
Customer success owns the winner’s hour. They own the relationship after the close, so they can ask what made the others lose without threatening anything. They also see the gap between what was sold and what was bought, which is the gap this whole exercise exists to expose.
One stool, three legs, one cadence. Not a process you bolt on. An organizational design decision, owned by a CRO who accepts that the findings will sometimes indict their own machine.
The game you weren’t told was being played
Now the hardest part.
Everything above assumes you knew the game existed. You knew about the deal, so you could debrief it. But there is a class of game you never knew was being played: the company that fit your market, evaluated its options, chose someone else, and never considered you. You weren’t outcompeted; you were not considered.
That means your competition is winning the game you should be in. You’re not on the field. You’re not in the dugout. You’re not in the parking lot. You’re not even in the same state. The game is played without you.
Your CRM has no column for this. No deal lost. No record at all. And the answers — why you never made their list, why someone else did — are the most important answers in this entire exercise, because that’s where the missing revenue lives.
Finding them takes work nobody’s job description includes: pick the companies you want as clients that already bought what you sell. Find them. Ask the questions anyway: were we ever on your list, how did the winner get on it, what did they do to earn the spot? Some will talk to you; a surprising number will, because you’re not selling, you’re learning.
Do this with the same three legs. CRO sets the target list. Product marketing runs the conversations. Customer success stays close because some of these companies will buy again someday from whoever taught them the most.
The answers are harder to get and more expensive to reach. They are also the only answers that tell you whether you have a selling problem or a consideration problem. The first is fixed with better reps. The second is fixed only with proof that reaches buyers before the list closes.
The work, in order
Pick the next ten wins and ten losses. Get the buyer, not the rep, on a call.
Run the outward questions. Loss: why did the winner win? Win: were we first, how did the others get on, what did we do to prove it, who did you never engage?
Staff the stool. CRO convenes. Product marketing conducts. Customer success covers the winners.
Build the never-listed. Ten target accounts that bought without you. Ask the same questions, with the same neutral legs.
Read the findings at the same table as the forecast. That’s the test of whether any of this was real.
None of it is easy. None of it pays this quarter. All of it removes a challenge that becomes insurmountable if you wait until you need the revenue to start learning why it never came.
~6 min read. Last week: The Room You’re Not In. Next: the five strategies: frontal, defend, fragment, flanking, delay, and how to know which one you’re actually running.