The Win-Loss Show

How to conduct a win-loss analysis interview like a pro | Win-Loss 101 Part 4


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A few months ago—after binge watching an entire season of the Great British Baking Show, I decided to try my hand at baking my favorite cookie. The raspberry rose macaron from the Jolly Holiday bakery at Disneyland. I assumed it would be easy.  After all, baking is just combining a bunch of ingredients in a bowl, then throwing it all in the oven, and voila, you have something delicious… right? Oooh how wrong I was. I tried baking these cookies 3 different times, and each time something went horribly wrong.  I was experiencing the Dunning Kreuger.

In case you need a quick refresher, the Dunning-Kruger effect is what happens when you completely overestimate your own competence while underestimating the difficulty of a task.

When most leaders hear about win-loss analysis, they make the same mistake I made with those raspberry rose macarons. They think, “All we need to do is call a few customers, have some conversations, and voila—we’ve got ourselves some valuable win-loss insights that can drive our strategy and help us generate more revenue. But if you’ve tuned into the past 3 episodes of this show, you know there’s a lot that needs to happen before you ever get on a call with a buyer if you want to build out a program that continuously impacts your business strategy, increases win rates, and drives more revenue.

In today’s episode, the rubber hits the road. Chase Pendleton and Scott Varner—two of our best win-loss program managers here at Clozd—are going to give you a crash course on how to conduct a top-notch win-loss interview that will reveal to you some of your greatest weaknesses as a company, and often some of your greatest strengths.

Buckle up and grab a notebook; this is going to be a great episode.

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The Win-Loss ShowBy Trenton Romph, Nate Bagley