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The Win-Loss Edition | 3 Win-Loss Takeaways | Win-Loss Guide

3️⃣ Three Things You Need to Know About Win-Loss 3️⃣

Ryan Sorley Win-Loss

Win-loss programs. So hot right now. 

It’s no wonder why. Insights drawn from a well-run win-loss program provide some of the most powerful competitive intel there is. 

Of course getting to those insights and then effectively distributing them is far from obvious. 

Thankfully there are a select few win-loss experts who know the ropes from hypothesis to interviewing to analyzing and distributing.

And we happened to convene three of them for last month’s inaugural Winner’s Circle Event!

Here are three takeaways from our win-loss session featuring Seismic’s Valerie Bonaldo, Forrester’s Derek O’Grady, and DoubleCheck’s Ryan Sorley.

1️⃣ BEFORE YOU DO ANYTHING… talk to your cross-functional partners and ask them what they would like to see from a win-loss program. 

“We always recommend going to product, customer success, customer experience, sales, product marketing and asking, Hey, what are you looking to learn through this effort? What’s most important to you right now?” – Ryan Sorley

 2️⃣ Give your most important stakeholders the two or three most key takeaways; let them (and whoever else) dig into the more detailed data at their discretion.

“Package the insights in a way that matters to them. Don’t throw 1000 things at them. Give them the top three headlines of what you learned and then what can be done with the takeaways.” – Derek O’Grady

3️⃣ Keep a consistent set of win-loss interview questions, adding new questions only when they pertain to a particular product launch or specific hypothesis you’re trying to validate. 

We have a core set of questions that we stick with…but maybe we want to measure how a recent product launch went, or how new messaging was presented in sales cycle.” – Valerie Bonaldo

At its best, win-loss brings together the art of interviewing and the science of qualitative research — leading to actionable insights that win more business.

And if you follow the advice of Ryan, Derek and Valerie, you’ll be one huge step closer to getting there. 

WATCH THE ENTIRE SESSION HERE.


📖 A Win-Loss Guide to Guide You Through Win-Loss 📖

win-loss analysis guide

In a lot of ways, the most critical (and most fun in my opinion) part of win-loss analysis are the interviews. 

But as anyone who’s ever conducted interviews knows, asking the right questions to elicit the most insightful answers can be incredibly difficult. 

That’s why earlier this year we put together a handy-dandy win-loss interview guide

In it, you’ll find more than 30 questions to ask, covering 10 points in the buyer journey. 

And since we’re here, I wanted to share four pro tips for gathering intel during your interviews. Here they are:

🗣 Keep it conversational – You’re not putting anyone on the stand — so don’t make it feel like an interrogation. Keep it natural, free-flowing and open. The more relaxed they are, the better their answers will be.

🙋‍♀️ Ask open-ended questions – Avoid questions that can be answered with a ‘yes’ or ‘no’. Instead, formulate your questions in a way that encourages elaboration on the part of your interviewee. 

🤔 Prioritize beforehand – Be clear on what it is you want from your win-loss interviews. Take the one or two hypotheses you have and look to validate it via your interviews. You want your conversations to be open-ended, not aimless. 

🙆‍♂️ Be flexible – Structure and direction are essential. But if your interviewee takes you down a path that is valuable, even if you weren’t expecting it, follow them down the path. You can always bring them back to your initial questions afterwards. 


👬 Coffee & Compete Community Corner 👭

Deal support. Rolling up your sleeves. Getting in the weeds. Some other overused metaphor.

PMMs and CI pros get their hands dirty all the time. But it can be hard to measure the impact you’re having. 

Luckily for us, Mr. Jason Oakley has a tip or 10

Take it away Oaks 👇


Thanks for reading this week’s edition of Coffee & Compete. As always, please reach out to me and the rest of the team with your thoughts and feedback. 

And If you know someone who isn’t already subscribed to Coffee & Compete, be a good friend and tell them about us.

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