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The 31 Best Win-Loss Questions You Should Be Asking

What are the best win-loss analysis questions to ask during an interview with a buyer after a deal?

An honest starting point for anyone looking to cut their teeth on win-loss analysis.

At the same time, this is the wrong way to go about it. 

Before we put on our detective hats, dust off our line of questioning, and channel our inner Sherlock Holmes… stop!

Take a breath. And read on.

In this blog, we’ll cover:

  • The questions you should be asking internally before you start conducting win-loss interviews
  • The categories of win-loss questions you should be asking your buyer after a deal
  • The questions to ask within each category
  • How to evolve your questions over time so that you can deliver insights that are most relevant to the business decisions your executive team is making today.
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The Win-Loss analysis questions you need to ask internally

The first win-loss questions you should be asking happen well before the buyer interview even begins.

Your initial questions need to be geared to your stakeholders, which when it comes to win-loss analysis, are the departmental leaders within your organization. 

These are the people who will make business decisions based off of your win-loss findings, meaning that your work should be tailored to what they’re looking to learn. 

This is called identifying your learning objectives.

“When launching your win-loss program, you need to know what the individual objectives are for each one of your functional areas, so I always recommend going to the leader within each group first,” said Ryan Sorley, CEO and Founder of DoubleCheck Research, at the Winner’s Circle event hosted by the Compete Network.

What are the internal questions you should ask, then?

It starts with two simple questions:

  • What is most important to you right now?
  • What are you looking to learn from win-loss analysis?

These are broad questions, obviously. But it sets the stage for you to dig deeper, by asking:

  • If you had this information today, what would you do with it?

Grab your shovel and keep digging. This is where you get a more coloured picture of how win-loss can bring value to different departments, and ensure that the insights you bring don’t just sit in a slide deck collecting dust.

  • Are you just going to keep it on your laptop and look at it? 
  • Will this bake into your product roadmap? 
  • Is this useful for sales enablement sessions you’re planning next quarter?
  • Does your next board meeting need better competitive intelligence brought to the table?

Conducting internal discovery not only makes you more confident entering a win-loss interview that you’re not tossing darts at a board blindfolded, but it’s also unlocks the secret to success for your win-loss program.

Internal buy-in.

“Those leaders start to lean into the program that much more. They get excited about the outcome that is yet to come, and they start to visualize what it is that you’ll be producing for them,” says Ryan Sorley.

“You end up getting a lot of people to have a sense of ownership of the win-loss program. It becomes stickier and the program takes off as a result of it.”

Keep a core list of Win-Loss analysis questions, but be agile

Think about your company’s messaging a year ago.

I’m sure it’s drastically different than today. More empathetic, considering the times that we’re currently in, perhaps?

This is just one example of how constantly you — and your competitor’s — go-to-market, product offerings and messaging are changing.

As such, you need to be asking questions that generate feedback relevant to these business decisions and strategies so that your executives can make more informed decisions, faster than the rest of the market.

While certain win-loss questions are evergreen, the ability to ask ones that unveil buyer intelligence on how your strategies are landing in the market today is what transforms a good win-loss program, into a great one explained Valerie Bonaldo, Director of Product Marketing Competitive Intelligence at Seismic, at the Winner’s Circle.

“When doing win-loss, we have a core set of questions that we stick with because we want to know the importance of what the buyer is looking for and how our sales team is engaging with them across the sales cycle.

But maybe we would want to measure how a recent product launch went? How some new messaging was presented in the sales cycle? We’ll pull out data specific to that within the interview guide and look for the qualitative results around what the customer’s real impressions were and how something resonated.”

It’s in those moments where win-loss can work its magic, especially when executives are dying to know why a big strategic bet they’ve made is (or isn’t) bringing desired results.

“The great thing about being able to do a quarter-over-quarter win-loss program is to be able to go back and look to see what was consistent in our surveying and in our questions, as well as where we see the conversations shift as we brought forth new initiatives and new features.”

Ask Win-Loss analysis questions covering the entire buyer journey

No matter what, make sure you’re asking questions that acknowledge every step in the buying process. 

Generally, there are 10 steps in the buyer journey you need to consider when conducting a win-loss analysis interview.

best b2b win-loss analysis questions

Here are a few questions that you can ask within each category:

The Role

  1. How did you play a role in the evaluation process?
  2. What are your responsibilities above and beyond evaluations like these?
  3. Tell me about your previous experience with vendors like us. 

Awareness

  1. What made you realize you needed a vendor partner in this space?
  2. How many voices at your company were asking for a change that led you to evaluate your options?
  3. What were the main issues with your previous vendor partner (if applicable)

Evaluation Bias

  1. What did you think of our company before the evaluation started?
  2. What did you think of [insert competitor] before the evaluation started?
  3. How have your thoughts about our company, our competitors and the space in general changed over time?

Requirements

  1. How did you go about requirements gathering?
  2. How well did [company] align with your requirements?
  3. What were your must-haves?

Consideration

  1. Who else did you evaluate in your decision? 
  2. Explain the factors that helped narrow down your decision-making.
  3. What were the strengths and weaknesses you saw across all vendors?

Buying committee

  1. Who was responsible for what in the buying process?
  2. Who were the most influential people in the decision-making process?
  3. How do you think the buying process would have been different had there been fewer voices at the table?

Product Demo

  1. What was the most memorable part of the demo experience?
  2. How did our demo compare with some of the other finalists?
  3. What would you have like to see more of?

Products and Services

  1. How would you describe our company’s product strengths and weaknesses?
  2. How much was customer service emphasized during the evaluation process?
  3. What would make our product better?

Price

  1. How did our pricing model compare to our competitors?
  2. How important was price to you and your team in the first place?
  3. To what extent did you feel like our pricing matched the value we offered?

Sales Process

  1. What was missing from the sales process and what did you like about it?
  2. How did our sales process differ from others?
  3. How can we make our sales process more effective?

That’s only 30 win-loss analysis questions…

Guilty! There is indeed a 31st question. It’s one that comes at the end of your interview — and happens to be the most fun of the bunch. 

If you want to check that question out, as well as the secret to nailing your win-loss interview courtesy of the experts over at DoubleCheck Research… it’s all here waiting for you.

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