The Five Questions you Need to Ask Your Buyer

Adam McQueen

Businesses making decisions based on gut feel are doomed to fail.

It’s why product marketers and Compete teams need to bring the voice of the buyer to the executive table; to deliver the unbiased (and unvarnished) truth from the people that matter most.

And if you’re not sure how to do this through win-loss analysis, we’ve got you covered. 

Here are the five most important questions you need to ask your buyer, why they matter, and what you’ll learn from them to give your team a competitive advantage.

And if you want our full guide on nailing your next win-loss interview, courtesy of our internal experts at Klue — including even more questions to ask — you can grab that here.

1. What business or technical problem led you to evaluate [company]? 

This question is foundational as it digs into the core issues your buyer is trying to solve. Understanding this provides context for:

• Crafting targeted messaging and positioning.
• Understanding the starting point for your market’s buyer journey
• Developing features that resonate with your audience.
• Equipping sales teams with crucial information for their pitches.

This question is your context-setter: without this foundation, you’ll go down rabbit holes that aren’t anchored in the core reason that they decided to evaluate you (and your competitors) in the first place.

2. What were the three most important factors in your decision?

This question complements your opener by highlighting the priorities and criteria that influenced the buyer’s decision. This uncovers:

• Core decision-making factors.
• Hierarchical importance of these factors.
• Key motivators and deal-breakers.

Check out what happened when our own Competitive Enablement manager, Hunter Sones, brought buyer insights to the executive table in the Coffee & Compete podcast.

3. Which other vendors did you seriously consider and why?

You’re not selling in a vacuum (unless you’ve found some giant blue ocean, then power to you!). At this point in the conversation, you can ask your buyer about the competitive alternatives they considered. This question helps you:

• Identify direct competitors.
• Understand if your buyer is looking at adjacent software to solve the problem
• Position your product favorably against competitors.

IMPORTANT! If you open your interview asking about competitors, it’ll quickly feel like an interrogation and limit the answers your buyer shares. Open with the two questions above, and then bring up competitors as they walk through their buyer journey. 

4. What are our strengths and weaknesses compared to competitors?

Don’t stop with who else the buyer evaluated. Dig for their perceptions of those competitors relative to your solution. This is where the conversation can go many paths; just make sure you’re open and not leading the buyer too heavily.

• Identifying strengths to amplify in your messaging.
• Recognizing weaknesses to address in future product iterations.
• Uncovering truthful, unbiased feedback.

If you’re conducting win-loss interviews on behalf of your company, it is critical that you check your bias at the door here; resist the urge to push back, ‘lead the witness’, or try to resell. 

Your job is to bring the buyer’s voice into your business.

(Psst, if you want more follow-up questions and tactics on getting the most of our win-loss interview, grab our full guide below 👇)

5. In comparing [company] with other vendors, did you find any appealing features elsewhere that were absent at [company]?

Our final question takes a specific focus on product feedback. This question helps to:

• Identify differentiators.
• Refine your product’s unique selling propositions (USPs).
• Communicate effectively why your product stands out.

Three more tips on nailing a win-loss interview

1. Avoid Closed-Ended Questions: Open-ended questions facilitate deeper discussions, revealing more nuanced insights. Closed-ended questions, like yes/no questions, limit the information you can gather.
2. Layering Questions: Start with broader, context-setting questions. Follow up with more specific, focused questions. This approach builds a logical flow and makes the interview feel like a natural conversation rather than an interrogation.
3. Adapt Based on Context: Tailor questions slightly based on the scenario – whether it’s a win, loss, churn, or renewal interview. 

Bring your buyers voice to the table

Don’t let business decisions get made by the loudest voice in the room.

Don’t let them get made based on hunches or hearsay.

Let your buyer — and your market — remove those biases for your business.

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