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Win-Loss Interviews: Asking the Right Questions to Solve the Right Problems



After many years in product management, marketing, and competitive sales roles, I know how few businesses understand the power of win-loss analysis. Win-loss analysis is a secret weapon for getting inside your customers' minds. Of course, it’s about figuring out what made them choose you—or what made them walk away. But it’s also about learning who made the choice and how they made it.

 

Most companies try to gather a mix of win-loss data from sales feedback, surveys, and more, but the real win-loss magic happens with buyer interviews.  There are many questions you can ask, but if you think getting someone to answer a survey is hard, getting them to agree to an interview is damn near impossible. Everyone is busy. Asking a buyer to give you the hour or more required to ask all your questions is a bridge too far for most. However, asking for only 15 to 20 minutes can make it palatable and increase your number of participants. That means you must tailor your win-loss interviews to target specific business goals.

 

Tailoring Questions to Fit Your Goals

The beauty of win-loss analysis is that you can customize it to fit whatever issue you’re dealing with

 

If You’re Looking to Improve Your Product

Ask: Which vendors did you evaluate? What features did you love? Where did our product miss the mark? How did we functionally compare to competitors?

 

Why It Matters: These questions help you identify your competitors and see where your product shines and where it needs a little polish.

 

If You Want to Boost Sales

Ask: How did our sales process work for you? What sales tools did you consume, and were they helpful? What influenced your decision to go with (or against) us?  What else could we have done to help you make your decision easier?

 

Why It Matters: By focusing on these questions, you can figure out what’s working with your sales approach and where you can improve.

 

If You Need to Sharpen Your Marketing Strategy

Improving marketing strategy is where win-loss shines. You want to ask the right questions to understand your target buyers and learn how they shop and eventually buy your products. These questions give you insights into how well your marketing campaigns and content connect with buyers and where you might need to tweak things.

 

Who Are Your Buyers

Ask: What is your job title?  What are your responsibilities?  What role did you play in the purchasing process? Who else was involved in the decision process?

 

Why it matters: These questions will help you identify and document buyer personas that describe the typical characteristics, preferences, and people involved in purchasing your product. This knowledge will help you accurately target your marketing programs and tailor your marketing message and tactics.

 

How Did They Realize They Had a Need

Ask: What problems were you trying to solve?  What negative impact did you experience related to those problems?

 

Why it matters: A deeper understanding of your customers’ problems can help you attract new shoppers by developing messaging that heightens their awareness of their problems and creates a sense of urgency to find a solution.

 

How Do They Identify Options

Ask: How did you research solutions?  How did you decide which solutions to evaluate?  Did any of our marketing content help you to determine our product was worth considering?

 

Why it matters: These questions can help you figure out how your awareness activities are working and where they can be improved.

 

Comparing Options

Ask: What competitive alternatives did you evaluate?  How would you describe the evaluation process?  Who from your organization was involved in the evaluations?  What were the evaluation criteria (e.g., economic impact, price, functionality)?  What type of product content did you find useful for your evaluation?

 

Why it matters: Knowing who and how your product is evaluated will inform your sales enablement efforts by making sure your channel’s sales motions are aligned with how your buyers buy. This will also help you create sales tools that effectively satisfy the buyer’s evaluation criteria and make sure your solution is seen as the perfect fit.

 

Making the Final Decision

Ask: Who made the final decision, and what sealed the deal for them?

 

Why it matters: Although you must understand the buying journey and the people who influence it, it is critical to know who makes that final buying decision and why. That knowledge will enable your sales channel to target the right people.

 

Wrapping It Up: The Power of Asking the Right Questions

Win-loss analysis is a fantastic tool for getting better at what you do, but it’s all about asking the right questions. Whether you’re trying to improve your product, make your sales team stronger, or fine-tune marketing, aligning your questions with your specific goals will help you get the insights you need to keep winning in the marketplace.

 

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