One of the most important parts of a Win/Loss interview is asking about the experience they had with the sales representative. If your customer acquisition process doesn’t include a live demo with a real salesperson, these questions won’t really be relevant to you. But for everyone else, getting a keen understanding of how the sales person did, what they did well, and how they could improve, are high value questions for a Win/Loss interview. 

One thing I’ve learned from doing so many Win/Loss interviews is that the salesperson is often one of the major variables for whether you win or lose a particular deal, which probably isn’t surprising, but the actual details themselves are.

The Big Blind-Spot

When a deal is lost because of the salesperson, the salesperson is rarely aware that they were the main reason the deal was lost, And if they are aware, they’re almost always wrong about the reasons. There’s a good reason for that. When a deal is lost because of the salesperson, it’s usually information that the customer is uncomfortable sharing back with the salesperson because it’s either a direct criticism of either their performance, or of them personally. There’s just no polite or normative way to share this type of information with the salesperson so it almost never happens. That’s why a Win/Loss interview with a 3rd party (or at least someone who’s not the salesperson) can be so enlightening on this topic. In this new context, if you ask them direct questions about the sales experience and salesperson they’ll just tell you. And you can use that information to better understand why the deal was lost, and as constructive feedback for the salesperson themselves. 

Resistance from the Sales Team.

When you’re setting up a Win/Loss program it’s pretty common to run into resistance from the sales team. The reason for this is because sales people aren’t dummies. They know you’re probably going to be asking about how they performed on a WIn/Loss call, and they’re worried that you may uncover a number of lost deals that were lost because of their performance. It makes them nervous. So while it’s true that a sales question in a WIn/Loss interview are tremendously illuminating, it’s also very important that you set up a plan with the Head of Sales for how this feedback is going to be handled. 

• Don’t share feedback about individual sales reps with the larger team. That may sound obvious on the face of it, but individual sales-rep feedback can accidentally sneak into your presentations to various teams. What if a high-stakes deal was lost because of personality quirks of the rep who was working on it? What if an important deal was lost because the sales rep forgot to tell them about a key feature, and they thought you didn’t offer that feature and chose a competitor? There are all kinds of ways a sales rep can lose a deal. But in your Win/Loss presentations back to your team you should use extreme caution in how you present these types of findings. A salesperson could literally lose their job if you point out their mistake in front of the whole company.
  
  
• Negative feedback about a salesperson should be handled with caution. Unlike any other type of feedback in a WIn/Loss interview, feedback about the sales experience can be very harmful to individuals, so it’s important to handle it with care. It’s also very important to keep in mind that when a deal was lost because of the salesperson, the salesperson probably has a different story worth hearing. Maybe the potential customer was very difficult. Maybe the salesperson just had an off day. Maybe it was an honest mistake that anyone could make. All kinds of things could be at play, so just because the customer pointed the finger at the salesperson doesn’t mean the salesperson should be in trouble. And if you call them out in any kind of group setting, it’s going to cause trouble. 
  
  If we’re sharing the details of an important deal and it’s clear that the salesperson was personally responsible for the loss, we’ll present the findings slightly differently when presenting it to a group vs. when we present it to the head of sales or to a few key executives. When presenting the findings in a group setting, we’ll usually share all the key details about why the deal was lost without making it personally damaging to the sales rep involved (keep in mind that there are usually at least a few reasons why a deal gets lost, so it’s rare that the salesperson’s performance was the only factor). When presenting to the Head of Sales or to a few key executives, we’ll usually share the full story about what happened. You’ll have to use your best judgment on these types of decisions. It’s important that the information does go somewhere, but it may be the case that it’s best that only the head of sales knows the full details. If the feedback is clearly damaging to an individual, it’s best to air on the side of caution and share it in a one-on-one conversation with someone who has the full context (like their boss)
  
  

Ask two key questions about the sales experience

We normally ask the following two questions about the person’s sales experience. “What do you think the salesperson did well?” and “what do you think the salesperson could improve on?”. Both of those questions are open-ended enough that what usually comes out is the participant’s authentic experience. Notice we’re not asking overly particular sales questions like “was the sales person responsive”, or “was the sales person on time to your calls”. If either of those things occurred, an open ended question about their experience will surface those issues. And if they arise via an open ended question, it’s much better data than if you ask them directly about responsiveness. Not to mention that those types of overly-specific questions are better handled by a survey anyway.

Organize Sales feedback into two big buckets (and by sales rep)

‍The two buckets of data for sales feedback are “what went well” and “what went poorly”. At a company level, once you’ve got all your data sorted into these two buckets you can start generating insights from within each dataset, and your company can start understanding the big trends or for strengths and weaknesses on the sales team.

But in addition to sales insights at the company level, there’s a unique opportunity to deliver feedback at the individual rep level. Every deal usually has a single sales representative that gave the pitch, did the demo, and had the relationship. So all of the feedback about a specific deal is all about a single individual. Another really valuable slice of the data is to split up the data into strengths  and weaknesses of each sales rep. Granted, these additional slices can take a fair amount of extra sorting work, but if you’re able to sort the data at this level, feedback on the strengths and weaknesses of each sales rep is an absolutely invaluable tool for the sales leader, and will quickly become a central piece of weekly 1-on-1s between sales leaders and sales reps. Additionally, this data often contains crucial information the salesperson can use to re-open these deals down the road, so there’s real winback opportunities that can occur from this data.

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Feedback about the sales experience is one of the most important parts of a Win/Loss interview. And the analysis about how to organize feedback about the sales experience is unique because of the personal criticism it contains, and the unusually high-impact it can have on whether the deal gets won. If you ask these questions in a structured way, and then organize feedback appropriately, you’ll start seeing improved sales performance from individuals as well as a meaningful uptick in closed deals.  

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