Ever been on a first date that didn’t go well?

Maybe they showed up late, were rude to the waiter, or talked WAY too much about their toxic ex who they’re “totally over.”

When you get home from a date like that, it’s easy to tell your friends about all the red flags you experienced.

But if that person reaches out a few days later asking for a second date, do you tell them the (awkward and potentially hurtful) truth about why you’re not interested … or do you just ghost them?

If you’re like most people, you simply don’t answer the call and leave the text on “read.”

This same thing happens in sales.

Once a buyer says, “No thanks,” they mentally and emotionally close the book on the relationship. When a sales rep calls back wanting to know why they didn’t buy (i.e., “Why don’t you want to see me anymore?”) buyers will avoid the conversation by suddenly becoming “too busy” to have a quick conversation.

And that’s a problem, because you can’t make necessary improvements to your sales process, products, and business strategy if you can’t get the truth about why you’re losing from your buyers. So what can you do to get reluctant buyers to show up to an interview to give you the cold hard truth? 

In this article, you’ll learn how to effectively set appointments for win-loss interviews with buyers. We’ll draw on the insights provided in our Win-Loss 101 course to help win-loss analysis program administrators understand how to optimize response rates and attendance for buyer interviews.

Start by identifying the right person to interview

These days, most B2B purchasing decisions are made by a buying committee. The first step in booking an interview is identifying the person (or people) who can provide you with the most information most relevant to the problem you’re trying to solve.

Sometimes that means talking to your main point-of-contact, which is likely to be the person you’ve had the most interactions with and built the most trust with throughout the sales process. They can typically provide you with candid feedback about your selling process, your product’s strengths and weaknesses, and how you could have helped them make a better internal business case.

But your champion may not have insight into the primary reason(s) their company made the decision to purchase (or not purchase) your product. Oftentimes the executive sponsor—or another member of the buying committee—has a more complete picture of the factors that played into the final decision. They’re likely to have the most comprehensive understanding of the buying process and can provide you with some valuable insights.

Other times, a more technical member of the buying committee will assess your solution for compliance issues, technical features, integrations, and whether or not it would be easier to build on their own solution in-house. That person might have a completely separate set of expectations, insights, and objections about whether your solution is a good fit for the company, and why.

It’s also important to remember from the first Win-Loss 101 lesson that your win-loss efforts are always tied to a specific goal. Other factors relevant to that goal might qualify (or disqualify) someone from being interviewed. For example, do you want to interview:

• Buyers you lost to a specific competitor?
• Buyers from deals of a certain deal size?
• Buyers from a specific region?
• Buyers who didn’t purchase a specific product?

The buyers you choose to interview should help you gather information related to the goals of your program. So, before you start reaching out to buyers to set interviews, make sure you have clarity around who you actually want to speak to.

Reach out to the buyer in a timely manner

Once you’ve identified the right person (or people) to interview, the next step is to reach out to them in a timely manner. According to Braydon Anderson, VP of operations at Clozd, it's best to reach out to the buyer within two weeks of the decision being made. This ensures that the buying process is still fresh in the mind of your buyer, and they’ll be more likely to provide you with accurate and detailed information.

When reaching out to the buyer, it's important to be clear about the purpose of the interview and how it will benefit both parties. Here’s a simple script you can use when reaching out:

Personalizing this outreach increases response rates.

One of the benefits of using a third party (like Clozd) to administer your win-loss analysis program is that they can automate and optimize this outreach for you. This takes a lot of the menial administrative work off your plate, empowering you to focus more on surfacing insights from your win-loss data and enacting positive, revenue-generating changes throughout your company.

Reach out more than once

Your buyers are busy, and they likely have cluttered email inboxes, so it’s important to invite them to participate in a win-loss interview more than once.

At Clozd, we’ve developed—and are constantly optimizing—a cadence of emails that get sent to buyers over the course of several days. The majority of win-loss interview appointments are booked on or after the second email.

Be polite but persistent.

Offer incentives

It’s rare to find a buyer who’s excited to tell you why they “broke up” with you. For most people, a conversation like this can trigger a lot of anxiety. 

One way to overcome this hurdle is to offer incentives to buyers in exchange for 30 minutes of their time.

Effective incentives could be as cheap as $25, or as expensive as several hundred dollars. Some buyers who aren’t able to accept gifts can be motivated by a donation in their name to a charity of their choice.

You can even increase the incentive amount over time. For example, on the first email you might offer $25, and then, on your fourth email, you might bump the incentive up to $50. Doing this can boost your response rate while also preserving your initial incentive budget, which you would have wasted had you offered everyone $50 out of the gate.

Be respectful of the buyer's time

At Clozd, our experience performing hundreds of thousands of win-loss interviews has shown that it's best to keep interviews to 30 minutes or shorter. This ensures that the buyer doesn't feel overwhelmed or burdened by the interview process.

It's also important to be flexible with scheduling. You can accommodate your buyer’s schedule by offering them multiple times and dates for the interview. This shows that you respect their time and are willing to work with them to make the interview process as convenient as possible.

Use a tool like Calendly to help make interview scheduling easy.

Follow up after the interview

After the interview, it's important to follow up with the buyer to thank them for their time and to ensure that you’ve captured all the relevant information. You should send a thank-you email or note within 24 hours of the interview. This shows that you appreciate their input and are committed to using it to improve your sales process.

Your Assignment

Today’s assignment is the last task you have to complete before you start conducting win-loss interviews. Identify a list of buyers who meet your criteria for helping you solve the primary problem your win-loss project is focused on—and then reach out to them!

Once you’ve booked a few appointments, it’s time to move on to the next lesson to learn how to conduct a best-in-class win-loss interview.

Want to use the email template we use for initial interview outreach? You can access it by signing up for the official Win-Loss 101 course. You’ll also get a bunch of other valuable bonus materials, and three free expert win-loss interviews from Clozd?

‍This article is the second in a six-part series to help you launch your first win-loss analysis project—so you can experience the value of getting feedback directly from your buyers. Click below to check out the rest of the series.