Win-Loss Analysis: Tracking Themes & Trends

Conducting an interview with one of your key B2B buyers is the most effective way to gain insight into why you won or lost the deal. You can transcribe the interview, distribute it to the relevant people, and make sure that your organization gets smarter about how it handles similar deals in the future. But in the end, there are limited benefits to taking a deep dive on any particular deal.

Where win-loss analysis becomes really powerful is when you begin to tag and track themes across interviews. This allows you to see what you’re doing well, what you’re doing poorly, where your efforts are yielding improvement, and where you need to focus next to improve your win rate. But while themes carry a lot of value, they bring pitfalls as well - after all, there is always some subjectivity involved in turning qualitative data (interviews) into quantitative data (trackable themes).

So how do you create and track win-loss themes effectively? Here are some guidelines we have developed based on our experience conducting hundreds of win-loss interviews.

Getting Started

When you first start interviewing buyers, do not start with a pre-set list of themes. Each company is unique, and trying to fit a new comment into an established mold can cause you to see problems that aren’t really there - or to miss the emergence of a new problem you’ve never encountered before.

For example, imagine that a software CEO sees the win-loss results which highlight a trend of buyer frustration with “the interface." In response, she plows money into a total UI overhaul. But as more interviews are conducted, and upon closer examination of the interview transcripts, she discovers that the buyers frustration wasn't with the core product “interface” but rather the interface of a particular product module or integration. Not only has she wasted a lot of money fixing something that wasn’t broken, but her customers are still dealing with the original problem.

The key to avoiding these kinds of situations is to listen to what the buyer is saying. Start broad, covering themes like “Product” and “Sales Experience." As you conduct more interviews and gather a critical mass of feedback, you can start to break those down into more targeted themes like “Support: Service Interface."

Consultation & Dialogue

A major consideration in tracking themes effectively is who should tag them. Having your interviews conducted by a third party who is unaffiliated with the company not only elicits more candid feedback, but also leads to more objective theme tagging.

Having just one third-party consultant conduct all of your win-loss interviews provides a lot of consistency in tagging themes, but also creates some room for bias and ambiguity. The consultant may know exactly what each theme means, but that provides no value to the company unless he can explain and justify how he categorizes feedback.

For this reason, it is ideal to have a consulting team working on your win-loss program. One consultant may take the lead in conducting most of the interviews and defining themes, but an additional one or two consultants can serve as a sounding board by reviewing themes for clarity and internal consistency. In addition, the lead consultant should confer regularly with stakeholders in the company to ensure that the theme names are consistent with the terminology used in the organization. This creates a healthy dialogue where themes can be discussed and refined.

Attach Quotes

At the end of the day, it’s what the buyer says that is going to help you get value from your win-loss program. While tracking themes allow you to zoom out and see the forest from the trees, direct quotes from the buyers help keep the feedback grounded and impactful.

Which of the following do you find more powerful to read?

  • “Buyers view us negatively on our service levels.”

  • “We were just totally underwhelmed with the way [Company X] delivered on our PoC. It was a mess from start to finish. If it weren’t for the dramatic price cuts they eventually gave us, there’s no way we would have rolled the contract.”

Every time your consultant tags an interview with a particular theme, he should also clip a quote that captures that sentiment in the buyer’s own words. This adds impact to the themes, but it also gives the consultant a chance to double-check and defend his assessment, ensuring he’s really tagged the right theme.

Themes Evolution

Over time, as the body of feedback grows, the ongoing dialogue and consultation process serves to develop and improve the themes.

As we have already discussed, this can happen by taking broader themes and making them more granular. Where you might start out talking about how the customer views “the product” as a whole, you could end up creating separate “product” themes that focus on things like ease of use, implementation, specific functionality, etc.

Sometimes it makes sense to merge themes. After analysis and discussion of the feedback, the consulting team and company stakeholders may decide that what they thought were two different themes actually represent one larger trend among buyers. “We thought buyers loved our discounts and our licensing model - but actually it looks like they’re really just excited about our overall price flexibility.” In cases like this, merging the two can add clarity - especially when the original themes didn’t seem to occur very often.


Themes give analytical depth to what would otherwise be just a stack of win-loss interview transcripts. But creating and curating an effective set of themes can be a lot of work. Your win-loss team should start with a blank slate, allowing themes to emerge organically over the first several interviews. They should regularly consult amongst themselves - and with you - to make sure that themes are internally consistent and easily understood within your organization. They should always back up their choice of themes with quotes from the buyer. And finally, they should be willing to rethink and redevelop the theme set as they uncover new data points.

Make sure you’re working with a win-loss team that follows these steps and you’ll be well on your way to edging your competition, delighting your buyers, and selling more!