The Complete Guide to Win-Loss

Posted on: August 22, 2022
By: Matthew Reeves

Businesses use win-loss analysis to diagnose why their prospects don’t buy from them.

They also use it to discover what their ideal customers love about their product or service.

This guide aims to be a primer on all things win-loss. It currently has major sections, each with its own subsections.

  1. Background to Win Loss
  2. Conducting a Win-Loss Analysis
  3. Win-Loss Results

I keep this post updated, so please email me or connect with me on LinkedIn here with suggestions and questions.

Background to Win Loss Analysis

What is Win-Loss Analysis?

Win-loss Analysis is the process of discovering why prospects buy from you and when they don’t, why not.

It’s a tool you can use to understand your prospects and customers in more detail.

After all, it’s rare that a business wants to know less about their customers.

The most common method is to interview prospects and buyers by phone, transcribing the audio and looking for running themes behind their behavior.

It’s not uncommon to use surveys.

People with very high sales volumes often use a survey-first approach.

Ok, that’s great. But, why do win-loss at all? That’s what we’ll cover in the next section.

Benefits of win-loss analysis

Four benefits arise from win-loss.

Combined, they lift the chances of a business or team being successful, and those are:

  1. You see your company, product, and processes through your customer’s eyes.
  2. You make business and team decisions from data and facts.
  3. You reduce your own bias in decision-making.
  4. You create a culture of being customer-centric.

More specifically, different teams derive their unique benefits. But win-loss also has its limits.

Benefits for Specific Teams

For Product Marketing: Create trustworthy buyer personas, backed created from current research, not cooked up eight years ago by an intern.

They know which features and benefits buyer cares about and which positioning simply isn’t working.

Win-Loss for Sales: Sales leaders understand what goals and problems your buyers genuinely face.

They understand if their sales team is being too pushy in their process or perhaps not understanding client pains as the competition.

When sales get their hands on win-loss, they often discover competitors aren’t as threatening as they once thought and learn how to lift demo-to-close rates by a few points just by highlighting the right things.

Content Marketing: Create content that buyers want to listen to, read, or watch. Know which sources of information buyers trust and which they think are fluff.

Win-Loss for Product Managers: Which functionality matters to buyers and prospects. What parts of the product are confusing

Competitive Intelligence: Understand how prospects perceive a competitor.

Do buyers think the latest feature is a game-changer or just PR puffery?

The Limits of Win-Loss

Win-loss can be severely limited when a single team fails to share the results.

For this reason, win-loss programs spearheaded by cross-functional teams such as Product Marketing tend to be the most successful.

Conducting a Win Loss Analysis

1. Assemble your Internal Customers.

Who would benefit from the results of a win-loss? Will it be used by sales, marketing, product marketing, or product?

While a project scope may be more focused on one part of the buyer journey, such as the sales experience, I firmly believe in looking across the entire buyer journey. Why?

Most of the time, we’d recommend beginning by researching the entire buyer’s journey.

2. Assemble your project team.

Who will conduct outreach, interviews, and analyze the data?

Deciding who is responsible for conducting win-loss and doing so early helps mitigate the risk that the project falls off the side of somebody’s desk.

Because you will ask interviewees to talk about Sales or Product experience, we recommend using the least-biased person you can.

As I mentioned earlier, that is often a Product Marketing person.

3. Decide an Interviewee Set

The interviewee set is who you will invite to participate in a win-loss interview. Many businesses interview a broad overview of their customers, but many also opt to ask customers of:

  • A particular product
  • A certain industry
  • Who chose a specific competitor

4. Write your win-loss questions and interview script

Most core win-loss questions map to the buyer journey:

  • Who did you buy from in the end?
  • What competitors or alternatives were considered?
  • What were your decision criteria?

But you will also have questions or ideas submitted by your team members. For example, a sales leader might want to know:

  • What do people think about competitor XYZ’s product?

When designing your interview script, you are dealing with compromises.

You need to:

  • Ask some questions to every interviewee so that you can assess trends
  • Give enough time so that you can have a real conversation and dive into insightful areas with your interviewees
  • Make sure you are providing answers to your team’s questions.

To do this, define a core set of “always ask” questions and a bunch of “nice-to-haves” questions.

Limit your Always-Asks to 3-5 questions.

5. Conduct the Outreach and Interviews

This section could warrant an entire guide, so I’ll start with a few tips for conducting your win-loss.

Top tips:

  1. Phoning your prospects to invite them to sit for an interview with you achieves a higher number of sign-ups but is more time-consuming than email.
  2. Emailing is cheap, easy, and can often be implemented via your existing marketing automation team.
  3. A downside of mass email is that interviewees may psychologically categorize it as spam or marketing.
  4. Most invitees will sign up for an interview on the same day or following. Make sure to keep enough calendar space free to accommodate that. Consider inviting people in waves.
  5. Give yourself lots more time during an interview than you expect. You can’t uncover exciting details if you don’t have time to let people talk and ask insightful, probing questions.
  6. Record your phone calls – use Zoom or similar – but ask the interviewee’s permission to record. Not only is it plain good manners, but it’s the law to disclose call recordings in many locations.
  7. Transcribe your calls. We recommend Otter.io or Zoom (which uses Otter) for most people.
  8. If you need to erase PII, many tools have an option to use AI to scan, find and hide any PII, such as people’s names or locations. AWS Transcribe is just one option, but you’ll need a developer to set it up.

Win-loss Analysis Results and Template

So, you’ve conducted your interviews. You have your calls recorded and transcribed. Now what?

Analyzing the Win-Loss Questions

Win-loss analysis — the data crunching — is the most time-consuming section of the whole process and one of the top reasons people hire Goldpan to conduct their win-loss.

If you want to do it in-house, you could be scrappy by simply using Excel or Google Sheets. The steps are simple but time-consuming:

  1. Make a list of every question you asked into the rows of Column A
  2. Copy and paste each answer into a new column from Column B onwards. You will have all the answers compiled next to each question. Make sure it’s clear which interview each came from.
  3. Categorize the Theme and Subtheme of each answer. E.g., a theme might be “Sales,” and a subtheme might be “Professionalism.”
  4. Use the theme and subtheme to begin to quantify how often a particular theme occurs. For example, you might find that to the question “What was your experience with sales like?” that the theme “Professionalism” occurs the most frequently.
  5. Repeat for each question.

Creating a Results Template

I strongly recommend creating a reusable Win-Loss Results Template.

Think of this as a slide deck with spaces for core information that can be used each time your re-run your analysis.

A results template has two halves:

  1. Core Win-Loss Elements (that will likely be repeated)
  2. Questions that were standalone or likely to change (often team-submitted ones).

By making a win-loss template early, you achieve several things:

  • You make an easy-to-delegate format that is easy for colleagues to pick up and contribute to.
  • You create a structure that executives and colleagues understand and recognize, reducing how much effort it is to analyze.

Four Elements Every Win-Loss Template Need

1. Top Win and Loss Reasons.

What is the most common reason or influence in you winning a deal? What is the most common reason you don’t? Are they similar?

2. Your Own Strengths and Weaknesses.

Group phrases or quotes that interviewees have provided into themes and subthemes, e.g., “Sales – Professionalism” or “Product Usability”

Count how often a particular theme arises as a strength and weakness.

By using departmental themes and sub-themes, you are able to see where your general strengths and weaknesses lie, but each of your teams will have its own relative successes to explore.

3. Competitive Insights.

Repeat the process you used to analyze your own strengths and weaknesses but for your competitors.

This allows you to draw powerful comparison charts that highlight where you outperform your competitors – things sales and marketing should be promoting.

4. Your Teams’ Submitted Questions

Your teams submitted questions are more likely to change over time for the simple reality that the market moves on.

You used to want to know how COVID impacted a client. Now you want to see if they are worried about inflation.

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