7 Top Actions and Outcomes from a Win-Loss Analysis

The obvious reason to conduct win-loss analyses is to discover why you win and lose deals. But knowing why you win or lose is just the beginning. You’re not just looking for good information, you want to drive concrete changes that will increase your competitiveness. The true value of a win-loss program comes when you turn your win-loss insight, into action.

While every company’s situation is unique, following are 7 typical outcomes from a win-loss analysis:

1. Better Deal Targeting and Segmentation
Once the win-loss analysis shows you why you win certain kinds of deals, you can gauge which new deals have the highest chance of success. Instead of treating every opportunity equally, focus your salespeople on the most promising deals.

2. Guidelines for Building Relationships with Prospects
Most prospects research your organization before they engage your sales team. During this research, they develop biases, opinions, and perspectives on how they should judge your product. Let your sales people know what your prospects are thinking. This will help them communicate in an intelligent manner. Share the insight from your win-loss analysis to develop the easiest, fastest… dare I say the most “delightful” experience across all touchpoints so that you stand out as the preferred vendor.

3. Product Development Insight
A key outcome of your win-loss analysis is what features or capabilities your product lacks to win – either because competitors have surpassed you or prospects have started looking for capabilities you simply don’t provide. This first-hand data couldn’t be more critical to your product development team as it plans future updates. Your win-loss analysis should help you to prioritize new developments.

4. A Clear, Defensible Vision
You need to present customers and prospects with a vision of where your company and its products are headed, and your vision needs to align with theirs. Win-Loss analysis can help you build a vision that is unique to you and your value proposition. See our blog post on Vision for more information on this subject.

5. Updated Competitive Strategies in Sales Tools and Enablement
Battlecards, training modules, whitepapers—all of your sales tools need to reflect what your prospects and customers actually say about you and your competitors, not what you think they are saying. Drawing on win-loss findings, you can advise your sales and marketing teams on ways to update your tools to better inform them on how your competitors have beaten you and how to better leverage your strengths (or the reasons that you win).

6. Sharpened Messaging
The competitive arena is dynamic. Presentations, websites, social media, collateral, elevator pitches – all need to reflect the latest in terms of customer needs and their outlook on your market. Your win-loss analysis provides superb insight to help you update your messaging on the buyer’s problems, your differentiation, and how your solutions can best meet the customer’s needs.

7. Better Informed Pricing Strategies
Understanding how your competitors have priced opportunities and gaining insight into the buyer’s need and decision process should prove invaluable when developing and updating the price for your solutions.

So, in summary, a win-loss program is not just for identifying why you win and lose… It’s about taking that insight and putting it into action to become a more competitive organization.

5 Reasons Why External Win-Loss Programs Improve Results

Companies that take the first step of doing a thorough review of why they win and lose deals often ask the question, “Why can’t we just do this internally?” Good question, but there are five good answers to say “no.”

1 – You Need an Unbiased Perspective.

If you have your own sales, marketing, or product development staff conduct interviews, review transcripts, and look for competitive advantages or issues, how can they be objective? That’s not to say that they’re trying to shape the truth, it’s that they’re going to start with a biased perspective.

An external win-loss consultant can present themselves as an objective third-party because they have no prior relationship to the customer/prospect, and they have no preconceived ideas.  Buyers are just more candid and open when taking with a third party.

An external win-loss consultant can also ensure the anonymity of the respondent. This is very important if you seek the truth and want your respondent to relax and tell it the way they see it.

Using a third party to conduct the interview removes bias due to these factors.

2 – You Can Benefit from Experience and a Proven Methodology.

Interviewing is an art. A methodology for uncovering key decision-making criteria is a science. Leveraging win-loss program professionals who, as a team, have performed thousands of interviews and hundreds of analyses can consolidate feedback into actionable recommendations. That’s where the art and science come together.

It also helps to work with win-loss consultants who have experience in your market. You won’t get insider, confidential information, but you’ll be working with people who know the data points and trends that you are looking for.

3 – It’s Cheaper to Outsource. Really.

It costs less to outsource this type of competitive research to a win-loss consultant than doing it internally. (Do I need to remind you ‘time = money’?). There’s the time to set up interviews, transcribe interviews, edit transcripts, translate transcripts from a foreign language, run win-loss analysis across transcripts, etc.

Ask the vendors who provide win-loss programs, “Do you have a toolkit, custom software, or processes that automate many of the tasks needed to produce a thorough win-loss analysis?” This is when you’ll understand that your company is not equipped to do this internally. And by doing your own competitive intelligence, you’ll find some win-loss providers are better equipped than others to get to the bottom of why you win and why you lose.

4 – You’ll Get Results Faster.

When you engage with an external service, you’ll have a dedicated team focused on delivering your results quickly.  The team approach means you’ll be able to get far more interviews (and an analysis) completed in a much shorter time frame than you can on your own.

5 – You Can Put Your Scarce Resources to Better Use.

Win-loss programs are very time consuming to implement, but easy to outsource. What you can’t outsource is implementing changes change. Focus your time and talent on how you’re going to evolve the parts of your business that will improve win rates: creating new sales messaging, developing JIT marketing materials, coaching sales execs on how to avoid landmines, launching new products that address gaps, responding to competitive “fear, uncertainty, and doubt”, and more.

Simply put, let an experienced, objective resource do the interviewing and analysis. You need to spend your time informing your organization about the findings – and advocating for changes that will deliver more wins.

8 Tips on Conducting Win-Loss Interviews


I love interviewing people. You learn a lot. Most people are in fact enjoyable to talk with. And, the subject matter is fascinating. I’m not going to give away ALL of my secrets on performing win-loss interviews, but below is a list of what I think are some really important ideas to employ when interviewing people.

1.)  Remove as much bias as possible.
You want to get respondents to tell you their thoughts – without influencing them to give certain responses. Minimize the use of answer “lists.”  If you provide a list, the respondent might select something that they thought they should have done, instead of what they actually did.  Or the list might be incomplete, missing something important, etc.  In order to determine the selection criteria, ask the respondents to explain what was important to them – in their own words.

You can prompt their memory afterwards by reviewing criteria other respondents have found to be important.  But do that after they give you their criteria.

2.)  Get the respondent to open up and relax at the beginning of the interview.
I like to start with open-ended questions about the context of the respondent’s decision – including the business need, the process that was used to make the selection, and the respondent’s role, etc.

For instance, my first question is most often “What motivated your company to look into solutions in this space?” These open-ended questions help your respondent to relax, open up, and start talking. Please, when your respondent starts talking, don’t say a word.  Listen only.  And let them talk as long as they want without interrupting them.  Resist the urge to interject comments or questions. Take notes and ask any clarifying questions after they are done.

3.)  Build rapport.
Enjoy your time with the respondent. Have a laugh together. Relate to them.

4.)  Show that you understand your respondent.
Who wants to spend their time explaining a complex thought to someone who doesn’t seem to get it? I like to give an indication with a short remark that shows that I understand and appreciate the respondent’s perspective or experience when they are explaining something.

Do your homework before you begin interviewing. You need to be well-versed in the market.  Review the key players and their differentiators.  Read the related analyst reports, competitive documents and the product (or service) descriptions, etc. If you are talking with someone in IT, you need to have knowledge of the technical issues. If your respondent starts talking about their integration architecture concerns and you don’t have a clue about REST APIs, OAuth 2,0, and LDAP – how can you ask the related follow-on questions to probe more deeply into the technical issues?

Similarly on the business side, you need to be able to speak the language of your respondent, and engage with them on their concerns.

5.)  Be interested in what your respondent has to say.
If a respondent says to me “the sky is green”, I might follow up with, “Hmm… that’s interesting, why is the sky green”? Again, you need to be conversant and interactive with your respondents if you expect to learn anything from them.

6.)  Get both qualitative and quantitative data.
To be most effective, you need both qualitative and quantitative data. Purely qualitative interviews have value, but they lack the ability to prioritize the importance of the information.

For example, you need to ask for the scores of each vendor across the criteria. “And for Company-X, how would you score them on ‘Ease of Use’”? Without scored responses, it’s very difficult to do a detailed, non-subjective analysis.

7.)  Ask my favorite question.
I often ask this question towards the end of the interview. “If you were meeting with the senior management from each of these vendors, what would you tell them they need to do in order to improve – and to better meet your needs?“

8.)  Make sure you are courteous, prepared, and professional.
You only have one shot… So get it right the first time.

Why Outsourcing a Win-Loss Program can be your “Secret Weapon”

You Need More Than ‘Internal Sales Debriefs’ To Increase Competitiveness

As we’ve recently spoken with a number of potential clients about Win-Loss Programs, more than a few people have told us that their company is already doing Win-Loss internally.  When asked for details, we’ve found that many companies think that they are doing Win-Loss when they are doing Internal Sales Debriefs instead.

While these internal debriefs serve a purpose, they are not a substitute for a professional win-loss program.

An “Internal Sales Debrief” is a post-deal discussion with a sales rep (or sales team) in which the details about a deal that recently closed (either won or lost) are discussed. It may be supported by a questionnaire. It’s most often done by the sales manager, but it can be done by product marketing or a competitive intelligence analyst as well.

Debriefs are an important activity and serve a purpose. The main beneficiary of the debrief is the sales team and the management who need to discuss what transpired, review their strategy, discuss the customer’s needs, the power base, and review what the competitors are doing in their account. In the case of a loss, the reasons for the loss should be discussed, etc.

Debriefs are not only helpful to the sales team, they are helpful to the Competitive Strategy and Intelligence team as well. If you attend enough of them  you will find examples of how a competitor operated, and that information should be incorporated into your competitor-specific battle cards.

However, if you are trying to become more competitive you need something more than debriefs, which have limitations, can be misleading and incomplete, and don’t give you a complete story.

  • Telephone Game In a debrief, you are not talking directly to the customer. Instead you are gathering data indirectly through the sales team, and that means that some of the information may not get passed on, or it may be modified before it gets to you. It reminds me of that telephone game I played as a kid – where you whisper something in someone’s ear – and by the time the information comes back around to you, it’s completely different.  And keep in mind that sales reps may be getting their information from someone other than the decision maker, such as a “friendly informant” (or “fox”), or even a partner who is speaking to the fox, etc. You get the idea.
  • Perception rather than fact You are asking the sales rep about his or her perception of what transpired. Some of the information is subject to interpretation.
  • Losing reps know far less than winning reps This may be obvious, but the losing sales reps know far less about the customer’s needs than the winning reps. But you do need to understand why you lose, so that you can understand your weaknesses and work on improving them.
  • Losing reps are concerned about being judged The data you seek in a debrief is masked by the sales rep’s need to be perceived as being valuable to the organization. As a result, some of the data might be “positioned” or changed before it gets to you. And when your losing sales reps are asked questions that they think they should know, but don’t, the losing sales rep may provide guesses. Hopefully they will precede this with “I don’t know that answer”, but these reps are very concerned about how they are being perceived…
  • Most losing sales reps will over emphasize “price” as a reason for losing
  • Sales teams are often not objective about their own performance It’s hard for sales reps to see themselves objectively.  And the problem is further reinforced by the fact that the customer will often not discuss what they didn’t like about the sales team directly with that sales team. Occasionally a sales rep will say “I screwed up”.  But how many times can that be reported before that sales rep is gone?
  • Winning reps use debriefs for self-promotion Have you ever asked a winning sales rep why they won – and the answer was “relationship”?  I remember asking one sales rep who clarified the response by saying “it was ALL relationship”.
  • Your team doesn’t know everything about the customer Your customers won’t tell your sales people everything because they are negotiating with your sales people, or using them for some other purpose. For instance, in some cases, your participation in a deal might be column fodder.  It could be that your participation is designed to lower the price of another vendor. Or it could be that the prospect loves your product so much that they’d have paid twice the price.  There are numerous reasons for why the customer may be holding back information from your sales team.
  • It’s impossible to get the normalized data you seek from your sales team. Except for the occasional spreadsheet that the customer has produced, which finds its way to the salesperson — it’s unusual for the sales team to deliver anything in terms of a full selection criteria list, the relative importance of the criteria, and ratings of the competitors across the criteria, etc.

By contrast, a win-loss program is specifically designed to provide insight and data so that you can identify the real reasons you win and lose, and provide the necessary recommendations across the organization to increase your competitiveness. Win-Loss is not easy to do, but this is the type of discipline that’s required to have a world-class winning team.

What needs to be done differently from an internal sales debrief approach?

  • Interview the Customer directly. The customer is the source of information you seek – so why not debrief the customer directly and bypass some of these issues?
  • Use an external consultant. There are a number of reasons for using an external consultant for win/loss interviewing and analysis.
    • Perform unbiased, anonymous interviews. Customers don’t want to disclose certain information to the vendor. It may seem counter-intuitive, but when customers engage in anonymous interviews, they will discuss the issues in a much more open and candid manner than they would if they know they are speaking to the vendor.
    • Remove as much bias as you can. Another benefit of using an external service, is that the approach provides you with an independent, unbiased interview. In contrast, having someone self-report the details of their performance has too much bias and spin.
    • Leverage the consultant’s experience and methodology.  There will be issues that will come up in managing this type of program. If you haven’t done it before, it’s fairly difficult to analyze win/loss data and make conclusions. Experience can help you avoid mistakes that might end your program.
  • Gather the right normalized data in a consistent, systematic manner. In order to help your organization become more competitive, you need to be able to draw conclusions and provide actionable recommendations.  Therefore, you need an approach that allows the data to be analyzed across the interviews. Your interview data should include – the customer’s selection criteria, the criteria importance weightings, and scores of the vendors across the criteria – along with the reasons behind the values that the customer gives you and your competitors.

For those of you who still think that an internal sales debrief may be good enough – consider this easy test. Compare the two approaches yourself.

But make sure your comparison includes two key aspects:

  • Interviews. Do some customer win-loss interviews conducted by a win-loss consultant, and then compare them to your internal sales debriefs. Try doing this on the same deals. We recommend a sample set of at least 5 interviews (2-3 wins and 2-3 losses).
  • Analysis. Compare the analysis that can be generated from an internal sales debriefs with an analysis generated by direct customer win-loss interviews. You can do this on the same set of 5 interviews.  Keep in mind that you probably won’t have enough data for statistical significance on such a small sample set.  However, you can still understand the process of how the analysis is performed so that you can get a sense of the types of conclusions that can come from one approach over the other.

Internal sales debriefs are useful – but they are very different from customer win-loss interviewing and analysis.  You need the latter to get the facts directly from the source, in an unbiased and complete manner; then you can draw conclusions and make changes in your approach that will lead to improved competitiveness and increased sales performance.