How to Conduct Win/Loss Analysis to Drive Strategic Growth

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Conducting win/loss analysis is one of the most cost-effective ways of generating the insights you need to increase revenue and grow your business. So why aren’t you doing it? Marketing strategist Sue Duris walks you through the process.

I have been involved with win/loss Analysis from the product and sales sides since the mid–1990’s and have written about the subject since 2009. To this day, I do not understand why more companies aren’t conducting win/loss interviews, analyzing results and implementing lessons learned.

When I speak with companies, many think they know the answers to the following questions:

  • Why did we win/lose this business opportunity?
  • Why were we selected over our competition or vice versa?
  • How are we perceived in the marketplace?
  • How does our value proposition align with our prospects and customers’ needs?
  • How do we differentiate ourselves from the competition?

These answers may come from market research, speaking with customers, competitive intelligence, and online surveys. The trouble with these methods is that they are subjective – we can manipulate data to get the results we want.

What these companies fail to consider is that win/loss analysis provides deeper and more accurate insights than the above methods provide, and frankly, it is more cost-effective.

Of course, end-to-end win/loss activities must be done accurately. For win/loss analysis to work, organization personnel must be open-minded to the entire process and win/loss analysis must be done in a timely and objective manner. When it is done properly, companies will gain valuable insights and be able to implement initiatives that will help them increase revenue and grow their business. It’s a win-win all around.

There are three parts to win/loss analysis:

  1. Pre-Interview
  2. Interview
  3. Post-Interview

In this post, I’ll be tackling the pre-interview and interview phases. In my next post, I’ll dive into the post-interview phase.

An Introduction to Win/Loss Analysis

What is it?

A process of understanding why one sales opportunity was won and another one was lost.

Why is win/loss analysis important?

It provides insights on:

  • How sales and marketing can better align
  • How to fine-tune your SWOT analysis
  • Whether your messaging is on track
  • How you are perceived in the marketplace
  • How your competition is perceived in the marketplace
  • How your value proposition is meeting the needs of prospects and customers
  • How well you are differentiating yourself and your products from the competition
  • How your competition are differentiating themselves from you
  • What criteria prospects and customers are really interested in when selecting your or similar products and services
  • How well your end-to-end sales processes are working

How do I get my sales team on-board?

It’s best if a member of the C-Suite is championing this effort and your Chief Sales Officer is on board. However, you may have to prove its worth first by showing examples of companies who implemented a win/loss analysis plan and how it helped them increase revenues. In order for your organization to grow effectively, you need to obtain accurate insights about your business, and win/loss analysis is an effective tool to accomplish that goal.

Setting up a strategy

You will want to create a win/loss analysis strategy to determine such things as criteria used to select those customers/prospects to be interviewed, as well as the overall framework of the process.

The Pre-Interview

What occurs during the pre-interview?

After the sales opportunity has been clearly won or lost, a pre-interview strategy session should occur with sales, marketing, product, customer service, and any other key stakeholders. Be sure to include the highest-ranking salesperson in the discussion. If you will use a third-party to conduct the interview, include them in the strategy session as they can help frame the entire win/loss analysis process and provide insights on questions that should be asked and discuss the appropriate interview format (later on they can also help you analyze results and put an implementation plan together). This should be a collaborative process with all stakeholders contributing in the session.

Key decisions to make

  1. Decide who will conduct the interview: While third-party interviews will typically provide the most unbiased, in-depth information since prospects and customers are more comfortable in sharing information with third-party sources, your company can conduct the interview. If you choose to go that route, ensure that the individual(s) conducting the interview are personnel independent of those who were involved in the sales opportunity in question.
  2. Determine questions to be asked: Questions should cover every aspect and touch every point of the sales opportunity. Get the sales team’s input as to the background, including how the company got involved in the proposal, the type of relationship they had/have with the customer/prospect, sales processes involved, the problem that was trying to be solved, products or solutions used to close the sale, how they felt the prospect/customer reacted to each phase of the sales cycle, the result, and whether they anticipated this result. Sales can also provide information as to appropriate customer/prospect personnel to be interviewed.
  3. Determine the logistics of the interview: Interviews typically run approximately 30 minutes and occur over the phone.
  4. Schedule the interview with the customer/prospect: Interviews should be scheduled immediately after the sale has closed (no longer than four weeks). Let them know in advance the topics you plan to discuss.

The Interview


If you are using a third-party, they will conduct the interview. If you are conducting the interview, make sure you have a script of everything you plan to say/ask in the interview (which you should create prior to the interview). This will enable you to spend more time taking notes.

For starters, introduce yourself and thank the prospect/customer for their time. Explain that the purpose of the interview is to learn as much as possible about their perceptions and experience during the recent sales process so your organization can continue to improve.

Discuss confidentiality with the prospect/customer, stating that while you want to communicate feedback throughout your organization, the prospect/customer should identify any sensitive aspects during the course of the conversation.

15 Questions to Consider

  1. Confirm the opportunity and products/solutions discussed. Was it a fit from the beginning? Why/Why not? What pain was customer/prospect trying to solve? What are the customer/prospect’s perceptions in your ability to solve that pain?
  2. Which other firms were in the competitive mix? Why were you included in the mix? How and why did the customer/prospect make it a competitive process?
  3. Why did/didn’t you win the business?
  4. Ask about the decision-making process. Who was involved in the decision? What was the key selection criteria used?
  5. What was the customer/prospect’s perception of the quality of the Sales team? Were they knowledgeable? How did they feel the Sales team managed the relationship? Who did the customer/prospect meet from the Sales team and what were their perceptions of them?
  6. What was the customer/prospect’s perception of the sales presentation and messaging used?
  7. Was the customer/prospect comfortable with your capabilities? Which capabilities were most/least important?
  8. What were the customer/prospect’s thoughts about your pricing? Was the customer/prospect able to determine true value from your pricing?
  9. How did you compare with the competition? What did the customer/prospect view as your strengths and weaknesses? What did the customer/prospect view as your competition’s strengths and weaknesses?
  10. Did the customer/prospect call your references? If so, were they helpful? Why/Why not?
  11. What was the customer/prospect’s perception of you prior to entering the buying cycle? How did their perception change? What were their perceptions of the overall experience?
  12. What advice would the customer/prospect give you for working with them in the future?
  13. Would the customer/prospect feel comfortable in recommending your solutions to others?
  14. If a win, would the customer feel comfortable in participating in a case study, testimonial, joint press release or beta program (for a future solution)?
  15. Does customer/prospect have any additional comments or suggestions?

Wrapping Up the Interview

Thank the customer/prospect and provide them with your contact information should they want to add anything at a later date.

Do you have any questions about the pre-interview or interview phases? Ask me in the comments, and stay tuned for my next post on the post-interview phase.

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Photo by Víctor Nuño

Director of Marketing and Customer Experience

  • Sue, agree that most sales/marketing professional don’t spend enough time analyzing their sales.nnnI beleive conducting a Won Sales Analysis, and knowing exactly why you won, is better than conducing a Lost Sales Analysis, and hoping you can figure out what to change in order to win next time.nnI think the four best questions to ask when you conduct your Won Sales Analysis are:nn1) WHAT EVENTS LEAD UP TO THIS PURCHASE? The answer to this question can tell what event triggered your new customer to have the time to look at your solution or the money to afford it.nn2) WHEN DID THESE EVENTS HAPPEN? The answer to this question will tell you what initially triggered your new customer to decide that that the Status Quo was not longer sufficient and start thinking about what could be a better solution to a problem or a better way to accomplish an outcome/objective. This is more important than question #1 because finding out what this trigger event was will help you identify other prospects you can get in front of before the competition and help them define the problem, design the solution, and develop a strong working relationship. I’ve seen research that says doing just the three things above results in getting the business 74% of the time.nn3) WHAT MADE YOU CHOOSE US? Notice I did not ask a why question – I’ve been told that why questions make people defensive and that asking what or how questions generate better insights. The answer to this question will tell you what was the outcome the customer received from using your product- we as sales or marketing professionals create content which customers use mental gymnastics to combine with their context and generate the real value of being your customer. Too often you lose a sale because the prospect either did not have the context to add to your content or could not do the mental gymnastics to understand the real value of being your customer. Once you know the answer to this question you make it easier for a prospect to become a customer.nnn4) HOW CAN WE MAKE IT EAISER TO BECOME OUR CUSTOMER? The answer to this question can tell you what barriers or obstacles exist within an organization and or the process you made the customer go through to become your customer. Make it easier to become your customer and the decision to buy happens faster and your minimize the likelihood of the dreaded ‘No Decision.’nnIf you want to learn more about the power of a Won Sales Analysis can:n* Download my Won Sales Analysisu2122 template and a video instructions on how to use it u2013 http://WonSalesAnalysis.comn* Request a free copy of my sales book SHiFT! that has a whole chapter on how to best conduct a Won Sales Analysis –* Access a webinar I did that explains all of the above in more detail, sharesnmore research on the topic and provides strategies and tactics to make timing happen u2013 hope this adds value to conversation and helps you win more sales.nnnGood Luck!nnnCraig Eliasn – The creator of Trigger Event Selling

  • Sue Duris

    Hi Craig.nnnThanks for reading and taking the time to respond. nnnI have to respectfully disagree with your comment that Loss Analysis should not be considered. You need to look at both because the losses are how you grow/learn. Additionally, if you only look at wins, you put yourself in a false sense of security situation. It’s like if you or I constantly get good feedback, how/where would we know where to improve?nnnI do agree that asking “what were the reasons” vs. asking “why” can be a better way to go. Of course, it depends on how you initially frame the question.nnnWith #1/#2, the company should already have answers based on info they have from their analytics and marketing automation. It should be included in #5/#6 above as more of a confirmation of the information you have and to get their feel of the entire nurturing process. Some of the info in your #1-#4 questions would be a better fit for your customer interviews, which are different from the win/loss process. Customer interviews help you fine-tune your buyer personas. I talk about this in Part 2 of the article. I hope you get a chance to read it. It will be available soon.nnnTake care.

  • Jeff McMurdy

    I appreciate the “Loss” with the Win analysis, to paraphrase a well-known thought, those who fail to learn from history are doomed to repeat it.

  • Jeff McMurdy

    I appreciate the “Loss” in the Win-Loss discussion for as a well known concept teaches – those who fail to learn from thier mistakes are doomed to repeat them!

  • Sue Duris

    Absolutely Jeff – you hit the nail right on the head!

  • Michael F. Boehne

    Analysis´s are important to get known about the reason of why any fact went wrong or right. Somebody who is not analysing the issues does not know how to act the next time when this point arises again. This is not only related to win or loss but needs to be performed in all processes. Do we need to change or can we repeat the same way we did before ?

    • Sue Duris

      Very well put @michaelfboehne:disqus. Thanks for commenting.

  • Hi Sue — I love your question set but I’m a little torn between making it all qualitative versus perhaps quantitative (“On a scale of 1-5…”). Where do you land on this? How do you report on the results?

    • Kim Carlos

      Adelle, I think it depends on if it’s a written survey or an in person/phone interview. I find the interviews need to be less formal and that it’s best to guide the prospect or customer with questions but let them tell their story. It’s really all about the “story” more so than data points at this stage. Just my two cents. 🙂

      • Sue Duris

        Be careful not to too overtly guide interviewee – let it come naturally. That’s why having a script in place is important. Yes, things will go off script. Listen/observe for cues on what people want to discuss. It will be there.

    • Sue Duris

      Hi Adelle – I think a healthy combination of quantitative/qualitative questions is fine. Ensure your questions are clear, unbiased and keep to what you need to know so that you are maximizing your and your interviewee’s time. Remember a few things. (1) if you “won” the business, the person is a customer, so first this should be separate of any on-boarding process and second, you are building a relationship with any customer touch point you have, so keep that forefront in your mind – commit to delivering a stellar experience that is memorable. This will help you convert this customer to a brand advocate. (2) if you “lost” the business today, that doesn’t mean you’ll “lose” the business tomorrow, so plant the seeds to build a relationship. You can still get this person to become a brand advocate so they will happily refer you potential customers.

  • Kim Carlos

    I really love this as a guide in creating a formal Win/Loss Analysis program. Very thankful for the insight Sue!

    • Sue Duris

      Hi Kim. See my part II here > This is the exciting part, analyzing results of your win/loss interviews and determining which insights to implement. The strategy here changes somewhat whether win/loss is being driven in-house or by a consultant. Try to review the results objectively. Determining which insights to implement is balancing act — supporting the brand, what your target segment wants and what your customer base expects. Let me know if Part II meets your need.

  • These are all good questions that likely yield the desired insight and understanding. However, the list of 15 questions actually contains 33 questions. I’m struggling to see how you can cover all this ground in 30 minutes.