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Why Isn’t Win/Loss Analysis Successful?

by Jeff Chamberlain  |  August 4, 2018  |  7 Comments

Closer Look

Having spent most of my career in Product Marketing prior to joining Gartner, I have been involved in win/loss analysis multiple times and from several angles. Normally, there is a concern bubbling up from sales or executives that we are not winning enough of the deals and we need to understand why. Win/Loss analysis seems tailor-made for that situation. Sometimes the win/loss analysis comes from a desire to better understand best practices in the sales force and this is one tool to help understand what is done differently on won deals versus lost deals. Occasionally, win/loss analysis is just a standard report requested by sales leadership or other executives within the company so there is an on-going process to provide the report.

In my experience, the motivation for the program is just one of the reasons why it can fail. Let’s look briefly at these three scenarios to understand why each can fail.

  1. Not winning enough deals – This situation is inherently an issue as normally the initiators of the analysis are looking for quick results. Unfortunately, gathering objective information on wins and losses that can really lead to valuable conclusions means gathering consistent and objective responses from the customer or prospect on enough deals to provide a statistically significant indication of what has worked and what hasn’t. Even if you have a good survey already developed, the time required to connect with prospects and customers will almost always take far longer than the patience of those desiring the analysis. Short cuts on the number of responses or the source of the responses can both lead to drastically incorrect information.
  2. Understanding best practices – This one is a tricky trap for win/loss analysis. While customers can provide objective information on what mattered and what didn’t during a sales execution, this data is very difficult to collect accurately. What’s important to one customer may not be important to another and given the number of variables between different sales reps, different customers/prospects across wins and losses, this takes an enormous amount of data to be significant. Also, you need to have sales cooperation for win/loss analysis to be successful. If sales feels that the program is primarily being used to evaluate their performance, they can definitely skew the data. How many times have you heard “You will receive a survey evaluating my performance.  If you plan to give me anything less than perfect, please let me know and I’ll fix the issue so you can give me a perfect rating.” Sales can definitely influence the responses. So, best not use win/loss analysis for this. Honestly, this is a sales management function and can be informed by some great industry research available on the topic (See Challenger Sales Method).
  3. Standard reporting requirement – Frankly, this is the right motivation for win/loss analysis. Unfortunately, these programs are normally implemented by including a win/loss reason field in the sales opportunity management solution. This is filled out by the sales representative (if required) when closing the opportunity. Ironically, this leads to a lot of conclusions that price and product features are the main reasons you are losing deals. Additionally, it is very difficult to provide a set of choices for sales that encompass all of the possible situations. So, sales will pick whatever they think is closest to accurate and/or whatever doesn’t implicate their execution on the deal as an aspect of the reasons. It’s not always blatant disregard for the truth that gets in the way, quite often sales doesn’t know the actual reason for the loss. Accurate information has to come from the horses mouth.

Look for more on this topic soon. In the meantime, I would love to hear from you.

Are you using or have you tried win/loss analysis?

Why were you using win/loss analysis?

Do you know if it was successful in improving your business or whatever your goals were for the program?

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Jeff Chamberlain
Research Director
1 years at Gartner
37 years IT Industry

Jeff Chamberlain is a Research Director focusing on software applications product marketing. He specializes in advising enterprise application software vendors on their go-to-market strategies. Read Full Bio


Thoughts on Why Isn’t Win/Loss Analysis Successful?


  1. Jeff. Great post. Our experience at Clozd definitely confirms each of the points you make. As you’ve pointed out, so many orgs rely on sales reps to self-report win/loss reasons in the CRM. And it just doesn’t work. The feedback has to come from the actual prospects/buyers. One additional challenge we routinely see is “inadequate executive sponsorship.” Too often it’s a lower-level product marketer, sales manager, or product manager that identifies the need for more rigorous win-loss analysis; but, they don’t have the authority or the budget to implement win-loss on a large enough scale to be meaningful. Even if they do secure budget they run into frustrations later when they don’t personally have the influence or authority to implement the feedback – they’re not high enough on the org chart. The best win-loss programs are executive-led initiatives, by detail-oriented leaders who aren’t afraid to hear critical feedback and who can fund a meaningful program with an adequate sample size (as you pointed out in #1). Thanks for posting.

  2. Richard Case says:

    Jeff, I have worked in the Win/Loss customer interviewing and analysis business ever since I left Gartner about 20 years ago. I have executed Win/Loss for many major companies. I agree with every single word in your post. And I also agree with Andrew Peterson about the need for executive sponsorship.

  3. Willem Maas says:

    Hi Jeff, thanks for a thought provoking post. WRT your #1 not winning enough deals, I’ve had a different experience. The insights win/loss interviews generate into how situation, status quo solution, trigger/problem, goal, etc correlate with winning and losing have been invaluable for building pipeline and better qualifying opportunities. So I think the key in #1 is setting expectations about the word quick, that pipeline build can improve within 1 quarter, and the timing of more wins will depend on deal cycle. The insights though are real and valuable, especially in the context of advice like Christy Ferguson’s to “Create Demand from Prospects Who Are NOT Planning a Purchase.”

  4. Goron Hogg says:

    I’m shocked anyone would even consider using a survey to capture win/loss information. If that’s the best a business can come up with, then they deserve the crappy results they get.
    Survey questions AND scripted interview questions restrict the buyers responses to a confined data set. Recent buyers offer-up incomplete or inaccurate data that we mistakenly take for truth. Even the best open-ended questions cannot extract good data.
    Buyer interviews that focus on the criteria for change, shift the bias from our “need-to-know” specific information to the buyers true discovery and decision-making process. The insights are pure gold!

  5. Nice post. While Sales is the primary beneficiary of the results of a Win / Loss exercise, I’ve found that the quality and relevance of a Win / Loss report goes up considerably if Sales is not involved in the process. Ideally, the exercise should be sponsored at CxO level, led by Marketing and the info gathering activity should be outsourced to an external agency, with prospect / customer contact info pulled out from CRM. But, as I said, this is ideal.

  6. There’s a lot in what you say, but that doesn’t invalidate WLA. Professor Efrem Mallach, Kea Company’s research director, has managed WLA for many vendors, so I asked for his thoughts. At the best-practice provider: “our WLA program was totally separate from sales management. We promised sales reps that their data would remain confidential. Once word got out that we had refused a vice-president’s request for information on a specific campaign, we had a great deal of credibility with the sales force and had no trouble getting data. We also picked two respondents at random each month to win American Express gift cards, for a good deal of money back. After a few months most of the sales reps knew someone who had won cards, so the word got around that we were for real in that regard as well.

    “One thing we learned is that win-loss analysis versus a single vendor is useless. When you win, the #1 reason is always good salesmanship. When you lose, it’s usually something like our price being too high or their consultant being in the competition’s pocket. What matters is differences from one vendor to another. When we compared the reasons we lost to one competitor with the reasons we lost to another the differences led to real insights – for example, price may have shown up more often, and higher on the list, in losses to one than to the other. This is useful even though looking at the reasons we lost to one told us nothing useful at all.”

  7. Nice post Jeff. I have been delivering win-loss interviewing and analysis over the past 4 years, and also have experience hiring and managing win-loss consultants. I agree with all of your points. I have found the effort to get the contacts from sales to be the biggest challenge, and executive sales sponsorship is very helpful. I have advised my clients to start slow (in terms of the expected numbers of interviews), and to work closely with sales leadership in establishing the program. Having someone in Sales Ops that can help source the contacts can be really helpful. Anonymizing the interviews, redacting negative comments about Sales personnel, and compensating sales people who do participate have all be helpful as well. – John



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