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  • Writer's pictureEric Doherty

Unveiling the Power of Win-Loss Reviews: A Crucial Business Strategy

Updated: Sep 19, 2023



Having lost and won deals over a career of 30 plus years in technology companies it can be a soul wrenching experience to delete that big deal from your forecast and try and provide an explanation.


.....and that is the problem, your own personal bias and the need to "cover your ass" does not allow a realistic and unbiased review of the real reasons why the deal "went south".


For CEOSs, CROs and CTOs a win-loss review, to put it simply, is an insightful interview designed to reveal the reasons behind the success or failure of a sales opportunity. Typically conducted via phone, these reviews can be executed either by an internal team member or an external party.


As a business consultant, I strongly recommend having a well-thought-out strategy before venturing into win-loss reviews. It should answer key questions like:


- Who will conduct the interview?

- On what basis will you choose customers or prospects for the interview?

- What questions will you ask?

- What will be the duration of the interview?

- When will the interview be scheduled?


A well-executed win-loss review strategy will significantly improve your team's success rate and increase your chances of winning more business deals. A recent study demonstrated that teams consistently utilising win-loss analyses were significantly more successful, seeing a 17.6% increase in seller achieved quota rates and a 14.2% increase in win rates.


The review process can be carried out internally or via a third-party, and the mode of interaction could range from an informal chat to a detailed survey.


Here is a list of essential questions you could incorporate into your win-loss review strategy. Please note that it's advisable to keep the in-person interviews within the 15-20-minute range.


Win-Loss Analysis Questions

1. What was the primary factor influencing your decision?

2. How well did we tailor our presentation/product/service to meet your needs?

3. Were your decision criteria well-defined? If so, what were they?

4. Did you speak with any references about our product/service? What was their feedback?

5. How was your overall experience interacting with our team?

6. How do you perceive the timing of our sales process? When did you initiate the search for a new product/service?

7. What are your thoughts on our product/service roadmap? Is there anything missing?

8. Can you share your decision-making process?

9. How would you rate our product/service? What did you like or dislike in particular?

10. Why did/didn’t you decide to buy now?

11. What would you suggest we change for next time?

12. What was the most significant difference between us and the other solutions you considered?

13. How easy did we make this decision for you?

14. How do you perceive our reputation within the industry?

15. Any additional suggestions or comments?


Template for Win-Loss Analysis


It's always helpful to have a predefined process when conducting win-loss reviews. Here's a useful framework:


1. Pre-Meeting Strategy Session - Identify the goals for the win-loss review, formulate questions, decide the interviewer, coordinate logistics, and determine the mechanism to share the findings with the team.

2. Conduct the Win-Loss Review - Keep the meeting concise (not more than 30 minutes) to respect the time of your prospect/customer. Ask your pre-decided questions and listen intently. Avoid defensiveness or unnecessary interruptions, and always conclude by expressing your gratitude for their time.

3. Disseminate Key Takeaways - Summarise the most pertinent points from your win-loss review and share the key takeaways with the relevant stakeholders within your organisation. If there was a lack in features, notify your product team. If it was your customer service package that gave you an edge, then give kudos to your customer service team.


By making win-loss reviews an integral part of your sales strategy, you will gain invaluable insights that will help refine your approach, boost your win rate, and ultimately, drive your business growth.

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