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Template: Win/Loss Review Questions

Setting the scene

  • Can you tell me a little bit about your role at [company] and your goals for this evaluation?

  • Can you walk me through your evaluation process in as much detail as you feel comfortable sharing?

  • How did you initially hear about [GreatCo.]? Do you remember anything in particular that caused you to investigate further?

  • What do you feel were the high-level strengths and weaknesses of [GreatCo.]? This could be about our product / our sales execution / our marketing materials. Anything about us that stands out one way or another.

Customer problem

  • What key pain point/business problem drove the purchase decision?

  • Did the need for this solution come from your executive team, or was it more a groundswell of user demand?

  • Did you have a hard requirement to implement a solution by a specific date? If yes, what was it?


  • When did you hear about [GreatCo.]? At the same time as other vendors or before/after?

  • Where did you find out most of the information on [GreatCo.]? On our website or social accounts? On review platforms? From current customers?

  • Which other vendors did you consider and how did you narrow down your list of vendors?

  • How were we priced relative to other vendors you evaluated?

  • Did an existing relationship with another vendor influence your decision?

  • Did you seek the opinion of an independent analyst? If so, who? What did they say about us? Were analysts more favorable to other vendors?

  • Did you involve consultants to help you with the selection? If so, who? What did they say about us? Were they more favorable to other vendors?

Decision Criteria

  • Could you share with me your most important evaluation criteria?

  • In addition to your role, who else was involved in the selection decision?

  • Did you include frontline reps in the evaluation?

  • Who was the ultimate decision-maker?

  • Which department did the budget come from?


  • What were your "must-have" features or capabilities?

  • What features of [GreatCo.] do you consider most important?

  • What do you feel were the key strengths and weaknesses of [GreatCo.]’s product?

  • In the case of a loss, what did you like about the product you finally purchased? What do you feel were the key strengths and weaknesses of the product that you purchased?

  • What concerns or shortfalls around Guru were raised by other people involved in the assessment?

Sales Process and other Info

  • Did [GreatCo.]’s messaging and positioning resonate with you?

  • What did / didn’t you like about the [GreatCo.] sales process? What did / didn’t you like about the other vendors' sales process?

  • Did other vendors raise concerns on [GreatCo.] that you felt were not satisfactory addressed by [GreatCo.] people?

  • In selecting a vendor, did you require:

    • Proof of Concept? If so, how did [GreatCo.] do? How did competitors do?

    • Reference calls? If so, how did [GreatCo.] do? How did competitors do?

  • Are there future projects or business needs whose requirements were factored into the decision? If so, what are those projects?

Looking forward

  • Would you feel comfortable in recommending our solutions to others?

  • In the case of a win, would you be interested in participating in a case study, testimonial, joint press release, or beta test (for a future solution)?

  • What advice would you give our team for working with you and teams like yours in the future?

  • Do you have any additional comments or suggestions?

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