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What? Who? Best Practices for Identifying the Best Opportunities for Win / Loss Interviews

Win / loss may seem simple: close a deal, call the buyer, find out why they selected you or a competitor. At a high level these steps may seem straightforward, but they are a lot more complicated than what meets the eye.

While debriefing with every single opportunity is a noble objective, it is unrealistic. If you have the right best practices though, you can select the right prospect organizations and the right contacts to engage with, and get on your way to developing a strong feedback mechanism. The following best practices can get you started:

At the Deal / Opportunity Level

There are a multitude of ways to segment or filter your deal-flow by in order to decide which of your prospects to call on. Here are some of the most beneficial to successful win / loss programs:

  • Revenue size: Establish a “floor” of deal size for which you will only inquire feedback for opportunities above that level. Doing this will filter out the smallest deals, which often did not receive the full extent of your resources to begin with.
  • Specific Competitor(s): Debriefing on deals in which you were up against your top competitors will give you valuable insights into how your rivals are positioning themselves and connecting with prospects. After you have built up a few data points from situations against a specific competitor, you can begin to construct “battle cards” to arm your sales team with so they can outperform the competition in the next heads-up sales situation.
  • Specific Sales Personnel / Teams: Have a new salesperson starting? Looking for data to help in coaching an underperforming individual on your team or want to learn from your most successful reps? Collecting feedback from the most recent deals completed by a salesperson and their team can provide you with a full debrief on their performance from the prospect’s point of view.

At the Contact Level

After deciding which deals to focus on, it is critical to make sure you speak with the right person at the prospect organization. Often in complex sales situations there is one key buyer, but many influencers from numerous different departments: the relevant line of business, IT, finance, and of course, procurement.

To gather the best win / loss feedback, remember to not get stuck in procurement. While the procurement department may have influence, they are often limited in the level of detail they can provide when describing the prospect’s full buying criteria and evaluation process. Getting in touch with the ultimate decision maker is the absolute best practice, as they will be able to provide access into their mindset throughout the sales process and ultimate decision.

In some scenarios there are heavy influencers or more than one decision maker, for instance a consultant may have been involved, or both IT and the line of business in a software sale. In these situations, it can be beneficial to interview multiple constituents to obtain the most well-rounded feedback possible.

After identifying who to contact for your interviews, remember some of the best practices for actually having the conversation with them. But by following the best practices above, you’ve already completed half the battle of conducting a win / loss interview.