Your salesperson hears that a prospect has bought from your competitor. It happens. When a long sales cycle ends with a closed lost sale, it can feel like you’ve missed more than just the revenue.
But there’s value to be gained from a loss. Make sure your sellers can brush themselves off quickly and capitalize on the experience with an effective post-sale analysis.
In my experience, most salespeople hesitate to determine what they could have done better during the sales process.
This may be because doing a lost deal analysis isn’t a commissionable activity. Maybe they’re worried they’ll get negative feedback that will feel too personal. Maybe they simply don’t care about doing a lost deal analysis. Maybe it’s because they already know why they lost.
The important thing for a sales leader, though, is to find out for yourself. A prospect who bought from your competitor can be a phenomenal resource. You can gain valuable insight into marketplace perception of your product, service, or company.
Closed Lost Sales: How to Learn What Went Wrong
Effective deal loss analysis requires both external feedback (from prospects) and internal reflection (from the sales team), helping sellers evolve from tactical to strategic thinking.
The question isn’t whether your sales team will lose deals, but whether they’ll learn enough to win more in the future. Here are five key recommendations for sales leaders to help their sellers learn from lost deals.
1. Encourage Direct Feedback from Decision Makers
Train your sellers to have post-loss conversations with decision makers using a professional approach: “As a professional courtesy, what could our company have done differently to be more successful with the next opportunity?”
When prospects give the universal “your price was too high” response, coach sellers to dig deeper by saying, “Let’s take price off the table. What can we do to be successful with the next opportunity?” This requires emotional resilience and professionalism from your team.
2. Conduct a Thorough Proposal Analysis
In today’s complex selling environment with multiple stakeholders, help your sellers evaluate whether they truly understood the internal organizational dynamics, spheres of influence, and company culture.
Did they recognize the different approaches and competing agendas of decision makers? Most importantly, did they have solid internal advocates or coaches guiding them through the process? This analysis reveals gaps in their discovery and relationship-building strategies.
3. Assess Perceived Emotional Cost
Most salespeople focus on price and features, but prospects think in terms of emotional cost. Opportunities can be lost to some perceived emotional cost that wasn’t recognized or addressed early in the buyer decision process.
Help your team identify what emotional concerns they may have missed: “Is this the right solution?” “Do I trust this salesperson?” “Is this a good career move for me?” “What’s the risk of changing vendors?”
4. Refine Your Qualified Prospect Definition
Many organizations lack clear criteria for what constitutes a qualified opportunity. Use lost deals to evaluate whether the opportunity truly met these criteria from the start.
They must have five core characteristics: the prospect has a need and is aware of it; someone has legitimate authority to say yes; there’s a sense of urgency with a defined timeframe; they trust you and your organization; and they’re willing to listen.
5. Foster Self-Awareness and Objective Analysis
Salespeople can be optimistic to a fault, believing they can win any opportunity. Create a culture where sellers honestly assess: “Did I do my best?” “Was this a realistic opportunity we could win?” “How well were we positioned against the competition?”
This self-reflection helps sellers better qualify and prioritize opportunities upfront, preventing future losses rather than just conducting post-mortems.
14 Questions to Guide a Closed Lost Sale Conversation
Once a buyer goes away, it can be difficult to get them to spend time with you; however, there are those who are willing to speak about their sales interaction.
Here are the types of questions you can ask a lost prospect. Use this list as a starting point to develop questions specific to your competitive environment, product, service, marketplace, and sales cycle.
- What did your vendor sourcing process look like?
- What did we do to earn the right to proceed as far as we did in your buying process?
- What was the main reason you decided not to buy from us?
- Do you feel as though you were given a clear understanding of our company, what we stand for, and how we could help you?
- What was most confidence-inspiring about our company? The least confidence-inspiring?
- Did the salesperson clearly articulate our value proposition?
- What did the salesperson do well? What could our salesperson have done better?
- Was the salesperson adequately prepared for the call? Why do you feel that way?
- Did the salesperson ask thoughtful, strategic questions about the business impact of our product or service?
- Did you feel that the salesperson’s recommendation was on target? Why or why not?
- At the end of each interaction, did the salesperson ask about next steps? If not, what did he or she do?
- What did our competitor offer that we didn’t, which compelled you to go in another direction?
- If you were managing this sales professional, what would you tell them was the reason you bought from the competition?
- Is there anything else you’d like to share?
The Importance of Lost Deal Analysis
Closed lost sales analysis isn’t about post-mortem finger-pointing. It’s about uncovering the hidden dynamics that drive buying decisions. In today’s increasingly complex sales environment, where deals involve stakeholders across multiple departments with competing agendas, the cost of losing opportunities extends far beyond a single salesperson’s quota.
Implementing a rigorous lost deal analysis shifts sales organizations from tactical to strategic thinking. Rather than simply reacting to RFPs and price requests, teams learn to become trusted advisors who understand the deeper implications of change for their prospects’ careers, relationships, and organizational dynamics.
Find out how sales training from The Brooks Group can help your sales teams win more deals.
