March 20, 2026 · Louie Bernstein
Sales Interview - Don't let them hide their mistakes
Do you want someone who hides from their mistakes, or someone who uses them as feedback to grow? During the interview, ask them this question:
"Walk me through the last deal you lost. What happened?"
Not the last deal they won. The last deal they lost.
This is the most revealing question you can ask a sales candidate.
Here's why and what You Are Listening For:
A weak candidate will do one of two things:
1. Blame the loss on external factors (“The pricing was off,” “The competitor got there first,” “The prospect was never serious”)
2. Tell you they cannot remember a specific loss (“I usually close my deals.” Red flag.)
A strong candidate will:
- Name the deal specifically without hesitation.
- Own their part in the loss (“I did not qualify the budget early enough” or “I waited too long to bring in the decision-maker”)
- Tell you what they did differently on the next deal as a result.
The ability to own a loss, and learn from it, is the single best predictor of long-term sales performance.
Sales is a sport of failure.
Whoever can process failure fastest and adjust their approach wins.
If your candidate cannot talk about a real loss with specificity and ownership, they are not the person you want representing your company.
Accountability is the ultimate predictor: A candidate who blames "pricing" or "the economy" for a loss will eventually blame your product for their missed quota.
Look for ownership, not excuses.
Sales Interview Strategy
Frequently Asked Questions (FAQs)
1. Why is asking about a lost deal better than asking about a win? Everyone has a "highlight reel" of successful deals where everything went right. While wins show talent, losses show character and process. Asking about a failure reveals whether a candidate takes accountability for their performance or if they habitually blame external factors like "the economy" or "product features."
2. What is the biggest "red flag" to look for in a candidate’s answer? The biggest red flag is a candidate claiming they cannot remember a specific loss or saying, "I usually close all my deals." This indicates either a lack of self-awareness or a lack of honesty. Sales is a high-rejection field; someone who can't point to a specific failure hasn't spent enough time reflecting on how to improve.
3. What specific traits characterize a "strong" answer? A strong candidate will provide three things:
Specificity: They name the company and the deal context immediately.
Ownership: They use "I" statements (e.g., "I failed to identify the true decision-maker").
Adaptability: They explain the specific change they made to their sales process to ensure that mistake didn't happen again.
4. Does blaming "pricing" or "the product" automatically mean I shouldn't hire them? Generally, yes. While pricing and product gaps are real challenges, a top-tier salesperson views those as hurdles to be navigated, not excuses for failure. A candidate who blames the product during an interview will likely use those same excuses to justify missing their quota once they are on your team.
5. How does this question predict long-term sales performance? Sales is a "sport of failure." Long-term success is determined by how quickly a rep can process a loss, extract the lesson, and adjust. Candidates who take ownership of their mistakes demonstrate a "growth mindset," which is the single best predictor of whether they will hit their quota consistently over time.
