Skip to main content

Tell me about a deal you lost and what you'd do differently.

Overview

This question is designed to see how you bounce back from failure and if you learn from your mistakes and misfortunes. Certainly, no one expects that you’re going to win over every single prospect. But they will expect you to rally when things fall apart and use these disappointing moments to fine-tune your approach to close future deals.

Answer framework

Lead with confidence.

Don’t avoid sharing a story about failure. Nearly every sales professional has lost a deal in their careers. Just dive in with a story that shows you’re an veteran of sales and have a variety of experiences to prove it.

Describe the scenario.

It’s good to be upfront about what happened. Maybe last time you underestimated the competition and they swooped in on you. Or, you thought you knew what your customers long-range plans were and you missed the mark. Perhaps you didn't ask the right discovery questions and fell short in estimating their biggest pain point. Whatever it was, being able to describe the scenario shows employers that you have a clear understanding of what was going on.

Share how you’d do it better next time.

Remember, the details on what unfolded matter less than what you learned from the experience. What employers would like to hear is how you improved your craft as a result. That’s the skill you’ll bring to the table in this job.

Sample answers
My company had just unveiled a new machine with advanced molding technology, and I couldn't wait to start selling it. But what I didn't realize was that as I began sharing the news with current customers, there were still bugs in the system. So, I was out there spreading the word, getting people excited about a game-changing product that wasn't ready. One of my long-time clients was so excited they jumped in and ordered three of the new machines, but shortly before our delivery date, our head of engineering informed me that we weren't going to be able to deliver on any of the promised machines for six months. That news was not well-received. And it went from bad to worse. One of our competitors launched a similar product a month later. Their machine wasn't as robust as ours, but it worked. So, the client canceled their order and bought their machines from the competition. That experience drove home the importance of collaboration and communication. I was so excited about having something new to sell that I didn't take the time to check in with the most important internal stakeholders: product development, engineering and marketing. Today, I make these things a top priority. I get out of my seat, go talk to the most important people, walk the manufacturing floor, meet with engineers and coordinate with marketing. I assume nothing and pay closer attention to the competition. Why this answer worked well: He answered candidly and in a way that shows self-reflection. He talked about what he learned from the experience. He shared what he does today to avoid repeating that disappointing situation.
Tips
  • Be upbeat and strategic as you answer - not apologetic.
  • Demonstrate self-awareness and share lessons learned.
  • Point to a success that resulted from you not making the same mistake twice.
Back to top