Our team sits in on a lot of sales interviews. Most of them follow the same script. The hiring manager asks predictable questions, the candidate gives rehearsed answers, and everyone walks away feeling good about it.
Then the hire doesn’t work out.
The problem is that good salespeople are good at interviews. They know what you want to hear. The trick is asking things they haven’t prepared for.
Here are ten questions we use that actually tell you something.
1. Walk me through your last deal.
Not the highlights. Start to finish. How they found the lead, what their approach was, where it stalled, and how they closed. A strong rep can walk you through this like they’re telling a story. If the answer is vague or they skip straight to the close, they’re leaving out the parts that didn’t go well.
2. What did you close last quarter?
We’re not asking this to hear a big number. We’re asking because real salespeople know their numbers without looking them up. If someone says “I’d have to check,” that tells you everything you need to know.
3. Tell me about a deal you lost.
Everyone loses deals. We want to know what they did after. Did they follow up to find out why? Did they adjust their approach? Or do they blame the prospect, the product, the timing? How someone handles a loss says a lot about how they’ll perform long term.
4. A prospect goes silent. What do you do?
This happens constantly in sales. The good reps have a system. They’ll tell you how many follow-ups they send, through what channels, on what timeline, and when they decide to move on. The ones who just say “I’m persistent” don’t usually have a plan behind it.
5. What’s your least favorite part of sales?
This one catches people off guard. There’s no wrong answer, but there are dishonest ones. If someone says they love everything about sales, they’re performing. If they say cold calling is tough but they still do it every day, that’s someone who pushes through discomfort. That’s who you want on your team.
6. What are your go-to deal questions?
A variant on the old “sell me this pen” angle. But we use this version because it works. Most candidates grab the pen and start listing features. The good ones ask questions first. What do you use a pen for? What are you using now? What’s wrong with it? This exercise uncovers thoughtful questions and the reasoning behind them.
7. What would you do in your first 30 days?
This tells us whether the candidate has thought about the job beyond getting the offer. The ones we want to place will ask about the pipeline, the CRM, the team, what’s working and what isn’t. The ones who give a speech about “making an impact” haven’t thought past the interview.
8. How do you research a prospect?
We want to hear specifics. Checking the company website, finding the decision maker on LinkedIn, reading recent news about the business. If their answer is “I just call and figure it out,” they’re going to waste a lot of leads before they close anything.
9. Tell me about a time you disagreed with your manager.
This is a coachability question. Did they raise the issue respectfully? Did they listen to the other perspective? Or did they just do things their own way? Both types of people exist in sales. Only one of them is manageable.
10. Why are you leaving your current job?
Simple question. Listen for two things. First, do they trash their current employer? If they do, they’ll do the same to you eventually. Second, is there real hunger behind the move? The best answer is usually that they’ve hit a ceiling and want more. That kind of motivation is hard to fake.
Put it all together
No single question tells you everything. But ten honest answers give you a much clearer picture than any resume.
If you need help finding the right candidates to sit across from, that’s what we do at SalesBountyHunter. Let us know what role you’re filling and we’ll go from there.