Hiring a sales executive isn’t just about finding someone who can talk a good game. You want someone who can consistently close deals, build genuine relationships, and adapt when the market shifts. The right hire can push your revenue into overdrive. The wrong one… well, let’s just say you’ll know soon enough.
After helping companies hire for over a decade, I’ve learned that the interview is where the real magic happens if you ask the right questions. Below are my top 10 tried-and-tested questions that help identify the salespeople who don’t just hit quota, they crush it.
1. “Tell me about a time you went beyond your sales target. How did you pull it off?”
You’re looking for specifics, not vague stories. Great candidates will walk you through numbers, strategy, and even a few war stories.
2. “How do you build relationships that actually last?”
Closing is great. Keeping is better. True high-performers think about customer lifetime value, not just this month’s target.
3. “What’s your playbook for a prospect who keeps saying no?”
Persistence, yes, but smart persistence. You want to hear about adjusting the pitch, not hammering the same line over and over.
4. “Walk me through the most complicated deal you’ve ever closed.”
This reveals if they can navigate long cycles, multiple decision-makers, and tricky objections without losing momentum.
5. “When you have too many leads, how do you decide who to call first?”
This tells you if they understand qualification or if they’re just playing the numbers game.
6. “Tell me about a deal you lost, and what you learned.”
The best salespeople are brutally honest about their misses and can show how they turned that pain into process.
7. “What tools or CRMs have you used, and how did they make you better?”
If they can speak confidently about Salesforce, HubSpot, or any CRM, that’s a good sign. Bonus points if they can explain how it improved their close rate.
8. “How do you stay on top of market trends and competitors?”
This separates the order-takers from the strategists.
9. “How do you handle pricing objections without giving a huge discount?”
You want value sellers, not discount dealers. Listen for how they reframe value in the customer’s mind.
10. “When sales are slow, what keeps you going?”
Some will say “money.” The great ones will talk about discipline, competition, and the thrill of the hunt.
A Few Pro Tips When Interviewing Sales Executives
- Don’t just take their word for it, ask for metrics and proof.
- Role-play a quick pitch to see them in action.
- Pay attention to their energy and communication style; sales is as much about presence as it is about process.
Where HireEazy Fits In
I’ll be honest, finding the right candidate is half the battle. That’s where HireEazy changes the game. Instead of sorting through piles of resumes, you get handpicked, pre-vetted sales executives who have a track record of smashing targets. We’ve already done the hard work, so you can spend your time on the interview — and skip the guesswork.
Bottom line: A great sales hire can transform your business. Start with these 10 questions, and if you want a shortcut to the good ones, HireEazy can deliver them straight to you.