Hiring Salespeople: Beyond the Resume

12 min read

Sales hiring is broken. Companies over-index on experience and under-index on everything else. A rep who crushed it at a well-known company might fail at yours because the selling environment is completely different. Meanwhile, you pass on candidates who could have been stars because they didn't have the "right" background.

What Actually Predicts Success

Research consistently shows weak correlation between sales experience and sales performance. What correlates more strongly:

Coachability: Can they receive feedback and improve?
Curiosity: Do they ask questions and want to understand?
Drive: Are they internally motivated to succeed?
Resilience: Can they handle rejection and keep going?
Preparation: Do they do the work before conversations?

Notice what's not on the list: years of experience, Rolodex of contacts, specific industry background. These matter for some roles but predict success far less than we assume.

Interview Questions That Reveal

"Tell me about a deal you lost that you should have won. What happened?"

Reveals self-awareness, accountability, and learning orientation. Beware candidates who blame external factors exclusively.

"Walk me through your last discovery call. What questions did you ask?"

Shows actual methodology versus claimed methodology. Good reps remember specific questions because they're intentional about discovery.

"What do you know about our company and product?"

Tests preparation. A candidate who hasn't researched you won't research prospects either.

"I'm going to give you some feedback on your answer. Let's see how you incorporate it."

Real-time coachability test. Give feedback, then ask a similar question. Do they adjust? How gracefully do they receive it?

"Describe a time you had to figure out how to sell something new without a playbook."

Reveals resourcefulness and adaptability. Early-stage companies especially need reps who can navigate ambiguity.

The Role Play Test

Don't just interview—simulate. Give candidates a realistic selling scenario and see how they perform. You'll learn more in 15 minutes of role play than 45 minutes of questions.

Provide context beforehand: company overview, target customer, product basics. Let them prepare for 24-48 hours. Then run the scenario: discovery call, demo, objection handling.

Look for: How do they open? What questions do they ask? How do they handle pushback? Do they listen or pitch? Can they think on their feet?

Reference Checks That Work

Candidates provide references who will say nice things. Go beyond the list:

Ask the candidate for their last three managers, not three people of their choosing. Patterns emerge across multiple data points.

Ask references specific questions: "What percentage of reps would you put them in, top 10%, middle, bottom?" "If you were hiring for a similar role, would you hire them again?" "What type of management did they need?"

Check LinkedIn for connections who worked with the candidate but aren't on their reference list. Back-channel references reveal what official ones hide.

The Hire Slow Principle

Bad sales hires are expensive—far more than the cost of having a seat unfilled longer. A failed hire means recruiting costs, ramp time, opportunity cost of deals lost, and team morale impact.

Don't rush. Add interview rounds if needed. Require multiple decision-makers to approve. Delay offers until you're confident. The cost of patience is lower than the cost of mistakes.