The 12 Interview Questions That Identify Great Roofing Sales Reps

Resumes lie. References are rehearsed. The only thing that predicts roofing sales success is how a candidate answers specific questions about their actual past behavior and thinks through specific scenarios. Here are the 12 questions I use and what to listen for in each answer.

Questions About Past Behavior

1. Walk me through your last sales day in detail

What you want to hear: specific times, specific locations, specific outcomes. "I knocked 60 doors between 10 AM and 6 PM in the Timberline neighborhood, got 8 inspections, scheduled 3, and closed one $22,400 deal."

Red flag: vague answers, generic descriptions, no numbers.

2. Tell me about your toughest close this year

What you want to hear: a real deal with a real problem solved. Homeowner objected, rep responded specifically, deal closed despite obstacle.

Red flag: cannot name a specific deal; talks only about easy deals; blames the customer for being difficult.

3. What was your close rate last quarter?

What you want to hear: a specific number they can defend. "About 32 percent from inspection to signed contract."

Red flag: "I do not really track that" or a wildly optimistic number (over 70 percent on cold inspections is fantasy).

4. How do you handle rejection?

What you want to hear: specific tactical answer. "I run 3 no-answer doors in a row without thinking about it, and I give myself 60 seconds after a hard no before knocking the next door."

Red flag: "I just stay positive" or any generic answer. Everyone claims to handle rejection well. You want to know how.

5. What was the most you ever earned in a month and how did you do it?

What you want to hear: specific month, specific deals, specific activity level. The story should be reproducible.

Red flag: cannot remember; fuzzy on deal count; claims numbers that do not add up (30 deals at 10 percent commission does not equal the stated income).

Questions About Scenarios

6. A homeowner says their deductible is too high. Walk me through your response.

What you want to hear: ACV vs RCV explanation, recoverable depreciation, financing options, never a discount or fee waiver suggestion.

Red flag: "I can work with them on it" (fraud territory) or "I would just give them a discount."

7. You are on an inspection and you find no damage. What do you do?

What you want to hear: honest conversation with homeowner, offer to inspect again after next storm, ask for referrals even without a sale, leave gracefully.

Red flag: "I would find something to write up" (fraud) or "I would argue about cosmetic damage to create a claim."

8. A competitor bids the job at 20 percent less. How do you respond?

What you want to hear: question what is included in their bid, compare warranties and materials, explain value, offer to match certain specs but hold price where it matters.

Red flag: "I would match it" or "I would just walk away" or "I would offer free add-ons."

9. You sign a contract on Tuesday. The homeowner calls Wednesday to cancel. What do you do?

What you want to hear: save call process, listen for real reason, isolate objection, offer specific save, let them out gracefully if unsalvageable, document everything.

Red flag: any version of "convince them they cannot cancel" or threats about material orders.

Questions About Motivation

10. Why roofing?

What you want to hear: specific reason. Maybe a family member in construction, maybe past work in insurance, maybe the income opportunity, maybe the storm chasing lifestyle. Specificity over generics.

Red flag: "I heard you can make good money" (true but shallow) or anything that sounds like they would switch to solar tomorrow.

11. What would make you quit within 6 months?

Surprising question, revealing answer. You want specifics: "If I was not making $6k per month by month 4" or "If leadership was dishonest."

Red flag: "Nothing, I am loyal" (unrealistic) or a list of things that apply to every shop (because they probably will quit).

12. Where do you want to be in 3 years?

What you want to hear: a specific path. Rep to closer to sales manager. Or rep building savings to start their own shop. Or rep moving into claims specialization.

Red flag: no answer; contradicts their compensation needs; or wants something your shop cannot offer.

Bonus Questions If You Have Time

• Describe your CRM workflow in your last job
• How do you prepare for a ride-along with a manager?
• What is your follow-up sequence on a no-show inspection?
• How do you handle a rep who is undercutting you on shared leads?
• What is the worst feedback a manager ever gave you?

The Ride-Along Test

After the interview, bring the top 2 candidates on a half-day ride-along with your best current rep. Watch for:

• Note-taking and attention
• Questions asked (good reps ask about objections and process, bad reps ask about commission)
• Body language on the driveway
• Willingness to knock a door themselves if invited
• Debrief quality afterward

The ride-along eliminates 70 percent of candidates who interview well but cannot execute. It is the most important step.

Reference Call Questions

When you call references, do not ask "was they a good employee." Ask:

• "What was their specific close rate?"
• "If you could hire them back today, would you?"
• "What was the hardest thing to manage about them?"
• "Would they be good in a W-2 role with daily accountability?"

The 30-Day Probation

Even after great interviews, write the offer with a 30-day probationary period. If the rep is not producing (15+ inspections, 2+ signed deals) by day 30, part ways. Do not hope for a month 2 turnaround. It rarely happens.

FAQ

How many candidates should I interview per hire?

5 to 8 phone screens, 3 to 4 in-person interviews, 2 ride-alongs, 1 hire. Volume gives you comparison and leverage.

Do I need a personality test?

Optional. DISC and 16Personalities can help filter but do not hire or reject on that alone. Behavioral questions and ride-alongs are more predictive.

What is the biggest mistake owners make in interviewing?

Hiring too fast when desperate. A bad hire costs 6 months and tens of thousands of dollars. Better to stay understaffed for 2 more weeks than to hire wrong.

Should I have multiple interviewers?

Yes. Have at least the sales manager and the owner interview. Different perspectives catch different issues. Final hire should have consensus.