First Week Check-Ins That Keep New Roofing Reps

Reps quit between day 14 and day 21 of a new job more than any other window. The primary driver is not comp, it is not territory, it is isolation. A new rep who goes home to their apartment on Friday of week 2 with no debrief, no scorecard, and no sense of whether they are doing well has nothing to anchor them over the weekend. Monday morning they either show up or they do not.

The Daily Debrief

15 minutes at end of day, every day, for the first 14 days. Not optional. If the manager is unavailable, a senior rep handles it.

Structure:

1. Numbers first (2 min): knocks, contacts, inspections booked today
2. Best moment (3 min): rep shares one interaction that went well
3. Hardest moment (3 min): rep shares one rejection or confusion
4. Coaching (5 min): manager gives one specific thing to try tomorrow
5. Preview (2 min): rep states tomorrow's plan and quota

That is it. 15 minutes, no scope creep. If the rep has a bigger issue, schedule time later in the evening or next morning.

The Call Scorecard

Beyond knocks and contacts, a new rep needs feedback on technique. The call scorecard is a 10-point checklist the manager uses while shadowing:

ElementScoreNotes Greeting within 5 seconds0/1Smile, eye contact Clear purpose stated0/1Storm inspection, no damage promised Permission asked0/1"Would it be ok if" Listening vs pitching0/2At least 50% listening Objection handling0/2Name it, validate, reframe Next step offered0/1Specific time proposed Professional exit0/1Thank even on no Business card delivered0/1Physical or digital

Total: 10. A new rep should hit 6/10 by day 7 and 8/10 by day 14. Below that trajectory is a coaching flag, not a firing flag.

Shadow Quota

Week 1: the rep shadows a veteran for 3 days, solo for 2 days. Solo days have 50% of the normal quota.

Week 2: solo all 5 days, 75% of quota. Veteran available by phone.

Week 3: 100% quota. Manager spot-shadows 2-3 hours on 1 day.

The error most owners make is skipping shadow in week 1. Shadow is where a rep learns the actual rhythm: how long to stand at a door, what to do when nobody answers, how to transition from small talk to the pitch. Telling a rep "just go knock" and handing them a script produces quitters.

Confidence Versus Competence

Separate these two things in your coaching. Confidence is mental state. Competence is skill. They fail in different ways.

• High confidence, low competence: rep is rolling through doors but closing nothing. Risk: burns territory, develops bad habits. Fix: slow them down, shadow more.
• Low confidence, high competence: rep knows the pitch cold but freezes at the door. Risk: quits. Fix: more shadow, more debrief wins, smaller daily goals.
• High both: your future top rep. Stay out of the way, reinforce.
• Low both: 90-day evaluation. Most reps move out of this bucket with good coaching. Some do not.

The 14-21 Day Quit Window

Research from sales training firms consistently shows the quit peak for commission reps at day 17-19. Why:

• Honeymoon energy from week 1 is gone
• First paycheck has not hit or was smaller than expected
• Numbers are real and some reps are behind
• Rejection has compounded
• Personal life has absorbed any remaining bandwidth

The check-in cadence above buys you through this window. Without it, retention at day 30 is typically 40-50%. With it, 70-80%.

Week 2 Specific Interventions

• Day 10: one-on-one lunch with the manager. Not a working meal, an actual conversation about how the rep is feeling.
• Day 12: the rep's best-scoring shadow session debrief is emailed to them with notes. Nobody does this. Reps who get it stay.
• Day 14: a text Saturday morning. "Proud of the week. See you Monday."

None of these cost anything. Together they shift retention double digits.

The Weekly Report a Rep Wants to See

Every Friday, the rep gets an automated weekly report showing:

• Their knocks, contacts, inspections booked vs team average and vs personal goal
• Where they sit on the leaderboard (even if last)
• Their close rate on inspections run (from week 3+)
• Their expected commission on pipeline jobs

RoofKnockers auto-generates this per rep. No manager time required after initial setup. See the weekly recap feature.

Related: burnout prevention, top rep retention, and weekly canvass competitions.

See pricing or start a trial.

FAQ

What if a new rep refuses the daily debrief?

That is a culture problem, not a check-in problem. Daily debrief is part of the job. A rep who refuses in week 1 is telling you how they will behave in month 6. Address it or release them.

Is 15 minutes really enough?

For most reps, yes. The occasional rep needs a longer sit-down. Schedule those outside the 15-minute slot so the routine stays predictable.

What about experienced reps joining from another company?

Still do the first week debriefs. The context is different but the check-in habit sets expectations and surfaces transitional issues fast. After day 14, taper to 2-3 debriefs per week.