Ride-Along Schedule — Days 9-12¶
Structured supervised practice between completing the quiz (Day 8) and going fully independent (Day 14).
The ride-along is where a new agent goes from "knows the script" to "can deliver the script credibly under live conditions." Supervisor presence is non-negotiable for this phase.
Day 9 — Pure observation (listening only)¶
Goal: new agent listens to 5 cold calls run by a senior agent. No participation.
| Activity | Duration |
|---|---|
| Pre-session: senior agent walks the new agent through what they'll hear | 15 min |
| 5 cold calls observed | ~1.5 hours |
| Debrief after each call (what went well, what would the new agent do differently) | 5 min per call |
| End-of-day reflection (3 things learned, 1 question) | 15 min |
Debrief questions after each observation:
- What was the opener? Did it work?
- How did the prospect react in the first 10 seconds?
- What objection came up? How was it handled?
- What was the close? Was it earned?
- What would you have done differently?
Day 10 — Discovery + demo observation¶
Goal: new agent observes 3 discovery calls and 1 demo call. Same listening-only posture, but the calls are deeper.
| Activity | Duration |
|---|---|
| 3 discovery calls observed | ~45 min |
| 1 demo call observed (30 min + setup) | ~45 min |
| Mid-day debrief | 30 min |
| Watch the senior agent's HubSpot logging at the end of each call | 20 min |
Specific things to look for:
- How does the senior agent set up the discovery call? What does the opener sound like?
- How does the senior agent handle a prospect who's vague about their pain?
- When does the senior agent transition from discovery into pitch?
- How does the senior agent close the discovery call — specific next step?
- During the demo: where does the senior agent let the product speak vs. talk?
- How does the demo close? Trial activation on the call?
Day 11 — Supervised cold calls (new agent runs them)¶
Goal: new agent runs 5 cold calls under supervision. Supervisor listens; can mute and intervene if necessary; debriefs after each.
| Activity | Duration |
|---|---|
| Pre-call brief: who they're calling, why, the opener | 15 min |
| Cold call #1 with supervisor listening | 10-20 min total |
| Debrief after #1 (15 min) — supervisor coaches | 15 min |
| Cold calls #2 through #5 (with debrief between each) | ~3 hours |
| End-of-day plan: 3 things to fix tomorrow | 15 min |
Coaching points the supervisor watches for:
- Speed of delivery (most new agents talk too fast)
- Tone (smiling-through-the-phone, energy without forcing)
- Pause after questions (silence is your friend)
- Active listening (mirroring the prospect's language)
- Handling rejection (gracefully, without taking it personally)
- Note-taking (writing down what the prospect says verbatim where useful)
- Closing with a specific next step
Day 12 — Supervised discovery + demo¶
Goal: new agent runs 3 discovery calls and 1 demo under supervision.
| Activity | Duration |
|---|---|
| Discovery call #1 (15 min) + debrief (15 min) | 30 min |
| Discovery call #2 (15 min) + debrief (15 min) | 30 min |
| Discovery call #3 (15 min) + debrief (15 min) | 30 min |
| Demo call (30 min) + debrief (30 min) | 60 min |
| HubSpot logging review (was every interaction captured correctly?) | 30 min |
| End-of-day: certification decision | 30 min |
Certification criteria at end of Day 12:
- Delivered all 4 supervised calls without supervisor intervention
- Logged every interaction in HubSpot per the lifecycle protocol
- Booked at least 2 next steps (discovery → demo, demo → trial, etc.)
- Handled at least 1 unscripted objection credibly
- Maintained brand voice throughout
- Self-debrief identifies their own weak spots
If criteria met: cleared for independent operations Day 13. If not: extended ride-along by 1-2 days; re-test Day 14 or Day 15.
Variants¶
For European-market agents¶
Days 9-12 should include at least 2 EU prospects (UK, NL, DE, or other target market) so the agent gets exposure to: - Local accent / cultural cadence in the conversation - EU-specific objections (GDPR, EU Accessibility Act, language fit) - EU-specific compliance citations (EN family vs. US standards) - Currency / VAT / Stripe-invoice complexity
For an agent specializing in one persona¶
Days 11-12 calls should all be the same persona (e.g., 5 cold calls to Maya-persona prospects + 3 Maya discovery + 1 Maya demo). Persona depth builds faster than persona breadth.
For an agent transitioning to senior¶
The same structure applies in reverse — a senior-track agent shadows the senior agent who's doing the most complex calls (large Team deals, Rig escalations). Different content, same structure.
What happens when ride-along reveals a problem¶
| Problem | Response |
|---|---|
| Scripts not memorized | Send back to Day 2 self-study; re-test Day 8 quiz |
| Tone problems (too pushy, too rushed, monotone) | Targeted coaching + 1-week probation |
| Compliance breach (made a forbidden claim, etc.) | Immediate stop; re-read Compliance; 1-week additional supervision |
| Brand voice drift | Targeted coaching with brand guide in hand |
| Inability to close | Specific work on sales-playbook/closing-and-pricing.md; additional supervised closes |
| Won't take coaching | Engagement conversation with call-center lead + Amir |
Recording for review¶
If the call center has call-recording infrastructure (HubSpot supports this; Stripe Connect supports this for invoiced calls):
- Record all ride-along calls
- Save in a shared library for the new agent to review
- Use for self-coaching (the agent listens to their own delivery)
- Use for cross-team learning (a great call becomes a training asset)
Recording requires consent in some jurisdictions; default to dual-consent + record. Pre-roll a "this call may be recorded for training purposes" statement.
After Day 14 — ongoing ride-along cadence¶
Even after independence, ongoing ride-along has value:
| Frequency | Purpose |
|---|---|
| Weekly | Supervisor listens to 1 call per agent for coaching |
| Monthly | Cross-agent ride-along: peer-to-peer learning |
| Quarterly | Senior agent + call-center lead ride-along: portfolio review of best practices |
The agents who stay sharpest are the ones who keep getting ride-along reps even after they're independent.
What ride-along is NOT for¶
- Performance evaluation (that's the monthly review, separate)
- Surveillance / micro-management (that breaks the working relationship)
- Backup for an agent who can't sell (if the agent can't sell, address that directly, not by hiding behind a supervisor)
Ride-along is for skill-building. Keep it focused there.