New Rep 30-60-90 Day Coaching Checklist

Use this to structure a new rep's first 90 days around scheduled coaching touchpoints and named, provable skill checkpoints — not around whatever comes up that week. Every checkpoint below should be demonstrated, not just covered in training. If a rep can't do the thing live or in a role-play, they haven't hit the checkpoint yet, regardless of what the curriculum says they finished.

Before Day 1 — Manager Prep

• Block recurring 1:1 slots for weeks 1–13 on both calendars now — don't schedule week to week
• Identify two peer partners: one tenured rep for shadowing, one rep at 12–18 months for relatable coaching
• Pull the onboarding curriculum and map which skills must be provable by Day 30 / 60 / 90
• Confirm call-recording or live-observation access is working before their first live call

Days 1–30 — Foundation (Watch, Absorb, First Reps)

Cadence: 2x/week 1:1 (15–20 min) · 1 shadow session every 2–3 days

• Day 3 — First 1:1: confirm they know where recordings live, how to book time with you, and who to ask when stuck
• Day 5 — Shadow debrief: rep names 3 specific things they noticed the tenured rep do, in their own words, not paraphrased from notes
• Day 10 — Skill checkpoint: rep delivers the opening/positioning statement unaided in a role-play, scoring 3+/4 on clarity
• Day 15 — First live call, rep-led, manager silent: review within 24 hours using a structured notes template — not a verbal "how'd it feel?"
• Day 20 — Skill checkpoint: rep asks 3 open discovery questions in sequence and follows the buyer's actual answer instead of reading the next scripted question
• Day 25 — Mid-point 1:1: rep self-rates against the Day-30 checklist below; manager rates the same list; compare gaps out loud
• Day 30 — Formal Day-30 review: documented sign-off against the checklist, with one named skill prioritized for Month 2

Day-30 skill checkpoints (must be demonstrable):

• Delivers core positioning/value statement unaided
• Runs structured discovery without going script-rigid
• Navigates the CRM/tool stack without help for routine tasks
• Has run at least one live call solo, even if the outcome was rough
• Knows where to escalate a stuck deal, and does so before it goes cold

Days 31–60 — Application (Handle Real Situations)

Cadence: 1x/week 1:1 (30 min) · 1 call review every week

• Day 35 — Skill checkpoint: rep acknowledges and isolates an objection live, even if the reframe is still weak (score the call with the Objection Handling Call Review Rubric)
• Day 40 — Peer role-play session: rep runs 2 scenarios from the Role-Play Script Library with a peer; manager observes silently
• Day 45 — 1:1 focused on ONE skill gap only, not a grab-bag review — pull it from the Day-30 gap list
• Day 50 — Skill checkpoint: rep runs a full call solo, start to next-step, with no manager pre-brief
• Day 55 — Manager reviews rep's own CRM notes for coaching-visible detail, not just completion
• Day 60 — Formal Day-60 review: documented sign-off, activity/pipeline checked against ramp benchmark, one skill prioritized for Month 3

Day-60 skill checkpoints:

• Scores 2+/4 on at least 3 of 4 dimensions on the Objection Handling Rubric across 2 real calls
• Runs discovery-to-next-step without manager intervention on routine calls
• Proactively flags a stuck or at-risk deal before being asked
• Self-assessment matches manager's observation within 1 rubric point

Days 61–90 — Independence (Consistency Under Real Conditions)

Cadence: 1x/week 1:1 (30 min) · 1 call review every 2 weeks, tapering toward standard cadence

• Day 65 — Skill checkpoint: rep handles a genuinely hard call (competitor comparison, multi-stakeholder, price pushback) with only light manager prep
• Day 70 — Rep leads their own 1:1 agenda for the first time; manager evaluates whether they're identifying their own gaps
• Day 75 — Cross-functional checkpoint: has the rep looped in support, deal desk, or leadership unprompted when needed?
• Day 80 — Skill checkpoint: rep coaches or peer-reviews a newer starter — teaching it back is the strongest ramp signal there is
• Day 85 — Manager drafts the Day-90 ramp assessment against the original hiring/ramp benchmark
• Day 90 — Formal Day-90 review: ramp sign-off, or a documented extension plan with named skills and dates; transition to standard 1:1 cadence

Day-90 full ramp bar:

• Meets or is trending to meet the activity/pipeline ramp benchmark for their cohort
• Scores 3+/4 average on the Objection Handling Rubric across the last 2 reviewed calls
• Runs discovery, objection handling, and next-step securing without manager support on standard-complexity deals
• Self-identifies coaching needs rather than waiting to be told
• Manager can honestly say: "I'd let this person run a call with a real prospect, unsupervised, today"

If a Checkpoint Is Missed

Don't let a missed checkpoint quietly roll forward. Log it, name the specific skill gap, set a new checkpoint date within 5 business days, and note it in the next formal review. A pattern of rolled-forward checkpoints is the earliest reliable signal of a ramp failure — catch it here, at Day 35 or Day 65, not at Day 90 when the runway is gone.