ThinkWork
Team/Manager Toolkit Free

New-Hire Skill Ramp Tracker

A week-by-week toolkit for the first 90 days that bundles checklists, milestone quizzes, and manager sign-offs into one tracker, so ramp is measured by skill milestones hit, not just tenure elapsed.

What's inside

  • Four 90-day phases (Foundation, Guided Practice, Independent Execution, Full Ramp)
  • A checklist for each phase
  • Sample milestone-quiz questions for each phase, with pass-mark guidance
  • A manager sign-off block gating advancement between phases
  • The hand-off point into the ongoing Skill-Gap Heatmap at day 90

Purpose

A week-by-week toolkit for the first 90 days: checklists, milestone quizzes, and manager sign-offs bundled into one tracker, so ramp is measured by skill milestones hit, not just tenure elapsed.

How the 90 Days Are Structured

PhaseWeeksFocus
1. Foundation1-2Product, ICP, process, tools — the knowledge layer under every skill
2. Guided Practice3-4First live reps of core skills, shadowed/paired
3. Independent Execution5-8Running full-cycle activity solo, coached closely
4. Full Ramp9-12Independent quota-relevant activity, ramp-to-target check

Phase 1: Foundation (Weeks 1-2)

Checklist

  • Completed product/ICP certification (pass mark: 80%+ on knowledge check)
  • Shadowed 5+ live or recorded calls across discovery, demo, and negotiation stages
  • Can articulate the company's value proposition unprompted, in their own words
  • Set up in CRM, dialer, call-recording, and enablement tools
  • Completed 1:1 with manager to walk through the Skill-Based 1:1 Template and the Rep Skill-Gap Heatmap they'll be scored against
  • Reviewed the Call Coaching Observation Scorecard so they know what "good" looks like before they're graded on it

Milestone Quiz — Foundation Check (sample questions)

  1. In your own words, what's the core problem we solve, and for whom?
  2. Name three questions you'd ask in a first discovery call to uncover business impact (not just surface pain).
  3. Walk through our sales process stage by stage — what has to be true to move a deal from Stage 2 to Stage 3?
  4. What's the difference between a feature and a value statement? Give one example of each for our product.

Pass mark: manager-graded pass/needs more time on all 4. Do not advance to Phase 2 on a "needs more time."

Manager Sign-Off — Phase 1

  • Foundation quiz passed: Y/N, date: ___
  • Manager comments: ___________________
  • Cleared for Phase 2: Y/N, signature: ___________________

Phase 2: Guided Practice (Weeks 3-4)

Checklist

  • Ran 3+ discovery calls paired with manager or peer buddy, debriefed against the Observation Scorecard
  • Completed 2 role-plays each on objection navigation and stakeholder mapping
  • Delivered first live demo (paired), scored on Value Articulation
  • First skill-based 1:1 completed with a named growth edge and commitment
  • Built first 5 pieces of self-sourced pipeline (or equivalent activity metric)

Milestone Quiz — Guided Practice Check (sample questions)

  1. Describe a real objection you handled this week. What was the surface objection, and what turned out to be the real concern?
  2. In your last paired discovery call, what business-impact question got the strongest reaction, and why do you think it worked?
  3. Who else, beyond your primary contact, do you now know is involved in at least one of your active deals? How did you find out?

Manager Sign-Off — Phase 2

  • Composite Observation Scorecard average across paired calls: ___ /4
  • Growth edge identified: ___________________
  • Cleared for Phase 3: Y/N, signature: ___________________

Phase 3: Independent Execution (Weeks 5-8)

Checklist

  • Running discovery calls solo, minimum 1 scored call/week using the Observation Scorecard
  • Composite scorecard average reaches 2.5/4 or higher across two consecutive scored calls
  • Has used at least one technique learned from a peer example (named, from the heatmap's top scorer on that skill)
  • Progressing at least one deal independently through negotiation stage
  • Self-sourced pipeline on pace vs. team ramp benchmark

Milestone Quiz — Independent Execution Check (sample questions)

  1. Pick your strongest scored call this phase. Which skill drove the result, and what specifically did you do?
  2. Pick your weakest scored call. What's the one thing you'd change, and what's your plan to practice it before it comes up again?
  3. Describe your current stakeholder map on your largest open deal — who, what role, what's still unknown?

Manager Sign-Off — Phase 3

  • Two consecutive scored calls at 2.5+/4: Y/N
  • Independent deal progressed to negotiation: Y/N
  • Cleared for Phase 4: Y/N, signature: ___________________

Phase 4: Full Ramp (Weeks 9-12)

Checklist

  • Operating at full quota-relevant activity level (calls/demos/pipeline generation at team benchmark)
  • Composite Observation Scorecard average at 3.0/4 or higher
  • First entry completed on the Rep Skill-Gap Heatmap (moves from "ramp tracker" to "ongoing team matrix")
  • 90-day skill-growth review completed with manager — one skill named as strongest, one as next growth focus for Quarter 2
  • Ramp retro completed: what worked, what to change for the next new hire

Milestone Quiz — 90-Day Ramp Check (sample questions)

  1. Across your ten core competencies, where would you rate yourself, and where would your manager rate you? Where's the biggest gap between the two, and why do you think that is?
  2. What's the one skill that, if you leveled up one point in the next two quarters, would change your results the most — and why that one?
  3. What's your plan, in your own words, for building that skill over the next 90 days?

Manager Sign-Off — 90-Day Ramp Complete

  • Full ramp achieved on schedule: Y/N
  • If not, extension plan and new target date: ___________________
  • First-quarter skill focus agreed: ___________________
  • Signed off by: ___________________ Date: ___________________

How to use it

Work through the four phases in order, gate advancement on the milestone quiz and manager sign-off at the end of each phase, and feed the Phase 4 scores directly into the ongoing Skill-Gap Heatmap so ramp data doesn't get thrown away at day 90.

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