onboarding-plan

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name: onboarding-plan description: > Design a 100-day customer onboarding plan with phase gates based on Never Lose a Customer Again by Joey Coleman. Use when user says "onboarding plan", "new customer onboarding", "customer kickoff", "first 90 days", "activation plan", "customer launch plan", "new customer journey", or "implementation plan" - even if they don't say "100 days" explicitly. Applies to CSMs designing structured onboarding programs that move customers from signed contract to full adoption.

Overview

Based on "Never Lose a Customer Again" by Joey Coleman, most customers who churn do so in the first 100 days - not because the product failed, but because the transition from buyer to user was never properly managed. Coleman's framework maps eight emotional phases every new customer moves through. Ignoring any phase creates a gap where customers feel abandoned or confused.

The core insight: onboarding is an emotional journey, not a technical checklist. Customers need to feel welcomed, capable, and successful - in that order - before they commit to the product.

Workflow

Step 1: Identify the customer's starting state

Before building the plan, answer these four questions:

1. What did they buy? - specific product tier, modules, or features contracted
2. What outcome did they buy it for? - the business problem stated during the sales process
3. Who will be using it? - end users, admins, execs (different onboarding needs for each)
4. What does success look like at day 100? - specific, measurable outcome, not "happy with product"

If you cannot answer all four, schedule a kickoff call before building the plan.

Step 2: Map the 100-day journey across Coleman's eight phases

Phase 1: Assess (Day 0-1) The customer is evaluating whether their decision to buy was correct. What they feel: anxiety, second-guessing, buyer's remorse.

Your job: Confirm the decision was right before they question it.

Actions:

• Send a personal welcome message from the CSM within 24 hours of contract signature
• Recap the outcome they're buying this for - use their exact words from the sales process
• Introduce the CSM team and set expectations for the first 30 days

Do not send a generic onboarding email. Send something that shows you read their contract.

Phase 2: Admit (Day 1-3) The customer acknowledges they need help setting this up. What they feel: vulnerability, need for guidance.

Your job: Make asking for help feel safe and normal.

Actions:

• Schedule kickoff call within 3 days - not a week
• Provide a clear "what to expect in the next 30 days" document
• Name a single point of contact for questions

Phase 3: Affirm (Day 3-14) The customer is looking for reinforcement that they made the right call. What they feel: hope mixed with doubt.

Your job: Provide early proof points that the product works for them specifically.

Actions:

• Show them 1-2 examples of customers similar to them who succeeded
• Share a case study or reference from their industry
• Identify the "quick win" - the fastest path to a visible result

Phase 4: Activate (Day 7-30) The customer is set up and using the product for the first time. What they feel: overwhelmed by the new tool, pressure to show ROI to their team.

Your job: Reduce friction. Get them to their first value moment as fast as possible.

Actions:

• Define the "first value moment" for this customer (specific action that signals adoption)
• Run a structured setup session - not a demo, an actual configuration of their environment
• Provide a 3-5 step quick-start checklist, not a 30-page user guide
• Check in at Day 14 specifically on blockers

Success gate for Phase 4: Customer has completed core setup and logged in independently.

Phase 5: Acclimate (Day 30-60) The customer is building habits with the product. What they feel: routine interrupted, adjusting to new workflows.

Your job: Embed the product into their existing workflows, not alongside them.

Actions:

• Identify the 2-3 core workflows they run today and map product features to each
• Conduct a mid-onboarding check-in call at Day 30
• Run a targeted training session on the features most relevant to their stated goals
• Address any adoption gaps identified in usage data

Success gate for Phase 5: Customer using core features independently at least 3x per week.

Phase 6: Accomplish (Day 45-75) The customer achieves their first meaningful business outcome. What they feel: pride, vindication of their purchase decision.

Your job: Make the win visible and attributable to the product.

Actions:

• Measure the outcome they contracted for and present the data
• Help the customer share the win internally (talking points for their exec, summary email)
• Connect the result back to their original stated goal from the sales process

This is the moment to lock in a reference or case study request.

Phase 7: Adopt (Day 60-90) The customer integrates the product into their standard operating procedures. What they feel: ownership, comfort with the product.

Your job: Expand adoption breadth - more users, more features, more integration points.

Actions:

• Present a 90-day adoption report with usage stats and outcomes
• Introduce adjacent features that address their next-tier goals
• Begin stakeholder mapping for expansion - who else in the org could benefit?

Success gate for Phase 7: Product embedded in at least one core recurring workflow.

Phase 8: Advocate (Day 90-100) The customer becomes a champion who refers others and defends the product internally. What they feel: loyalty, pride in their decision.

Your job: Give them a way to express that loyalty.

Actions:

• Ask for a reference or case study
• Invite to user community, customer advisory board, or beta programs
• Schedule first QBR to carry the relationship into the next quarter

Step 3: Build the 100-day plan document

Structure the plan as a two-column table: your actions and their actions.

Week	Your Actions	Customer Actions	Success Gate
Week 1	Welcome message, kickoff call	Assign internal admin, attend kickoff	Kickoff completed
Week 2-4	Setup session, quick-start checklist	Complete setup, first login	Core setup done
Week 5-8	Workflow mapping session, Day 30 check-in	Attend training, run core workflow	3x/week active use
Week 9-12	Mid-point outcomes review	Share data, identify gaps	First outcome measured
Week 13-14	Adoption report, expansion preview	Review report, identify next use case	Product in SOPs

Step 4: Define success gates and escalation triggers

Success gate: measurable condition that must be true before advancing to the next phase. If a gate is missed, do not simply proceed - diagnose and intervene.

Escalation triggers (flag to manager immediately):

• No kickoff scheduled by Day 5
• No independent login by Day 21
• No response to 3 consecutive outreach attempts
• Day 60 with no measurable outcome progress

Anti-Patterns

1. Technical-only onboarding Bad: Onboarding plan is a list of configuration tasks and training webinars. Good: Map technical milestones to emotional phases. A setup session without a success gate and check-in misses why customers disengage.

2. No defined "first value moment" Bad: Onboarding ends at "training complete." No measurement of actual value delivered. Good: Define the specific action or outcome that signals the customer got value. Track it.

3. Reactive cadence instead of proactive Bad: Only contacting the customer when they raise a problem. Good: Phase-gated check-ins at Day 1, 7, 14, 30, 60, and 90 regardless of customer behavior.

4. One-size onboarding Bad: Same plan for a 5-person team and a 500-person enterprise. Good: Segment the plan by customer size, complexity, and stated goals. The phases are universal; the content within them is tailored.

5. Skipping the Advocate phase Bad: Day 90 is just "first QBR scheduled." No ask for reference, no community invite. Good: Day 90-100 is intentionally designed to convert satisfied customers into active advocates.

Quality Checklist

• Customer's stated outcome from sales process captured and used throughout
• All 8 Coleman phases addressed in the plan (even if brief)
• First value moment defined with a specific measurable signal
• Success gate defined for each major phase (not just "training complete")
• Escalation triggers documented with owner and response time
• Plan distinguishes your actions from customer actions
• Phase 6 (Accomplish) includes a plan to make the win visible internally at the customer
• Phase 8 (Advocate) includes a specific ask (reference, case study, community)
• No personal names, internal tool names, or company-specific references in template