Designing Effective Client Onboarding Checklists for Success Managers
Designed for Enterprise SaaS Success Managers responsible for onboarding new clients to sophisticated workflow platforms to spark real collaboration and high-energy learning.
A 90-minute virtual workshop for Success Managers who manage onboarding for enterprise clients. Many participants report feeling overwhelmed by checklist complexity and struggle to maintain client engagement during onboarding. The session focuses on practical checklist design, real-world pitfalls, and communication strategies to ensure client adoption.
Checklist Curiosity Countdown
Kick off with a rapid-fire 'mystery' checklist challenge: share three anonymized onboarding checklist steps from well-known SaaS brands (e.g., Slack, Salesforce, HubSpot) and ask participants to guess the product and why that step is pivotal. Participants post their guesses in chat, sparking curiosity about best-practice structures.
Tap to view the full activity.
Why this works
Curiosity spikes engagement and primes participants to notice nuances in checklist design by connecting unfamiliar steps to familiar brands.
Myth-Busting Checklist Bingo
Distribute a virtual 'Bingo' card with common onboarding misconceptions (e.g., ‘Clients always read every step,’ ‘Checklists should be one-size-fits-all’). As you read statements aloud, participants mark their card and shout 'Bingo!' when they get five. Debrief each myth with real outcomes.
Tap to view the full activity.
Why this works
Addressing misconceptions directly clears cognitive bias and opens space for designing checklists grounded in reality.
Silent Sticky Note Share
All participants write (or type) one checklist step they believe is frequently missed or misunderstood during onboarding. On a shared board (e.g., Miro, Jamboard), everyone posts their note silently. Facilitator reads out a few and validates the low-pressure sharing.
Tap to view the full activity.
Why this works
Silent, asynchronous input lowers anxiety, ensures contributions from quieter voices, and surfaces overlooked checklist points.
Checklist Relay Race
Split participants into small breakout teams. Each team is given a client persona and must build a quick five-step onboarding checklist (timer: 4 min). Teams then pitch their checklist in rapid-fire format. Facilitator awards playful badges for most creative, clearest, or most client-friendly checklists.
Tap to view the full activity.
Why this works
High-energy, time-bounded creativity activates teamwork and reinforces practical checklist design under pressure.
Onboarding Dilemma Live Poll
Present a real onboarding dilemma (e.g., ‘Client skips the data integration step, causing delays’). Launch a live poll with 3 response options for how to handle it within the checklist. Facilitate brief group discussion on poll results, focusing on integrating prevention into checklist design.
Tap to view the full activity.
Why this works
Anchoring abstract checklist concepts to real dilemmas boosts relevance and helps participants practice problem-solving.
Personal Checklist Commitment
Invite everyone to write one actionable change or improvement they’ll make to their onboarding checklist based on today’s session. Participants share in chat or on sticky notes, and the facilitator encourages ‘micro-commitments’ for follow-up accountability.
Tap to view the full activity.
Why this works
Personal reflection and commitment bridge learning to real-world behavior, increasing transfer and accountability.
Sign up to unlock 3 more activities
Get the full pack, facilitation flow, and more ready-to-run ideas.