Designing 30-60-90 Day Onboarding Plans for New Managers
Designed for Newly promoted engineering managers in SaaS organizations who have never formally managed teams before and are expected to lead technical teams with high autonomy. to spark real collaboration and high-energy learning.
A 90-minute hybrid workshop with a mix of remote and in-person participants. Managers are transitioning from high-performing individual contributor roles and struggle with ambiguity, balancing team trust, and getting early wins without overwhelming their new teams.
Onboarding Bingo: Curiosity Kickoff
Each participant receives a digital or physical 'Onboarding Bingo' card with 16 squares labeled with typical onboarding activities (“Meet team individually”, “Review past project post-mortems”, etc). They mingle virtually/in-person to find peers who've already done each activity. First to fill a line yells 'Bingo!' and shares their most surprising onboarding experience.
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Why this works
This energizes participants, surfaces diverse onboarding tactics, and prompts curiosity about what counts as 'essential'. Peer-to-peer interaction builds engagement from minute one.
Myth Smash: The Manager Timeline
Facilitator presents 3 bold statements about onboarding plans (e.g., 'Managers should set objectives in week 1', 'The 90-day plan must be followed exactly'). Participants vote digitally or by raising hands: True or False. Facilitator reveals data from leadership studies and real quotes from seasoned managers, debunking common myths.
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Why this works
Revealing misconceptions prevents flawed approaches and builds more realistic mental models. It leverages group polling to foster safe disagreement.
Silent Plan Sketch: No Wrong Answers
Participants are given a blank 30-60-90 grid. Silently, they fill in one milestone they’d include at each phase. Facilitator collects grids anonymously, shuffles, and shares highlights. No names attached—no pressure, just sharing creative ideas.
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Why this works
Low-pressure activities reduce performance anxiety and encourage beginners to contribute, fostering psychological safety.
Milestone Dash: Race the Clock
Divide participants into small teams. Each team has 90 seconds to list as many critical onboarding milestones as possible for new managers. Teams present their lists rapid-fire. Facilitator awards points for unique, actionable milestones. High-energy and competitive!
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Why this works
Timed, collaborative challenges increase adrenaline and unlock group creativity. Competition boosts engagement and retention.
The Day 31 Dilemma
Facilitator shares a real case: A newly minted manager is thriving until Day 31, when a team member suddenly resigns. Small groups debate—should onboarding plans be flexible or rigid? Groups brainstorm real-time pivots, then share their reasoning and dilemmas.
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Why this works
Connecting learning to real-world dilemmas increases relevance and encourages critical thinking. Teams get practical practice in adapting plans.
Personal Check-In: Manager Map
Participants use sticky notes or a digital board to answer: ‘What’s the most important conversation you wish you’d had in your first 30 days?’ They post, read others, and write a brief self-reflection—how their onboarding plan will ensure this happens for their team.
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Why this works
Encourages deep, active reflection and personal connection to content. People learn best when relating new concepts to their own experiences.
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