Navigating the First 90 Days of an Executive Leadership Role
Designed for Newly appointed C-suite executives in mid-size tech companies, transitioning from functional leadership roles to enterprise-wide responsibility to spark real collaboration and high-energy learning.
A 90-minute hybrid workshop. Audience is high-performing leaders feeling pressure to quickly demonstrate value, but struggling to balance strategic vision with cultural adaptation and relationship-building. Common pain points: unclear role expectations, information overload, and fear of early missteps.
The 90-Day Map Reveal
Participants start by voting (anonymously via a digital poll or sticky notes) on what they believe are the top three priorities for a new executive’s first 90 days. As priorities are revealed, the facilitator overlays actual examples from major leadership books and real C-suite onboarding plans, sparking curiosity about the differences and drivers.
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Why this works
This approach leverages curiosity and cognitive surprise, helping participants see the gap between instinct and evidence-based practice, which primes the brain for learning.
Pitfall Truth-or-Lie Game
Facilitator presents five statements about common early executive mistakes. Participants guess which are real pitfalls and which are urban myths (truths or lies), using a quick thumbs-up/thumbs-down or chat poll. Facilitator then shares brief stories illustrating the real pitfalls.
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Why this works
This method reveals misconceptions and corrects faulty mental models, a critical step in preparing for realistic challenges.
Stakeholder Speed Sketch
Each participant quickly sketches (literally or in words) their perceived 'stakeholder map'—the five people/groups they think will most impact their early success. Then, share one key name in a low-pressure round-robin or chat.
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Why this works
This activity lowers pressure by focusing on simple, personal mapping. It encourages sharing without forcing deep vulnerability and builds initial engagement.
Rapid Network Mix-Up
Facilitator runs a fast-paced networking challenge: participants pair or group up and, in one minute, share their top strategy for building credibility with a tough stakeholder. Groups rotate twice, collecting ideas rapidly.
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Why this works
High-energy sharing ignites creativity and reduces hesitancy. It also spurs participants to tap into their own experience, which boosts retention.
The Real Dilemma Dash
Present a realistic executive dilemma: ‘You discover mid-way through your onboarding that two key stakeholders are at odds with your vision, but you need both on board.’ Small groups brainstorm immediate next steps, then compare approaches to highlight diverse real-world solutions.
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Why this works
Anchoring learning in real dilemmas builds relevance and transfer, while the group format encourages collaborative problem-solving.
Personal Credibility Timeline
Participants privately create a timeline of their first 90 days, pinpointing one action per week they will take to build credibility. They then share one action with a partner, reflecting on how it connects to their leadership values.
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Why this works
Active reflection ties learning to personal context, deepening commitment and connecting practical steps to individual identity.
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