Day 4 challenge

Goal: automate daily agenda preparation with actionable insights

Theme: foundation week - calendar intelligence & communication

Time investment: ~10 minutes

Welcome to Day 4! Yesterday you experienced how Sidekick analyzes your schedule and drafts stand-up updates. Today we’re advancing to comprehensive daily agenda preparation—having Sidekick create detailed meeting notes and draft follow-up emails based on your calendar context.

This is where you see agents move beyond simple scheduling to strategic daily management.

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What you’ll accomplish today

  • Generate a comprehensive daily agenda with meeting-specific notes
  • Have Sidekick draft context-aware email templates for meeting follow-ups
  • Experience predictive meeting preparation and action item management
  • Learn how agents connect calendar data to communication strategies

This isn’t about copying calendar entries. Sidekick analyzes meeting types, attendees, and context to suggest specific talking points, potential outcomes, and strategic follow-up actions.

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Step 1: Request your daily agenda preparation

Building on yesterday’s calendar intelligence, let’s have Sidekick create a comprehensive agenda for your day:

Ask Sidekick:

Based on my calendar today, can you prepare my daily agenda with contextual notes for each meeting?
Include suggested talking points, potential outcomes, and any preparation I should do beforehand.

Daily Agenda Preparation

Watch how Sidekick:

  • Analyzes each meeting’s purpose based on title, attendees, and timing
  • Suggests specific talking points relevant to each meeting type
  • Identifies potential decisions or outcomes to prepare for
  • Recommends pre-meeting preparation based on attendee profiles
  • Notes optimal meeting flow and transition strategies

Agent learning moment notice how Sidekick infers meeting context and purpose from minimal calendar data. it’s using pattern recognition to suggest relevant business outcomes and conversation topics.

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Step 2: Generate meeting-specific preparation notes

Let’s get more specific about your most important meeting today:

For my most important meeting today, can you create detailed preparation notes?
Include background research on attendees, suggested agenda items, potential objections or questions I might face, and key outcomes I should aim for.

Meeting Preparation Notes

Sidekick provides:

  • Attendee context: roles, recent company news, potential interests
  • Strategic talking points: relevant to meeting objectives and attendee priorities
  • Anticipated challenges: common objections or difficult questions to prepare for
  • Success metrics: clear outcomes to aim for and how to measure meeting success

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Step 3: Draft follow-up email templates

Now for the powerful part—having Sidekick prepare email follow-ups before meetings even happen:

Based on my agenda today, can you draft email templates for potential follow-up actions?
Create templates for: meeting recap emails, action item assignments, scheduling next steps, and sharing relevant resources.
Tailor each template to the specific meeting type and attendees.

email Template Generation

Sidekick creates customized templates such as:

  • Meeting recap emails: structured summaries with key decisions and next steps
  • Action item assignments: clear task delegation with deadlines and context
  • Follow-up scheduling: templates for booking next meetings based on outcomes
  • Resource sharing: contextual document or link sharing based on discussion topics

Pro insight Sidekick tailors language, formality, and content based on attendee relationships, meeting types, and your communication history.

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Step 4: Strategic day optimization

Ask Sidekick to go beyond agenda creation to strategic optimization:

Looking at my full agenda, what strategic opportunities should I watch for today?
Are there any cross-meeting synergies, networking possibilities, or ways to maximize the value of my time?

Sidekick might identify:

  • Cross-meeting connections: “your 2 PM discussion about budget could inform your 4 PM vendor meeting”
  • Relationship opportunities: “two attendees from different meetings work on related projects—consider introducing them”
  • Information leverage: “insights from your morning client call could strengthen your afternoon proposal presentation”
  • Energy management: “schedule your most challenging conversation after your team win at 11 AM”

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What just happened?

In 10 minutes, you’ve experienced sophisticated daily intelligence:

Predictive preparation Sidekick doesn’t just read your calendar—it anticipates meeting needs, potential outcomes, and required follow-up actions

Context-aware communication email templates aren’t generic—they’re tailored to specific relationships, meeting types, and expected outcomes

Strategic management Beyond individual meetings, Sidekick identifies cross-meeting opportunities and day optimization strategies

Proactive action planning Rather than reactive follow-ups, you now have prepared templates that anticipate common meeting outcomes

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The power of contextual intelligence

Unlike basic calendar apps or generic email templates, Sidekick understands the flow of business relationships and decision-making. It connects the dots between meetings, anticipates outcomes, and prepares you for the communication strategies that drive business forward.

Tomorrow - Day 5

Reflection Friday - Sidekick summarizes what it learned about you this week and reflects on your agent interaction patterns for continuous improvement.

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Pro tip for today

After each meeting today, tell Sidekick what actually happened:

My 2 PM meeting with [person] went differently than expected. Here's what actually happened: [brief summary].
How should I adjust my follow-up approach and what can you learn for future meeting preparation?

This teaches Sidekick to improve its meeting prediction accuracy and follow-up suggestions based on real outcomes.

Time to complete: ~10 minutes

Skills learned: agenda preparation, predictive meeting analysis, email template generation, strategic day optimization, contextual intelligence

Next day 5 - reflection and optimization based on week’s learning

Remember each interaction teaches Sidekick more about your meeting patterns, communication style, and business context. The agent is learning to anticipate not just what you’ll need, but when and how you’ll need it.