What Are Kickoff Sessions?
The first official mentorship sessions held after a mentee purchases a bundle.These sessions (typically lasting 40–60 minutes) are designed to set a clear direction, define measurable goals, and co-create a personalized roadmap for the mentorship journey.
It’s the stage where insight turns into action — Ensure the plan aligns with the mentee’s goals, feels comfortable for them, and focuses on areas you can confidently mentor in.
Purpose of Kickoff Sessions
🎯 Alignment
Both mentor and mentee should already be aligned on the main goals and expectations from the intro session. Use this time to briefly confirm that nothing has changed and that you’re both ready to move forward with the agreed priorities.🧭 Goal Definition
Translate the mentee’s ambitions into 2–3 clear, measurable goals with success indicators and realistic targets.🧩 Roadmap Building
Co-create a structured plan that defines what will be done, when, and how progress will be tracked.🔄 Accountability
Establish the rhythm of work — how sessions will run, what mentees should complete between them, and how progress will be reviewed.Before the Session
Preparation Checklist
- Review the intro session summary and mentee’s notes.
- Open your Kickoff Session Form before starting.
- Make sure your internet, camera, and audio work smoothly.
- Prepare any templates or resources you’ll reference (e.g., roadmap template)
Managing Cancellations
Sessions are automatically approved when mentees book them. In case something urgent came up that prevented you from attending, it’s important to cancel the session:- Cancel at least 24 hours prior to the session
- Use the platform’s cancellation feature to notify the mentee
Last-minute cancellations negatively impact the mentee experience and your reputation as a mentor. Always cancel with proper notice when necessary.
Session Structure
Session Duration: 40-60 minutesKeep Kick off Session Evaluation Form open on your screen during the session to capture key notes in real-time. Immediately after the session, complete and submit the form.
| # | Title | Duration | Description |
|---|---|---|---|
| 1 | Welcome & Framing | 3-5 min | Start with a warm welcome, restate the goal of this session: to set a clear roadmap and define success. Briefly revisit the intro discussion. |
| 2 | Confirm Intro Summary | 5 min | Confirm what was discussed in the intro: mentee’s main objective and selected focus area (e.g., Job Search, Skill Mastery, Career Transition). |
| 3 | Current State Assessment | 10–15 min | Explore the mentee’s current level — experience, portfolio, strengths, and gaps. Identify top 2–3 areas for development using evidence (projects, CV, etc.). |
| 4 | Define Goals & Success Measures | 10-15 min | Co-create 2–3 main goals. For each goal, define success metrics, timelines, and how progress will be tracked. Make sure the goals are realistic, measurable, and achievable within the duration of the purchased bundle. |
| 5 | Co-Build the Roadmap | 10-15 min | Turn goals into a sequence of milestones. Outline key steps, resources, and approximate session allocation per milestone |
| 6 | Next Steps & Assignments | 5 min | Assign clear, actionable tasks before the next session. Confirm next session’s date and communication channel ( Pumble) |
After the Session
📝 Submit the Kickoff Session Form
Immediately after the session, fill out the Kickoff Form with all details:- Goals, milestones, and success measures
- Agreed roadmap
- First assignment
🧾 Update Session Status
Mark the session as completed on the Silah platform.This ensures tracking and progress visibility for both mentor and mentee.
Always update the Kickoff Session status immediately after the session. This is essential for tracking progress, maintaining alignment, and ensuring the community team can support the mentee throughout the mentorship bundle.
📂 Share Materials
If you promised templates, examples, or learning resources — share them right after the call through Pumble.Achieving the Purpose of the Kickoff
The session is successful when: ✅ You and the mentee have a shared, written roadmap.✅ There are 2–3 measurable goals agreed upon.
✅ Both sides know what’s next before ending the session.
Remember: This roadmap will be your anchor in all following sessions.
Achieving the Purpose of the Kickoff Session
The Kickoff Session works best when it is structured around three core objectives:1. Lead with clarity to define goals and roadmap
- Use structured questions to confirm the mentee’s goals and current state.
- Explore priority areas, milestones, and timelines to ensure the plan fits the mentee’s bundle duration.
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Keep the session focused and on schedule; politely steer the conversation back if it drifts off-topic.
- Example redirect: “That’s helpful context. To make the best use of our time, can you clarify which milestone you’d like to tackle first?”
2. Decide and co-create the roadmap
- By the end of the session, define 2–3 main goals with success metrics, targets, and tactics.
- Agree on milestones, timeline, and responsibilities — what the mentor will provide vs. the mentee’s assignments.
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Document the plan as the source of truth for the mentorship bundle.
Important: Ensure goals and milestones are realistic and achievable within the bundle duration — overloading the plan may hinder progress.
3. Leave the mentee motivated and prepared
- Share high-level advice, resources, or actionable steps that the mentee can start working on immediately.
- Highlight potential gaps and explain how they will be addressed through the roadmap.
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Even if challenges exist, ensure the mentee feels confident and supported.
- The goal is for the mentee to walk away thinking: “This session gave me a clear path, and I know exactly what to work on next.”
Best Practices
Prepare in advance
Prepare in advance
- Review the intro session notes and the mentee’s profile before the kickoff to start the session with clarity and continuity.
- Prepare a draft structure for the mentorship roadmap, but remain flexible to co-create and adjust it with the mentee during the session.
Co-Create the Roadmap
Co-Create the Roadmap
- Define 2–3 main goals with clear success metrics, milestones, and timelines that fit the bundle duration.
- Ensure goals are realistic and both sides know their responsibilities.
Maintain Structure and Flow
Maintain Structure and Flow
Keep the session focused within 40–60 minutes. Politely redirect if the conversation drifts off-topic and summarize key decisions as you go.
Ensure Alignment and Motivation
Ensure Alignment and Motivation
Confirm mutual understanding of goals, expectations, and next steps. End the session with clarity and motivation for the journey ahead.
Follow-Up and Documentation
Follow-Up and Documentation
Document the agreed roadmap and update the session status immediately after the session. This keeps progress visible and enables the community team to provide support.Common QuestionsCommon QuestionsCommon QuestionsCommon Questions
Common Questions
What if I need to adjust the roadmap after the session?
What if I need to adjust the roadmap after the session?
Minor adjustments are fine if they help improve progress, but major changes should be discussed with the mentee and clearly documented. Keep the mentorship plan consistent with the agreed bundle duration
How will communication happen between sessions?
How will communication happen between sessions?
All communication takes place through Pumble. We’ll invite the mentee after the payment and use it for follow-ups, updates, and sharing resources.
What if I disagree with the mentee on the roadmap or priorities?
What if I disagree with the mentee on the roadmap or priorities?
Handle disagreements constructively — listen to their perspective, explain your reasoning, and aim for a shared solution. If misalignment continues, contact the community team for guidance.
How are future sessions scheduled?
How are future sessions scheduled?
You can discuss and agree on upcoming session times during the kickoff. Once confirmed, the mentee will book them through the paid sessions calendar.
What if the mentee doesn’t engage after the session?
What if the mentee doesn’t engage after the session?
Reach out once on Pumble to check in. If there’s no response, inform the community team so they can follow up. Don’t chase repeatedly — your role is to guide, not to manage attendance.
Resources & Tools
- Roadmap Template: [link to template]
- Kickoff Session Form: [link to Google Form]
- Communication Tool: Pumble - for mentor updates, team coordination, and managing engagement with mentees.