A strong coaching plan gives structure to your work together, sets expectations, and helps clients clearly see their progress over time. It turns abstract goals into a clear, actionable journey — and this clarity is what builds confidence, trust, and momentum.
1. Start With the Client’s Goals
Begin every coaching plan by understanding:
What they want to achieve
Why it matters to them
Their timeline
Their starting point (experience, knowledge, skills, etc.)
This ensures the plan is tailored, not generic.
2. Break the Goal Into Milestones
Big goals feel overwhelming. Break the journey into smaller, digestible steps.
Examples:
MBA Application → Brainstorm → Resume → Essays → Recommendations → Interviews
GRE Tutoring → Diagnostic → Concept Review → Practice Sets → Test Strategy → Mock Exams
Milestones create visible progress, which keeps motivation high.
3. Decide How You’ll Work Together
Clarify the structure of the engagement:
Number of sessions or weekly cadence
What happens between sessions (feedback, check-ins, assignments)
How you’ll communicate (Leland messages, shared docs, etc.)
This prevents confusion and builds reliability.
4. Create a Shared Workspace
Use a simple, shared document where both you and the client can track progress.
This could be:
A Google Doc
A Notion page
A shared folder with worksheets
A checklist or timeline
The exact tool doesn’t matter — consistency does.
5. Revisit and Adjust
Goals evolve. Good coaching plans aren’t rigid — they adapt.
Check in regularly:
What’s working well?
What needs to shift?
Are we still aligned with the main goal?
This makes the coaching feel supportive and collaborative.
In Summary
A great coaching plan:
Starts with the client’s goals
Breaks them into clear milestones
Defines how you’ll work together
Lives in a shared workspace
Evolves as the client grows
When clients can see the path and feel the progress, they stay engaged, confident, and motivated — and that’s what leads to strong results and great experiences.