Designing a Coaching Session Sequence
5 min read
Turn Sessions Into a Story
Coaching works better when sessions build on each other instead of standing alone. Here's how to create that flow:
The Session Structure
Beginning (First 2-3 minutes)
Remind the coach where you're at: "Last time I committed to having a conversation with my manager. I did it." "I'm still working on my goal to delegate more. Didn't make much progress this week." "This is my first session. I want to figure out if I should switch teams."
Name how you're arriving today: Energized? Scattered? Stuck? Anxious? Clear? This context helps the coach calibrate
Middle (Main part of session)
Explore one concrete situation or decision: Not 5 problems. One. Bring the actual details (not abstract thinking) Ask the coach to help you see options, trade-offs, patterns
End (Last 2-3 minutes)
Crystallize one action: Ask: "What's one specific thing I should do before we talk again?" Write it down (phone note, goal step, whatever) Say when you'll do it Say when you'll come back
Creating the Loop
Session 1: You commit to "send that email Friday"
Session 2 (a few days later): Start by reporting: "I sent the email. It was terrifying. But I got a good response." Explore what surprised you Get the next action
Session 3: Start: "I did that thing we talked about last time." Build on what you learned
The Magic
After 3-4 sessions with this structure, you're not just thinking out loud. You're on a journey. You can see progress. You can see patterns. That's when coaching gets powerful.
Between Sessions
Do the action you committed to (or at least try) Notice what happened Write down any insights Come back and report
You're not failing if you didn't do the action. Report what happened instead. "I didn't send the email. I got scared." That's useful information. The coach works with what's real.
A Note on Continuity
You don't need the same coach for every session. But if you can, it helps them remember your arc. If you switch coaches, just recap: "Here's what I've been working on."
The continuity comes from *your* commitment, not from the coach's memory.