Playbook

One-on-One Coaching — Short Template & Prompts

A reproducible, interactive one-on-one template with guided coaching prompts, a simple development tracker, and saveable meeting logs to make one-on-ones predictable, development-focused, and results-oriented.

Interactive Tool

One-on-One Coaching — Short Template & Prompts

Simple reproducible structure (30–40 minutes)

This interactive one-on-one log follows a compact, repeatable structure: Check-in, Wins & Progress, Current Challenges, Career/Development, Commitments & Next Steps. Use it to keep meetings predictable, help the person grow, and track commitments over time so conversations lead to observable progress.

Coaching prompts (pick a few):

  • "What’s one win since we last talked?"
  • "What’s blocking you right now?"
  • "If you could get one thing done this week, what would you choose?"
  • "What skill do you want to build and what small experiment could you try?"
  • "How can I or the team support you this week?"

Coach tips: Ask open questions, listen more than you speak, resist solving immediately, turn insights into a small experiment, and agree clear commitments with owners and dates.

YYYY-MM-DD or friendly date (e.g., 'Weekly - Wed')
Typical: 30
1 = Needs attention, 5 = Energized
What went well since the last meeting? What progress did you notice?
Which blockers or decisions are in the way? What assumptions are uncertain?
What skill, stretch assignment, or learning step is the focus? What small experiment can we try?
Describe the action, owner (if not the participant), and a due date or timeframe. (e.g., 'Draft proposal — Jordan — by 2026-08-25')
What will you do before the next meeting? Which obstacles will you remove?
1 = worse, 3 = same, 5 = much better
Record notable questions, observations, or coaching techniques you tried.
e.g., 'Weekly', '2026-08-18', or 'Every other Tuesday'
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