AI-Enhanced One-on-Ones

Monday, November 3, 2025 - 06:54 am

Turn One-on-Ones from Routine Check-Ins into Impactful Conversations

Live, 75-minute workshop — January 7th, 2026 at 6:00–7:15 PM ET

Make your one-on-ones the most valuable 75 minutes on the calendar. In this hands-on session, you’ll learn a repeatable, AI-powered system for preparing, running, and following up on one-on-ones using ChatGPT and Microsoft Copilot—so you build trust, surface insights faster, and turn conversations into forward motion.

What you’ll walk away with

A proven, reusable workflow to prep, facilitate, and follow up with intention (templates included).
Personalized, insight-driven agendas that reflect goals, context, and working styles—created in minutes.
Clear, accountable follow-ups (summaries, action trackers, nudges) that keep momentum without micromanaging.
Strategic confidence to show up as a thoughtful, human-centered partner—consistently.

How it works

Live session: One class, 6:00–7:15 PM ET
Interactive format: Live demos, short exercises, and guided discussion
Real tools: We’ll practice with ChatGPT or Copilot to analyze notes, draft agendas, and generate personalized follow-ups
Immediate takeaways: Prompt templates, a customizable one-on-one tracker, and an AI workflow you can use the next day

Who this course is for

Executive Assistants / Executive Business Partners who prepare leaders to show up prepared and present.
Chiefs of Staff / Ops Leads who need crisp alignment, fast decisions, and visible progress.
People Managers & Team Leads who want less status reporting and more real conversation.

Transform your one-on-ones into strategic superpowers

AI-Enhanced Preparation
Turn scattered notes into a tailored agenda with context, priorities, and timing cues.

Stronger Relationships
Use prompts that surface what matters: wins, blocks, emotional temperature, and long-term goals.

Actionable Follow-Ups
Auto-draft summaries, decisions, and next steps—plus light-touch accountability trackers.

Strategic Confidence
Run a consistent cadence that feels human, organized, and genuinely useful.

What you get

Prompt pack: Prep, in-meeting, and follow-up prompts (ChatGPT + Copilot ready).
One-on-One Toolkit: Customizable tracker (topics, decisions, actions, next review), plus a light CRM tab for relationship notes.
Agenda blueprints: First 5 minutes, mid-course corrections, and “stuck conversation” rescue patterns.
Follow-up library: Summary scaffolds, decision logs, and gentle accountability nudges.

Sample prompts you’ll master

“Given these notes and goals for Q4, draft a 25-minute one-on-one agenda that prioritizes roadblocks and role clarity. Include 3 questions to check alignment and 2 to uncover risks.”
“Summarize today’s one-on-one into decisions, owners, and dates. Add a 2-sentence context note I can paste into the project channel.”
“Suggest 3 questions to deepen trust without veering into therapy, based on this teammate’s style and last week’s feedback.”

Accessibility & tooling

Bring any modern browser. Copilot or ChatGPT (free or paid) both work—prompts are tool-agnostic. All templates are delivered in editable formats.

FAQ

Do I need advanced AI skills?
No. We’ll show you exactly what to copy, paste, and tweak.

Will this work if my exec/teammate hates AI?
Yes. The workflow is human-first; AI accelerates prep and polish behind the scenes.

Can I use this across multiple reports/executives?
Absolutely—the tracker and prompts scale across people and cadences.

Make every one-on-one count

Stop status updates. Start progress. Leave with a simple system you can run tomorrow—one that earns trust, reveals insight, and keeps work moving.