Most operating-system coaches show up for the two-day annual and the quarterlies, then go quiet in between. Rob and John do it differently. They call it embedded coaching.

In this episode, Coach Rob Simons and Coach John Lund break down what it actually means to be embedded inside a client's Microsoft 365 environment: in the weekly leadership team meeting, in the Teams channels, on the same email, working right inside the client's tenant.
What they cover:
- Why a Teams ping gets answered faster than a quarterly email
- Staying connected even when you miss a meeting (recaps, notes, dashboards, shared docs)
- How being AI-native lets them get a client unstuck in five minutes instead of a back-and-forth email chain
- Accelerating AI activation by getting teams over the hump on Copilot and Claude
- Why staying inside the Microsoft environment answers the data security question most owners ask
- Treating the coach like part of the leadership team, the way you'd think about a fractional CFO
If you've ever wondered what it looks like to have a coach who's actually in the room, this one's for you.
Subscribe to: @coachdotwin
Visit our website: 🌐 https://coach.win/Follow us on Linked: 👉 https://www.linkedin.com/company/coach-win/#EmbeddedCoaching #BusinessCoaching #Microsoft365 #Teams #Copilot #AINative #LeadershipTeam #SMBLeadership #DigitalAdoption #ExecutiveCoaching

Transforming the Pace of Coaching: By utilizing AI tools like Claude, Copilot, and Whisper Flow during live meetings, coaches can help clients visualize and adjust results in real-time. Foundational business tools like accountability charts and scorecards, which used to take three to six months to develop, can now be created and refined in a single session.

Next-Level Pre-Meeting Prep: The "AI native" approach fundamentally upgrades how coaches handle pre-meeting surveys. AI synthesizes the organization's current strategy and state to generate highly meaningful prep documents and even custom podcasts, ensuring leaders walk into the room better prepared than ever before.

An "Assistant in the Room": Utilizing project spaces with institutional memory (like Claude Co-work) functions as a live assistant during client meetings. Coaches can instantly query historical data—such as generating a chart of all past Employee Net Promoter Scores (ENPS)—without manually digging through files or folders.

Comprehensive Post-Meeting Follow-up: Leveraging AI tools for post-meeting recaps generates incredibly detailed content, ensuring that no crucial action items or insights are missed.

More Strategy, Less Admin: The ultimate benefit of AI native coaching is the shift in focus. By automating administrative tasks, both the coach and the leadership team can dedicate significantly more time to deep strategic thinking, robust conversations, and effective facilitation

Great meetings don't happen by accident.



In this episode, Coach John Lund sits down with Christina Johnson, Digital Adoption Manager at Coach.Win, to introduce the new Meeting Excellence program. It's a 12-week engagement designed to help up to 10 leaders in your company run consistently great meetings across the board, not just the weekly leadership meeting.



Most companies have gotten pretty good at their weekly meeting. But client kickoffs, one-on-ones, department meetings, and project check-ins are often inconsistent. Meeting Excellence fixes that by standardizing how your leaders prep, run, and follow up on every recurring meeting.



What you'll learn in this episode:



• Why meeting excellence matters for communication, alignment, and accountability
• What the 12-week Meeting Excellence program looks like and who it's for
• How to standardize recurring meetings across your company
• Microsoft Teams setup best practices most leaders miss
• How to use AI tools like Copilot, Claude, and ChatGPT before, during, and after meetings
• How better meetings make your team look sharper to clients, vendors, and each other



Ready to bring Meeting Excellence to your team?