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?

𝗪𝗵𝗮𝘁 𝗱𝗼𝗲𝘀 𝗴𝗿𝗲𝗮𝘁 𝗰𝗼𝗺𝗽𝗮𝗻𝘆 𝗰𝘂𝗹𝘁𝘂𝗿𝗲 𝗮𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗹𝗼𝗼𝗸 𝗹𝗶𝗸𝗲?

Coach Rob Simons and Coach John Lund didn't plan to find the answer at a bar after a client meeting; but that's exactly what happened.

Their bartender wasn't just doing her job. She knew her company's mission cold, believed in it, and could tell you exactly why her GM was the real deal. Including the moment he fired a service manager who wasn't pulling his weight.

No hesitation. No letting it drag on. Just clear standards and the courage to act on them.

That's what A-player culture feels like from the inside. And it's what Rob and John help leadership teams build every day.

𝗜𝗻 𝘁𝗵𝗶𝘀 𝗲𝗽𝗶𝘀𝗼𝗱𝗲:

- Why engaged employees are your best culture signal

- What happens when leaders actually remove C-players

- How to build a team where people talk about their company like 𝙩𝙝𝙖𝙩

If this resonated, subscribe and leave a comment. More stories coming.

Connect with Rob Simons:

rob@simons.coach
https://www.linkedin.com/in/rwsimons/

Connect with John Lund:

john@entresmart.com
https://www.linkedin.com/in/johnlund1/

Subscribe to: @coachdotwin

Visit our website: 🌐 https://coach.win/

Follow us on Linked: 👉 https://www.linkedin.com/company/coach-win/

#CompanyCulture #EmployeeEngagement #Leadership #APlayerCulture

Coach.Win Podcast - F'ing Engaged Employees (NSFW).mp4

AI isn’t optional anymore. The question is: What stage is your organization in?

In this episode of the Coach.Win Podcast, Rob Simons and John Lund break down the 4 stages of AI adoption they’re seeing across organizations heading into 2026.

Coming out of annual planning sessions and SWOT assessments, one theme is clear: nearly every leadership team has AI on their objectives. But most companies don’t know how to move from experimentation to real impact.

John outlines the four stages:

1️⃣ Explorer – Getting comfortable with tools like ChatGPT, Copilot, and Claude. Small wins. Faster daily tasks.
2️⃣ Thinker – Using AI as a thought partner to elevate strategic thinking and problem-solving.
3️⃣ Builder – Creating structured prompts, GPTs, bots, and internal tools that scale capability.
4️⃣ Leader – Scaling AI across the organization to increase productivity, alignment, and strategic leverage.

If you’re asking:
• How do we start using AI without overwhelming the team?
• How do we make our people smarter and more strategic?
• How do we grow without hiring 3–6 more employees?
• How do we scale AI across the organization?

This episode gives you a roadmap.

1. Learn How to Define "What Winning Looks Like" (WWLL) Before hiring a coach, you must understand how to align your team behind a unified vision. This video explains the concept of "WWLL"—ensuring every employee knows exactly what a good day, week, or year looks like. The speakers discuss why the traditional 5-year plan is becoming obsolete due to the pace of technology, and why focusing on a crystal-clear 3-year plan provides the agility modern businesses need.

2. Discover the Role of AI as a Strategic "Thought Partner" A modern strategic coach shouldn't just facilitate; they should leverage technology to sharpen your focus. The hosts demonstrate how to use AI during planning sessions—not to replace human leadership, but to generate tough questions and refine "squishy" goals into concrete, measurable objectives. This ensures you aren't just copy-pasting AI results, but using them to challenge your leadership team's thinking.

3. Understand the Value of an "Embedded Coach" This video introduces a shift from the traditional "drop-in" consultant to an "embedded coach" who integrates directly into your daily workflow (such as Microsoft Teams). By having a coach who sees your dashboards and chats daily, you get real-time course correction rather than waiting for quarterly reviews to discover you are off track.

4. Move From Vague Objectives to Actionable OKRs Many businesses set generic goals like "implement a new CRM" without defining the specific business impact. This discussion highlights the importance of Objectives and Key Results (OKRs), teaching you how to demand measurable metrics—such as "better accuracy on prospect lists"—so you know exactly when to celebrate a win.

5. Prevent Burnout by Validating Plans with Your Team Hiring a coach isn't just about setting ambitious goals; it’s about ensuring they are achievable. The speakers outline a critical validation process: drafting the plan, stepping away, and allowing the team to review it for capacity. This prevents setting your staff up for failure by ensuring no one is inadvertently assigned impossible workloads across multiple objectives.

Why do some people naturally step up like owners while others avoid responsibility?

In this episode, Coach John Lund sits down with Byron McFarland, a leading expert in exit strategy, succession planning, and M&A readiness. Byron shares what he has learned from years of assessing leadership teams and explains the real behaviors that define an ownership mindset.

They also dive into expectancy theory, a practical way to predict whether a leader or team will truly pursue a goal before you commit to it in planning.

💡 In this episode:

• The five behaviors that signal a true owner mindset
• How to use the Ownership Mindset Assessment with your team
• Why “owner like” employees are most likely to get recruited by private equity
• How expectancy theory reveals if a goal will stick or stall
• Tips for structuring incentives that actually motivate

How do you keep your entire team aligned from leadership to the frontlines?

In this episode, John Lund sits down with Emre Ok, Product and Content Marketing Manager at Teamflect and host of The Team Check-In, one of the fastest-growing HR podcasts today. Emre is an active voice in the HR Tech space, known for championing the human side of technology and for his conversations with leading experts in human resources, leadership, and innovation.

Together they explore how Teamflect, an all-in-one performance management tool built for Microsoft Teams, helps organizations turn strategy into daily action through goal alignment, meaningful recognition, and connected conversations that drive growth.

💡 In this episode:

• Why visibility and alignment are everything in goal setting
• How cascading OKRs connect company vision to individual impact
• The importance of peer-to-peer recognition and building team culture
• Using AI as the “observer” to surface insights and support real human connection
• What’s ahead for Teamflect with its next evolution, Teamflect Agent

Learn more about Teamflect:https://www.teamflect.com

Subscribe to: ‪‪‪@coachdotwin

Visit our website: 🌐 https://coach.win/

Follow us on Linked: 👉https://www.linkedin.com/company/coach-win/

#CoachWinPodcast #MicrosoftTeams #Teamflect #Leadership #GoalSetting #EmployeeEngagement #AIInHR

John Lund Rob Simons