Coach.Win

John Lund and Rob Simons
  • 5.0 (4)
  • Entrepreneurship
  • Updated Weekly

Coach John and Coach Rob have over 1500 Facilitated Session with SMB Leadership Teams. We are Strategic and AI Forward.  

  1. Oct 11

    Winning with Numbers

    Most leadership teams have one numbers person and everybody else nodding along. Coach Rob Simons built WinCFO to fix that.   In this episode, Coach Rob and Coach John Lund walk through the tool they created to turn financial data into something a whole leadership team can read, understand, and act on. John calls it operational accounting: not tax, not audit, just the numbers you need to move levers and make decisions.   What they cover:   - Connecting your data: import a standard P&L and balance sheet, or direct-connect to QuickBooks Online and load a couple years in minutes  - Simplifying the chart of accounts down to about 10 to 15 lines so the team sees what matters (and why Greg Crabtree says some businesses only need four)  - Building a KPI dashboard with trends, sparklines, and comparisons, and putting an owner on each of your 8 to 10 metrics  - Setting realistic targets against your last 12 months, including a "just get 5% better" option  - Why the rolling twelve month view beats the annual snapshot for actually running the business  - The forecast tool that runs an AI-guided Q&A and builds a proposed budget you can edit and export  - Forecast versus actual with variance as real data comes in  - The "What If" tool: model a new hire, a revenue miss, or a scenario and see the full picture in minutes  - Power Plays: the seven levers that show what a 1 to 3% change does to profit and cash  - Reporting, a valuation framework, and where you sit on the multiple, so you can build a business that's sustainable and transferable whether or not you ever sell   Perfect timing heading into annual planning season. Load your data now and bring it into your session.   𝗦𝗲𝗲 𝗶𝘁 𝗳𝗼𝗿 𝘆𝗼𝘂𝗿𝘀𝗲𝗹𝗳 𝗮𝗻𝗱 𝗯𝗼𝗼𝗸 𝗮 𝗱𝗲𝗺𝗼 (𝟯𝟬 𝘁𝗼 𝟱𝟬 𝗺𝗶𝗻𝘂𝘁𝗲𝘀) 𝗮𝘁 𝗵𝘁𝘁𝗽𝘀://𝘄𝗶𝗻𝗰𝗳𝗼.𝗰𝗼𝗮𝗰𝗵.𝘄𝗶𝗻/   Subscribe to:   ⁨@coachdotwin  Visit our website: 🌐 https://coach.win/ Follow us on Linked: 👉 https://www.linkedin.com/company/coach-win/   #WinCFO #OperationalAccounting #CFO #FinancialForecasting #KPIs #BusinessCoaching #QuickBooks #CashFlow #BusinessValuation #AITools #Microsoft365 #SMBLeadership #AnnualPlanning

  2. Jul 22

    Embedded Strategy Coach = What Winning Looks Like

    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

  3. Jun 25

    The AI Native Coach Advantage: Accelerating Strategy and Results

    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

  4. Apr 20

    Great meetings don't happen by accident.

    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?

  5. Mar 21

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

    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

  6. Feb 24

    4 Stages of AI Adoption in SMB

    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.

  7. Jan 31

    Mastering Strategy Execution: How AI, OKRs, and an "Embedded Coach" Can Define Your Wins

    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.

  8. 11/20/2025

    The Ownership Mindset

    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 mindsetHow to use the Ownership Mindset Assessment with your teamWhy “owner like” employees are most likely to get recruited by private equityHow expectancy theory reveals if a goal will stick or stallTips for structuring incentives that actually motivate

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Ratings & Reviews

5
out of 5
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About

Coach John and Coach Rob have over 1500 Facilitated Session with SMB Leadership Teams. We are Strategic and AI Forward.  

Information

  • Creator
    John Lund and Rob Simons
  • Years Active
    2024 - 2026
  • Episodes
    21
  • Rating
    Clean
  • Copyright
    © 2026 Coach.Win
  • Show Website
    Coach.Win