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/

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#WinCFO #OperationalAccounting #CFO #FinancialForecasting #KPIs #BusinessCoaching #QuickBooks #CashFlow #BusinessValuation #AITools #Microsoft365 #SMBLeadership #AnnualPlanning

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.
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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