Reporting on strategy isn't just about raw data; it's about telling a story. While standard executive summaries provide a high-level overview, stakeholders often need a balanced view of what is going right and where roadblocks exist.

In this lesson, we will explore the Wins and Challenges configuration within Cascade’s AI Executive Reporting. This tool automatically synthesizes your qualitative and quantitative data to create a "feedback sandwich"—celebrating success while transparently highlighting obstacles.

What is the 'Wins and Challenges' Widget?

The Wins and Challenges widget is a specific configuration of Cascade's AI reporting engine. Instead of a general paragraph summary, it specifically isolates:

• The Top 3 Wins: Positive progress, completed milestones, and high-performing metrics.
• The Top 3 Challenges: Blockers, overdue items, and risks.

Context-Aware Scoping

The most powerful aspect of this widget is its adaptability. The AI analyzes the specific scope of the report you are building.

• Strategy Level: It draws broad conclusions about organizational health.
• Project Level: It identifies specific task-based blockers or milestone achievements.
• Team Level: It highlights team-specific velocity and resource issues.

Note: The AI reads every piece of data—both the hard numbers (quant) and the written updates (qual)—to generate these insights.

How to Configure and Customize

1. Generating the Report

When you add the AI Executive Reporting widget to your dashboard or report, select the Wins and Challenges default configuration. The AI will immediately spin up, analyze the data within your current scope, and generate the text.

2. The Editorial Process

By default, Cascade injects personality into these updates, often using emojis to make the report visually engaging (e.g., specific icons for wins vs. challenges).

However, you retain full editorial control. If the tone doesn't match your corporate style, or if you want to rephrase a specific insight:

1. Click Edit Report.
2. Delete emojis, rewrite sentences, or remove specific bullet points.
3. Save your changes.

The AI provides the first draft, but you make the final call.

Pro Tip: Stacking AI Configurations

You don't have to choose between a standard summary and a Wins/Challenges list. Cascade’s flexible grid allows you to mix and match reporting styles for a comprehensive narrative.

Try this layout for your next Board Report:

1. Top Widget: Use the Executive Summary configuration for a high-level introduction.
2. Bottom Widget: Add a second AI widget configured for Wins and Challenges.
3. Resize & Arrange: Drag the widgets to resize them. You might make the Summary wide across the top, with Wins/Challenges sitting below specific KPI charts.

This approach gives your stakeholders the "Bottom Line Up Front" (BLUF) via the summary, followed immediately by the specific drivers of that performance.

Summary

• Balance: Use the Wins and Challenges widget to ensure your reporting celebrates success before tackling problems.
• Scope: Remember that the AI adapts to the report's filter—ensure you are looking at the right project, portfolio, or plan.
• Control: Always review and edit the AI text to ensure it aligns with your voice.
• Combine: Stack multiple AI widgets to create a rich, multi-layered report instantly.