diff --git a/README.md b/README.md
index cd2b54a..4e96576 100644
--- a/README.md
+++ b/README.md
@@ -418,7 +418,7 @@ challenge isn't adding this function to the base class a bad idea?
 Normally, your favorite coding agent will enthusiastically reply with **“You’re absolutely right!”**—then proceed 
 to completely reverse the _correct_ strategy, without ever explaining why you're wrong.
 
-**[📖 Read More](docs/tools/challenge.md)** - Critical thinking tool for validating ideas
+**[📖 Read More](docs/tools/challenge.md)** - Challenge an approach or validate ideas with confidence
 
 ### 4. `planner` - Interactive Step-by-Step Planning
 Break down complex projects or ideas into manageable, structured plans through step-by-step thinking.
diff --git a/docs/tools/challenge.md b/docs/tools/challenge.md
index 8141b11..796974a 100644
--- a/docs/tools/challenge.md
+++ b/docs/tools/challenge.md
@@ -1,4 +1,4 @@
-# challenge - Critical Challenge Tool
+# challenge - Challenge an approach or validate ideas with confidence
 
 The `challenge` tool encourages thoughtful critical thinking instead of automatic agreement with the dreaded **You're absolutely right!** responses - especially 
 when you're not. This tool wraps your comment with instructions that prompt critical thinking and honest analysis instead of blind agreement.
@@ -6,10 +6,20 @@ when you're not. This tool wraps your comment with instructions that prompt crit
 ## Quick Example
 
 ```
-challenge but the new function you added duplicates the hashing method, no?
+challenge but do we even need all this extra caching because it'll just slow the app down?
 ```
 
-The tool wraps your statement with instructions that explicitly tell Claude to think critically and disagree if warranted, rather than automatically agreeing.
+```
+challenge I don't think this approach solves my original complaint
+```
+
+Here’s a more fluid and natural version:
+
+Normally, your favorite coding agent will enthusiastically reply with **“You’re absolutely right!”**—then proceed to 
+reverse the _correct_ strategy entirely, without stopping to consider that you might actually be wrong, missing the 
+bigger picture or ignoring architectural constraints.
+
+`challenge` fixes this.
 
 ## Why Use Challenge?