diff --git a/src/crewai/conditional_task.py b/src/crewai/conditional_task.py
index 023355076..67f9f0c7b 100644
--- a/src/crewai/conditional_task.py
+++ b/src/crewai/conditional_task.py
@@ -1,4 +1,4 @@
-from typing import Callable, Optional
+from typing import Callable, Optional, Any
 
 from pydantic import BaseModel
 
@@ -18,7 +18,7 @@ class ConditionalTask(Task):
         super().__init__(*args, **kwargs)
         self.condition = condition
 
-    def should_execute(self, context: TaskOutput) -> bool:
+    def should_execute(self, context: Any) -> bool:
         print("TaskOutput", TaskOutput)
         if self.condition:
             return self.condition(context)
diff --git a/src/crewai/crew.py b/src/crewai/crew.py
index 06a3c1458..91c44b6bb 100644
--- a/src/crewai/crew.py
+++ b/src/crewai/crew.py
@@ -224,6 +224,17 @@ class Crew(BaseModel):
                     agent.set_rpm_controller(self._rpm_controller)
         return self
 
+    @model_validator(mode="after")
+    def validate_first_task(self) -> "Crew":
+        """Ensure the first task is not a ConditionalTask."""
+        if self.tasks and isinstance(self.tasks[0], ConditionalTask):
+            raise PydanticCustomError(
+                "invalid_first_task",
+                "The first task cannot be a ConditionalTask.",
+                {},
+            )
+        return self
+
     def _setup_from_config(self):
         assert self.config is not None, "Config should not be None."
 
@@ -400,7 +411,7 @@ class Crew(BaseModel):
         for i, task in enumerate(self.tasks):
             if isinstance(task, ConditionalTask):
                 # print("task_outputs", task_outputs)
-                previous_output = task_outputs[-1] if task_outputs else None
+                previous_output = task_outputs[-1].result() if task_outputs else None
                 # print("previous_output type", type(previous_output))
                 if previous_output is not None:
                     if not task.should_execute(previous_output):
@@ -451,7 +462,6 @@ class Crew(BaseModel):
                 task_output = task.execute_sync(
                     agent=task.agent, context=context, tools=task.tools
                 )
-                print("task executed res:", task_output)
                 task_outputs.append(task_output)
                 self._process_task_result(task, task_output)
         if futures: