diff --git a/src/crewai/cli/cli.py b/src/crewai/cli/cli.py
index 9d748715a..bc6d5c21d 100644
--- a/src/crewai/cli/cli.py
+++ b/src/crewai/cli/cli.py
@@ -60,10 +60,17 @@ def version(tools):
     default=5,
     help="Number of iterations to train the crew",
 )
-def train(n_iterations: int):
+@click.option(
+    "-f",
+    "--filename",
+    type=str,
+    default="trained_agents_data.pkl",
+    help="Path to a custom file for training",
+)
+def train(n_iterations: int, filename: str):
     """Train the crew."""
-    click.echo(f"Training the crew for {n_iterations} iterations")
-    train_crew(n_iterations)
+    click.echo(f"Training the Crew for {n_iterations} iterations")
+    train_crew(n_iterations, filename)
 
 
 @crewai.command()
diff --git a/src/crewai/cli/templates/crew/main.py b/src/crewai/cli/templates/crew/main.py
index 94ac35b93..86beeeaca 100644
--- a/src/crewai/cli/templates/crew/main.py
+++ b/src/crewai/cli/templates/crew/main.py
@@ -25,7 +25,7 @@ def train():
         "topic": "AI LLMs"
     }
     try:
-        {{crew_name}}Crew().crew().train(n_iterations=int(sys.argv[1]), inputs=inputs)
+        {{crew_name}}Crew().crew().train(n_iterations=int(sys.argv[1]), filename=sys.argv[2], inputs=inputs)
 
     except Exception as e:
         raise Exception(f"An error occurred while training the crew: {e}")
diff --git a/src/crewai/cli/train_crew.py b/src/crewai/cli/train_crew.py
index cd880db5d..12c5191b1 100644
--- a/src/crewai/cli/train_crew.py
+++ b/src/crewai/cli/train_crew.py
@@ -3,19 +3,22 @@ import subprocess
 import click
 
 
-def train_crew(n_iterations: int) -> None:
+def train_crew(n_iterations: int, filename: str) -> None:
     """
     Train the crew by running a command in the Poetry environment.
 
     Args:
         n_iterations (int): The number of iterations to train the crew.
     """
-    command = ["poetry", "run", "train", str(n_iterations)]
+    command = ["poetry", "run", "train", str(n_iterations), filename]
 
     try:
         if n_iterations <= 0:
             raise ValueError("The number of iterations must be a positive integer.")
 
+        if not filename.endswith(".pkl"):
+            raise ValueError("The filename must not end with .pkl")
+
         result = subprocess.run(command, capture_output=False, text=True, check=True)
 
         if result.stderr:
diff --git a/src/crewai/crew.py b/src/crewai/crew.py
index d7998ecff..f3f032294 100644
--- a/src/crewai/crew.py
+++ b/src/crewai/crew.py
@@ -34,7 +34,9 @@ from crewai.telemetry import Telemetry
 from crewai.tools.agent_tools import AgentTools
 from crewai.types.usage_metrics import UsageMetrics
 from crewai.utilities import I18N, FileHandler, Logger, RPMController
-from crewai.utilities.constants import TRAINED_AGENTS_DATA_FILE, TRAINING_DATA_FILE
+from crewai.utilities.constants import (
+    TRAINING_DATA_FILE,
+)
 from crewai.utilities.evaluators.crew_evaluator_handler import CrewEvaluator
 from crewai.utilities.evaluators.task_evaluator import TaskEvaluator
 from crewai.utilities.formatter import (
@@ -388,7 +390,7 @@ class Crew(BaseModel):
         del task_config["agent"]
         return Task(**task_config, agent=task_agent)
 
-    def _setup_for_training(self) -> None:
+    def _setup_for_training(self, filename: str) -> None:
         """Sets up the crew for training."""
         self._train = True
 
@@ -399,11 +401,13 @@ class Crew(BaseModel):
             agent.allow_delegation = False
 
         CrewTrainingHandler(TRAINING_DATA_FILE).initialize_file()
-        CrewTrainingHandler(TRAINED_AGENTS_DATA_FILE).initialize_file()
+        CrewTrainingHandler(filename).initialize_file()
 
-    def train(self, n_iterations: int, inputs: Optional[Dict[str, Any]] = {}) -> None:
+    def train(
+        self, n_iterations: int, filename: str, inputs: Optional[Dict[str, Any]] = {}
+    ) -> None:
         """Trains the crew for a given number of iterations."""
-        self._setup_for_training()
+        self._setup_for_training(filename)
 
         for n_iteration in range(n_iterations):
             self._train_iteration = n_iteration
@@ -416,7 +420,7 @@ class Crew(BaseModel):
                 training_data=training_data, agent_id=str(agent.id)
             )
 
-            CrewTrainingHandler(TRAINED_AGENTS_DATA_FILE).save_trained_data(
+            CrewTrainingHandler(filename).save_trained_data(
                 agent_id=str(agent.role), trained_data=result.model_dump()
             )
 
diff --git a/src/crewai/utilities/file_handler.py b/src/crewai/utilities/file_handler.py
index 68c33241d..1125cae4e 100644
--- a/src/crewai/utilities/file_handler.py
+++ b/src/crewai/utilities/file_handler.py
@@ -1,7 +1,5 @@
 import os
 import pickle
-
-
 from datetime import datetime
 
 
@@ -32,14 +30,16 @@ class PickleHandler:
         Parameters:
         - file_name (str): The name of the file for saving and loading data.
         """
+        if not file_name.endswith(".pkl"):
+            file_name += ".pkl"
+
         self.file_path = os.path.join(os.getcwd(), file_name)
 
     def initialize_file(self) -> None:
         """
-        Initialize the file with an empty dictionary if it does not exist or is empty.
+        Initialize the file with an empty dictionary and overwrite any existing data.
         """
-        if not os.path.exists(self.file_path) or os.path.getsize(self.file_path) == 0:
-            self.save({})  # Save an empty dictionary to initialize the file
+        self.save({})
 
     def save(self, data) -> None:
         """
diff --git a/tests/cli/cli_test.py b/tests/cli/cli_test.py
index 509b9193a..4f606e213 100644
--- a/tests/cli/cli_test.py
+++ b/tests/cli/cli_test.py
@@ -15,18 +15,18 @@ def runner():
 def test_train_default_iterations(train_crew, runner):
     result = runner.invoke(train)
 
-    train_crew.assert_called_once_with(5)
+    train_crew.assert_called_once_with(5, "trained_agents_data.pkl")
     assert result.exit_code == 0
-    assert "Training the crew for 5 iterations" in result.output
+    assert "Training the Crew for 5 iterations" in result.output
 
 
 @mock.patch("crewai.cli.cli.train_crew")
 def test_train_custom_iterations(train_crew, runner):
     result = runner.invoke(train, ["--n_iterations", "10"])
 
-    train_crew.assert_called_once_with(10)
+    train_crew.assert_called_once_with(10, "trained_agents_data.pkl")
     assert result.exit_code == 0
-    assert "Training the crew for 10 iterations" in result.output
+    assert "Training the Crew for 10 iterations" in result.output
 
 
 @mock.patch("crewai.cli.cli.train_crew")
diff --git a/tests/cli/train_crew_test.py b/tests/cli/train_crew_test.py
index 9d0d3d4a7..036dd7c2f 100644
--- a/tests/cli/train_crew_test.py
+++ b/tests/cli/train_crew_test.py
@@ -6,7 +6,6 @@ from crewai.cli.train_crew import train_crew
 
 @mock.patch("crewai.cli.train_crew.subprocess.run")
 def test_train_crew_positive_iterations(mock_subprocess_run):
-    # Arrange
     n_iterations = 5
     mock_subprocess_run.return_value = subprocess.CompletedProcess(
         args=["poetry", "run", "train", str(n_iterations)],
@@ -15,12 +14,10 @@ def test_train_crew_positive_iterations(mock_subprocess_run):
         stderr="",
     )
 
-    # Act
-    train_crew(n_iterations)
+    train_crew(n_iterations, "trained_agents_data.pkl")
 
-    # Assert
     mock_subprocess_run.assert_called_once_with(
-        ["poetry", "run", "train", str(n_iterations)],
+        ["poetry", "run", "train", str(n_iterations), "trained_agents_data.pkl"],
         capture_output=False,
         text=True,
         check=True,
@@ -29,7 +26,7 @@ def test_train_crew_positive_iterations(mock_subprocess_run):
 
 @mock.patch("crewai.cli.train_crew.click")
 def test_train_crew_zero_iterations(click):
-    train_crew(0)
+    train_crew(0, "trained_agents_data.pkl")
     click.echo.assert_called_once_with(
         "An unexpected error occurred: The number of iterations must be a positive integer.",
         err=True,
@@ -38,7 +35,7 @@ def test_train_crew_zero_iterations(click):
 
 @mock.patch("crewai.cli.train_crew.click")
 def test_train_crew_negative_iterations(click):
-    train_crew(-2)
+    train_crew(-2, "trained_agents_data.pkl")
     click.echo.assert_called_once_with(
         "An unexpected error occurred: The number of iterations must be a positive integer.",
         err=True,
@@ -55,10 +52,13 @@ def test_train_crew_called_process_error(mock_subprocess_run, click):
         output="Error",
         stderr="Some error occurred",
     )
-    train_crew(n_iterations)
+    train_crew(n_iterations, "trained_agents_data.pkl")
 
     mock_subprocess_run.assert_called_once_with(
-        ["poetry", "run", "train", "5"], capture_output=False, text=True, check=True
+        ["poetry", "run", "train", str(n_iterations), "trained_agents_data.pkl"],
+        capture_output=False,
+        text=True,
+        check=True,
     )
     click.echo.assert_has_calls(
         [
@@ -74,13 +74,15 @@ def test_train_crew_called_process_error(mock_subprocess_run, click):
 @mock.patch("crewai.cli.train_crew.click")
 @mock.patch("crewai.cli.train_crew.subprocess.run")
 def test_train_crew_unexpected_exception(mock_subprocess_run, click):
-    # Arrange
     n_iterations = 5
     mock_subprocess_run.side_effect = Exception("Unexpected error")
-    train_crew(n_iterations)
+    train_crew(n_iterations, "trained_agents_data.pkl")
 
     mock_subprocess_run.assert_called_once_with(
-        ["poetry", "run", "train", "5"], capture_output=False, text=True, check=True
+        ["poetry", "run", "train", str(n_iterations), "trained_agents_data.pkl"],
+        capture_output=False,
+        text=True,
+        check=True,
     )
     click.echo.assert_called_once_with(
         "An unexpected error occurred: Unexpected error", err=True
diff --git a/tests/crew_test.py b/tests/crew_test.py
index 0c49d51f2..be7ec1da3 100644
--- a/tests/crew_test.py
+++ b/tests/crew_test.py
@@ -8,6 +8,7 @@ from unittest.mock import MagicMock, patch
 
 import pydantic_core
 import pytest
+
 from crewai.agent import Agent
 from crewai.agents.cache import CacheHandler
 from crewai.crew import Crew
@@ -1806,7 +1807,9 @@ def test_crew_train_success(task_evaluator, crew_training_handler, kickoff):
         agents=[researcher, writer],
         tasks=[task],
     )
-    crew.train(n_iterations=2, inputs={"topic": "AI"})
+    crew.train(
+        n_iterations=2, inputs={"topic": "AI"}, filename="trained_agents_data.pkl"
+    )
     task_evaluator.assert_has_calls(
         [
             mock.call(researcher),
@@ -1890,7 +1893,7 @@ def test__setup_for_training():
     for agent in agents:
         assert agent.allow_delegation is True
 
-    crew._setup_for_training()
+    crew._setup_for_training("trained_agents_data.pkl")
 
     assert crew._train is True
     assert task.human_input is True