diff --git a/src/khoj/processor/conversation/prompts.py b/src/khoj/processor/conversation/prompts.py
index 346db020..dcfc1bf4 100644
--- a/src/khoj/processor/conversation/prompts.py
+++ b/src/khoj/processor/conversation/prompts.py
@@ -4,7 +4,7 @@ from langchain.prompts import PromptTemplate
 
 ## Personality
 ## --
-personality = PromptTemplate.from_template("You are Khoj, a friendly, smart and helpful personal assistant.")
+personality = PromptTemplate.from_template("You are Khoj, a smart, inquisitive and helpful personal assistant.")
 
 
 ## General Conversation
@@ -77,7 +77,9 @@ conversation_llamav2 = PromptTemplate.from_template(
 ## --
 notes_conversation = PromptTemplate.from_template(
     """
-Using the notes and our past conversations as context, answer the following question.
+Using my personal notes and our past conversations as context, answer the following question.
+Ask crisp follow-up questions to get additional context, when the answer cannot be inferred from the provided notes or past conversations.
+These questions should end with a question mark.
 Current Date: {current_date}
 
 Notes:
diff --git a/tests/test_openai_chat_director.py b/tests/test_openai_chat_director.py
index a28c3d04..4f05fc52 100644
--- a/tests/test_openai_chat_director.py
+++ b/tests/test_openai_chat_director.py
@@ -280,7 +280,6 @@ def test_answer_general_question_not_in_chat_history_or_retrieved_content(chat_c
 
 
 # ----------------------------------------------------------------------------------------------------
-@pytest.mark.xfail(reason="Chat director not consistently capable of asking for clarification yet.")
 @pytest.mark.chatquality
 def test_ask_for_clarification_if_not_enough_context_in_question(chat_client):
     # Act
@@ -289,10 +288,10 @@ def test_ask_for_clarification_if_not_enough_context_in_question(chat_client):
 
     # Assert
     expected_responses = [
-        "which of them is the older",
-        "which one is older",
-        "which of them is older",
-        "which one is the older",
+        "which of them",
+        "which one is",
+        "which of namita's sons",
+        "the birth order",
     ]
     assert response.status_code == 200
     assert any([expected_response in response_message.lower() for expected_response in expected_responses]), (