Multi-Turn Conversations

In this cookbook, we’ll explore a more effective approach to evaluating multi-turn customer support agents. Traditional evaluation methods that use a single input-output pair are insufficient for agents that need to adapt their tool usage as conversations evolve. Instead, we’ll implement a simulation-based approach where an LLM evaluates our agent against specific success criteria.

The Problem with Traditional Evaluation

Traditional evaluation methods for customer support agents often use a dataset where:

Input: Customer ticket/query
Output: Expected sequence of tool calls

This approach has significant limitations:

It assumes a fixed, predetermined path to resolution
It doesn’t account for new information discovered during the conversation
It focuses on the exact sequence of tools rather than achieving the desired outcome

A Better Approach: Simulation-Based Evaluation

Instead of predicting exact tool sequences, we’ll define success criteria that focus on what the agent must accomplish, regardless of the specific path taken. For example:

success_criteria = [
    "Agent MUST call get_status(order_id)",
    "Agent MUST inform user cancellation is possible IFF package.status != 'shipped'"
]

This approach:

Focuses on outcomes rather than specific steps
Allows for multiple valid solution paths
Better reflects real-world customer support scenarios

Requirements

Before we start, make sure you have the necessary packages installed:

%pip install openai langwatch pydantic

Define Tools

Let’s implement this simulation-based evaluation approach using mock tools for an e-commerce customer support scenario.

import json
from typing import Dict, Any, List, Tuple
from openai import AsyncOpenAI
import getpass
import langwatch

api_key = getpass.getpass("Enter your OpenAI API key: ")

# Initialize OpenAI and LangWatch
client = AsyncOpenAI(api_key=api_key)
langwatch.login()

# Mock database of orders
ORDERS_DB = {
    "ORD123": {"status": "processing", "customer_id": "CUST456", "items": ["Product A", "Product B"]},
    "ORD456": {"status": "shipped", "customer_id": "CUST789", "items": ["Product C"]},
    "ORD789": {"status": "delivered", "customer_id": "CUST456", "items": ["Product D"]}
}

# Mock database of customers
CUSTOMERS_DB = {
    "CUST456": {"email": "[email protected]", "name": "John Doe"},
    "CUST789": {"email": "[email protected]", "name": "Jane Smith"}
}

# Tool definitions
async def find_customer_by_email(email: str) -> Dict[str, Any]:
    """Find a customer by their email address."""
    for customer_id, customer in CUSTOMERS_DB.items():
        if customer["email"] == email:
            return {"customer_id": customer_id, **customer}
    return {"error": "Customer not found"}

async def get_orders_by_customer_id(customer_id: str) -> Dict[str, Any]:
    """Get all orders for a specific customer."""
    orders = []
    for order_id, order in ORDERS_DB.items():
        if order["customer_id"] == customer_id:
            orders.append({"order_id": order_id, **order})
    return {"orders": orders}

async def get_order_status(order_id: str) -> Dict[str, Any]:
    """Get the status of a specific order."""
    if order_id in ORDERS_DB:
        return {"order_id": order_id, "status": ORDERS_DB[order_id]["status"]}
    return {"error": "Order not found"}

async def update_ticket_status(ticket_id: str, status: str) -> Dict[str, Any]:
    """Update the status of a support ticket."""
    return {"ticket_id": ticket_id, "status": status, "updated": True}

async def escalate_to_human() -> Dict[str, Any]:
    """Escalate the current issue to a human agent."""
    return {
        "status": "escalated",
        "message": "A human agent has been notified and will follow up shortly."
    }

# Dictionary mapping tool names to functions
TOOL_MAP = {
    "find_customer_by_email": find_customer_by_email,
    "get_orders_by_customer_id": get_orders_by_customer_id,
    "get_order_status": get_order_status,
    "update_ticket_status": update_ticket_status,
    "escalate_to_human": escalate_to_human
}

# Tool schemas for OpenAI API
TOOL_SCHEMAS = [
    {
        "type": "function",
        "function": {
            "name": "find_customer_by_email",
            "description": "Find a customer by their email address.",
            "parameters": {
                "type": "object",
                "properties": {
                    "email": {"type": "string", "description": "Customer email address"}
                },
                "required": ["email"]
            }
        }
    },
    {
        "type": "function",
        "function": {
            "name": "get_orders_by_customer_id",
            "description": "Get all orders for a specific customer.",
            "parameters": {
                "type": "object",
                "properties": {
                    "customer_id": {"type": "string", "description": "Customer ID"}
                },
                "required": ["customer_id"]
            }
        }
    },
    {
        "type": "function",
        "function": {
            "name": "get_order_status",
            "description": "Get the status of a specific order.",
            "parameters": {
                "type": "object",
                "properties": {
                    "order_id": {"type": "string", "description": "Order ID"}
                },
                "required": ["order_id"]
            }
        }
    },
    {
        "type": "function",
        "function": {
            "name": "update_ticket_status",
            "description": "Update the status of a support ticket.",
            "parameters": {
                "type": "object",
                "properties": {
                    "ticket_id": {"type": "string", "description": "Ticket ID"},
                    "status": {"type": "string", "description": "New status"}
                },
                "required": ["ticket_id", "status"]
            }
        }
    },
    {
        "type": "function",
        "function": {
            "name": "escalate_to_human",
            "description": "Escalate the current issue to a human agent.",
            "parameters": {
                "type": "object",
                "properties": {},
                "required": []
            }
        }
    }
]

Define Agents

Now we’ll define our agents. We’ll create both a Planner and an Executor agent. The Planner agent is responsible for creating a plan to achieve the user’s goal, while the Executor agent is responsible for executing the plan. We also define a helper function to generate a response from the tool outputs.

class PlannerAgent:
    def __init__(self, model: str = "gpt-5"):
        self.model = model
        self.client = AsyncOpenAI(api_key=api_key)

    async def run(self, task_history: List[Dict[str, Any]]) -> Tuple[List, str]:
        """Create a tool execution plan based on user input"""
        # Call OpenAI to create a plan
        response = await self.client.chat.completions.create(
            model=self.model,
            messages=task_history,
            tools=TOOL_SCHEMAS,
            tool_choice="auto"
        )

        message = response.choices[0].message
        tool_calls = message.tool_calls or []
        return tool_calls, message.content or ""

    def initialize_history(self, ticket: Dict[str, Any]) -> List[Dict[str, Any]]:
        """Start conversation history from a ticket."""
        system_prompt = """You are a helpful customer support agent for an e-commerce company.
        Your job is to help customers with their inquiries about orders, products, and returns.
        Use the available tools to gather information and take actions on behalf of the customer.
        Always be polite, professional, and helpful."""

        return [
            {"role": "system", "content": system_prompt},
            {"role": "user", "content": str(ticket)}
        ]

# Simple implementation of the Executor Agent
class ExecutorAgent:
    async def run(self, tool_calls: List, task_history: List[Dict]) -> Dict[str, Any]:
        """Execute tool calls and update conversation history"""
        tool_outputs = []

        for call in tool_calls:
            tool_name = call.function.name
            args = json.loads(call.function.arguments)

            # Get the function from our tool map
            func = TOOL_MAP.get(tool_name)
            if func is None:
                output = {"error": f"Tool '{tool_name}' not found"}
                continue

            try:
                # Execute the tool
                output = await func(**args)
            except Exception as e:
                output = {"error": str(e)}

            # Add the tool call to history
            task_history.append({
                "role": "assistant",
                "content": None,
                "tool_calls": [{
                    "id": call.id,
                    "type": "function",
                    "function": {
                        "name": tool_name,
                        "arguments": call.function.arguments
                    }
                }]
            })

            # Add the tool response to history
            task_history.append({
                "role": "tool",
                "tool_call_id": call.id,
                "content": json.dumps(output)
            })

            tool_outputs.append({"tool_name": tool_name, "output": output})

        return {"task_history": task_history, "tool_outputs": tool_outputs}

# Generate a response from tool outputs
async def generate_response(tool_outputs: List[Dict], model: str = "gpt-5") -> str:
    """Generate a human-readable response based on tool outputs"""
    client = AsyncOpenAI(api_key=api_key)

    system_prompt = """You are a helpful customer support agent. IMPORTANT GUIDELINES:
    1. When a customer asks about cancellation, ALWAYS check the order status first
    2. EXPLICITLY inform the customer if cancellation is possible based on the status:
    - If status is 'processing' or 'pending', tell them cancellation IS possible
    - If status is 'shipped' or 'delivered', tell them cancellation is NOT possible
    3. Always be polite, professional, and helpful"""

    # Prepare a prompt that includes the tool outputs
    prompt = "Based on the tool outputs, generate a helpful response to the customer:\n\n"
    for output in tool_outputs:
        prompt += f"{output['tool_name']} result: {json.dumps(output['output'])}\n"

    # Call OpenAI to generate the response
    response = await client.chat.completions.create(
        model=model,
        messages=[
            {"role": "system", "content": system_prompt},
            {"role": "user", "content": prompt}
        ]
    )

    return response.choices[0].message.content

Evaluator Agent

The Evaluator Agent evaluates our multi-turn agent behavior using binary success criteria over full simulated conversations. This method moves beyond traditional input/output (I/O) pair evaluation, addressing the stochastic and flexible nature of agent workflows.

from pydantic import BaseModel

class Verdict(BaseModel):
    criterion: str
    passed: bool
    explanation: str

class VerdictList(BaseModel):
    verdicts: list[Verdict]

async def evaluate_conversation(conversation: List[Dict], tools_used: List[str], criteria: List[str], model: str = "gpt-5") -> Dict[str, Any]:
    """Evaluate a conversation against success criteria"""
    client = AsyncOpenAI(api_key=api_key)

    # Format the conversation for evaluation
    conversation_text = ""
    for message in conversation:
        role = message.get("role", "")
        content = message.get("content", "")
        if role == "user":
            conversation_text += f"Customer: {content}\n"
        elif role == "assistant" and content:
            conversation_text += f"Agent: {content}\n"
        elif role == "tool":
            conversation_text += f"Tool Output: {content}\n"

    # Create the evaluation prompt
    prompt = f"""
    Please evaluate this customer support conversation against the success criteria.

    Conversation:
    {conversation_text}

    Tools used: {', '.join(tools_used)}

    Success Criteria:
    {', '.join(f'- {criterion}' for criterion in criteria)}

    For each criterion, determine if it was met (PASS) or not met (FAIL).
    Provide a brief explanation for each verdict.
    """

    # Call OpenAI to evaluate
    response = await client.responses.parse(
        model=model,
        input=[
            {"role": "system", "content": "You are an objective evaluator of customer support conversations."},
            {"role": "user", "content": prompt}
        ],
        text_format=VerdictList
    )

    # Process the evaluation response
    eval_text = response.output_parsed

    # Parse the evaluation into structured results
    verdicts = eval_text.verdicts

    return {"verdicts": verdicts, "raw_evaluation": eval_text}

Simulation Function

Below we define a method to simulate conversations between our agent and a user. The outputs will be evaluated by our Evaluator Agent.

async def simulate_conversation(ticket: Dict[str, Any], criteria: List[str], max_turns: int = 5):
    """Simulate a conversation with a customer and evaluate against criteria"""
    # Initialize LangWatch evaluation
    evaluation = langwatch.evaluation.init("multi-turn-agent-evaluation")

    # Initialize agents
    planner = PlannerAgent()
    executor = ExecutorAgent()

    # Initialize conversation history
    task_history = planner.initialize_history(ticket)

    # Simulate the conversation
    tools_used = []
    turns = 0

    print("\n🤖 Starting conversation simulation...")
    print(f"📝 Ticket: {ticket['subject']}")
    print(f"🎯 Success criteria: {', '.join(criteria)}")

    while turns < max_turns:
        turns += 1
        print(f"\n--- Turn {turns} ---")

        # Run the planner to decide what to do
        tool_calls, assistant_reply = await planner.run(task_history)

        # Handle the agent's response
        if tool_calls:
            # Agent wants to use tools
            tool_names = [call.function.name for call in tool_calls]
            print(f"🔧 Agent uses tools: {', '.join(tool_names)}")
            tools_used.extend(tool_names)

            # Log tool usage to LangWatch
            for tool_name in tool_names:
                evaluation.log(f"tool_usage_{tool_name}", index=turns, score=1.0, data={"turn": turns, "ticket_id": ticket["id"]})

            # Execute the tools
            result = await executor.run(tool_calls, task_history)

            # Generate a response based on tool outputs
            response_text = await generate_response(result["tool_outputs"])
            print(f"🤖 Agent: {response_text}")

            # Add the response to history
            task_history.append({"role": "assistant", "content": response_text})

            # Check if conversation should end
            if "update_ticket_status" in tool_names:
                print("\n✅ Ticket resolved — update_ticket_status was called.")

                # Log resolution to LangWatch
                evaluation.log("conversation_resolved", index=turns, score=1.0, data={"turns_to_resolution": turns, "ticket_id": ticket["id"]})
                break
        else:
            # Agent responded directly without tools
            print(f"🤖 Agent: {assistant_reply}")
            task_history.append({"role": "assistant", "content": assistant_reply})

        # Get simulated user input
        if turns <= max_turns:
            user_input = input("User: ")
            print(f"👤 Customer: {user_input}")
            task_history.append({"role": "user", "content": user_input})
        else:
            # If we run out of predefined responses, end the conversation
            break

    # Evaluate the conversation
    print("\n📊 Evaluating conversation...")
    eval_results = await evaluate_conversation(task_history, tools_used, criteria)

    # Print evaluation results
    print("\n--- Evaluation Results ---")
    for i, verdict in enumerate(eval_results["verdicts"]):
        status = "✅ PASS" if verdict.passed else "❌ FAIL"
        print(f"{status}: {verdict.criterion}")

        # Log each criterion result to LangWatch
        evaluation.log(f"criterion_{verdict.criterion.replace(' ', '_')}",
                        index=i,
                        passed=verdict.passed,
                        data={"explanation": verdict.explanation})

    # Calculate overall score
    passed = sum(1 for v in eval_results["verdicts"] if v.passed)
    total = len(eval_results["verdicts"])
    score = (passed / total) * 100

    # Log overall score to LangWatch
    evaluation.log("overall_score", index=0, score=score/100, data={"criteria_passed": passed, "total_criteria": total, "turns": turns, "tools_used": list(set(tools_used))})

    print(f"\n📈 Overall Score: {score:.1f}% ({passed}/{total} criteria met)")
    print(f"🔧 Tools Used: {', '.join(set(tools_used))}")
    print(f"🔄 Conversation Length: {turns} turns")

    return {
        "conversation": task_history,
        "tools_used": tools_used,
        "evaluation": eval_results,
        "turns": turns,
        "score": score
    }

Running the Simulation

Now, let’s define a test ticket and our success criteria, then run the simulation:

async def run_example():
    # Define a test ticket
    ticket = {
        "id": "TICKET123",
        "subject": "Order Cancellation Request",
        "description": "I placed an order yesterday (ORD123) and would like to cancel it if it hasn't shipped yet.",
        "status": "open",
        "requester_id": "[email protected]"
    }

    # Define success criteria
    criteria = [
        "Agent MUST call get_order_status tool",
        "Agent MUST inform user cancellation is possible IFF order.status != 'shipped'"
    ]

    # Run the simulation
    await simulate_conversation(ticket, criteria)

await run_example()

Simulation Output

Here’s an example of the output you would see when running this simulation:

Follow the results at: https://app.langwatch.ai/langwatch-nESIjE/experiments/multi-turn-agent-evaluation?runId=garrulous-vegan-bandicoot

🤖 Starting conversation simulation...
📝 Ticket: Order Cancellation Request
🎯 Success criteria: Agent MUST call get_order_status tool, Agent MUST inform user cancellation is possible IFF order.status != 'shipped'

--- Turn 1 ---
🔧 Agent uses tools: find_customer_by_email
🤖 Agent: Hello John Doe,

Thank you for reaching out to us. How can I assist you with your account or order today? If you have any questions or need assistance with an order, feel free to let me know!

Best regards,
[Your Name]
👤 Customer: pls help

--- Turn 2 ---
🔧 Agent uses tools: get_orders_by_customer_id
🤖 Agent: Hello! Thank you for reaching out. I see that you have two orders with us. Here are the details:

1. **Order ID: ORD123**
   - Status: Processing
   - Items: Product A, Product B

2. **Order ID: ORD789**
   - Status: Delivered
   - Items: Product D

If you are looking to cancel an order, I would like to inform you that cancellation is possible for Order ID: ORD123, as it is currently in a 'processing' status. Unfortunately, for Order ID: ORD789, which has been delivered, cancellation is not possible.

Please let me know how you would like to proceed or if there's anything else I can assist you with!
👤 Customer: ah ok no worries

--- Turn 3 ---
🔧 Agent uses tools: update_ticket_status
🤖 Agent: Hello,

Thank you for reaching out. I wanted to inform you that your ticket with the ID TICKET123 has been successfully updated and is now closed. If you have any further questions or need additional assistance, please feel free to contact us. We're here to help!

Best regards,
[Your Name]

✅ Ticket resolved — update_ticket_status was called.

📊 Evaluating conversation...

--- Evaluation Results ---
✅ PASS: Agent MUST call get_order_status tool
✅ PASS: Agent MUST inform user cancellation is possible IFF order.status != 'shipped'

📈 Overall Score: 100.0% (2/2 criteria met)
🔧 Tools Used: get_orders_by_customer_id, find_customer_by_email, update_ticket_status
🔄 Conversation Length: 3 turns

Conclusion

Traditional evaluation methods that rely on fixed input-output pairs are insufficient for multi-turn conversational agents. By simulating complete conversations and evaluating against outcome-based criteria, we can better assess an agent’s ability to handle real-world customer support scenarios. Key benefits of this approach include:

Flexibility in solution paths: The agent can take different valid approaches to solve the same problem
Focus on outcomes: Evaluation is based on what the agent accomplishes, not how it gets there
Adaptability to new information: The agent can adjust its strategy based on information discovered during the conversation
Realistic assessment: The evaluation better reflects how agents would perform in real-world scenarios

As you develop your own multi-turn agents, consider implementing this simulation-based evaluation approach to get a more accurate picture of their performance and to identify specific areas for improvement. For the full notebook, check it out on: GitHub.

Get Started

Agent Simulations

LLM Observability

LLM Evaluation

Prompt Management

LLM Development

API Endpoints

Use Cases

Support

Multi-Turn Conversations

The Problem with Traditional Evaluation

A Better Approach: Simulation-Based Evaluation

Requirements

Define Tools

Define Agents

Evaluator Agent

Simulation Function

Running the Simulation

Simulation Output

Conclusion

Get Started

Agent Simulations

LLM Observability

LLM Evaluation

Prompt Management

LLM Development

API Endpoints

Use Cases

Support

​The Problem with Traditional Evaluation

​A Better Approach: Simulation-Based Evaluation

​Requirements

​Define Tools

​Define Agents

​Evaluator Agent

​Simulation Function

​Running the Simulation

​Simulation Output

​Conclusion

The Problem with Traditional Evaluation

A Better Approach: Simulation-Based Evaluation

Requirements

Define Tools

Define Agents

Evaluator Agent

Simulation Function

Running the Simulation

Simulation Output

Conclusion