End-to-end roadmap to evolve a plain LLM chatbot into a production-grade agentic AI system. It’s organized as maturity levels so you can climb one rung at a time without breaking things.


0 → 1: Robust Chatbot (baseline you can trust)

Goal: Deterministic, instrumented, secure LLM app.

Do:

  • Spec the job: Narrow, measurable tasks + success criteria.
  • Structured I/O: Force JSON outputs with schemas (pydantic/JSON Schema).
  • Guardrails: Prompt templates, content filters, allow/deny lists.
  • Telemetry: Log prompts, tool calls, tokens, lat/latency, errors, user satisfaction tags.
  • Eval harness: Golden tests + regression suites (unit + scenario tests).

KPIs: response validity %, latency p95, hallucination rate, CSAT.


1 → 2: Tool-Using Assistant (from “talker” to “doer”)

Goal: LLM can call tools/APIs deterministically.

Do:

  • Tool registry: Each tool has a contract: name, description, strict JSON args, auth scope, rate limits, cost.
  • Router: Model chooses a tool via function-calling; you validate args before execution.
  • Idempotency: Use request IDs + retries + timeouts.
  • Sandboxing: Separate service accounts for read vs write tools.

KPIs: tool-call success %, invalid-arg rate, external error rate.

Tool contract example (concise):

{

  “name”: “search_db”,

  “description”: “SQL read-only over analytics”,

  “schema”: {

    “type”: “object”,

    “properties”: { “query”: {“type”: “string”} },

    “required”: [“query”],

    “additionalProperties”: false

  },

  “auth_scope”: “analytics.read”,

  “rate_limit_qps”: 5,

  “timeout_ms”: 8000

}


2 → 3: Add Memory (short-term, long-term, episodic)

Goal: The assistant remembers context and learns across sessions.

Do:

  • Memory layers:
    • Working: conversation buffer (windowed).
    • Episodic: “events” with outcomes & metadata.
    • Semantic long-term: vector store for facts, docs.
    • Profile/State: key–value store (preferences, configs).
  • Write policy: What gets saved, for how long, and why (avoid hoarding).
  • Read policy: Retrieval filters (freshness, scope, PII constraints).
  • PII & compliance: Field-level encryption; TTLs; user “forget me”.

Minimal schemas:

episode:

  id: uuid

  ts: datetime

  task: string

  actions: [tool_name, args, result_ref]

  outcome: success|failure|partial

  notes: text

profile:

  user_id: string

  prefs: {key: value}

  scopes: [string]

KPIs: retrieval hit rate, memory precision/recall (offline eval), PII leakage = 0.


3 → 4: Planning & Multi-Step Execution (the agentic loop)

Goal: Break big goals into actionable steps; recover from errors.

Plan–Act–Observe loop (core):

  1. Plan: LLM produces a structured plan (steps with tools/inputs/expected outputs).
  2. Act: Execute step N (validate + run tool).
  3. Observe: Capture results, update state/memory.
  4. Revise: Re-plan if blocked; stop when success criteria met.

Design choices:

  • Shallow vs deep planning: Cap max steps; prefer re-planning over long initial plans.
  • Critic model: Lightweight verifier scores step outputs (pass/fail/explain).
  • Self-consistency: Re-ask the model for plan variants when confidence is low.

Task graph spec (example):

{

  “goal”: “Produce a weekly sales summary slide”,

  “constraints”: [“read-only db”, “finish < 3 mins”],

  “steps”: [

    {“id”:”s1″,”tool”:”query_sales”,”args”:{“week”:”2025-W35″}},

    {“id”:”s2″,”tool”:”summarize”,”args”:{“input”:”$s1.rows”}},

    {“id”:”s3″,”tool”:”make_slide”,”args”:{“markdown”:”$s2.text”}}

  ],

  “success_check”:”slide has totals, trend, top 3 SKUs”

}

KPIs: task success rate, average steps per success, auto-recovery rate.


4 → 5: Multi-Agent Orchestration (specialists that collaborate)

Goal: Decompose roles (Researcher, Planner, Executor, Critic, Guard).

Do:

  • Roles with charters: Each agent has tools & success metrics.
  • Conversation protocol: Turn-taking with budgets (tokens/time/tool calls).
  • Arbiter: A controller that stops loops, resolves conflicts, enforces costs.

KPIs: marginal gain vs single-agent baseline; overhead (tokens, latency).


5 → 6: Proactivity & Autonomy Controls

Goal: Let agents initiate work safely.

Do:

  • Triggers: CRON, webhooks, event streams (“new lead added”, “SLA breach”).
  • Policy engine (OPA/Rego or custom): who/what/when the agent may act.
  • Approval ladder:
    • Tier 0: read-only, always.
    • Tier 1: low-risk writes, batch gated.
    • Tier 2: high-risk writes, human review with diff.
  • Budgeting: Per-goal caps (tokens, spend, API calls).

KPIs: % proactive actions accepted, budget adherence, incident rate (target ≈ 0).


6 → 7: Production Ops, Safety, and Governance

Goal: Treat your agent like a microservice—observable, auditable, upgradable.

Do:

  • Observability: Tracing across plan→tool→result; redaction at log sinks.
  • Risk controls: Rate limits, circuit breakers, kill switch, sandbox envs.
  • Policy packs: Data residency, IP hygiene, model usage constraints.
  • Model mgmt: Canary deploys, shadow tests, rollback, eval-gated releases.
  • Human-in-the-loop: Review queues with structured feedback → fine-tuning/RLAIF.

KPIs: MTTR, change failure rate, eval pass rate pre-release.


Reference Implementation (minimal, production-leaning pseudocode)

class Tool(Protocol):

    name: str

    schema: Dict

    def run(self, **kwargs) -> Dict: …

class Registry:

    def __init__(self, tools: list[Tool]): self.tools = {t.name: t}

    def validate(self, name, args): …  # jsonschema.validate

    def run(self, name, args): return self.tools[name].run(**args)

class Memory:

    def read(self, query): …

    def write_episode(self, episode): …

class AgentController:

    def __init__(self, llm, registry: Registry, memory: Memory, critic):

        …

    def plan(self, goal, context) -> dict: …

    def act(self, step): return self.registry.run(step[“tool”], step[“args”])

    def loop(self, goal, context, budget):

        plan = self.plan(goal, context)

        for step in plan[“steps”][:budget[“max_steps”]]:

            self.registry.validate(step[“tool”], step[“args”])

            out = self.act(step)

            ok, reason = self.critic.check(step, out)

            self.memory.write_episode({…})

            if not ok: plan = self.replan(goal, context, reason)

        return self.finalize(plan)


Testing & Evaluation (make this non-negotiable)

  • Offline: 50–200 canonical tasks with ground-truth; measure success & constraint violations.
  • Simulated users: Synthetic conversations to probe edge cases.
  • Chaos tests: Tool timeouts, 429s, malformed responses; verify recovery.
  • Red-team: Prompt-injection, data exfiltration, jailbreaks, tool-misuse.

Automatic checks per run:

  • “No-op tool spam” ≤ threshold
  • External call budget not exceeded
  • PII never leaves approved sinks
  • All writes have diffs + approvals where required

Stack Suggestions (pick one from each row)

  • Orchestration: LangChain | Semantic Kernel | Autogen | CrewAI
  • Memory (semantic): pgvector/SQLite-Vec | Pinecone | Weaviate | Milvus
  • State store: Postgres | Redis
  • Eval: Ragas | E2E eval scripts + human review queues
  • Policy: OPA/Rego | custom middleware
  • Observability: OpenTelemetry + ELK/Grafana | vendor APM
  • Models: Hosted LLMs (for reliability) + small local models for critics/parsers

Security & Compliance Quicklist

  • Least-privilege API keys; rotate + scope.
  • Output-to-action gap: show diffs for any write; require approvals per policy.
  • Prompt-injection defenses: input sanitization, origin tagging, content sandboxing.
  • Data handling: classify fields; encrypt at rest & in transit; region pinning.
  • Third-party risk: vendor DPAs, SOC2/ISO evidence, incident SLAs.

Cost & Latency Controls

  • Caching (prompt + retrieval) and distilled “fast path” models for simple steps.
  • Early-exit heuristics and confidence-based reruns only when needed.
  • Batch tool calls when safe; cap step counts; compress traces.

Migration Plan (pragmatic 6–8 weeks)

  1. Week 1–2: Instrument current chatbot; add eval harness + guardrails.
  2. Week 2–3: Introduce 2–3 high-value tools; ship read-only flows.
  3. Week 3–4: Add memory (episodic + semantic); ship retrieval-augmented tasks.
  4. Week 4–5: Implement plan–act–observe loop with critic + re-planning.
  5. Week 5–6: Limited autonomy with approvals; add proactive triggers.
  6. Ongoing: Multi-agent roles for complex domains; harden ops & governance.

Common Failure Modes (and fixes)

  • Endless loops → step caps + critic + “no-progress” detector.
  • Tool over-calling → per-tool budgets + cost-aware planner.
  • Hallucinated tools/params → strict schema validation + tool name canonicalization.
  • Memory hoarding → write policy + TTLs + size caps + periodic compaction.
  • Prompt-injection → signed content sources, retrieval isolation, tool-call allowlists.