//pragmatic leaders

Technical Challenges in AI Product Development

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The real margin lives in nuanced recommendations — not telling users where their package is.
Talvinder Singh, from a Pragmatic Leaders AI product leadership session

AI product development is fraught with technical challenges that can derail projects if unaddressed. The trap is not just building AI — it is building AI that actually delivers value reliably in production. Most teams underestimate the complexity of operationalizing AI, especially in India’s data and infrastructure environment.

This lesson walks you through the technical pitfalls you will encounter, the diagnostic mindset you must adopt, and how to scope your AI initiatives to succeed beyond the prototype stage.

The margin is in decision support, not chatterbots

Many companies start with FAQ bots or simple chatbot demos. These projects feel tangible but rarely create strategic value.

The real margin lies in nuanced recommendations that help users make complex decisions. This is what differentiates a chatbot that just repeats scripted answers from an AI system that meaningfully impacts business outcomes.

For example, in an e-commerce context, telling a customer where their package is does not move the needle. But helping them choose between multiple products based on detailed specs and preferences unlocks value.

This distinction guides your technical approach: you will need richer data, better embeddings, and more sophisticated retrieval and ranking — not just canned responses.

Common failure modes in AI systems

Incorrect indexing and chunking

A common mistake is naïve text chunking for retrieval-augmented generation (RAG). For instance, chunking PDFs or documents without preserving structure leads to garbled context.

Example: If you index a product manual PDF by blindly splitting on fixed character limits, tables break mid-row, and the model receives nonsensical fragments. This causes hallucinations or irrelevant answers.

Fix: Use layout-aware chunking tools. For example, Unstructured.io can parse PDFs preserving tables and headings, improving retrieval quality.

Embeddings mismatch

Embedding models convert text into vectors for similarity search. Using a generic embedding model for domain-specific data causes poor recall.

Case study: A retail chatbot using all-MiniLM-L6-v2 embeddings for fashion product search returned irrelevant results because the model was trained on generic text, not fashion descriptions.

Fix: Use domain-specific embeddings or fine-tune embeddings on your product descriptions or user queries. This improves semantic matches and retrieval relevance.

Partial context hallucinations

Sometimes the model generates answers based on only one of multiple retrieved documents, ignoring contradictions in others.

Detection: Tools like TruLens provide faithfulness scores to detect when the model’s output is unsupported or conflicted.

Mitigation: Add prompt instructions like “If documents conflict, state uncertainty.” Also, consider retrieval strategies that prioritize consistent documents or aggregate multiple sources carefully.

The debugging workflow for RAG systems

Diagnosing AI failures requires a systematic approach:

  1. Validate retrieval: Manually inspect the top-k retrieved documents for a sample query. Are they relevant and complete? Irrelevant docs indicate indexing or embedding problems.

  2. Check embeddings: Measure cosine similarity between query and retrieved docs. Low similarity scores suggest embedding mismatch or poor query formulation.

  3. Audit prompts: Test if the model respects prompt instructions. For example, does it obey a “Do not answer if unsure” directive? Prompt engineering is crucial.

  4. Use tracing tools: Platforms like LangSmith help trace the full RAG pipeline, from query to retrieval to generation, exposing where failures occur.

Proactive mitigations

  • Preprocessing: Clean and redact personally identifiable information (PII) before indexing. Microsoft Presidio is useful for automated PII detection and redaction.

  • Embedding calibration: Dynamically adjust similarity thresholds to balance recall and precision, avoiding noise in retrieval.

Technology Readiness Levels (TRL) in AI projects

TRL is a framework to grade your AI initiative’s maturity and risk. It helps set realistic expectations with leadership and finance.

  • TRL 4-6: Prototype phase. You have a working prototype tested in controlled environments but not yet deployed at scale. For example, a Python script generating comparison articles for phones on your laptop.

  • TRL 6: Operational prototype. The prototype runs in a staging environment with real or simulated traffic. Docker-compose setups with test users exemplify this.

  • TRL 7-9: Production readiness. The system is scalable, reliable, and serving hundreds or thousands of users. This is the “on the menu” phase where you have proven ROI.

Why TRL matters: CFOs care about risk and ROI. Technical teams care about functionality. Aligning on TRL ensures you scope projects that can realistically deliver value soon, instead of chasing research-level ambitions.

The AI Opportunity Matrix: Filtering ideas strategically

After TRL grading, filter ideas against these criteria:

  • Strategic Fit: Does this AI project directly help you sell more, save costs, or widen competitive gaps? For example, will automating spec comparisons increase sales velocity on 91mobiles?

  • Impact Potential: Is the measurable impact in rupees, user engagement, or market share significant? Quantify expected gains.

  • Feasibility: Can your current team build this with existing tools? Or do you need PhDs and years of development?

  • Data Readiness: Is the data you need clean, accessible, and ready today? Messy or siloed data kills AI projects before they start.

Role matching in AI components

Understanding which AI component handles which function is essential:

FunctionCorrect ComponentCommon Mistake
Stores numerical vectorsVector DBLLM
Converts text to vectorsEmbedding ModelReranker
Improves retrieval rankingRerankerPrompt Constructor
Generates final answerLLMEmbedding Model

Confusing these leads to architectural mistakes and debugging headaches.

Hands-on system exploration: A 91mobiles use case

Learners test queries like:

  • “Battery capacity of iPhone 15 Pro” → Should return exact specs with source citation.

  • “Compare camera quality Pixel 8 Pro vs Galaxy S24 Ultra” → Table comparing sensor size, aperture, lens count, with sources.

  • “Phones under ₹40k with 120 Hz AMOLED & wireless charging” → Multi-criteria filter outperforming hardcoded SQL.

These experiments reveal where the system succeeds and where it fumbles, highlighting real-world technical challenges.

Field exercise: Diagnose and debug your AI prototype (20 min)

  1. Pick an AI feature your team is building or considering.

  2. Run 3-5 typical user queries through the prototype or MVP.

  3. Note any incorrect, irrelevant, or hallucinated outputs.

  4. For each failure, identify if it stems from:

    • Indexing/chunking issues

    • Embedding mismatch

    • Retrieval ranking problems

    • Prompt engineering errors

  5. Propose one concrete fix from the debugging workflow.

  6. Share your findings with your team to prioritize improvements.

Test yourself: Scoping an AI initiative at 91mobiles

// learn the judgment

You are PM at 91mobiles, leading an AI content generation project. Your engineering lead wants to build a prototype that generates phone comparison articles using GPT-4, but warns it will take 2 months to build a reliable pipeline. Marketing wants to launch a demo in 3 weeks to impress advertisers.

The call: How do you scope the project timeline and set expectations with marketing and engineering?

Your reasoning:

// practice

You are PM at 91mobiles, leading an AI content generation project. Your engineering lead wants to build a prototype that generates phone comparison articles using GPT-4, but warns it will take 2 months to build a reliable pipeline. Marketing wants to launch a demo in 3 weeks to impress advertisers.

Your task: How do you scope the project timeline and set expectations with marketing and engineering?

your reasoning:

0 chars (min 80)

Meeting scene: Aligning AI expectations at a mid-stage startup

// scene:

Product review meeting at a Bangalore-based AI SaaS startup

CEO: “I want this AI feature live next month. Our competitors are moving fast.”

Engineering Lead: “We can build a prototype in 3 weeks but production readiness will take at least 2 more months.”

You (PM): “Let's define the TRL milestones so we can communicate what we can deliver when, and manage stakeholder expectations.”

CEO: “I don’t care about acronyms. I want results.”

You (PM): “Results come from reliable systems. We risk customer trust if we launch too early. Let's align on a phased approach.”

This conversation sets the tone for realistic AI delivery, balancing ambition with operational rigor.

// tension:

The tension between speed and reliability in AI product launches.

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