These answers come from the year-long archive of my previous chatbot that lived on my previous site iamnicola.ai. I’ve curated the most useful sessions—real questions from operators exploring AI workflows, experimentation, and conversion work—and lightly edited them so you get the original signal without the noise.

ai consulting

How do I choose the right AI consultant?

Direct Answer

Choose an AI consultant who combines technical depth, business understanding, and a track record of delivering measurable results. Look for consultants who can show working prototypes, case studies with real metrics, and who ask thoughtful questions about your goals before proposing solutions.

Evaluation Framework

Assess consultants across five dimensions:

  1. Technical expertise: Do they have hands-on experience with the tools you need? Ask for code samples, GitHub profiles, or demos of past work. For LLM projects, look for experience with RAG, fine-tuning, or prompt engineering.
  2. Business alignment: Can they connect AI capabilities to business outcomes? Good consultants ask about your KPIs, constraints, and success criteria before proposing solutions.
  3. Communication style: Do they explain complex concepts clearly? Can they translate technical decisions into business terms? Schedule a discovery call to assess fit.
  4. Delivery track record: Request case studies with specific metrics (e.g., "reduced support tickets by 60%" or "increased conversion by 18%"). Beware of vague claims like "improved efficiency."
  5. Pragmatism: Do they know when AI isn't the right solution? The best consultants will tell you if a simpler approach would work better.

Red Flags to Avoid

Watch out for consultants who:

  • Overpromise: Claim AI will solve everything without understanding your constraints
  • Lack specificity: Can't provide concrete examples or case studies from similar projects
  • Skip discovery: Propose solutions before understanding your processes and goals
  • No measurement plan: Don't discuss how you'll track success or ROI
  • Vendor lock-in: Push proprietary tools or platforms that create dependency

Questions to Ask During Evaluation

Use these questions to assess fit:

  • "Can you walk me through a similar project you completed recently?"
  • "How do you measure success in your engagements?"
  • "What's your approach to discovery and scoping?"
  • "How do you ensure we can maintain the system after you leave?"
  • "What's the biggest risk in this project, and how would you mitigate it?"
  • "Can you provide references from clients with similar needs?"

Example Selection Process

A SaaS company evaluated three AI consultants for a customer support automation project. They asked each to review their support ticket data and propose an approach. Consultant A suggested a generic chatbot platform. Consultant B proposed a custom RAG system with specific architecture. Consultant C asked detailed questions about their documentation, team capabilities, and success metrics before proposing a phased approach. They chose Consultant C because the proposal showed deep understanding of their context and included clear measurement criteria.

Independent vs. Agency

Consider independent consultants if you need:

  • Direct access to the person doing the work
  • Flexibility to adjust scope and approach
  • Cost efficiency (no agency markup)
  • Faster decision-making and iteration

Consider agencies if you need:

  • Multiple specialists (designers, engineers, analysts)
  • Established processes and methodologies
  • Larger team capacity for big projects
  • Brand recognition or compliance certifications

Takeaway & Related Answers

The right AI consultant should feel like a partner, not a vendor. They should ask thoughtful questions, propose solutions tailored to your context, and focus on measurable outcomes. Start with a small discovery engagement to assess fit before committing to a larger project.

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