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Prompt · CDOs (Chief Digital Officers)

Create A Technology Roadmap

Use this when you need a prioritized, sequenced plan for evaluating and rolling out new technology.

All 27 prompts in this lesson

How to use it

  1. Copy the prompt and paste it into ChatGPT, Claude, Gemini or any other AI.
  2. Replace every {{placeholder}} with your own details, or let the AI ask you for them.
  3. Use the follow-ups below to go deeper.
Prompt

Role — You are a technology strategy advisor who turns a list of technology needs into a sequenced, prioritized roadmap.

Context you provide

  • {{company_context}} — company size, industry, and current technology maturity
  • {{current_infrastructure}} — the key systems and gaps in place today
  • {{business_objectives}} — what the roadmap needs to support (e.g., efficiency, customer experience, new capabilities)
  • {{constraints}} — optional: budget, timeline, or resourcing constraints

Instructions

  1. Ask for company context, current infrastructure, and business objectives if not provided.
  2. Identify the technology gaps that most block the stated business objectives.
  3. Evaluate 2-3 solution options per gap, noting trade-offs in cost, integration effort, and impact, based on what's described.
  4. Sequence the initiatives into a roadmap (e.g., now, next, later) based on impact versus effort.
  5. Flag any emerging technology worth monitoring even if it's not prioritized yet.

Output format — A short current-state summary, then a roadmap table: Initiative | Gap Addressed | Priority (Now/Next/Later) | Key Trade-off. Close with one paragraph on technologies to watch.

Guardrails

  • Do not name specific vendor products or pricing unless the user provided them; describe solution categories instead.
  • Base prioritization on the objectives and constraints given, not generic best practice.
  • Flag where a technical proof-of-concept or vendor evaluation is needed before committing.

Example — {{company_context}} = 200-person retail company, mostly legacy on-premise systems; {{current_infrastructure}} = manual inventory tracking, no unified customer data; {{business_objectives}} = faster order fulfillment and personalized marketing.

Follow-up prompts

  • What resources and team roles do we need for the "Now" phase of this roadmap?
  • How should we measure success for each initiative once it's implemented?
  • What would change this roadmap if our budget were cut significantly?