AI Transition Plan Checklist for Small Business

A few years back, I was part of an IT company thriving in the niche of IBM Lotus Notes, particularly favored by banking sectors.

Opportunity v Pivots

When a pan-European livestock crisis broke out, we adapted one of our internal projects into a track-and-trace solution and started to apply for Government contracts. This was a real turning point. We rapidly expanded, on-boarded new talent and opened two new offices.

All in! Within a few month, we shifted focus from a service-based to a product-oriented powerhouse.

However, as our product gained traction, it also drew in larger competitors. Meanwhile, as we’d overlooked servicing our legacy Lotus Notes projects, the recurring revenue dried up, as did the government tenders.

Download the Transition Plan Template

Enter AI

Now, let’s talk about AI.

It’s everywhere. It feels like on the precipice of a revolution. Companies are ripping up roadmaps and going all in on AI.

So, what does this mean if your company have stable revenue and with a dedicated client base?

Diving headfirst into AI might seem tempting, but let’s remember our lesson.

I’d suggest a more nuanced, phased approach.

That is, look to develop a transition plan that will, by degrees, weave AI into your business model while retaining your core strengths. This way, you can pivot back if needed.

AI Transition Plan Checklist for a Small Company

To integrate AI into your operations effectively, we’ve developed the following AI Transition Plan Checklist.

It will help reduce risks, optimize resources, engage employees, and position your company for sustainable growth while protecting your current income streams.

Let’s look at what’s involved

Phase 1: Preparation and Assessment

1. Understand AI and Its Implications

  • [ ] Educate team leads and key staff about AI, its capabilities, and limitations. Keep things practical. That is, develop case studies that show how companies of a similar size/industry implemented AI into their workflow.
  • [ ] Identify the specific areas where your business could benefit most from AI integration. For example, choose a specific department, say HR, set specific OKRs, and implement AI tools to meet those objectives.

2. Conduct Current State Analysis

  • [ ] Assess current business processes, technologies, and data systems.
  • [ ] Identify inefficiencies or pain points in current operations.

3. Set Clear Objectives and KPIs

  • [ ] Define specific goals for AI integration (e.g., cost reduction, efficiency improvement, customer experience enhancement).
  • [ ] Establish Key Performance Indicators (KPIs) to measure AI implementation success.

4. Evaluate Technical Infrastructure

  • [ ] Assess existing IT infrastructure and its readiness for AI integration.
  • [ ] Plan for necessary upgrades or changes in IT infrastructure.

5. Legal and Ethical Compliance

  • [ ] Review relevant AI regulations and ethical guidelines.
  • [ ] Ensure compliance with data privacy laws and ethical AI practices.

Phase 2: Planning and Development

Next, start the planning phase. Here’s you’re going to develop your strategic plan, identify the most appropriate solutions (this might involve testing a few tools until you find what seems suitable), prepare sample data, then get started.

6. Develop a Strategic AI Implementation Plan

  • [ ] Create a detailed roadmap for AI integration, including timelines and milestones.
  • [ ] Allocate resources (budget, personnel, technology) for the AI project.

7. Select the Right AI Solutions

  • [ ] Research and identify appropriate AI technologies and platforms.
  • [ ] Consider partnerships with AI vendors or service providers.

8. Staff Training and Capacity Building

  • [ ] Train staff on AI tools and technologies.
  • [ ] Hire or develop internal AI expertise, if necessary.

9. Data Preparation

  • [ ] Ensure availability of quality data for AI training and operations.
  • [ ] Implement data governance and management practices.

10. Pilot Testing

  • [ ] Start with a pilot project to test AI solutions in a controlled environment.
  • [ ] Gather feedback and adjust the approach based on pilot results.

Phase 3: Implementation and Integration

11. Gradual Roll-out of AI Systems

  • [ ] Implement AI solutions in phases, starting with less critical areas.
  • [ ] Monitor the performance and impact of AI on business processes.

12. Manage Change and Transition

  • [ ] Communicate regularly with employees about AI integration and its benefits.
  • [ ] Address concerns and manage resistance to change.

13. Integration with Existing Systems

  • [ ] Ensure seamless integration of AI solutions with existing business systems.
  • [ ] Maintain business continuity during the integration process.

14. Continuous Monitoring and Adjustment

  • [ ] Regularly review the performance of AI systems against set KPIs.
  • [ ] Make adjustments based on performance data and feedback.

Phase 4: Evaluation and Scaling

15. Evaluate AI Implementation

  • [ ] Conduct a comprehensive evaluation of the AI implementation against initial objectives.
  • [ ] Analyze ROI and impact on business operations.

16. Plan for Future Expansion

  • [ ] Identify opportunities to expand or enhance AI capabilities.
  • [ ] Develop a scaling plan based on the initial success and learnings.

17. Ongoing Learning and Adaptation

  • [ ] Stay informed about new AI developments and best practices.
  • [ ] Continuously evolve AI strategies to align with business growth and technological advancements.


Today is Day 1 in the age of AI. In the next five years, new industry leaders will emerge, incumbents will be phasing out. It’s tempting to go all in and not get left behind. FOMO is just as real in IT as on social media.

As you start your AI Transition Plan, aim to combine innovation with calculated caution. Embrace AI, but do so with a plan that respects your roots and safeguards your future.

Use this checklist to guide your company through a structured and strategic transition to an AI-enabled setup. You’ll need to tweak it according to your needs but it should help minimize disruption to your current operations while laying a foundation for an AI-enabled future.

Download the Transition Plan Template