As we approach the end of 2023, it’s the perfect time for small business owners to reflect on their AI journey and prepare for the opportunities ahead. Whether you’ve already begun implementing AI solutions or are just starting to explore the possibilities, this checklist will help you assess where you stand and plan strategically for 2024.

Assessing Your Current State

Before looking ahead, take stock of where your business stands with AI today.

Technology Audit

Current AI Tools in Use

  • List all AI-powered tools and services your business currently uses
  • Include both obvious AI tools (chatbots, writing assistants) and embedded AI (email filtering, recommendation features in software)
  • Note the monthly cost for each tool

Effectiveness Evaluation

  • Which tools are delivering measurable value?
  • Which are underutilized or disappointing?
  • Are there redundancies where multiple tools serve similar purposes?

Integration Assessment

  • How well do your AI tools work with existing business systems?
  • Are there data silos preventing AI from accessing important information?
  • What manual workarounds have you developed due to integration gaps?

Skills and Knowledge Inventory

Team Capabilities

  • Who on your team has experience with AI tools?
  • Have any employees shown particular aptitude or interest in AI?
  • What training have team members received this year?

Knowledge Gaps

  • What AI topics do you wish you understood better?
  • Are there specific use cases you’ve considered but felt unprepared to tackle?
  • How comfortable is your team with evaluating AI vendor claims?

Identifying Opportunities for 2024

With a clear picture of your current state, you can identify where AI can make the biggest impact next year.

High-Value Use Cases

Consider these questions for each area of your business:

Customer Service

  • How many hours weekly does your team spend on repetitive customer inquiries?
  • Could AI-powered chatbots or knowledge bases reduce this burden?
  • What customer service metrics would you want AI to improve?

Marketing and Content

  • How much time do you spend creating marketing content?
  • Which content types could AI help generate or improve?
  • Are there personalization opportunities you’re missing due to resource constraints?

Operations and Administration

  • What administrative tasks consume disproportionate time?
  • Where do data entry errors frequently occur?
  • Which processes involve manual data transfer between systems?

Sales and Revenue

  • How effectively are you using data to identify sales opportunities?
  • Could AI help with lead scoring or customer segmentation?
  • What insights about customer behavior would be valuable?

Prioritization Framework

For each opportunity identified, assess:

  1. Impact: How significantly would this improvement affect your business?
  2. Effort: How complex would implementation be?
  3. Cost: What’s the expected investment required?
  4. Timeline: How quickly could you see results?

Focus on opportunities with high impact and reasonable effort for your first 2024 initiatives.

Budget Planning for AI

Approaching AI investment strategically will help you maximize returns.

Categories to Consider

Software and Subscriptions

  • AI-powered SaaS tools (writing assistants, analytics platforms)
  • API access for AI models
  • Platform fees for AI-enabled services

Infrastructure

  • Cloud computing costs for AI workloads
  • Hardware upgrades if running AI locally
  • Data storage for AI training and outputs

People and Training

  • Employee training programs
  • Consulting or implementation support
  • Potential new hires with AI expertise

Experimentation Budget

  • Set aside funds for testing new tools and approaches
  • Allow for some initiatives that may not succeed
  • Budget for proof-of-concept projects

Setting Realistic Expectations

AI investments often require several months to show full returns. Plan for:

  • Initial setup and learning curve periods
  • Iterative refinement based on early results
  • Gradual expansion as you gain confidence

Data Readiness

AI effectiveness depends heavily on data quality and accessibility.

Data Quality Check

  • Is your customer data clean and up-to-date?
  • Are there duplicates, inconsistencies, or gaps in key datasets?
  • When was your last data cleanup effort?

Data Organization

  • Can you easily access the data AI tools would need?
  • Are important insights trapped in spreadsheets, emails, or documents?
  • Do you have consistent formats and naming conventions?

Data Privacy Compliance

  • Are you compliant with relevant data protection regulations?
  • Do your data practices support AI use while protecting privacy?
  • Have you documented how customer data is used and stored?

Skills Development Plan

Investing in your team’s AI capabilities pays dividends.

Training Priorities

  • Identify 2-3 specific AI skills that would benefit your team
  • Research available training resources (online courses, workshops, certifications)
  • Schedule dedicated learning time

Practical Experience

  • Plan small AI projects that let team members learn by doing
  • Encourage experimentation with AI tools in low-stakes situations
  • Create opportunities to share learnings across the team

Vendor and Partner Evaluation

The AI vendor landscape is evolving rapidly.

Current Vendor Assessment

  • Review contracts and renewal dates for existing AI services
  • Evaluate whether current vendors are keeping pace with the market
  • Consider consolidation opportunities

New Vendor Research

  • Identify categories where better AI solutions may exist
  • Create evaluation criteria aligned with your business needs
  • Plan time for demonstrations and trials

Creating Your 2024 AI Roadmap

Pull everything together into an actionable plan.

Q1 2024 Focus

  • Complete any data cleanup or preparation work
  • Finalize budget allocations
  • Launch your highest-priority AI initiative

Q2 2024 Focus

  • Evaluate early results and adjust
  • Begin second wave of AI implementations
  • Conduct team training activities

Q3-Q4 2024 Focus

  • Scale successful initiatives
  • Explore more advanced applications
  • Plan for 2025

Final Thoughts

The businesses that will thrive with AI in 2024 are those that approach it strategically rather than reactively. Use this quiet end-of-year period to honestly assess your current state, identify meaningful opportunities, and create a realistic plan for the year ahead.

AI is not about implementing technology for technology’s sake. It’s about solving real business problems and creating genuine value for your customers and team. With thoughtful planning now, you’ll be well-positioned to make 2024 a year of meaningful AI progress for your small business.