AI Skills Training

This blog was originally featured on the September 25th, 2025 newsletter found here: INBOX INSIGHTS, September 24, 2025: AI Skills Training, Process Documentation with AI

How to Advocate for AI Skills Training

Today, let’s answer a reader question: “How do we convince executives and enablement leaders to invest in improving AI skills across the workforce?”

This is happening in organizations everywhere—executives are investing in AI technology while completely neglecting the human side of the equation. They love AI in theory, but they’re often blind to the fact that their people don’t know how to actually use it effectively.

Start with the Business Case, Not the Technology

When I work with teams trying to get executive buy-in for AI training, I tell them to flip their approach entirely. Don’t start with “We need AI skills training.” Start with “Here’s how our current skill gaps are costing us money and opportunities.”

Use the 5P Readiness Assessment from the AI Strategy Kit to document exactly where your team stands. This assessment evaluates your organization’s readiness across five critical dimensions: Purpose, People, Process, Platform, and Performance. When you can show leadership that 60% of your marketing team scores below a 3 on AI literacy, and connect that to slower campaign development or missed optimization opportunities, suddenly you’re speaking their language.

Connect Skills to Strategic Objectives

The Goal Alignment Worksheet is perfect for this. This tool helps you map your AI initiatives directly to specific business objectives, ensuring every AI investment has a clear strategic purpose. Take your organization’s current strategic priorities and map them against your team’s AI capabilities. If your company wants to increase personalization by 40% this year, but your team doesn’t know how to implement AI-driven content optimization, that’s a problem executives can understand.

For this, I recommend creating a simple visual (like a matrix) showing what your organization wants to achieve, what AI skills are required to get there, and where your current gaps exist. Make it visual. Make it obvious.

Quantify the Opportunity Cost

Nothing gets executive attention like lost revenue potential. Use the ROI Calculator to project what improved AI skills could deliver. This tool helps you quantify both the financial investment and expected returns from AI initiatives, translating operational improvements into dollars and cents. For example, if better prompt engineering could reduce content creation time by 30%, calculate what that means in terms of output capacity and cost savings.

But don’t stop there. Also calculate the cost of doing nothing. How much business could you lose to competitors who are leveraging AI more effectively? What opportunities are you missing because your team lacks the skills to execute?

Present a Phased Roadmap, Not a Wishlist

Executives hate open-ended training requests that feel like education for education’s sake. Instead, use the 12-Month AI Marketing Roadmap Template to show how skills development directly supports business milestones. This template helps you sequence AI initiatives across quarters while addressing all dimensions of successful implementation—from people development to platform integration.

Quarter 1 might focus on foundational prompt engineering tied to improving campaign development speed. Quarter 2 could tackle data analysis skills needed for better audience segmentation. Each phase should have clear business outcomes attached.

Address the Real Resistance Points

Let me be honest about what’s really happening in those executive meetings. Leaders are worried about training costs, time away from “real work,” and whether people will actually apply what they learn. They know you need the training, and they want you to have it. They are struggling to figure out how to make it work. This is where you can help. You need to address these concerns head-on.

Show them how the TRIPS framework can help prioritize where AI training will have the highest impact. TRIPS evaluates potential AI use cases across five factors: Time consumed, Repetition, Importance, Pain points, and Sufficient data availability. Demonstrate that you’re not asking for generic AI education, but targeted skill development that directly improves processes they care about.

Make it About Competitive Advantage

Frame AI skills as competitive intelligence. When your team can effectively use AI for market analysis, content optimization, and campaign performance prediction, you’re not just keeping up with competitors—you’re potentially leaping ahead of them.

The bottom line is this: executives will invest in AI skills when they see the direct connection between those skills and business results. Your job isn’t to convince them AI is important. Your job is to show them exactly how AI skills translate into the outcomes they’re already trying to achieve.

Stop asking for a training budget and start presenting skill development as the missing piece of their strategic puzzle. That’s when you’ll get their attention—and their investment.

Click here to get your free copy of the AI-Ready Marketing Strategy Kit

How are you making the case for more AI training? Reply to this email or join our free Slack group, Analytics for Marketers.

– Katie Robbert, CEO

Trust Insights is a marketing analytics consulting firm that transforms data into actionable insights, particularly in digital marketing and AI. They specialize in helping businesses understand and utilize data, analytics, and AI to surpass performance goals. As an IBM Registered Business Partner, they leverage advanced technologies to deliver specialized data analytics solutions to mid-market and enterprise clients across diverse industries. Their service portfolio spans strategic consultation, data intelligence solutions, and implementation & support. Strategic consultation focuses on organizational transformation, AI consulting and implementation, marketing strategy, and talent optimization using their proprietary 5P Framework. Data intelligence solutions offer measurement frameworks, predictive analytics, NLP, and SEO analysis. Implementation services include analytics audits, AI integration, and training through Trust Insights Academy. Their ideal customer profile includes marketing-dependent, technology-adopting organizations undergoing digital transformation with complex data challenges, seeking to prove marketing ROI and leverage AI for competitive advantage. Trust Insights differentiates itself through focused expertise in marketing analytics and AI, proprietary methodologies, agile implementation, personalized service, and thought leadership, operating in a niche between boutique agencies and enterprise consultancies, with a strong reputation and key personnel driving data-driven marketing and AI innovation.