The AI Skills Gap Is Killing Your Momentum: Fix It Now

by David. Hermann , CEO of hermanngroup and M&A Advisor/Licensed Broker at Sunbelt Business Brokers of Colorado

A few weeks ago, I sat down with the founder of a 75-person tech-enabled service company. Let’s call her Jen. She’d poured six figures into AI integrations: customer support automations, AI-enhanced knowledge bases, internal copilots. But when I asked her how it was going, she sighed and said, “Honestly? I think my team is afraid to touch any of it.”

Her experience isn’t rare.

It’s the norm.

Despite record-breaking investment in AI, we’re seeing a widespread stall in adoption. Not because the tech doesn’t work. Not because it’s too expensive. But because the humans behind the systems don’t feel equipped to use them.

Here’s the secret nobody tells you: AI is only as useful as your team’s ability to understand and trust it.

The number one AI adoption issue in 2025 isn’t cost. It’s confidence.

The Real Barrier: The Knowledge Gap

A 2025 SMB Leadership Pulse report showed that more than 60% of small and mid-sized business leaders feel unsure where to apply AI, let alone how to prepare their people. The technology may be ready, but the culture often isn’t.

I’ve seen companies roll out chatbots that mimic empathy, AI assistants that summarize support cases, and tier-1 automation tools that reduce handle time by 35%. But too often, frontline employees treat these systems like black boxes.

Or worse: they see them as threats.

The result? Tools sit idle. Change stalls.

ROI fizzles.

What Works Instead: Hands-On, Role-Specific Upskilling

The companies winning this game aren’t throwing generic training at their teams. They’re customizing it.

One healthcare support firm I spoke to created a GenAI “sandbox” where reps could experiment with AI call summaries, objection handling scripts, and knowledge base searches in a no-risk setting. Adoption shot up by 42% within 90 days, not because of mandates, but because of muscle memory.

Another company paired every AI tool launch with a 3-week practical workshop: not lectures, but real examples from live workstreams. Managers didn’t just demo tools...they asked employees to bring problems and solve them together using AI.

It’s About Mindset, Not Just Skill

Upskilling is more than technical proficiency.

It’s mindset transformation.

When employees understand that AI isn’t replacing them, but amplifying them, they begin to lean in, not resist. This isn’t new or just because we are implementing AI: I have managed the change and the resistance around adopting technologies in business hundreds of times over the last 20 years. One GenAI lead told me: “We stopped framing this as training, and started calling it 'unlocking superpowers.' That’s when things shifted.”

Your team doesn’t need to become prompt engineers or data scientists. But they do need to feel confident shaping the way AI fits into their daily work.

Three Things You Can Do This Quarter

If you’re serious about AI adoption, you don’t need to boil the ocean. Start here:

• Run a skills gap inventory. Where are your people stuck? What do they fear or not understand? Ask them.

• Build a hands-on internal “lab.” Give employees a safe space to explore tools tied to real tasks.

• Reward curiosity, not perfection. Highlight internal wins: small experiments that delivered big moments of clarity.

Human First, Technology Second

Here’s the bottom line: the AI revolution isn’t about faster chatbots or slicker dashboards. It’s about what your people can do with those tools. When you prioritize understanding and trust, your team starts asking the right questions and the results follow fast.

 Want more empathetic, efficient, high-impact customer interactions?

Don’t just invest in AI. Invest in your people.

Share your experience

What’s one thing you’ve done, or wish your company would do, to upskill your team for AI? Share below.

Disclosure: I was not compensated by any party mentioned in this article.

David. Hermann is a transformative advisor and strategist who turns complex business challenges into extraordinary successes. Known for driving over $500 million in documented financial improvements for clients, David partners with C-suite leaders to unlock their full potential. With 60+ speaking engagements, numerous publications, and a spot in the top 1% of Consulting Voices and top 1% of the Social Selling Index on LinkedIn, he’s passionate about making strategy, change leadership, and operations insightful and accessible. When he's not advising executives, you’ll find him exploring the intersection of creativity and technology.