What AI Can't Upskill For You, And What To Do About It

The obsession with AI literacy has produced a blind spot.

Everyone is racing to learn the tools, the prompting skills, the agents, and workflows. That's not wrong. But the practitioners getting the most out of AI share something that doesn't show up on a tools list. They have the judgment to know when an output is wrong, the creativity to ask questions the models haven't encountered, and the self-direction to act when no one hands them a plan.

The problem is that human skills require active investment to maintain, and many professionals are so focused on keeping up with AI that they've quietly stopped making that investment.

We asked five UNBOUND 2026 speakers the same question: as AI upskilling dominates the conversation, what's the one human skill people need most right now and aren't investing in enough? Here's what they said.

The Skill: Share What You Actually Care About

David Meerman Scott (Marketing Strategist)

The Blind Spot: Most people treat business communication as a performance of competence, keeping personal enthusiasm separate from their work identity. As AI generates more competent-sounding output for everyone, the actual human behind the work becomes the differentiator and most people have stopped showing that person.

"Not sharing your passions, the genuine enthusiasm you bring to your work and to what you love to do outside of work, means missing out on the most magnetic, human force in any team or organization and the counterpart to AI,” Scott shares.

Passion is visible and contagious in ways that polished output isn't. The more AI levels the floor on execution quality, the more the ceiling belongs to people who show up with real enthusiasm.

Try this: Instead of being all business on LinkedIn, consider sharing what you love to do, who you are, and what you're a fan of with your professional network.

“Without passion, you risk becoming replaceable and uninspiring, blending into a sea of sameness just as AI commoditized routine skills." — David Meerman Scott

The Skill: Self-Leadership

Jen Spencer (Chief Growth Officer, Booth)

The Blind Spot: Decades of management structure have conditioned professionals to wait for direction before acting. AI is making this habit worse by positioning itself as the source of the next right answer, which means fewer people are practicing the capacity to decide and move without a green light.

"We've gotten comfortable waiting to be told what to do, and AI is making that worse by selling the idea that the right answer is always one prompt away,” Spencer adds.

Without self-leadership, your growth trajectory ends up controlled by how much attention someone above you can spare. And the work that fills that gap is exactly what AI is best positioned to absorb.

Try this: Choose one problem you've been waiting on someone else to address. Take a real first step on it this week, then loop in whoever would normally own it after you've already started.

"Almost nobody is practicing the thing that actually moves a career or a company: deciding to lead yourself when no one is coming to do it for you." — Jen Spencer

The Skill: Creative Thinking

Beth Dunn (Head of Product Experience, Agent.ai)

The Blind Spot:: AI produces output that is, by design, statistically probable. It’s a synthesis of what has already been said. That makes it useful for execution and dangerous as a creative starting point. Professionals who rely on it for ideation are training themselves out of the capacity to think originally.

“AI is still an 'average' machine. It's very good at giving you the most probable answer based on what you've told it and trained it on so far,” notes Dunn.

The longer you go without generating original ideas—messy, impractical, weird ones included— the harder it becomes to access that capacity when a new problem actually requires it.

Try this: Set aside 15 minutes a day to write something with no purpose. Think, stream of consciousness, strange observations, whatever comes out. The point is to keep the creative muscle working on its own terms, separate from any deliverable.

“New problems require new thinking, not old answers that revert to the mean. If you outsource your creativity, your creative thinking will die." — Beth Dunn

The Skill: Emotional Discernment

Karen McFarlane (Founder, CMO, Board Director; Kaye Media Partners)

The Blind Spot:: Data has always been easier to act on than observation, and AI makes data faster and more abundant than ever. The result is that leaders are increasingly making decisions based on what's measurable rather than what's actually happening, and those two things are rarely the same.

"AI can hand you reams of data on low performance, but it can't tell you if the team feels unmotivated or undervalued. It can't tell you your team leader has stopped raising new ideas in meetings because her team is burned out and can't take on anything new. That only comes from sitting in the room, not from the data,” McFarlane adds.

Data tells you something is wrong, but discernment tells you why. When leaders skip the observational work in favor of the analytical, they often end up solving the measurable symptom rather than the actual problem.

Try this: Show up to one meeting this month that you'd normally skip or delegate. Afterward, write down one thing you learned that wouldn't have appeared in any report or dashboard.

“Never let AI output be the last step before a decision. Without discernment, you may end up with a solution that was never aimed at the right problem.” — Karen McFarlane

The Skill: Curiosity and Humility

Eric M. Bailey (President, Bailey Strategic Innovation Group)

The Blind Spot: In a world where everyone has access to the same tools and information, the instinct to project certainty becomes a liability. Efficiency at processing information is table stakes when everyone has access to the same tools. The ability to stay curious about people is where real differentiation happens.

"We spend so much of our conscious time projecting our intelligence, our rightness, and our certainty. In a world where everyone has the same access to the same technology and information, our ability to know and understand people becomes the true differentiator,” Bailey adds.

Certainty closes off the information that would have changed your answer. Curiosity keeps that channel open, and in roles that depend on persuasion, relationships, or judgment calls, that channel is the work.

Try this: In a meeting, review, or conversation, ask a follow-up question when you'd normally move on. Resist the pull toward resolution long enough to find out what you'd have missed.

“By turning to judgment and certainty rather than curiosity, we miss out on building connections, relationships, and being truly persuasive." — Eric M. Bailey

Read these five responses together and the throughline is hard to miss. None of them are technical and every one points to a capacity that requires practice, exposure, and friction. Passion, self-direction, creative resistance, reading a room, staying open when you'd rather be right: these are the things AI can use as an input but cannot produce as an output.

Those who will benefit the most from AI advancement will be the ones who kept developing the human skills no tool can supply.

These are the conversations happening at UNBOUND in September. Catch these speakers, plus many other experts in their field as they share insights and takeaways powering the next era of growth.

Explore the UNBOUND agenda and register now.