Emma Grede has built billion-dollar brands with the Kardashians, sits on the Obama Foundation board, and is one of the sharpest operators in fashion and retail.
But when Mark Cuban pulled out his phone and showed her the 60 AI apps he had installed, she had to laugh and admit:
“I’ve been using AI like a 42-year-old.”
- Emma Crede, Self-made multimillionaire behind $4 billion Skims empire
That line (from her interview with Fortune) is funny because it’s honest. It’s also a mirror moment for every business leader right now.
You probably think you’re keeping up with AI because your team is using it.
But are you personally fluent? Or are you watching from the stands while others play the game?
Here’s the truth: if you’re not hands-on with AI yourself, you’re already behind.
The Illusion of AI Readiness
A lot of executives mistake their team’s adoption for their own readiness.
Marketing is experimenting with ChatGPT.
Finance has found a way to make reports faster.
Someone in customer service built a bot that saves 30 minutes a day.
Great. But let’s be blunt: none of that means you understand what’s possible.
Leaders often end up in what I call “spectator mode.”
They’re watching the game, cheering their team on, but never picking up the ball. And let’s be honest…cheering from the sidelines doesn’t make you an athlete. If it did, I’d have a gold medal in musical theater.
The problem? Spectators don’t shape the playbook. They don’t see the unexpected moves. They don’t drive the competitive advantage.
And that’s dangerous.
Because AI isn’t a side project. It’s shaping the way companies sell, serve, and scale right now.
👉 Want a quick maturity snapshot?
Check out Ready or Not? Let’s Talk About Your AI Readiness for a straight-talking view of where you really stand.
Why Delegating Isn’t Enough
Delegating AI exploration feels efficient — let the younger, tech-savvy folks play around, right? Wrong. Handing AI off to the ‘digital natives’ on your team is like asking your teenager to explain TikTok trends or emojis — you’ll get half the story and all the eye rolls.
Here’s why:
Innovation gets watered down. By the time insights bubble up to you, the magic has been averaged out.
You don’t know what to ask for. If you’ve never prompted an AI tool yourself, you can’t tell whether the answer your team gives you is the best answer or just a decent one.
You miss the leadership moment. Culture starts at the top. If you’re not visibly curious and engaged, your team will treat AI like a side hustle instead of a core skill.
If you want adoption, model it. Try Show & Fail — let your team watch you prompt, flub, fix, and learn out loud. Learning together beats hiding mistakes. Collaboration beats isolation.
Emma Grede spotted this gap herself. She incentivized her staff with cash bonuses for using AI (smart move) and it completely transformed their work.
But she realized she’d let them become the experts while she was stuck at “search engine” level. That’s not leadership.
The Competitive Pressure Is Real
Mark Cuban put it bluntly on Emma’s hit podcast show Aspire:
“If you don’t get your hands on AI, you’re already falling behind. That’s like saying back in the day, ‘I don’t need a PC. I don’t need the internet. I don’t need a cell phone.”
- Mark Cuban - American Businessman and Shark Tank star
He’s not exaggerating.
Think back to leaders who dismissed the internet, email, or smartphones. They didn’t just fall behind — they became irrelevant.
Bill Gates recently admitted AI is moving faster than even he expected. Former Google execs are warning that CEOs celebrating efficiency gains today might be tomorrow’s cautionary tales.
This is not about hype. It’s about pace.
The companies where leaders embrace AI are already pulling ahead. The ones where leaders hesitate are writing their own “too late” case studies.
Your First 3 Moves
So, how do you close the gap between knowing you should use AI and actually doing it? You don’t need 60 apps on your phone like Cuban.
You just need to start.
1. Experiment yourself
Spend 15 minutes this week playing with an AI tool. Don’t overthink it. Ask it to solve a problem, analyze a dataset, or draft a scenario. The point is to get hands-on.
👉 Not sure what to type? Try my PREPARED framework so your prompt has teeth, not fluff.
2. Apply AI to a decision, not just a task
Next time you’re weighing a big choice — pricing, product launch, expansion plan — use AI to test assumptions or surface blind spots. Don’t outsource this. See what it feels like to make a strategic decision with AI as your copilot.
👉 Want a simple way to structure this? Use my 20-60-20 framework: you set the context, AI does the heavy lift, you polish the result.
3. Commit to AI fluency, not just awareness
Make a plan to actually learn AI — not at a coding level, but at a leadership level. This is about understanding capabilities, asking better questions, and leading smarter conversations. You don’t need to code a robot army, but you do need to know enough to stop looking like you’re sending faxes in a Slack world.
Why This Matters
“Your team can’t outrun your blind spots. If you’re only dabbling in AI while competitors are designing strategy around it, you’ll eventually lose.”
Emma Grede didn’t need Cuban’s 60 apps. She needed that spark to get into action. And many leaders do too. The wake-up call isn’t about AI itself — it’s about leadership.
If you’re not experimenting, not learning, not leading on this… you’re risking more than productivity. You’re risking relevance.
What’s Next
Your Homework
If this post felt like your own wake-up call, here’s where to go from here:
- Take my AI Readiness Assessment to see exactly where you are on the adoption curve and what to do next
- Join my weekly AI Newsletter for the latest strategies, tools and ideas on using AI to sell more, serve better and think smarter
Next week, we’ll bust the biggest myth in AI: that it’s just about productivity.
Spoiler alert: it’s not.