How to stop overthinking AI and just start seeing value

For many of us in leadership, mastering AI can feel like an overwhelming swirl of promises, pitfalls, and “gamechanger” headlines every other day. According to Justin Massa, owner of Midwest Quality Consulting and former partner at IDEO, the key is simpler than you might think: dedicate a few days to hands-on experimentation then watch what happens.

In this conversation, Justin shares why companies need to stop waiting for some grand, multi-million dollar AI rollout. Instead, get scrappy. Start building “AI jigs,” the small, custom hacks that provide near-instant ROI and practical results. Below, we unpack his three-day approach, debunk some security fears, and outline how leaders can navigate the bigger strategic questions AI poses.

Meet Justin Massa: Consultant, board member, AI enthusiast

Justin has an eclectic background. He started consulting at IDEO, and now advises executives and small businesses on how to integrate GenAI effectively. He also sits on the board of the Northern Illinois Food Bank, weaving together humanitarian interests with cutting-edge tech. His mantra? “Learn AI by doing AI.” That’s the only way to truly understand it, he argues, especially if you’re a busy executive who’s not exactly a “spring chicken” in the digital realm. Justin’s top tip if you’re feeling stuck or intimidated: Set aside three consecutive days in your calendar to be at your desk, mostly meeting-free, and force yourself to use a generative AI tool for every single thing you do. Here's how to get started:

Pick a tool & pay for it- ‍Choose a frontier model like ChatGPT (Plus version), Claude 2, or another paid tier. Why pay? Because it often unlocks more features and better privacy settings, so you can worry less about data training

‍Use it for literally everything - Morning Emails? Ask the AI to rewrite them or give you a bullet-point summary of your inbox. Strategy Docs? Dump in transcripts or notes and let the AI brainstorm. Random Problem-Solving? Say, “Here’s a thorny issue from today’s leadership meeting, how would you approach it?”

‍Push through the awkwardness - Day 1 can feel clumsy and weird. You might not sleep great after Day 2 because you’ll realize how big AI’s implications are. By Day 3, you’ll have a tangible sense of how and where AI can help.

Justin’s top tip: “Set aside three consecutive days in your calendar to be at your desk, mostly meeting-free, and force yourself to use a generative AI tool for every single thing you do."

Stop learning from junior staff alone

One big mistake? Relying on junior employees to teach you AI best practices. Research shows that junior folks approach AI mainly from a “task” or “project” perspective. But as a senior leader, your lens is strategic: you need to see how AI shifts entire systems, processes, and potentially your competitive edge. If you only view AI as a “writing assistant” or a “code generator,” you’ll miss the bigger transformations. Senior leaders must develop an internal AI mindset through direct usage, so they can sense how it impacts strategy, operations, and the business model as a whole. Rather than waiting for the perfect enterprise-grade solution, Justin suggests adopting an “AI jig” approach: a riff on the idea that in a woodworking shop, you build quick “jigs” for specific tasks, for example:

Lightweight experiments: using GPT-based projects or agent frameworks for a couple of hours to automate a sales funnel task or create 100 test accounts for QA.
Immediate ROI: if it works well enough, great...you got your ROI on day one.
Iterate or discard: if it’s not good, you can toss it without major sunk costs.

Addressing security & training concerns

Worried about data leaks? Many executives fear “Samsung-like” fiascos where corporate info allegedly bled into an AI model. But Justin points out that those stories are often misunderstood or revolve around older, now-fixed vulnerabilities, such as paid tiers that usually let you opt out of training, and robust security certifications and compliance pages by major AI labs. In reality, the biggest threat might be human error, not the AI. That said, watch your input. For highly sensitive data, you might choose self-hosted or specialized enterprise models with advanced privacy controls.

Finding time to tinker and “expert-ify” yourself

“No one has used AI for 10,000 hours yet,” Justin reminds us. That means nobody is a true “expert.” The advantage? Anyone can become one, especially in the niche that matters for your business. He recommends three ways to grow your expertise. First, budget weekly play time to explore new models, agent frameworks, or code it unexpectedly spits out. Second, work on refining prompts. Accept that your first prompt might be 30% right. Keep iterating just like you would in a design sprint. And last but not least, stay curious! The frontier evolves weekly maybe even daily. Keep an eye on new developments and re-test your assumptions.

“Anyone can become an expert, especially in the niche that matters for your business.”

How to get started tomorrow

Step 1: Pick a model (ChatGPT, Claude, etc.) and pay for the premium tier.
Step 2: Set aside a few consecutive days where you can experiment relentlessly.
Step 3: Use it for everything: project summaries, rewriting emails, strategy sessions, random problem-solving.
Step 4: Identify your business’s core differentiation. Build a test or prompt library to gauge AI’s abilities in those areas.
Step 5: Rinse and repeat. The market is moving fast, and so should you.

“This wave is different,” Justin says. “Email revolutionized how we communicate; generative AI is about to revolutionize how we think, and it’s only 20 bucks a month.”

So, block out the calendar, give yourself permission to feel awkward at first, and see what unfolds. Because as Justin puts it, “We’re all beginners here. Let’s start exploring and become the experts our businesses need.”

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Want to hear more from Justin?

LinkedIn: Justin Massa
Website: Midwest Quality Consulting