Jeff's Daily Dose: Meaty Info for National Pizza Day

If your Super Bowl spread didn't include pizza, the universe is giving you a mulligan.

Today is National Pizza Day. Yes, it's a real thing. And the deals are everywhere. 🍕

Pizza Hut has a $10 Big New Yorker. Domino's is running a mix-and-match at $6.99 per item. Little Caesars is knocking $2 off orders over $12. Papa Murphy's will take $10 off $25 with the code PZDAY26. Chuck E. Cheese is doing $5 large one-topping pizzas through Wednesday. And if you're feeling lucky, Sal's Pizza is selling 19-inch cheese pies for literally one cent to the first 100 online orders.

The full list (here it is) is longer than a CVS receipt. Bottom line ... you have no excuse not to eat pizza today.

Now here's where I deliver a different kind of slice...

Most companies approaching AI upskilling make the same mistake. They train everyone on the same tools at the same time & call it a strategy. That's not a strategy ... that's a pizza party without the pizza.

The leaders getting this right are doing something different. They're segmenting their teams by proximity to impact ... and it changes everything.

Not every role will be transformed by AI at the same speed or in the same way. Your marketing team's relationship with AI looks nothing like your finance team's. Treating them identically is like ordering one topping for 50 people ... someone's going to be unhappy.

Start by mapping your team into these 3 tiers.

Tier 1:

Immediate impact. These roles will change dramatically in the next 6 months. Think content creation, data analysis, customer support, SDRs. These folks need hands-on tool training now ... not a webinar, but actual workflow integration. Block 90 minutes this week to sit with your Tier 1 managers & identify the 3 tasks in each role that AI can improve today. Then assign a specific tool to each task. ChatGPT for drafting. Claude for analysis. Copilot for code. Get specific or nothing happens.

Tier 2:

Emerging impact. These roles will shift meaningfully in 6-18 months. They need foundational AI literacy plus exposure to use cases in their function. The move here is a monthly "AI Lab" ... a 60-minute working session where they bring a real problem & leave with a real prompt or workflow. Not theory. Not demos. Actual reps.

Tier 3:

Longer horizon. The work changes eventually, but not yet. A quarterly awareness session is enough for now ... save your training dollars where the dough rises fastest.

This tiered approach does 2 things. It makes your investment more efficient. And it reduces the anxiety that comes when people feel like they're drinking from a firehose.

Now here's the move that separates the contenders from the pretenders.

Pick your 3 "early adopter" people from Tier 1 and appoint them internal AI Champions. Give them 4 hours a week of protected time to experiment. Give them a $500 tool budget. Give them explicit permission to fail. Then have them run a biweekly "show and tell" where they demo what's working for the rest of the team.

I've seen this single move compress a 6-month adoption curve into 6 weeks. Why? Because people don't trust the CEO's slide deck about AI. They trust the colleague sitting next to them who just cut a 4-hour process down to 40 minutes.

One more tactical piece:

Create a shared doc ... call it your "AI Wins Log." Every time someone saves time, improves output, or eliminates a manual step using AI, they add it. With the task, the tool, and the time saved. Within 30 days, you'll have an internal playbook that no consultant could build for you. (And you'll have proof of ROI when your CFO starts asking questions.)

That's how you build a culture of learning ... not from the top down, but from the middle out. Not with a training mandate, but with visible proof that this stuff actually works.

What's the biggest obstacle you're facing when it comes to upskilling your team on AI ... is it budget, buy-in, knowing where to start, or something else? 🤷‍♂️

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