Apr 14, 2025

What 40+ SMB Leaders Are Saying About Generative AI in 2025 (So Far)

Over the past five months, I've interviewed more than 40 leaders / owners of SMBs about the value they're finding, and not finding, with generative AI. Here's what I've observed new in the first quarter of this year.

1. From "on the list" to "top of the list"

In Q4 of last year, most leaders I spoke with had generative AI on their list of priorities, but it wasn't at the top of that list. Many of them referenced mainstream press articles about how AI improvement curves were flattening.

Since the start of this year, and especially the last 6 weeks, this has radically shifted. Figuring out how to identify and capitalize on generative AI opportunities seems to be at the top of every leadership team's priority list. At least in SMBs, budget for to accelerate generative AI is being allocated and spent.

2. Leaning into experimentation

Last year, I'd regularly be talking with a leader who would share an idea about how generative AI might help them. I'd ask if they'd tried it, and most would confess they hadn't attempted it. As they spoke, I'd turn on screen share and "prototype" their idea while they spoke.

While this still happens, it's a far less common occurrence this year. More and more, leaders are getting their hands dirty with generative AI, using the tools directly - and reaping the rewards.

3. Getting AI "into the room"

The objection / myth that "generative AI is going to train on / steal all our secrets" is increasingly less common (although not completely gone). More and more companies are getting serious about connecting their internal data to AI as well as diligently capturing transcripts of human conversations.

The organizations that are prioritizing this, even if their data is still "messy," are finding real value, fast. Don't let the perfect be the enemy of good enough.

My goal is to complete 100 of these interviews by the end of October of this year, and I'd love your help in figuring out who I should talk to next! Tag an SMB owner / leader that you think would benefit from one of these chats, or sign-up yourself if you haven't done one yet!

In these conversations, we’ll talk about what’s working well and creating value - and what seems to be AI snake oil. We’ll talk about the thing you’re dying for gen AI to be capable of - and the things you’re terrified it will be able to do.

I’d like to speak with folks who are directly involved in exploring, setting, activating generative AI strategy inside of your company. You're likely a director, VP, or member of the c-suite. Maybe you're running an SMB-sized business unit inside of a large, multinational.

✨ ✌🏻 ✨

Justin Massa
Ratings
justin-massa

Owner @ Midwest Quality Consulting

Chicago, IL

Publisher of AI for SMBs Weekly and founder of MQC, helping SMBs innovate with tech. Former SVP at Newlab and partner at IDEO. Board member at Northern Illinois Food Bank and 1848 Ventures.

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