With nearly 60% of small businesses currently using generative AI and 96% planning to adopt emerging technologies, artificial intelligence has become an essential entrepreneurial tool. Yet as more business owners experiment with AI, many are finding the hard part isn’t learning the technology itself—it’s sorting through the noise and navigating the many platforms to turn AI’s promise into practical results.
According to Bill Furlong, Founder and CEO of SquareStack and Author of “ASAP: AI in SMB,” the challenge with using AI successfully is “less about code and more about connecting the dots.” Based on his extensive experience working with and building tech solutions for small businesses, Furlong shared four practical ways for business owners to thoughtfully and strategically get started with AI.
Start simple
Start your AI journey by focusing on small, real-world tasks that help you save time or uncover areas for improvement. Furlong advised starting with a single file and a single question: Upload a financial report, a sales deck, or an internal form and ask AI to analyze it. Here are a few example scenarios and prompts you could apply to different parts of your business:
- Finance: “Here’s last quarter’s P&L. What trends or risks should I watch?”
- Sales: “Here’s our sales deck. Recommend improvements for clarity and conversion.
- HR/operations: “Create a first-year employee evaluation template tailored to our roles.”
- Training: “Draft a plan for how we’ll educate the team on using AI in our workflow.”
These questions can give you a starting point to build on the insights you gain from these initial prompts and identify additional use cases for AI.
“Upload it, ask it, learn from it,” said Furlong. “Momentum matters more than mastery.”
[Read more: Leveraging AI for Business Idea Testing and Improvement]
Make sure your tech tools talk to each other
Small businesses often rely on a patchwork of platforms for marketing, sales, accounting, scheduling, and operations. But without a way to integrate these various systems, it’s harder to get comprehensive, meaningful insights from AI. In fact, Salesforce research found that over 80% of IT leaders cite “data silos” as a hindrance to their digital transformation.
Small businesses that treat AI as an iterative process—not a one-and-done experiment—tend to see the strongest results.
Platforms like SquareStack act as a “translator” across a small business’s tech stack, using an agentic framework that connects and is trained on a company’s own software. This allows business owners to ask cross-functional questions and get answers that pull from all internal data sources rather than fragmented manual inputs.
One print shop Furlong works with built an agent that automatically compiles weekly ad performance from Instagram and Facebook and shares a summary with the team, which saves hours of manual reporting. A real estate firm created a similar agent to generate weekly reports from its scheduling software and agent workloads, which allowed them to balance showings and reduce bottlenecks.
“The magic isn’t in any one tool—it’s in how they talk to each other,” Furlong said.
Be intentional about the data you input (and where you’re feeding it)
In “ASAP AI,” Furlong reminds small businesses that AI is only as good as the data you give it, so it’s important to audit your inputs, set naming conventions, clarify decision rules, and keep your documentation fresh when incorporating AI into a workflow. By carefully controlling the flow of information into your AI tools, you and your team can use this technology safely, confidently, and with much greater accuracy.
This recommended approach involves what Furlong refers to as “internal AI”—AI platforms that work as a private personal assistant for your files, workflows, and use cases, with guardrails you build. External AI, on the other hand, are the public platforms that scrape your data and analyze you in “invisible, often manipulative, often unregulated” ways.
“If you can’t tell what the AI platform is doing with your input, it’s probably not acting in your best interest,” Furlong writes in his book.
[Read more: AI for Small Businesses: How to Stay Competitive]
Keep evolving and building on your AI outputs
Small businesses that treat AI as an iterative process—not a one-and-done experiment—tend to see the strongest results. Citing data from the U.S. Chamber of Commerce, Furlong noted that small businesses that commit to small, sustained adoption of AI see improvements in sales, profits, and hiring.
Furlong advised starting with a few concrete use cases and then evolving those workflows as you learn from the outputs. The goal is to let each AI interaction surface the next opportunity for improvement.
“You're never done with one prompt,” he told CO—. “It's amazing how the answers will reveal the next question for you.”
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