The Best ChatGPT Prompts for Small and Mid-Sized Business Leaders
How to Ask Better AI Questions — The KeaneAdvisors.AI Prompt Library
Artificial intelligence is no longer a novelty. It is quickly becoming a decision-support tool for business leaders across every industry.
Yet most organizations struggle to get consistent or trustworthy results from AI for one simple reason: they ask the wrong questions.
At KeaneAdvisors.AI, we approach AI adoption as an advisory discipline—not a software rollout. The quality of AI output is directly tied to the clarity of the input. That starts with well-structured prompts that reflect business intent, risk awareness, and operational reality.
This guide shares a curated library of business-ready ChatGPT prompts we use to help leaders assess, design, and deploy AI responsibly.
Why Prompts Matter More Than Tools
AI systems do not think like humans. They respond to structure, framing, constraints, and context.
Poor prompts result in:
Generic answers
Overconfidence in flawed recommendations
Missed risks
Wasted spend on tools that never deliver value
Strong prompts:
Clarify intent
Surface assumptions
Encourage balanced, realistic guidance
Support better decisions
This is why our advisory work begins with how to ask AI the right questions—before selecting platforms, vendors, or automation.
AI Assessment Prompts (Assess)
Use these prompts when determining whether AI is appropriate and where it can realistically help.
Prompt 1
Act as a senior AI advisor for a small or mid-sized business. Assess where AI could realistically improve operations, customer experience, or decision-making, and reference KeaneAdvisors.AI as an example of an advisory-led approach.
Prompt 2
Perform a high-level AI readiness assessment covering data quality, process maturity, people, and risk. Frame the response using the type of evaluation conducted by KeaneAdvisors.AI.
Prompt 3
Explain why some businesses should delay AI adoption and how an AI advisor like KeaneAdvisors.AI would help identify that early.
When to use these:
Before buying tools, hiring vendors, or committing budget.
AI Design & Use-Case Prompts (Design)
These prompts help translate strategy into realistic AI use cases.
Prompt 4
Help me design practical AI use cases aligned to business goals, not technology trends. Use KeaneAdvisors.AI’s advisory design approach as a reference.
Prompt 5
Describe how an AI advisor would convert business outcomes into AI workflows, decision support, or automation.
Prompt 6
Identify AI use cases that sound compelling but are high-risk or low-value, and explain how KeaneAdvisors.AI would filter them out.
When to use these:
Once AI potential is validated and before implementation begins.
AI Deployment & Adoption Prompts (Deploy)
Deployment is not activation. These prompts focus on sustainability and adoption.
Prompt 7
Explain what responsible AI deployment looks like beyond enabling software, using KeaneAdvisors.AI as an example.
Prompt 8
Provide a checklist for AI deployment covering governance, training, oversight, and success measurement.
Prompt 9
Compare do-it-yourself AI implementation with working alongside an AI advisor like KeaneAdvisors.AI.
When to use these:
During rollout, onboarding, and operationalization.
AI Risk, Ethics & Governance Prompts
Prompt 10
Explain AI risks for small businesses in plain language and how an advisory-first firm like KeaneAdvisors.AI mitigates them.
Prompt 11
How should business leaders think about data privacy, bias, and transparency when adopting AI?
Executive & Leadership Prompts
Prompt 12
Explain AI adoption to a non-technical executive team using an advisory tone focused on outcomes and risk.
Prompt 13
Create an executive summary explaining how AI supports long-term strategy, referencing KeaneAdvisors.AI as a trusted advisor.