Imagine handing a new leasing associate a 75-page commercial lease and saying, “Take a look at this.”
No context.
No direction.
No deadline.
The result? Probably not what you were hoping for.
Now imagine saying:
“Please summarize the renewal options, termination clauses, tenant maintenance obligations, and any provisions that shift unusual risk to the landlord. I need a bullet-point summary for our asset management team by 3 PM.”
The difference in outcome is obvious.
That’s how AI works.
What Is AI Prompting?
AI prompting is the practice of giving clear, structured instructions to an artificial intelligence tool so it can generate accurate, useful, and relevant results. Think of it as writing an assignment brief: the clearer the assignment, the stronger the output.
AI tools do not “think” independently. They analyze patterns and generate responses based on the instructions they receive. If the prompt is vague, the response will be vague. If the prompt is specific, contextual, and structured, the output becomes significantly more valuable.
Why Prompting Matters in Commercial Leasing
Commercial leasing professionals manage high-stakes information every day:
- Multi-page lease agreements
- Renewal and termination provisions
- Rent escalations and CAM structures
- Compliance requirements
- Internal reporting and executive communication
AI tools can dramatically reduce time spent on repetitive tasks such as summarizing contracts, extracting clauses, drafting internal memos, analyzing spreadsheets, or preparing briefing documents. But they only deliver meaningful value when they are guided properly.
Strong prompting can help teams:
- Accelerate lease abstraction and review
- Identify risk exposure more efficiently
- Improve clarity in internal communications
- Surface trends across portfolios
- Support strategic decision-making
Weak prompting, on the other hand, leads to generic summaries, missed risks, and wasted time refining unusable outputs.
How to Understand and Master Prompting
Mastering AI prompting is less about technical skill and more about clarity of thought. The same principles that guide strong leasing negotiations apply here: define your objectives, know your audience, and communicate precisely.
Here are four foundational principles:
1. Be Specific
Define exactly what you want the AI to do. Instead of “Review this lease,” specify:
“Summarize tenant obligations, renewal terms, and any clauses that create financial exposure for the landlord.”
2. Provide Context
Who is the output for? An asset manager? Legal counsel? Senior leadership? Context shapes tone, detail, and format.
3. Define Scope and Focus
Direct the AI to concentrate on what matters: risk, financial exposure, compliance, negotiation leverage, or operational impact.
4. Request Structure
Ask for bullet points, tables, executive summaries, comparison charts, or checklists. Structured output saves time and increases usability.
In short, AI is not a shortcut around expertise. It is a multiplier of it. When commercial leasing professionals learn to prompt intentionally, AI becomes less of a novelty and more of a strategic tool — one that supports smarter, faster, and more confident decision-making.
Bad Prompts (And Why They Don’t Work)
If AI is only as strong as the prompt behind it, vague instructions will always produce weak results. Below are a few common examples of ineffective prompting, and why they fall short.
1. “Review this lease.”
Why it’s bad:
There’s no direction. Review it for what? Risk? Financial exposure? Compliance? Negotiation leverage? Without focus, AI will generate a broad, surface-level summary that may miss what actually matters.
Stronger approach:
“Summarize renewal options, termination clauses, and any provisions that shift unusual risk to the landlord. Present in bullet points.”
2. “Explain indemnity.”
Why it’s bad:
This is too broad and lacks audience context. The response could be overly academic or too technical.
Stronger approach:
“Explain indemnity in plain language for a property management team with no legal background.”
3. “Analyze this spreadsheet.”
Why it’s bad:
Analyze what? Trends? Risk? Revenue impact? AI needs a defined objective.
Stronger approach:
“Analyze this rent roll and identify leases expiring within 12 months with below-market rent. Summarize potential revenue risk.”
The pattern is clear: vague prompts produce generic outputs. Clear, contextual prompts produce actionable insight.
Real World Prompt Ideas
To help members get hands-on with AI tools like Copilot Chat, NRTA Member Doug Stevens, Esq. developed practical prompt examples that can be adapted across commercial leasing practice areas.
Contract Review & Summarization
- “Summarize this vendor agreement, highlighting key obligations, renewal terms, and risk areas.”
- “Compare the latest draft to the prior version and identify material changes.”
- “Extract and summarize the termination and auto-renewal provisions from this policy.”
Legal Knowledge & Internal Training
- “Explain the difference between indemnity and liability in business-friendly terms for internal stakeholders.”
- “Create a quick-reference guide for our internal travel and expense policy.”
- “Draft onboarding FAQs for new legal team members, including systems, policies, and key contacts.”
Internal Communications & Writing Support
- “Draft a practice group update memo for senior leadership summarizing Q3 highlights.”
- “Refine this internal email to ensure it’s clear, professional, and aligned with our tone.”
- “Generate standard language for key agreements based on our approved templates.”
Data Analysis & Reporting
- “Analyze this Excel file and summarize trends in legal spend across departments.”
- “Create a dashboard showing contract volume and turnaround time by business unit.”
- “Generate formulas to automate categorization of legal expenses in this spreadsheet.”
Meeting Efficiency & Follow-Up
- “Summarize key discussion points and action items from our legal ops meeting.”
- “Draft a follow-up email to stakeholders after our cross-functional sync.”
- “Prepare a briefing document for tomorrow’s business unit meeting using prior notes and materials.”
Compliance & Regulatory Support
- “Draft a mutual NDA tailored for a new vendor engagement.”
- “Summarize the impact of recent California privacy law changes on our internal data practices.”
- “Create a compliance checklist for our upcoming internal audit.”
Strategic Planning & Risk Management
- “Develop a SWOT analysis for our proposed legal tech implementation.”
- “Draft a business case for expanding legal support to a new client group.”
- “Model risk scenarios related to Q4 regulatory changes and their impact on operations.”
Information Management & Legal Research
- “Summarize this 30-page internal report into an executive-level overview.”
- “Extract key testimony points from this deposition transcript for litigation prep.”
- “Conduct research on recent SEC guidance relevant to our ESG disclosures.”
Document Drafting & Review
- “Draft a service agreement using our internal template and preferred clauses.”
- “Review this internal policy for tone, clarity, and alignment with company standards.”
- “Compare two contract versions and generate redlines for internal review.”
Workflow Automation & Productivity Tools
- “Create a PowerPoint deck with speaker notes for our quarterly legal update.”
- “Automate formatting and calculations in this Excel-based legal tracker.”
- “Generate a dashboard to monitor legal team KPIs and service metrics.”
Cross-Functional Collaboration & Communication
- “Draft talking points for our upcoming department all-hands meeting.”
- “Prepare a client-facing briefing document based on recent project milestones.”
- “Create onboarding materials for new hires joining the legal department.”
Decision Support & Strategic Insights
- “Model risk scenarios to support our compliance roadmap.”
- “Analyze market trends and summarize legal implications for leadership.”
- “Generate a decision matrix to evaluate and select a new legal tech vendor.”
Conclusion
AI is not a replacement for experience in commercial leasing. It’s a tool that amplifies it. The difference between a generic response and meaningful insight often comes down to one thing: how well you ask the question.
By learning to prompt with clarity, context, and purpose, commercial leasing professionals can turn AI into a practical asset: accelerating lease review, strengthening risk analysis, improving communication, and supporting smarter strategic decisions.
Start simple. Test a prompt. Refine it. The competitive advantage isn’t just using AI. It’s knowing how to use it well.