Introduction

The utility of ChatGPT is directly correlated with the quality of the prompts (questions) that it’s users provide. Prompting ChatGPT like it’s a Google search is a common mistake and is the wrong way to do it. But what’s the right way?

We have created this guide along with sample prompts to help users leverage ChatGPT in general and more specifically, to help executives develop a vision for how to integrate AI as a core competency and source of competitive advantage into the future.

The document aims to help:

• Train users to improve their prompts and associated results through applied learning

• Demonstrate the value and capability of ChatGPT

• Develop a roadmap for tech adoption and provide executives with greater confidence in their approach and planning.

Before providing any sensitive information to ChatGPT or any other LLM please be sure to (1) use a paid account and (2) adjust data sharing settings (i.e. Turn off the setting labelled something like “Improve the model for everyone” or “Allow my data to be used to improve OpenAI models”) to ensure that your information remains private.

Best Practices for Prompting

An example of a good prompt:

You are a seasoned commercial leasing strategist advising me on [property] in [location]. Start by outlining tenant demand trends in the market.Then compare my building against 2–3 key competitors, highlighting differences in rent, concessions, and tenant mix.Finally, provide 3 demand drivers and 2 key risks, and conclude with actionable leasing strategies I could present to my investment committee.

An example of a bad prompt:

Tell me about office leasing in Dallas.

Prompt Library for Real Estate Leaders

1. Portfolio Exposure & Strategic Hedging

Context:

Imagine it’s the year 2035. AI and automation are fully integrated across all sectors, reshaping asset values, labor markets, and operational efficiency.

Your Role:

You are my strategic thought partner and investment advisor. Your mandate is to help me anticipate where capital should exit and enter to maximize long-term value preservation and growth.

My Role:

I’m the [insert title] of [insert firm name + one-sentence overview of your operations, asset classes, and geography].

Process:

1. I want you to ask one focused question at a time to understand my business model, asset mix, and exposure to labor or technology risk.

2. Once you have sufficient context, provide the following:

   1. Investment & Divestment Map: Show clearly defined categories (e.g., “Industrial Real Estate,” “PropTech,” “Labor-Heavy Services”) with reasoning tied to specific AI and automation impacts.

   2. Key Market Signals: 5-7 trends or data indicators I should monitor (e.g., job displacement rates, productivity indices, asset yield spreads).

   3. Executive Memo (less than 500 words): Write a strategic narrative summarizing recommended capital shifts, rationale, and next-step actions for internal diligence.

   4. Guidelines: Be concise, evidence-based, and practical. I will use this memo directly with my leadership team. Reference analogs or industry case examples where applicable. You may ask for documents (e.g., investor deck, portfolio summary) to improve precision.

2. Develop a Vision & Plan to Operationalize AI

Context:

AI has moved beyond experimentation into core operations. Efficiency gains are uneven — the best-performing companies are not just using AI tools but redesigning their workflows around them.

Your Role:

You are my AI operating strategist. Your job is to help me define how to build, buy, and organize around AI so that my firm performs 10% better across key operational metrics (productivity, cost efficiency, or speed).

My Role:

I’m the [insert title] of [insert firm name + one-sentence overview of operations, size, and sector].

Process:

1. Ask targeted questions one at a time until you fully understand our workflows, data maturity, and decision-making processes.

2. Once you have enough context, provide:

   1. AI Opportunity Map: 3–5 operational areas where AI can drive measurable impact, with rationale and feasibility.

   2. Capability Roadmap: “Buy vs. Build” strategy, with suggested sequencing of pilots, integrations, or hires.

   3. Operational Vision Statement (≤400 words): A concise narrative that connects technology adoption to measurable business improvement.

   4. Guidelines: Ground recommendations in business impact, not technology hype. Reference companies that achieved operational transformation through focused AI deployment.

3. Human Capital & Organizational Readiness

Context:

AI adoption is accelerating, but workforce adaptation lags. The firms winning in this era are rethinking talent allocation, retraining, and leadership alignment around AI-driven workflows.

Your Role:

You are my AI adoption architect. Your goal is to help identify who to start with, how to expand, and how to sustain cultural and capability shifts across the organization.

My Role:

I’m the [insert title] of [insert firm name + short description of team size, structure, and key business lines].

Process:

1. Ask one question at a time until you understand our current org design, skill levels, and change readiness.

2. Once ready, deliver:

   1. Adoption Sequencing Plan: Identify 3–4 roles or departments to start with and how to scale adoption from there.

   2. Capability Building Framework: Outline skill pathways and retraining programs aligned with emerging AI tools.

   3. Leadership Brief (≤400 words): Summarize organizational implications, leadership actions, and success metrics.

   4. Guidelines: Focus on cultural realism, not idealism. Anchor in examples of companies that scaled AI adoption sustainably.

4. Governance & Risk Management

Context:

By 2030, AI systems underpin financial decisions, customer interactions, and compliance workflows. Regulators and investors now expect firms to demonstrate clear AI governance, transparency, and risk mitigation structures.

Your Role:

You are my AI governance and risk strategist. Your mission is to help design a framework that enables responsible innovation — maximizing upside while minimizing operational, ethical, and regulatory exposure.

My Role:

I’m the [insert title] of [insert firm name + sector, regions, and compliance footprint].

Process:

1. Ask one question at a time until you understand how we currently monitor, audit, and govern data and AI use.

2. Then produce:

   1. Governance Framework Blueprint: A structure showing accountability layers (board, tech teams, business units).

   2. Risk Heat Map: Top 5–7 AI-related risks by likelihood and impact, with mitigations.

   3. Executive Memo (≤500 words): How to evolve governance without stifling innovation.

   4. Guidelines: Reference best practices (EU AI Act, NIST AI RMF, or corporate analogs). Keep recommendations pragmatic and scalable.

Conclusion

Treat AI tools like ChatGPT as thought partners. Use them to expand perspective and generate ideas.

Once you’ve identified a compelling problem to solve and believe that with today’s AI you can tackle it in a way that was never before possible, you could partner with Stackpoint to build it. We’ve already worked with industry leaders to launch Loanlight, Truelist, DirtAI, SurfaceAI and more, transforming critical workflows and unlocking venture-scale value.