How to Train Your Team to Think With AI—Not Just Use It

Let’s talk about one of the most important (and overlooked) skills in commercial real estate today: AI intuition. 

We're all seeing the explosion of artificial intelligence across business sectors. In CRE, it’s showing up in rent roll analysis, refinancing scenarios, offering memo summaries, lease abstraction, even investor communication drafts. Adoption is happening, and it's happening fast. 

But here’s the hard truth: Using AI is not the same as thinking with AI. 

It’s easy to get your team set up with ChatGPT, a few plug-ins, or an AI-powered financial modeling tool. What’s not easy is building a team that knows how to think alongside those tools, questioning them, guiding them, and applying their outputs with judgment and domain expertise. 

Why This Matters in CRE 

Commercial real estate is a uniquely complex and regulated industry. There are moving parts in every deal: equity structures, loan covenants, tax strategies, operating partners, local market dynamics, and forward curves that change by the hour. 

Generic AI can look impressive on the surface, but without understanding the nuances of CRE, it can lead to oversights that aren’t just costly; they’re damaging to reputation, investor trust, and decision timelines. 

That’s why training your team to think with AI and not just use it is the next frontier of leadership and competitive advantage in CRE. 

What It Means to “Think With AI” 

Thinking with AI is about integrating it into your team’s decision-making process without outsourcing critical thinking. 

Here’s how you build that: 

1. Train for Judgment, Not Just Usage 

It’s not enough to know how to generate a prompt or use a prebuilt model. Train your team to ask: 

  • Is this the right model for the problem? 

  • Are these assumptions valid? 

  • What’s missing in this AI-generated output? 

  • Would I sign off on this if my name were on the line? 

2. Make AI Part of Strategic Conversations 

When discussing a refinancing option or acquisition model, bring AI into the room as a thought partner. Make it a standard part of your workflows. Let the team analyze where AI added clarity or confusion. 

3. Benchmark Against Human Intelligence 

Encourage your team to compare AI outputs to their own analysis and experience. Don’t just accept the answer. Ask: 
"Would we arrive at the same conclusion using just our own judgment?" 
This keeps the human-in-the-loop where it belongs: at the top. 

4. Foster Creative Problem-Solving 

AI is a tool. But the real unlock is in the questions your team asks it. Train your team to be curious, creative, and scenario-driven. Teach them to iterate and refine their prompts based on market feedback. 

5. Use Real CRE Scenarios, Not Hypotheticals 

Build your training and development around actual operating challenges: 

  • How would AI help underwrite this specific asset? 

  • Can it improve how we evaluate a forward curve scenario? 

  • Will it flag inconsistencies in our offering memo or cashflow forecast? 

The more you ground AI usage in your data, your models, and your market dynamics, the faster your team will build real intuition. 

The Risk of Not Evolving 

Here’s the big risk: if your team doesn’t build this muscle, they’ll fall into one of two traps: 

  • Blindly trusting AI and making avoidable mistakes, or 

  • Avoiding AI altogether and falling behind more nimble, tech-enabled competitors. 

Neither of those outcomes is acceptable in today’s CRE environment. 

The firms that win over the next few years will be those that merge human insight, data fluency, and AI intuition. These teams will be able to move faster and smarter because of it. 

What This Means for CRE Leaders 

As a leader, your job is to build capabilities and not just choose tools. 
That means: 

  • Encouraging experimentation 

  • Embedding AI into cross-functional collaboration 

  • Supporting ongoing learning 

  • Reinforcing that human judgment still leads the way 

This isn’t just a tech upgrade; it’s a leadership shift. And your teams aren’t just executing tasks anymore; they’re interpreting intelligence and deciding what to do with it. 

So here’s the question: How are you helping your team build stronger AI judgment?