What to Ask Before You Hire an AI Consultant for Your Real Estate Agency

Everyone’s an AI expert now.

Scroll LinkedIn for five minutes and you’ll find a dozen consultants promising to “transform your business with AI.” Half of them were crypto experts two years ago. The other half discovered ChatGPT six months ago, built a few automations for their cousin’s accounting firm, and now they’re pitching real estate principals on five-figure engagements.

Here’s the thing — AI genuinely can make a massive difference for real estate agencies. We’ve seen it firsthand. But the gap between a good AI consultant and someone who’s going to waste your money is enormous. And right now, there’s no accreditation, no industry standard, and no easy way to tell the difference.

So we wrote this article to arm you with the right questions.

These are the 10 questions every principal should ask before signing anything. We’ll also cover the red flags that should send you running, the green flags that signal genuine expertise, and — because we believe in radical transparency — exactly how we’d answer each question ourselves.

Use this to evaluate us. Use it to evaluate our competitors. We’re confident about where we land.

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The 10 Questions Every Principal Should Ask

1. “Can you show me ROI from a real estate client?”

Not “a client.” Not a café or a law firm or a generic small business. A real estate agency.

Real estate has specific workflows, specific software, specific compliance requirements, and a specific rhythm to how deals move. An AI consultant who’s delivered results for an accounting practice hasn’t proven they can deliver results for you.

Good answer: Specific numbers — hours saved on property descriptions, reduction in response time for buyer enquiries, measurable efficiency gains. They walk you through the before and after.

Bad answer: “We’ve worked with lots of small businesses” or vague “productivity gains” without specifics.

2. “What specific workflows will you implement?”

This is where vague consultants get exposed. “We’ll integrate AI into your business” means nothing. You need to hear specific workflows.

Good examples: automated property description drafting from listing data, AI-assisted buyer-match emails, follow-up sequence generation for open home attendees, vendor report drafting, social media content from new listings, review response management.

If they can’t name at least three to five workflows that are specific to how a real estate agency actually operates day-to-day, they’re selling you a concept, not a solution.

Good answer: “We’d start with property descriptions, buyer-match communications, and follow-up sequences — then expand based on where we find the biggest time savings.”

Bad answer: “We’ll assess your needs and find opportunities for AI.” That’s not an answer. That’s a stall.

3. “Do you know what CRM we use?”

This one’s a litmus test. If you mention you’re on Rex and they don’t know what that is, the conversation should be over. If they’ve never heard of Reapit, VaultRE, Agentbox, or Eagle, they haven’t worked in Australian real estate.

Your CRM is the backbone of your agency. Any AI implementation worth doing needs to work with your existing systems, not require you to rip them out and start fresh. A consultant who knows Australian real estate CRMs can talk about what integrates cleanly and what needs workarounds. A consultant who doesn’t is going to burn your time figuring out basics you shouldn’t be paying them to learn.

Good answer: “You’re on Rex? Great — we’ve built workflows that pull listing data directly from Rex to generate descriptions, vendor reports, and buyer communications.”

Bad answer: “What’s Rex?“

4. “Will we need to hire someone to maintain this?”

One of the biggest hidden costs of bad AI consulting is the aftermath. They build something clever, hand it over, and three weeks later it breaks because nobody in your team knows how to fix it. Now you’re either paying them ongoing fees or hiring someone technical.

Good AI implementations should be low-maintenance by design. Monthly check-ins to optimise and adjust, sure. But the day-to-day should run itself.

Good answer: “No. We build everything to run autonomously with monthly check-ins. Your team doesn’t need to touch anything beyond light review of outputs.”

Bad answer: “You’ll probably want someone technical on staff” — or worse, silence on the topic entirely.

5. “What happens if the AI gets something wrong?”

AI is powerful, but it’s not perfect. Anyone who tells you otherwise is lying or inexperienced. The real question isn’t whether the AI will make mistakes — it will. The question is what safeguards are in place.

This is especially critical in real estate, where a wrong price in a property description, an incorrect claim about a property’s features, or an off-brand message to a vendor can damage trust and potentially create legal exposure. If you want to understand more about common AI mistakes in real estate, we’ve written about that too.

Good answer: “Every client-facing output goes through a human review step. The AI drafts, your team approves. Over time the review gets faster — but it never disappears entirely.”

Bad answer: “Our AI is 99% accurate” — or any answer that doesn’t include the words “human review.”

6. “Are you selling us a platform or an outcome?”

This distinction matters more than almost anything else.

A platform is a software subscription. You pay monthly, you get access to tools, and it’s up to you to figure out how to use them. If it doesn’t work, tough — you’re still paying.

An outcome is a result. The consultant is accountable for delivering measurable improvements to your workflows, your efficiency, or your bottom line.

Some consultants are really just reselling software with a consulting wrapper. They’ll set you up on a platform, do some training, and move on.

Good answer: “We’re selling you outcomes — fewer hours on descriptions, faster response times, more consistent follow-up. You’re paying for results, not software.”

Bad answer: “You’ll get access to our proprietary AI platform” — especially if that platform comes with its own monthly fee on top of the consulting engagement.

7. “How long until we see results?”

This is a reality-check question. Anyone who promises overnight transformation is either lying or planning to implement something so surface-level it won’t move the needle.

Good AI implementation follows a predictable timeline. First workflows should be live within two to four weeks. You’ll feel it quickly — a property description that used to take 45 minutes now takes five, follow-up emails that fell through the cracks go out automatically.

Full impact — where AI is woven into daily operations — takes around three months. It takes time to refine voice, optimise workflows based on real usage, and build your team’s confidence.

Good answer: “First workflows in two to four weeks. Full impact in about three months.”

Bad answer: “You’ll see results immediately” or “it’s a six-to-twelve-month journey.” The first is unrealistic. The second is designed to maximise billable hours.

8. “What do you need from our team?”

Your team is already flat out. If an AI consultant needs 20 hours of your team’s time for workshops, interviews, and training sessions, that’s a significant hidden cost — and a sign their process isn’t very efficient.

The upfront investment should be minimal: two to three hours to capture your agency’s voice and communication style. After that, light ongoing review — glancing at AI-drafted content before it goes out and flagging anything that doesn’t sound right.

Good answer: “Two to three hours upfront, then maybe 15 to 20 minutes a day reviewing outputs. We do the heavy lifting.”

Bad answer: “We’ll need your team for a full-day workshop” or “we’ll need a dedicated point person.” That’s offloading work onto your team.

9. “Can we see it work before we commit?”

This might be the most important question on the list. A good consultant is confident enough in what they deliver to let you see it in action before you sign a contract.

That might be a free assessment where they audit your current workflows. Or a pilot project — one or two workflows implemented so you can see the quality firsthand.

If a consultant won’t let you see the work before you pay for it, ask yourself why.

Good answer: “Absolutely. We offer a free 30-minute AI assessment where we walk through your workflows and show you exactly what we’d implement.”

Bad answer: “We require a signed engagement before we begin any work.” In a market this new, you deserve proof before you pay.

10. “What do you do that we couldn’t do ourselves with ChatGPT?”

This is the real question. And honestly, it’s a fair one.

ChatGPT is incredibly capable. Your team can absolutely use it to write property descriptions and draft emails. So what does a consultant actually add?

Process. Knowing which workflows to automate and in what order. Building systems that run consistently without relying on one person remembering to open ChatGPT.

Integration. Connecting AI to your CRM, your listing data, your templates. Making it seamless rather than manual.

Voice-tuning. Training the AI to sound like your agency — not generic, not robotic, but genuinely on-brand.

Maintenance. Keeping it running, optimising over time, adapting as models improve.

You could do most of this yourself — if you had the time and technical knowledge. A good consultant is worth it because they’ve already done that work. Use our ROI calculator to see whether the numbers stack up for your agency.

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Red Flags: Walk Away If You Hear This

Not every AI consultant is dodgy, but here are the warning signs that should make you think twice:

• They promise to “replace” staff. Good AI augments your team. It takes repetitive tasks off their plate so they can focus on relationships and deals. Anyone promising to replace your property managers or admin staff with AI either doesn’t understand real estate or doesn’t care about the disruption they’ll cause.

• They can’t name specific real estate workflows. If the conversation stays at the level of “AI can improve your productivity,” they’re selling a concept, not a solution.

• They’re selling a platform, not outcomes. If the pitch centres on software you’ll be subscribing to — especially if it’s “proprietary” — you’re buying a product, not consulting.

• They have no real estate industry experience. AI expertise without industry context is incomplete. They’ll spend your money learning your business instead of improving it.

• They won’t do a free pilot or assessment. Confidence in your own work means being willing to prove it. If they won’t, ask yourself what they’re afraid you’ll see.

• They quote in the tens of thousands without a clear scope. A $30,000 engagement isn’t inherently wrong — but it should come with a crystal-clear scope, timeline, and expected outcomes. If the proposal is vague and the number is large, you’re funding their learning curve.

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Green Flags: Signs You’ve Found a Good One

On the flip side, here’s what genuine AI consulting expertise looks like in the real estate space:

• They start with an audit. Before proposing anything, they want to understand how your agency actually works. What’s your tech stack? Where are the bottlenecks? What’s already working well?

• They know your CRM by name. Rex, Reapit, VaultRE, Agentbox, Eagle — they should know these systems and have opinions about how AI integrates with each one.

• They show you the math. Hours saved per week, cost per property description, time-to-response improvements. Real numbers, not vibes.

• They offer a pilot. They’re willing to prove the value before you go all-in.

• They talk workflows, not features. “We’ll automate your follow-up sequences” beats “our platform has 47 AI features” every time.

• They’ve done it for similar agencies. Not identical — every agency is different. But they should have relevant experience with agencies of a similar size, market, and tech setup to yours.

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How We’d Answer: Headland Digital’s Take on All 10 Questions

We said we’d be transparent, so here it is. This is how Headland Digital answers every question on this list.

1. ROI from a real estate client? Yes. We work exclusively with real estate agencies. We can show you specific time savings and efficiency improvements from agencies we’ve worked with — including agencies on the Mid North Coast and across Australia.

2. What specific workflows? We typically start with property description generation, buyer-match emails, open home follow-up sequences, vendor report drafting, and social media content creation from listing data. But we always audit first — your agency might have different priorities.

3. Do you know our CRM? We know Rex, Reapit, VaultRE, Agentbox, and Eagle. We’ll ask which one you’re on in our first conversation, and we’ll already know how AI integrates with it.

4. Will we need to hire someone? No. Everything we build is designed to run with minimal oversight. We do monthly check-ins to optimise and adjust, but your team shouldn’t need any technical skills beyond reviewing AI-generated content.

5. What if the AI gets it wrong? Every workflow includes human review checkpoints. The AI drafts, your team approves. We also build feedback loops so the AI learns from corrections and improves over time.

6. Platform or outcome? Outcome. Always. We use best-in-class tools behind the scenes, but you’re paying for results — time saved, consistency improved, follow-up that actually happens.

7. How long until results? First workflows are live in two to four weeks. Full impact — where AI is genuinely embedded in your daily operations — takes about three months.

8. What do you need from our team? Two to three hours upfront to capture your voice and preferences. After that, 15 to 20 minutes a day reviewing outputs. We handle everything else.

9. Can we see it before we commit? Yes. We offer a free 30-minute AI Assessment where we audit your workflows and show you exactly where AI would save you time and money. No commitment. No pitch.

10. What can you do that we can’t do with ChatGPT? We build integrated, automated systems that run consistently — connected to your CRM, trained on your voice, and maintained over time. ChatGPT is a powerful tool, but it’s a tool. We build the workshop.

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The Bottom Line

AI consulting for real estate is a buyer’s market — but only if you know what to ask. The right consultant will welcome these questions. They’ll have specific, confident answers. They won’t flinch when you push for proof.

The wrong consultant will get vague, change the subject, or try to dazzle you with jargon instead of results.

You now have the questions. Use them ruthlessly.

We answer all 10 of these questions in our free 30-minute AI Assessment. No pitch — just a breakdown of what AI can (and can’t) do for your agency. Book at headlanddigital.com.au/assessment.

Want to do some homework first? Our Database Value Calculator shows you what’s hiding in your CRM, and the article on your database’s real worth breaks down the maths. For a practical starting point, see how to write listing descriptions in 60 seconds with AI.