5 Questions Every Executive Must Ask Tech Vendors

It is easy to fall victim to "shiny object syndrome." A smooth demo promises to save your team time, stretch your budget and revolutionize your workflow. But after signing the contract and spending countless hours onboarding, many executives realize the software delivers half of what was promised.

Whether you lead an MLS, manage an association or run a brokerage, evaluating new software requires getting through the sales pitches. Grounded in real-world leadership experience, these five foundational questions ensure your next tech investment delivers real value.

1. What problem is this product solving?

Ask the vendor to walk you through the core issue they intend to fix. Their answer quickly reveals their depth of industry knowledge. Real estate has a unique ecosystem: the dynamics between brokers, agents, MLSs and associations are intricate. This question identifies whether the vendor built a tailored solution for your world or is simply trying to force a generic tool into a complex market.

2. What kind of companies are using your product and how are they using it?

Inquire about previous implementations. Where is the tool running, and what were the lessons learned during onboarding? Pay close attention to adoption metrics: for non-core software, a consistent monthly active user rate of 10–15% represents strong engagement. Ask to speak with both their smooth implementations and their bumpier onboardings to get a realistic picture of rollout.

3. What does your 12- to 24-month product roadmap look like?

Understand the vendor’s development lifecycle and innovation cadence. Are they releasing enhancements every two weeks or running on a six-month update cycle? A fast, responsive release cadence indicates that feature requests and user feedback will actually make it into future builds.

4. What is your pricing structure?

Pricing models reveal how well a vendor understands real estate economics. Be cautious of forced company-wide licensing if actual user adoption typically settles around 15%. Look for flexible, scalable pricing models, such as baseline minimums combined with usage tiers.

5. What does the relationship look like after the contract is signed?

Determine whether the vendor operates as a technology provider or a true strategic partner. Will they actively assist with ongoing education, host joint training sessions and hold monthly check-ins; or do they vanish until renewal time? You need partners invested in driving long-term user adoption.

Finding the Right Fit

You do not need perfect answers on day one, but this framework provides a clear foundation for vendor discussions. Always evaluate multiple options or consider complementary tools outside the real estate industry to ensure you see the full picture.

Need help evaluating your MLS or association’s technology options? The T3 Sixty Organized Real Estate team conducts comprehensive product suite reviews, contract evaluation and vendor vetting to help leadership teams select the best tools for their organizations. 

Connect with our team to refine your organization’s tech suite