Article

Commercial Real Estate - How to Ask Your Discovery Questions

Topic: Real EstateBy Craig HigdonPublished Recently added

Legacy signals

Legacy popularity: 1,862 legacy views

Legacy rating: 2/5 from 2 archived votes

In order to make a successful commercial real estate investment you need to know the right questions to ask and the right way to ask them. Since purchasing commercial real estate is a negotiation between the buyer and the seller (and probably their prospective brokers), it is important that you, as the buyer, are prepared. Asking the right questions could help you avoid owning an underperforming asset.

Remember, both parties are trying their best to get what they want, but their goals are diametrically opposed. The seller is trying his or her best to get the highest possible price, while the buyer is trying just as hard to get the property for the least possible amount of money. There’s an old saying in the business: “All sellers are liars, all buyers are thieves.” While I don’t believe in either scenario as a way to do business, those commercial real estate investors who are able to create a win-win transaction will enjoy huge advantages over their more combative competition. And the key to doing that is in your questioning technique.

Finding and creating these win-win deals isn’t easy, but making them happen is the basis of successful real estate investment. In many ways, finding the best deals boils down to knowing which questions to ask and is one of the most important of all real estate “secrets.”

The key is to ask plenty of open ended questions of either the seller or his agent and to not accept a simple “yes” or “no” answer. If you ask an open ended question and get a yes/no answer, your immediate reaction should be to follow up with additional open ended questions! Obviously, if you keep getting yes/no’s to your questions, it may be time to find a more cooperative and serious seller.

Some of the leading questions smart real estate investors use include:

  • What can you tell me about this piece of property?
  • What makes this particular property a good investment?
  • What is it like dealing with the city?
  • Tell me about your tenants … neighbors … city, etc.
  • What can you do to help me get into this property?
  • What financing are you willing to carry?
  • What are your neighbors like? Or “how easy are the adjacent property owners to deal with?
  • How quickly do you need to close? Why?
  • Why are you selling the property … now?
  • What is the existing financing? How can it be assumed?
  • What are the down payment requirements?

While the straightforward approach and strategy generally works the best, many successful real estate investors have also found success at using the “Columbo Technique.” For those of you too young to remember, Columbo was a dumpy-looking fictional detective who always seemed a couple of cents short of a dollar. However, he had this process where he’d get up to leave after seeming to conclude his suspect interviews and would say something like: “Oh, Mr. Jones, one more thing …” And that question would usually catch the perpetrator off guard. I suggest trying it during your discovery process. It can be very enlightening!

You’ll need to develop your own list of questions as you do more transactions and I suggest even rehearsing them or incorporating them into some form of due diligence checklist. The bottom line is that the better you question, the better your deals will be.

Article author

About the Author

WANT TO USE THIS ARTICLE IN YOUR E-ZINE OR WEB SITE? You can, as long as you include this complete statement with it: ‘“The Investment Property Insider” is published by Craig S. Higdon, a veteran commercial mortgage banker. He publishes the e-zine and blog, InvestmentPropertyInsider.com, for commercial real estate investors, developers, and industry professionals. Visit the blog and get this free report: “The 7 Biggest Loan Mistakes Real Estate Investors Make And How To Avoid Them.” ’

Further reading

Further Reading

4 total

Article

The Evolution of the Resident Experience Imagine a property manager named Alex. Alex oversees three hundred apartment units across a bustling metropolitan area. A few years ago, Alex’s day began and ended with a symphony of ringing phones. Between leaky faucets, lost keys, and prospective tenants asking about square footage, the actual work of managing a property—strategy, inspections, and community building—was often buried under a mountain of missed calls and frantic

February 20, 2026

Article

The American housing market, a dynamic and often bewildering entity, is influenced by a myriad of factors – interest rates, supply and demand, economic stability, and even global events. Yet, beneath the surface of these well-documented drivers, an unexpected force has been quietly at work, contributing significantly to its current boom: the thriving call centers in Pakistan. This might seem like an unlikely connection, but a closer look reveals a sophisticated symbiotic re

July 3, 2025

Article

The Search for Serenity Life in the city can be overwhelming—constant noise, endless traffic, and the relentless rush of daily responsibilities. Sometimes, all one needs is a quiet retreat, a place where time slows down, and nature takes over. Surprisingly, such havens exist just beyond Islamabad’s bustling streets. Tucked away in the Margalla foothills and the surrounding countryside, serene farmhouses in Islamabad offer a perfect escape from urban chaos. A Glimpse into

June 25, 2025

Article

Dubai's skyline is a testament to ambition, a dazzling display of architectural marvels rising from the desert. Its real estate market, much like its towering structures, is a landscape of unparalleled dynamism and fierce competition. In such an environment, merely having a property to sell, or even a prospective buyer, is no longer enough. The true currency of success lies in something far more refined: the qualified lead. The Illusion of Abundance: Quantity vs. Quality Once

May 21, 2025