20 Questions Every CRE Broker Should Be Asking

Let me ask you a question:
Why would a prospect take your call?
Seems simple enough, but most brokers can’t answer it clearly.
And if you can’t answer it, your prospects won’t either.
Here’s the truth: the best brokers aren’t just great at pitching, they’re great at asking questions. Especially the ones they ask themselves before they ever make a call or walk into a meeting.
In commercial real estate, your success isn’t just built on market knowledge or deal experience. It’s built on your ability to position yourself in the mind of your prospects.
And positioning starts with asking the right questions.
The Science of Asking
Research shows that when we ask ourselves questions, we trigger a process called instinctive elaboration. That means our brain starts searching, consciously and subconsciously, for answers.
This is why simply asking the right question can change how you show up.
It can influence how you prospect, how you present your value, and ultimately how you close.
But most brokers never stop long enough to ask themselves the questions that really matter.
Let’s change that.
20 Questions Every CRE Broker Should Ask Themselves
You don’t have to answer all of these right now. In fact, I recommend sitting with them over the next few days. Write some down. Journal on a few. Let them simmer.
They will give you clarity, and in this game, clarity builds confidence.
- Why would a prospect take my call?
- Why would they agree to meet with me?
- Why would they choose to work with me?
- What specific benefits do I offer my clients?
- What specific benefits does my company offer?
- What problems do I solve better than anyone else?
- What proof do I have that I get results?
- If someone asked “Why now?”, what would I say?
- Who is my ideal client?
- What objections do I hear most often?
- How do I respond to those objections?
- What are my three most valuable success stories?
- Where is the biggest opportunity in my market right now?
- What’s holding me back from taking full advantage of it?
- What does my current pipeline really look like?
- What’s the next action I should take with every prospect in it?
- What do I want my reputation in the market to be?
- What do I want it to be 12 months from now?
- What am I doing today to build that reputation?
- What does “success” look like for me this year—and what am I doing to make it happen?
Start with One
It’s probably the weekend at the time you’re reading this, which is the perfect time to pick a question from this list and reflect on it.
Important: You don’t need to have all the answers.
But start with just one question and really sit with it.
Your brain will do the rest.
Everyone’s heard of the phrase, “work smarter, not harder.” And to a degree, that’s true. However, in CRE brokerage, the brokers who win aren’t always the ones with the most innovative tools or the most experience. They’re the ones who think better. Who asks smarter questions. Who get clear on their value and then communicate it consistently.
If you’re not getting the results you want, don’t chase a new tactic. Start by asking a better question.
Want help turning these questions into real conversations, meetings, and momentum?



