"When we get stuck, we tend to think the reason is because we don't have the right answer. My experience is that finding the 'right' answer is rarely the problem. What keeps us stuck are inferior questions that produce tactical or unattractive choices." -Keith J. Cunningham

"When we get stuck, we tend to think the reason is because we don't have the right answer. My experience is that finding the 'right' answer is rarely the problem. What keeps us stuck are inferior questions that produce tactical or unattractive choices." -Keith J. Cunningham

The Power of Asking the Right Questions

Most real estate owners and operators don’t have an answer problem. They have a question problem. Weak questions lead to weak decisions and mediocre financial performance. Strong questions unlock insights, better strategies, and higher profits.

The quality of the questions you ask determines the quality of the results you get. Let's explore high-impact business questions that actually move the needle in real estate.

Weak vs. Strong Real Estate Questions

Accountability & Operations

Weak Question: "Are our staff following procedures?" Better Question: "What specific metrics can we track daily to ensure our team is executing on our highest-priority activities?" Why? Procedures alone don't generate results. Measuring the right activities reveals where accountability is breaking down.

Leasing & Tenant Experience

Weak Question: "How can we get more leases?" Better Question: "What's the exact moment prospects are saying 'no' in our leasing process, and what's the specific objection they're raising?" Why? The first question is too general. The second forces you to identify the exact conversion bottleneck and fix it.

Weak Question: "How do we increase renewal rates?" Better Question: "What are the top three reasons our best residents leave, and how can we eliminate these pain points entirely?" Why? Renewals aren't just about keeping anyone. They're about retaining your highest-value residents who pay on time and respect your property.

Pricing & Revenue Management

Weak Question: "Should we offer concessions to fill vacancies?" Better Question: "What amenities or services could we add to justify a higher rent than our competitors?" Why? Concessions erode your financial foundation. Value-creation lets you charge premium rates.

Weak Question: "Are our rental rates competitive?" Better Question: "Which specific unit types are underperforming in rent growth compared to the market?" Why? The first question leads to blanket adjustments, while the second pinpoints precise revenue opportunities.

Maintenance & Asset Preservation

Weak Question: "How can we cut maintenance costs?" Better Question: "Which three maintenance issues are consuming 80% of our budget, and how can we invest in permanent solutions rather than ongoing repairs?" Why? Cost-cutting often leads to deferred maintenance and bigger expenses later. Prevention and permanent solutions build asset value.

Weak Question: "How do we improve response times?" Better Question: "What's the specific bottleneck in our maintenance workflow that adds the most delay, and how can we eliminate it completely?" Why? Faster responses don't come from just working harder—they come from redesigning broken processes.

Marketing & Lead Generation

Weak Question: "How do we get more leads?" Better Question: "What's the profile of our ideal resident who pays rent on time, and how do we build our entire marketing strategy to attract exclusively these prospects?" Why? Volume of leads alone doesn't matter. Quality and targeting do.

Weak Question: "What's the best way to advertise vacancies?" Better Question: "What specific pain point or desire is our ideal resident experiencing that our property solves better than any competitor, and how do we make that the centerpiece of our marketing?" Why? Marketing isn't just about the properties—it's about solving resident problems and desires.

Resident Retention & Customer Experience

Weak Question: "How can we improve resident satisfaction?" Better Question: "What are the three moments in the resident experience that create the highest emotional impact, and how can we make these moments extraordinary?" Why? Satisfaction often comes from peak experiences, not just avoiding problems.

Weak Question: "How do we reduce negative online reviews?" Better Question: "What systematic failure in our operation leads to negative reviews, and what's our plan to fix the root cause rather than the symptoms?" Why? Focusing on damage control won't fix the underlying operational issues driving complaints.

Financial Performance & ROI

Weak Question: "How can we increase NOI?" Better Question: "Which specific property in our portfolio has the largest gap between current and budgeted NOI, and what's the one change that would close that gap?" Why? General goals don't drive action. Targeted opportunities with clear actions do.

Weak Question: "Are we spending too much on expenses?" Better Question: "Which three expense categories have grown faster than revenue over the past 24 months, and what specific operational changes would reverse this trend?" Why? The first question leads to arbitrary cuts. The second drives strategic efficiency.

Asking better questions will help refine your strategy and tactics to achieve your goals.

"Strategy is how you choose to allocate your limited resources against unlimited options ."

--Alex Hormozi

A Real-World Example: The Power of Better Questions

We had a new construction property that was experiencing frustratingly slow leasing. When we asked the management company about it, they gave us the standard excuse: "It's just a slow time of year."

Instead of accepting this, we asked a better question: "Are our leasing agents actually at the property during business hours?"

We instructed an assistant to call the property three times daily—at 10am, 2pm, and 4pm—to verify staff presence. Despite paying for two full-time leasing agents, we discovered they were only on-site 1-2 days per week and frequently left early. They were primarily working from a home office, leaving our property unstaffed.

Once we identified and addressed this issue, our leasing activity immediately spiked. While there were other contributing factors, simply ensuring staff were present at the property was the first and most critical fix. The better question revealed the true problem and led to a simple solution that dramatically improved performance.

Your properties don't perform better just because you "work harder." They thrive because you ask better questions and take decisive action on the right things first. The right question doesn't just give you information—it forces action that drives results.

Your biggest problem isn’t what you think—it’s the questions you’re not asking. Fix that, and you fix everything.