The 6 Most Expensive Words in Property Management

Every industry has phrases that quietly drain its potential. In property management, I have come to believe the most expensive words we can say are: “We’ve always done it this way.” 

On the surface, it sounds harmless, even comforting. It is a defense mechanism we all use when we do not have the energy to rethink a process or when the risk of change feels greater than the reward. But after more than two decades in multifamily operations, I have seen those six words derail portfolios, undermine compliance, and erode resident trust faster than any market downturn or maintenance backlog. 

Especially in affordable housing, where margins are razor thin and compliance carries real consequences, comfort becomes the silent killer of excellence. 

The Cost of Comfort 

I once walked into a property where the leasing team was still using a paper logbook to track prospects even though three different software systems had been implemented over the prior decade. When I asked why, the answer was predictable: “We’ve always done it this way.” 

That habit meant half the data in their property management system was incomplete, renewals were being tracked inconsistently, and reports to ownership painted a skewed picture of performance. It was not malicious. It was familiar. But the real cost showed up as missed renewals, strained occupancy, and lost credibility with stakeholders. 

The same pattern repeats itself everywhere: 

• Legacy processes nobody questions 

• Metrics that measure vanity numbers instead of impact 

• Quick fixes that became permanent SOPs 

• Compliance tools left idle between audits 

• Leasing procedures designed for software versions retired years ago 

Each of these comfort zones creates operational blind spots. In an industry where one compliance misstep can trigger cascading consequences, outdated knowledge is not just inefficient. It is a liability. 

The Leadership Blind Spot 

The deeper problem is that leaders often reward stability over curiosity. Teams are praised for error-free execution but rarely for challenging outdated practices. Consistency is emphasized, which is essential, but consistency without relevance becomes dangerous. 

I have seen managers shut down new ideas because “ownership will not go for it.” I have seen staff hide behind procedures long after they stopped serving residents effectively. I have seen cross-functional teams avoid collaboration because the way they have always done it is easier than the friction of change. 

What gets lost in that culture is the opportunity to innovate. And innovation in property management is not about flashy new tech or sweeping reforms. It is about continuously asking whether the process in place still serves its purpose. 

A Case From the Field 

Several years ago, I worked with a regional team struggling to manage delinquency. Their escalation process was slow, resident communication was inconsistent, and write-offs were piling up. When I asked why they were handling collections the way they were, the answer was predictable: “We’ve always done it this way.” 

The truth was that their process had been built around a local court requirement that changed years earlier. They were still following an outdated playbook even though the environment had shifted. 

Once we restructured the process to align with current regulations, leverage better software tools, and clarify ownership of each step, delinquency dropped by double digits in six months. Nothing about the team had changed. Only the willingness to challenge the old script had. 

Building Cultures That Question 

The real challenge for leaders is building environments where questioning the status quo feels safe and expected. That requires more than slogans. It requires habits: 

• Making “Why do we do it this way?” a legitimate question at every level 

• Treating “Because that is how we do it” as an unacceptable answer 

• Actively soliciting feedback on outdated processes from frontline teams 

• Rewarding innovation, not just punishing mistakes 

• Structuring regular cross-functional reviews to optimize workflows 

I have seen the difference this makes. When staff know their perspective matters, they bring forward the small inefficiencies that leaders often miss. Those micro-shifts such as changing how work orders are assigned, revising how compliance files are stored, or adjusting how budgets are tracked add up to real performance gains. 

The Risk of Standing Still 

The danger is not just inefficiency. In today’s environment, processes that worked even a few years ago may no longer protect you. 

Consider compliance. Regulations evolve. Software platforms update. Funding requirements shift. If you are still running procedures written in 2020, you may already be out of alignment in 2024. 

Or think about resident expectations. The pandemic permanently changed how people interact with service providers. Residents expect digital communication, faster response times, and clearer transparency. If your processes have not adapted, you are not just inefficient. You are eroding trust with the very people you serve. 

Action Steps for Leaders 

So how do we fight back against the six most expensive words? Start small. This week, pick one process that has been running on autopilot. Sit down with your team and ask three questions: 

• Why do we do it this way? 

• Who does this serve? 

• What would we do differently if we started fresh today? 

Then, listen. The answers may surprise you. 

At one property I worked with, that exercise led to a simple change in how maintenance tickets were prioritized. The result was a noticeable improvement in resident satisfaction scores in just one quarter, not because the team worked harder, but because they worked smarter. 

Closing Reflection 

In property management, comfort is tempting. Familiarity feels safe. But the cost of those six words, “We’ve always done it this way,” is often far higher than we realize. 

The best leaders I have known do not chase change for its own sake, but they also do not allow processes to calcify. They balance consistency with curiosity. They build cultures where innovation is not a disruption but a discipline. 

So here is the challenge: what is one “we’ve always done it this way” process in your organization that is overdue for scrutiny? Because in affordable housing and multifamily operations alike, excellence is not built on comfort. It is built on the courage to ask better questions.