The ever-changing, often unpredictable nature of their industry requires professional property managers to be adaptable. On any given day, a manager might find him- or herself dealing with issues ranging from managing a major capital repair project at one property to balancing a budget at another, to de-escalating a resident dispute at a third. Each scenario presents a challenge, as well as an opportunity to problem-solve, learn, and improve. 

CooperatorNews polled property managers across the industry to find out some of the best lessons they’ve learned throughout the years, and came away with six key takeaways:

Lesson #1: Clear Communication + Transparency Build Trust

Communication breakdowns, inconsistent decision-making, and a lack of trust among board members and residents can swiftly spiral into deep dysfunction that can be very tough to correct. A clear plan and transparency can bring things back on track before they get to that point.

Chicago-based PRG Management’s Director of Management Todd Rowan recalls a time when their management team assumed responsibility for a 10-building, 60-unit townhouse association facing significant operational and financial challenges. “Compounding the issue was limited financial transparency from the previous management company, which left the board without a clear understanding of the association’s true financial position, their reserve balances, vendor obligations, and overall budget health,” he explains.

“One of our first priorities was to establish clarity and restore confidence in the management process. We conducted a comprehensive review of the association’s financial records, contracts, account balances, and operating procedures. Through this process, we identified gaps in reporting, inconsistencies in budgeting, and areas where expenses were not aligned with the association’s actual income from dues.

“Equally important was rebuilding the functionality of the board itself,” Rowan continues. “We worked closely with board members to improve communication, define responsibilities, and implement more structured and productive meetings. By introducing transparent reporting practices, clear agendas, and actionable follow-up items, the board gradually became more collaborative, informed, and effective in its decision-making.

From there, he says, “Financial stabilization became a key focus of the transition. We developed a realistic operating budget that accurately reflected the association’s expenses while remaining aligned with the dues being collected. This included prioritizing necessary maintenance, evaluating vendor relationships, and creating a clearer roadmap for reserve planning and long-term financial sustainability. Regular financial reporting and open discussions with the board helped establish accountability and trust throughout the process.”

As a result of the management transition, the association moved from an uncertain, reactive position to one that was organized, transparent, and financially responsible. The board evolved into a functional and productive leadership group, residents gained greater confidence in the community's direction, and the association was placed on a stronger foundation for long-term success.

​Lesson #2: Strong Relationships Save Time

​Along with financial and legal advisors, it’s also vital for boards to maintain strong relationships with experts like plumbers, electricians, and engineers—for both everyday maintenance and for support in emergencies. Their experience and expertise are invaluable when quick decisions need to be made, regardless if they are directly contracted by the property or are a part of your professional network.

​Thomas Chilenski, president and CEO of New Jersey’s Cedarcrest Property Management, remembers a time when leaning on his network came in handy. He notes that “I was doing an inspection, and I walked into the boiler room to find a leak coming from the main water line. It was just large enough to be an issue. We needed to immediately shut off the water supply to the building. I called up one of my friends who works in the field and knows the building.” Chilenski sent his friend photos of the pipes and valves in front of him, and his friend was able to talk him through the steps to shut off the water and prevent the leak from causing serious damage before it could be repaired. 

​“He gave me all of the information I needed and told me how to shut all of the water off,” Chilenski says. “Because of his knowledge and the ability to get in touch with him so quickly, we were able to get the issue isolated, fixed, and get the water back on within 45 minutes. It was a challenge that ended up in a good place pretty quickly.”

​Property managers tend to be experts at networking, and know the value of having reliable pros available for any situation that might pop up at one of their client buildings. When there’s a weather emergency, a security issue, or when a building system goes offline, time is of the essence; having a deep bench of professionals on call gives boards and residents alike some peace of mind.

Lesson #3: Imperfection is Okay ​

Residential buildings are living communities that change constantly. Successfully managing them depends not on avoiding mistakes, but on acknowledging and learning from them.​

"In this ever-evolving industry,” says Michael Mintz, founder and CEO of New York-based MD Squared Property Group, “we view every day as an opportunity to refine our craft. We are committed to a culture of continuous improvement and transparency. By encouraging our managers to take proactive ownership of every situation, we create a foundation of trust that drives innovation and strengthens the entire industry."  

From managing emergencies to meeting resident expectations, property managers work long hours and often have unpredictable workloads. 

"We empower our managers to move beyond the pressure of being flawless and instead focus on being solutions-oriented,” says Mintz. “We believe that the best way to build confidence is to view challenges as vital teaching moments. By asking ourselves how we can optimize our response and prevent future hurdles, our team grows more resilient and skilled in their roles."  

Lesson #4: Plan Ahead with the Big Picture in Mind

When undertaking a capital improvement or repair project, planning ahead and staying locked in on the long term goal is essential. This is much easier said than done, of course; capital projects by their very nature are complex jobs, with multiple, time-sensitive layers of planning and strategy required before the first hammer even falls. Some delays and bureaucratic hassles are inevitable, but having that anchor plan in place with an eye to the big picture allows for adjustments to be made without derailing the project. 

Georgia Lombardo Barton, president of NYC-based Barton Management, recalls an example of this: “For several years, a landmark condominium building in Brooklyn had been planning and preparing to finance and launch a major structural vault reinforcement project. Because access to the vaults required demolition of the existing sidewalks, the scope of work inevitably included installation of new sidewalks as part of the overall project.”

“At the same time,” Lombardo Barton continues, “the surrounding block was included in a six-plus-year public infrastructure improvement program involving ongoing street and sidewalk excavation for new underground electrical conduits, water mains, and related utility upgrades.

A contractor change mid-project enabled the condo to re-bid the scope of work, and they eventually secured a new proposal that not only saved the condo substantial money, but gave the building an opportunity to coordinate its vault work with what the City had planned.

“In 2025, we met with City representatives and their subcontractors to coordinate schedules,” says Lombardo Barton, “and it was agreed that the City’s reconstruction efforts would not interfere with our planned work.

“Given that the vault was located directly in front of the building, we strategically organized the project in three phases to minimize disruption to the building’s main entrance, parking garage access, and the on-site day care school,” she continues. “Safety remained the top priority throughout the project, particularly for pedestrians, residents, and parents and children utilizing the day care, while the exposed vault areas were securely protected with barriers and 10-foot fence enclosures.”

Through careful planning, collaboration, consistently updating residents, meeting weekly with the building engineer and contractor, and strong oversight, the project was completed safely, efficiently, and with minimal disruption to daily building operations.

Lesson #5: Prioritize Tasks & Manage Expectations

​Residents, boards, and staff members all have their own needs, wishes, and priorities when it comes to how their building is run, and frequently the property manager is the one receiving all that input and then trying to deliver on those demands. It’s a tall order—and one that can eventually lead to burnout, if a manager isn’t able to prioritize, set boundaries, and manage expectations for both their clients and themselves.  

"In the early stages of my career, my primary focus was on immediate responsiveness and a 'yes-first' approach,” says Mintz. “However, I soon discovered that the most sustainable path to excellence involves proactive communication. I realized that by aligning with our clients on a clear, achievable vision of service, we can provide a higher quality of work while maintaining the energy and focus needed to serve them long-term."  

"We have a very disciplined approach to meetings where we align on key priorities,” he continues. “Even with a long list of goals, we find success by focusing on the most impactful needs and setting a clear timeline for each. This strategic focus ensures every task gets the attention it deserves and makes our progress more intentional and rewarding."   

​Chilenski agrees with prioritization and adds that slowing down during the planning process can save time in the end. “It’s better to take five or 10 minutes to think through the different possibilities to come to the right decision rather than making a quick snap decision,” he says. 

Lesson #6: You Know Your Building Best

​Though it’s certainly helpful to have experts to call on when needed (see #2 above), a stacked contacts list still doesn’t replace a competent property manager’s own expertise. Mintz cautions that “the vendor you have the best relationship with is not always necessarily going to get the best outcome, so you need to be thoughtful and make sure that you really are going to the best vendor who knows how to service your building’s particular type of equipment.” And that requires taking an active, attentive approach to getting at least passing familiarity with the various systems and equipment in use at client properties, knowing how old they are, what their active useful life expectancy is, and their service history, for example. 

​That intimate familiarity can come in very handy when planning budgets, scheduling reserve studies, and charting a community’s financial game plan for or five years ahead. “I have definitely learned over time that professionals—whether they’re attorneys or engineers—are not always strategic,” Mintz adds. “They can be focused on their silo of what they’re doing without knowing about the bigger picture.” It’s the property manager's responsibility to take a holistic approach and make sure their advice is applicable.

​Along with people skills and good communication, adaptability is one of the hallmarks of a successful property manager. The best managers know that organization, proactive planning, building solid relationships, and transparency can turn the job’s inevitable challenges into stronger communities.  

Kate Mattiace is associate editor of CooperatorNews.