10 Questions Every Condo Board Should Ask Before Hiring a Property Manager

Hiring a property management company is one of the most important decisions a condo board will make. The wrong choice affects everything from reserve fund planning to how quickly a resident's maintenance request gets resolved. Before signing any management agreement, boards need to ask pointed questions that go beyond the sales pitch.

It's easy to assume every management company offers the same level of service because the proposals often sound alike. Almost all of them mention responsiveness, financial reporting, and trusted contractors. What really matters is how those promises translate into everyday management. That's something boards should uncover during interviews, before committing to a contract.

Questions That Reveal Experience and Operational Fit

These first questions establish whether a firm actually understands the realities of managing a condominium corporation in Ontario, where aging building stock, tight trade availability, and Condominium Act compliance all intersect.

Note: Ontario boards should confirm that any proposed condominium manager or management provider is appropriately licensed. Verify here >

1. How many condominium corporations do you currently manage, and what size range? 

A firm managing mostly small residential buildings may struggle with a high-rise that has complex mechanical systems, elevators, and a larger reserve fund. Ask for a breakdown, not a vague total.

2. Who will be our dedicated property manager, and what is their background?

Boards often meet with an executive sales team and are later assigned a junior manager they’ve never spoken with. Ask specifically who will handle your account, what their licensing status is, and how the management company supports them to prevent burnout. 

As industry expert Nicholas Chirametli explains, choosing the right manager is critical to avoiding costly mistakes.

To read more about selecting and supporting the right talent for your building, check out our collaborative industry piece on Stratastic >

3. What is your average client retention rate? 

Turnover among management companies signals dissatisfaction. A firm confident in its service record should be willing to discuss retention, even in general terms.

4. How do you handle emergencies outside business hours? 

Water leaks, elevator failures, and security issues don't wait for office hours. Ask about the actual escalation process, not just "we have 24/7 support." 

A standard-setting firm should have a structured, audited emergency protocol. Under our ACMO 2000 guidelines, City Sites Property Management utilizes clear, standardized operating procedures (SOPs) for after-hours dispatching, ensuring a licensed manager is always reachable and emergency trades are deployed in minutes, not hours. 

5. What is your approach to vendor management and contractor oversight? 

This matters more than boards often realize. A management company's vendor network affects pricing, response time, and workmanship quality on everything from HVAC repairs to garage remediation.

Instead of relying on traditional preferred vendor lists that can be difficult to verify, many property management companies now use digital procurement platforms to improve transparency and accountability. At CSPM, we use VendorPM to manage vendor sourcing, request competitive bids from qualified local contractors, and confirm that everyone working on your property meets licensing, insurance, and WSIB requirements before any work begins.

Questions That Reveal Financial Controls and Communication Standards

Financial oversight and communication are where boards face the most friction with property managers, and where the differences between firms become most apparent.

1. How do you handle reserve fund planning and budget forecasting? 

A capable manager should be able to explain how they work alongside the reserve fund study, not just process invoices. Ask how they flag upcoming capital expenses before they become emergencies.

2. What financial reporting will the board receive, and how often? 

Monthly financials, arrears tracking, and expense variance reports should be standard. If a firm is vague about reporting frequency or format, that's worth noting.

3. How do you communicate with the board between meetings? 

Boards should know whether they'll get a single point of contact, a shared portal, or an inconsistent mix of emails and phone calls. Response time expectations should be set explicitly, not assumed.

4. How do you handle owner complaints and disputes?

 This is increasingly relevant given how the Condominium Authority Tribunal evaluates whether a corporation responded reasonably to a complaint. A management company should have a consistent, documented process, not an ad hoc approach.

5. Can you provide references from current condo boards? 

Reference checks remain one of the most underused tools in the hiring process. A board in a comparable building size and municipality can speak directly to responsiveness, transparency, and follow-through. . A reputable firm backed by strong community partnerships will gladly connect you with active board members who can verify their track record. 

The Ultimate Test for a Management Firm 

Most proposals cover the same ground. You'll see promises about responsive service, clear communication, and experienced staff in almost every one. What you won't find as easily is how the company works when something goes wrong. That's where the interview becomes valuable. Ask about a difficult repair, a challenging board decision, or a situation that didn't go as planned. The way they describe those experiences often tells you more than a list of services ever could.

Choosing a management company isn't simply a matter of comparing features or fees. Every condominium corporation has its own priorities, its own challenges, and its own expectations. A company that's a great fit for one building may not be the right choice for another. That's why it's worth spending time getting a sense of how the team thinks, communicates, and works with boards before making a decision.

A management company will become part of your community's day-to-day operations, sometimes for many years. Taking the time to ask thoughtful questions at the beginning can make the decision easier and help build a stronger working relationship from the start.