Hiring a property manager is a big decision. Whether you own a small one-bedroom condo, a vacation rental, or a large home with multiple bedrooms, a pool, and a hot tub, the person or company managing your property can have a significant impact on your investment.
I've managed properties myself and worked with property managers over the years. My experience ranges from studio and one-bedroom condos to 14-bedroom homes with pools, hot tubs, and numerous guest amenities. I've seen firsthand how different the management requirements can be depending on the size, type, and complexity of a property.
One thing I've learned is that hiring a property manager isn't simply about finding someone to handle guest communications, coordinate cleanings, and fix things when they break. It's about finding a partner you can trust to protect your investment, operate the property efficiently, and provide a great experience for your guests.
The challenge is knowing what to ask before signing an agreement.
A property manager might have an impressive website, offer an attractive management fee, and promise excellent results. There are many management companies to consider. But how do you know whether they can actually deliver?
Here are the questions I'd ask before hiring a property manager, along with what I'd be looking for in their answers.
1. How Will You Communicate With Me and Keep Me Informed?
If I had to identify one characteristic that separates a good property manager from a bad one, it would be communication.
And more specifically, proactive communication.
As a property owner, you shouldn't have to constantly chase your property manager for updates or discover problems after they've become bigger and more expensive.
You want someone who keeps you informed, communicates clearly, and brings potential solutions to the table.
Questions to Ask About Communication
How often will I receive updates about my property?
Will I receive monthly performance and financial reports?
How quickly will you notify me when something goes wrong?
Who is my primary point of contact?
What's the best way to reach you: phone, email, or text?
How do you handle emergencies or urgent maintenance issues?
Will you provide recommendations and potential solutions when issues arise?
What a Good Answer Looks Like
I believe every property manager should establish a consistent communication schedule with their owners, even when everything is going well.
For example, I'd expect at least a monthly update covering:
How the property performed during the previous month.
Revenue, occupancy, and upcoming reservations.
Ongoing maintenance issues.
Items that may need attention in the coming weeks.
Any recommendations for improving the property.
Of course, owners should always have the ability to reach their property manager outside of those scheduled updates.
But there's an important distinction between keeping owners informed and overwhelming them with every little detail.
If a lightbulb burns out or a minor issue can be resolved without the owner's involvement or additional expense, there's probably no reason to interrupt their day.
On the other hand, if the air conditioning stops working, there's a water leak, or a major appliance needs replacing, the owner should know immediately.
My opinion: A property manager shouldn't just tell you there's a problem. They should present solutions.
For example, if a water heater needs replacing, I'd expect the manager to explain the situation, provide available repair or replacement options, share cost estimates, and make a recommendation.
The owner ultimately makes the decision, but the property manager should provide enough information to make that decision confidently.
Establish Spending and Decision-Making Authority Upfront
Another important conversation is determining how much authority the property manager has to make decisions without your approval.
For example:
Repairs under $150 can be approved by the property manager.
Repairs between $150 and $500 require notification.
Expenses above $500 require owner approval.
The actual amounts will vary depending on the property and owner's preferences.
The important thing is establishing these expectations before management begins.
If the owner wants to be involved in every decision, that's something the property manager should understand. If the owner prefers a more hands-off arrangement, the manager needs sufficient authority to operate efficiently.
Get these expectations in writing.
2. What Are Your Management Fees, and Are There Any Additional Costs?
When evaluating property managers, it's tempting to focus on the management percentage or monthly fee.
But that's only one part of the financial picture.
Different property management companies offer different fee structures and services. Some charge a flat monthly fee, while others charge a percentage of the property's rental revenue.
Neither approach is necessarily better. What matters is understanding exactly what you're paying for and what you're receiving in return.
Questions to Ask About Fees and Expenses
Do you charge a flat management fee or a percentage of rental revenue?
What services are included in your management fee?
Are there additional onboarding or setup fees?
Do you charge separately for maintenance coordination?
Are there markups on supplies, inventory, or maintenance services?
How are cleaning fees collected and distributed?
Are there additional fees for guest communication, inspections, or emergencies?
Are there any circumstances where additional fees may apply?
Understand the Difference Between What Guests Pay and What Vendors Receive
One area I'd pay particular attention to is cleaning fees.
For example, let's say guests are charged a $150 cleaning fee for each reservation, but the cleaning company actually charges $125.
What happens to the remaining $25?
Does the property manager retain it? Is it included in their management compensation? Is it passed along to the owner?
There isn't necessarily one right answer, but you should understand exactly how these arrangements work.
The same applies to maintenance, supplies, replacement inventory, and other expenses associated with operating the property.
Ask whether the property manager receives any additional compensation from vendors or service providers.
You want to understand where your money is going.
Review the Management Agreement Carefully
Don't rely exclusively on what a property manager tells you during an introductory conversation.
Ask for a copy of the management agreement and review the financial terms.
Pay particular attention to:
Management fees and how they're calculated.
Additional charges and service fees.
Maintenance and repair expenses.
Cleaning arrangements.
Supply and inventory costs.
Cancellation and termination provisions.
Like most business arrangements, there may be flexibility in the terms.
If you have a particular property, operating arrangement, or financial requirement, discuss it. A good property manager should be willing to have that conversation and determine whether an arrangement can work for both parties.
My advice: Don't automatically hire the property manager with the lowest fee. Understand the complete financial arrangement and determine which company offers the best overall value.
3. Who Handles Cleaning, Maintenance, and Day-to-Day Operations?
This is one of the most important areas to evaluate, and it's something I don't think property owners spend enough time investigating.
A property manager is only as good as the people and systems supporting them.
You might be hiring one company, but that company is relying on an entire network of people to keep your property running.
That includes cleaners, maintenance technicians, handymen, plumbers, electricians, landscapers, pool technicians, and potentially several other service providers.
You need to understand who these people are, how they're managed, and whether they're reliable.
Questions to Ask About Cleaning
Who handles the cleaning between reservations?
Do you use the same dedicated cleaning team for my property?
How long have you worked with your cleaning crews?
How do you communicate with them?
What happens if a cleaner doesn't show up?
How quickly can they return if something wasn't cleaned properly?
Do you have a cleaning checklist and quality-control process?
Who handles staging and restocking supplies?
Why Your Cleaning Team Matters So Much
Here's something I've learned from managing short-term rentals: A good cleaner is worth their weight in gold.
Think about the guest experience.
The cleaning crew is often the last person to touch the property before a guest arrives. They're responsible for making sure everything is clean, organized, staged, and ready for check-in.
Their work creates the first impression of the property.
A great cleaning team doesn't just clean. They notice things.
They might identify a broken kitchen appliance, a damaged piece of furniture, missing inventory, or something a previous guest left behind.
That information can help prevent small problems from turning into bigger ones.
On the other hand, an unreliable cleaning team can create significant problems:
A late check-in because the property wasn't ready.
A negative guest review because something wasn't cleaned properly.
Missing supplies or inventory.
A reservation that needs to be delayed or canceled because the cleaning crew never showed up.
You don't want a revolving door of different cleaners who have no familiarity with your property.
Ideally, you want dedicated cleaners who know the property, understand its setup, and take pride in their work.
The relationship between the property manager and the cleaning team is absolutely critical.
Questions to Ask About Maintenance
Who handles routine maintenance and repairs?
Do you have dedicated maintenance personnel?
What types of repairs can your team handle internally?
Which repairs require outside contractors?
How quickly can you respond to urgent maintenance requests?
Do you have established relationships with local vendors?
How do you evaluate the cost and quality of outside service providers?
You want a property manager who has reliable people they can call when something breaks.
For example, a trustworthy handyman who knows the property can often resolve minor issues quickly and affordably without needing to bring in an expensive contractor.
However, you also want someone who understands their limitations and knows when a licensed professional is necessary.
Questions to Ask About Inspections and Inventory
Beyond cleaning and maintenance, find out how the property is inspected and monitored.
Ask:
How frequently do you physically inspect the property?
Who performs those inspections?
Do you have a recurring maintenance checklist?
How do you track missing or damaged inventory?
How do you ensure supplies are restocked before each reservation?
How are issues documented and followed up on?
A property manager should have systems in place to ensure things actually get done.
It's not enough to tell you they have a great cleaning crew or maintenance team. They should be able to explain how they manage those relationships and hold everyone accountable.
My advice: Spend as much time evaluating the property manager's team as you do evaluating the property manager themselves. The people behind the scenes are often what determine whether the operation succeeds or fails.
4. What Experience Do You Have Managing Properties Like Mine?
Not all properties are created equal.
Managing a one-bedroom condo is very different from managing a 14-bedroom home with a swimming pool, hot tub, outdoor entertainment areas, and multiple amenities.
The operational requirements, maintenance demands, cleaning logistics, and guest expectations can be dramatically different.
You want someone who understands the type of property you're asking them to manage.
Questions to Ask About Experience
How many properties do you currently manage?
What types of properties do you specialize in?
Have you managed properties similar to mine?
How many reservations or guests have your properties accommodated?
Can I see examples of properties you've managed?
Can you provide references from current property owners?
What are some of the biggest challenges you've encountered managing properties like mine?
Look Beyond the Number of Properties Managed
Having 50 properties under management doesn't automatically make someone better than a company managing 15.
You want to understand the quality of their operation, not just its size.
If you're hiring someone to manage a large vacation rental, ask for examples of similar properties they've operated.
A manager who primarily handles smaller condos may not have the systems, staffing, or vendor relationships necessary to manage a large home with extensive amenities.
Likewise, someone who specializes in luxury vacation rentals may not be the best fit for an owner looking for straightforward, affordable management of a long-term rental.
Check Their Track Record and References
Ask to see their property management profiles, where applicable, and review the properties they've managed.
Look at:
Guest reviews and ratings.
Number of reservations completed.
Number of properties managed.
Consistency of guest feedback.
How they respond to negative reviews.
References from current or former property owners.
Don't just look at the five-star reviews.
Pay attention to how the manager handles problems and complaints. No property manager will have a perfect track record, but how they respond when things go wrong can tell you a lot about their professionalism.
If possible, speak directly with a few property owners they currently work with.
Ask those owners whether the manager communicates well, handles problems efficiently, and follows through on commitments.
5. How Do You Forecast Revenue and Measure Property Performance?
Before hiring a property manager, you should have a reasonable understanding of what your property can generate.
This is particularly important for short-term rental owners who are evaluating whether professional management makes financial sense.
A property manager should be able to provide a revenue projection based on market data, comparable properties, and historical performance.
Questions to Ask About Performance
How do you estimate potential rental revenue?
What comparable properties are you using?
What occupancy rate do you anticipate?
What average nightly rate do you expect?
How do you account for seasonality?
How frequently do you review pricing and adjust rates?
What performance metrics will you share with me?
How will you identify opportunities to improve revenue?
Ask for Data, Not Just Promises
There are several legitimate analytical tools available to help evaluate short-term rental markets and forecast potential property performance.
A property manager should be able to leverage these tools to provide insight into:
Historical occupancy rates.
Average daily rates.
Revenue potential.
Seasonal demand.
Comparable property performance.
Local market trends.
The goal is to understand what your property could reasonably generate before committing to a management arrangement.
Be cautious of anyone promising exceptionally high revenue without supporting their projections with actual market data.
I'd rather see a conservative, well-supported forecast than an inflated projection designed to win your business.
Understand What Success Looks Like
Revenue is important, but it shouldn't be the only measure of performance.
You should also consider:
Occupancy and average daily rate.
Guest satisfaction and reviews.
Maintenance and operating expenses.
Cleaning quality and consistency.
Property condition over time.
Owner profitability after management fees and expenses.
Ultimately, a property manager should help you operate a successful investment, not simply generate reservations.
6. How Do You Handle Mistakes and Take Accountability?
Here's something worth remembering: Your property manager is going to make mistakes.
Everyone makes mistakes. That's part of running a business and managing people.
The question isn't whether something will eventually go wrong. It's how the property manager responds when it does.
Questions to Ask About Accountability
Can you share an example of a mistake your team has made and how you handled it?
What happens when a guest experience falls short?
How do you handle situations where your team fails to complete a task?
How do you communicate mistakes to property owners?
What steps do you take to prevent the same issue from happening again?
Look for Ownership, Not Excuses
I want a property manager who takes responsibility when something goes wrong.
That means they're willing to:
Acknowledge the mistake.
Communicate what happened.
Take responsibility when it's their fault.
Explain how they're going to make things right.
Put processes in place to prevent it from happening again.
What I don't want is someone who immediately becomes defensive, points fingers at vendors, or makes excuses.
If the cleaning crew doesn't show up, it's ultimately the property manager's responsibility to have a backup plan.
If a maintenance issue goes unresolved because someone dropped the ball, I want the manager to own that and fix it.
Mistakes happen. Repeated mistakes without accountability are a different story.
My opinion: I'd rather work with a property manager who admits when they've made a mistake than one who tries to convince me they've never made one.
7. What Does Your Management Agreement Look Like, and How Can I Terminate It?
Even if everything sounds great during the interview, make sure you understand the agreement before signing.
A property management relationship should feel like a partnership. You shouldn't feel trapped in a contract if the arrangement isn't working.
Questions to Ask About the Contract
Is there a minimum contract length?
Does the agreement automatically renew?
How much notice is required to terminate?
Are there early termination fees?
Is the agreement exclusive?
What happens to future reservations if we terminate?
Who controls the listing and guest information?
Who owns the property photos, descriptions, and marketing materials?
Are there any restrictions on hiring another management company?
Understand the Exit Strategy
One area I'd pay particular attention to is what happens when the relationship ends.
For example, if the property manager controls the listing on Airbnb or another booking platform, what happens to that listing if you decide to move on?
What happens to reservations that have already been booked?
Can you continue operating the property without disruption?
These are important questions to resolve before the relationship begins, not after you've decided to terminate it.
I'd also want to understand whether there are any restrictions on working with other management companies or handling certain aspects of the property independently.
The agreement should clearly explain everyone's responsibilities and what happens if either party wants to end the relationship.
8. What Are the Biggest Red Flags When Hiring a Property Manager?
Sometimes what a property manager doesn't tell you is just as important as what they do tell you.
There are a few things I'd watch for when evaluating potential managers.
Their Pricing Seems Too Good to Be True
If one property manager is significantly cheaper than everyone else, I'd want to understand why.
They could be newer to the industry, have less experience, or be offering fewer services.
That doesn't automatically make them a bad choice. Everyone has to start somewhere, and a newer company may offer competitive pricing while building its client base.
But you need to understand exactly what you're getting.
Are they providing dedicated cleaning crews? Do they have established maintenance relationships? Are they handling guest communications around the clock? Are inspections included?
A low management fee doesn't mean much if you're constantly paying additional fees or dealing with operational problems.
They Can't Explain Their Systems and Processes
If a property manager can't clearly explain how they handle cleaning, maintenance, inspections, inventory, and guest communications, that's a concern.
You don't necessarily need to know every detail of their operation, but they should be able to explain how things work.
A professional management company should have established processes rather than relying on someone remembering to get things done.
They Make Big Promises Without Supporting Data
Be cautious of managers who promise exceptionally high revenue or occupancy without showing you how they arrived at those numbers.
Ask for comparable properties, market data, and realistic projections.
You want someone who understands the market, not someone who simply tells you what you want to hear.
They Aren't Transparent About Fees
If you have to repeatedly ask about additional charges, vendor markups, cleaning fees, or other expenses, that's a red flag.
You should be able to understand the financial arrangement before signing anything.
They Don't Take Ownership
Pay attention to how they discuss problems.
If every issue is someone else's fault, whether it's the cleaner, maintenance provider, guest, or previous manager, I'd be concerned.
A good property manager understands that they're responsible for coordinating the operation, even when they rely on outside vendors.
9. The Most Important Question: How Involved Do You Want to Be as an Owner?
After asking all these questions, there's one final question I'd encourage every property owner to ask themselves:
How involved do I actually want to be in managing this property?
This is an important consideration because not every owner wants the same thing.
Some owners want to be completely hands-off. They want someone to handle everything, provide monthly updates, and only involve them when a major decision needs to be made.
Others want more involvement. They might want to approve maintenance expenses, review cleaning invoices, communicate with vendors, or have input on pricing and guest-related decisions.
Neither approach is wrong.
But you need to find a property manager whose operating style aligns with your expectations.
If you want to be completely hands-off, you need someone with reliable systems, established vendor relationships, and enough authority to make day-to-day decisions.
If you want to be more involved, you need someone who is comfortable working collaboratively and communicating more frequently.
The important thing is establishing those expectations upfront.
Final Thoughts: Hiring a Property Manager Is About Finding the Right Partner
I've managed everything from small condos to large homes with extensive amenities, and if there's one thing I've learned, it's that successful property management comes down to a few fundamentals.
You need someone you can trust, someone who communicates proactively, and someone who has the right people and systems in place to operate your property.
If I were hiring a property manager today, I'd prioritize three things above everything else:
1. Communication and transparency. I want someone who keeps me informed, brings solutions instead of just problems, and is upfront about what's happening with my property and my money.
2. Reliable people and systems. I want dedicated cleaning crews, trustworthy maintenance providers, and established processes that ensure the property is being properly maintained and prepared for every guest.
3. Trust and accountability. I want someone who treats my property as if it were their own, takes ownership when something goes wrong, and understands that we're working together toward the same goal.
Ultimately, you're not just hiring someone to manage a property. You're trusting them with an investment that you've likely put a significant amount of time and money into.
Take the time to ask the right questions, understand what you're paying for, and make sure the expectations are clear before signing an agreement.
The right property manager can make owning an investment property significantly easier and more profitable. The wrong one can create more work, more expenses, and more headaches than managing it yourself.
Choose your property manager carefully. You're not just hiring a service provider. You're choosing a business partner.
