Most cleaning companies will give you a quote. Few will tell you what you actually need to know. We've been cleaning Chicago offices since 2019, and we've heard the horror stories — companies that showed up once, damaged property, or disappeared mid-contract.
Quick Answer: Before hiring a commercial cleaning company, ask about insurance and bonding, employee screening, references from similar clients, products used, scheduling flexibility, contract terms, and service guarantees. If they hesitate on any answer, keep looking.
### Why These Questions Matter
You're giving someone access to your office after hours. Keys. Alarm codes. Employee belongings. Sensitive documents. The cleaning company you choose needs to be trustworthy, reliable, and properly insured.
Chicago has hundreds of cleaning companies. Some are excellent. Some are one person with a vacuum. Some will quote low and deliver less. These questions help you tell the difference.
### Question 1: Are You Licensed, Bonded, and Insured?
This is non-negotiable. Any commercial cleaning company should have:
General Liability Insurance
Covers damage to your property. If a cleaner breaks a computer, damages carpets, or causes a fire, liability insurance pays for it. Ask for a certificate of insurance. Verify the policy is current. Minimum coverage should be $1 million.
Workers' Compensation
Covers injuries to their employees. If a cleaner gets hurt on your property, workers' comp pays for it. Without this coverage, you could be liable. Ask for proof.
Bonding
Protects against theft. If an employee steals from your office, bonding covers the loss. Bonding is different from insurance — ask for both.
What to look for: A reputable company will provide certificates of insurance and bonding within 24 hours of request. If they hesitate or can't provide documentation, move on.
### Question 2: How Do You Screen Your Employees?
Your cleaning crew has access to your office after hours. You need to know who's entering your space.
Background Checks
Ask if they run criminal background checks. Ask what offenses disqualify someone from working. Not every company screens employees thoroughly.
Drug Testing
Some companies drug test. Some don't. If this matters to you, ask.
Employment Verification
Do they verify employment history? Do they check references? How long do employees typically stay?
What to look for: Companies that invest in screening tend to have better retention and fewer problems. Ask about their hiring process. A good company will explain their screening without hesitation.
### Question 3: Can You Provide References from Similar Businesses?
A cleaning company that serves medical offices is different from one that serves warehouses. You want references from businesses similar to yours.
Ask for Specific References
"I need references from law firms" or "I need references from medical offices." A good company will provide 3-5 relevant references.
Call the References
Don't just collect names. Call them. Ask:
- How long have you worked with this company?
- Have you had any problems?
- How do they handle complaints?
- Would you hire them again?
Check Online Reviews
Google, Yelp, industry directories. Look for patterns. One bad review might be a fluke. Consistent problems are a warning sign.
What to look for: References from businesses like yours. Consistent positive feedback. A willingness to provide contact information.
### Question 4: What Cleaning Products Do You Use?
Cleaning products matter for employee health, surface preservation, and environmental impact.
Health Considerations
Harsh chemicals can trigger asthma and allergies. Ask what products they use. Ask if they have green cleaning options.
Surface Compatibility
Wrong products damage surfaces. Marble floors need different cleaners than vinyl. Hardwood needs different treatment than carpet. Ask how they choose products for different surfaces.
Environmental Impact
Many Chicago businesses prioritize sustainability. Ask about green cleaning products. Ask about recycled paper products. Ask about equipment efficiency.
What to look for: Companies that can explain their product choices. Willingness to accommodate requests (unscented products, green products, etc.). Knowledge about surface-appropriate cleaning.
### Question 5: What's Your Scheduling Policy?
You need cleaning that works around your business, not the other way around.
Flexibility
Can they clean early morning? After hours? Weekends? Can they adjust for special events? What if you need extra cleaning before a client visit?
Consistency
Will you have the same cleaning crew each time? Consistent cleaners learn your space. Rotating crews start fresh every visit.
Reliability
What happens if a cleaner calls in sick? Do they have backup coverage? How do they handle weather emergencies?
What to look for: Scheduling flexibility. Commitment to consistent crews. A backup plan for absences.
### Question 6: What Are Your Contract Terms?
Contracts matter. Understand what you're signing.
Contract Length
Avoid long-term contracts initially. A 30-90 day trial period lets you evaluate service. Month-to-month after that is standard. Be wary of contracts longer than one year.
Cancellation Policy
What notice do you need to cancel? Is there a penalty? How do you end service if it's not working?
Price Guarantees
How long is the quoted price valid? When can prices increase? What triggers a price change?
Scope Changes
What if you need to add services? Reduce frequency? Change schedule? How are changes handled?
What to look for: Flexible terms. Reasonable cancellation policies. Clear pricing. A company that wants to earn your business, not lock you in.
### Question 7: What Happens If Something Goes Wrong?
Problems happen. How they're handled matters more than whether they occur.
Complaint Process
Who do you call if something is missed? How quickly do they respond? What's the process for fixing problems?
Damage Policy
If a cleaner damages property, what happens? Who pays? How quickly is it resolved?
Service Guarantee
Do they guarantee their work? Will they come back if something isn't clean? Is there a money-back guarantee?
What to look for: A clear process for handling problems. A commitment to making things right. A service guarantee in writing.
### Red Flags to Watch For
Quotes Without Seeing Your Space
If a company gives you a firm quote without visiting your office, be careful. Accurate quotes require seeing the space, understanding your needs, and assessing the work.
Prices Far Below Market
If a quote is significantly lower than others, something is missing. They may cut corners, skip tasks, or send undertrained staff. Cheap cleaning costs more when you have to hire someone else to fix problems.
No Physical Address
A legitimate company has an office, equipment storage, and staff. A PO box or residential address might mean the company is one person with a vacuum.
Pressure to Sign Now
A good company gives you time to decide. Pressure to sign immediately is a warning sign.
### What a Good Answer Looks Like
When you ask these questions, good companies answer clearly:
- "Yes, we're licensed, bonded, and insured. I'll send certificates of insurance today."
- "We run background checks on all employees. We verify employment history for the past 5 years."
- "Here are references from three law firms we currently clean. I've included phone numbers."
- "We use EPA Safer Choice products. We can adjust for employees with allergies."
- "We can clean after 6 PM or before 8 AM. You'll have the same crew every visit."
- "We start with a 30-day trial. After that, it's month-to-month. 30 days notice to cancel."
- "If something is missed, call me directly. I'll send someone back within 24 hours at no charge."
Need a quote for your Chicago office? Get a free quote or call 630-349-2862. We're licensed, bonded, and insured. References available.