Office Cleaning in Chicago, IL

“Will you add us as an "additional insured" on your general liability policy and send a Certificate of Insurance (COI)?”

Additional-insured status means their policy responds first if their crew causes damage or injury on your site — being only a "certificate holder" does not give you that protection.

Red flag: They can only list you as a certificate holder, or hesitate to send a COI.

“What are your general liability limits, and do you carry workers’ compensation and a janitorial bond?”

Look for at least $1M per occurrence / $2M aggregate, active workers’ comp (so a crew injury is not your liability), and a bond that covers theft.

Red flag: Limits below $1M, lapsed workers’ comp, or no bonding.

“Are cleaners W-2 employees or 1099 subcontractors, and do you run background checks and verify work authorization (E-Verify)?”

W-2 employees mean the company carries payroll taxes, training, and supervision. Background checks and E-Verify reduce theft, liability, and compliance risk for after-hours building access.

Red flag: An all-1099 crew with no screening or documented training program.

“Who supervises the crew, and how is training documented?”

A named supervisor and a written training program are what separate consistent quality from turnover-driven inconsistency.

Red flag: No on-site supervision and no training records.

“Can you share references for facilities like ours, and are you ISSA CIMS certified?”

References in your facility type prove relevant experience. ISSA’s CIMS (Cleaning Industry Management Standard) certification signals mature management systems and quality processes.

Red flag: No references in your vertical, or vague, unverifiable claims.

“What is your client retention and average account tenure?”

High retention is the clearest signal that a provider actually delivers — cleaning is a relationship business, and churn hides service problems.

Red flag: Evasive answers or a portfolio of only very new accounts.

“Can I see a detailed scope of work and your quality-inspection cadence?”

A written SOW (tasks, frequencies, areas) plus scheduled inspections and reporting is what makes quality measurable instead of a matter of opinion.

Red flag: A one-line quote with no task list and no QA process.

“How is pricing calculated, and how do you handle communication and issue response?”

Transparent pricing (per square foot or documented labor hours) and a guaranteed response time let you compare quotes fairly and hold the provider accountable.

Red flag: A flat number with no basis, or no clear point of contact.