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68% of businesses switch IT providers because promises weren’t delivered. If you're searching for managed IT services in Chicago, this guide gives you the 10 questions you must ask before signing a contract. From SLAs and cybersecurity to compliance and response time, we break down how to separate real IT partners from smooth sales pitches— so your business doesn’t pay for someone else’s learning curve.

When a Chicago law firm’s systems go down mid-day, it is not just an inconvenience. It is lost billable hours, missed deadlines, and potential compliance risk. Yet many firms still choose IT support based on price, rely on remote-only providers, or assume backups work without testing them. In a legal market driven by speed, confidentiality, and ARDC compliance, local response time is not a luxury. It is a safeguard for revenue, reputation, and client trust.

Most security problems inside CPA firms don’t begin with sophisticated hackers. They begin with good people under pressure. During busy season, helpful staff take shortcuts to meet deadlines, unknowingly creating Shadow IT, visibility gaps, and compliance risk. This guide explains why locking systems down fails, how guardrails work better than restrictions, and what leadership must redesign to protect client data without slowing productivity.

Law firms do not just manage cases. They manage confidential data, financial records, and privileged communications. In Chicago’s competitive legal market, one security slip can trigger downtime, lost billable hours, client distrust, and insurance complications that cost more than your malpractice policy ever will. Strong IT support is no longer optional. It is the foundation of protecting client privilege, compliance, and your firm’s reputation.