Question 1

What types of businesses does Sterling & Associates represent?

Accepted Answer

We represent businesses of all sizes across virtually every industry — from solo entrepreneurs and startups to established mid-market companies with hundreds of employees. Our clients include technology companies, manufacturers, professional services firms, healthcare organizations, real estate developers, restaurants and hospitality groups, and financial services firms. The common thread is that our clients need sophisticated corporate legal counsel tailored to their specific business needs.

Question 2

How is Sterling & Associates different from a large law firm?

Accepted Answer

We offer the same caliber of legal expertise you'd find at a large national firm — our attorneys trained at top law schools and practiced at major firms — but with several key advantages: direct partner attention on every matter, faster response times, more predictable fees, and a deep focus on the Chicago business community. We don't have the overhead of a 500-attorney firm, which means our clients get better value without sacrificing quality.

Question 3

Do you offer free initial consultations?

Accepted Answer

Yes. We offer a complimentary 30-minute initial consultation for prospective clients. During this meeting, we'll discuss your legal needs, explain your options, and provide a clear sense of the scope and cost of engagement. There's no obligation and no pressure — it's simply an opportunity for us to understand your situation and for you to evaluate whether we're the right fit.

Question 4

What geographic areas do you serve?

Accepted Answer

While our office is located on Wacker Drive in downtown Chicago, we serve clients throughout the Chicagoland area, across Illinois, and nationally for transactional matters that don't require local court appearances. Many of our clients operate in multiple states, and we regularly coordinate with local counsel in other jurisdictions when needed.

Question 5

How quickly can you respond to urgent legal matters?

Accepted Answer

We understand that business doesn't wait for business hours. For existing clients, we aim to respond to all communications within 4 business hours during weekdays. For truly urgent matters — such as threatened litigation, emergency injunctions, or time-sensitive transactions — we are available after hours and on weekends. Every client has their attorney's direct phone number and email.

Question 6

Can you serve as our company's outside general counsel?

Accepted Answer

Absolutely. Many of our clients engage us as their outside general counsel, which means we serve as their go-to legal resource for day-to-day questions, contract reviews, compliance issues, and strategic planning — without the cost of a full-time in-house attorney. We offer retainer arrangements that provide predictable monthly costs and priority access to our team.

Question 7

What's the best business entity for my company — LLC, S-Corp, or C-Corp?

Accepted Answer

The right entity depends on your specific situation, including the number of owners, funding plans, tax preferences, and long-term goals. LLCs offer the most flexibility and are ideal for most small businesses. S-Corps can provide tax advantages for owner-employees earning above a certain threshold. C-Corps are typically best for companies planning to raise venture capital or eventually go public. We recommend using our free Business Entity Selection tool for initial guidance, then scheduling a consultation for personalized advice.

Question 8

How much does it cost to form a business in Illinois?

Accepted Answer

The Illinois Secretary of State filing fee for an LLC is $150, and for a corporation it's $175 (both as of 2025). However, the filing fee is just the beginning. A proper formation includes drafting an operating agreement or bylaws, obtaining an EIN, setting up your corporate records, and ensuring compliance with Chicago and Cook County business licensing requirements. Our all-inclusive formation packages start at $1,500 for a basic LLC and include everything you need to start operating with proper legal protection.

Question 9

Do I really need an operating agreement for my LLC?

Accepted Answer

Yes — emphatically. While Illinois law doesn't technically require an operating agreement, operating without one is one of the biggest mistakes we see. Without an operating agreement, your LLC is governed entirely by the Illinois Limited Liability Company Act's default rules, which may not reflect your intentions regarding profit sharing, management authority, or what happens if a member leaves. More critically, courts have used the absence of an operating agreement as evidence to pierce the corporate veil, which means you could lose your personal liability protection.

Question 10

How long does it take to form a business in Illinois?

Accepted Answer

Standard processing with the Illinois Secretary of State takes approximately 5-7 business days for online filings. Expedited processing (1-2 business days) is available for an additional fee. We typically have all organizational documents — articles, operating agreement, EIN, and initial resolutions — completed within 1-2 weeks. If you need to form an entity urgently for a time-sensitive transaction, same-day filing is possible.

Question 11

Should I form my business in Delaware or Illinois?

Accepted Answer

For most Chicago businesses, Illinois formation is the better choice. Delaware's advantages — such as its specialized business courts and well-developed corporate law — primarily benefit large publicly traded companies or venture-backed startups anticipating institutional investment. If you're forming a Delaware entity but operating in Illinois, you'll need to register as a foreign entity in Illinois anyway, resulting in double filing fees and franchise taxes. We recommend Delaware formation only for companies specifically planning to raise institutional venture capital.

Question 12

What ongoing compliance requirements does my business have after formation?

Accepted Answer

Illinois LLCs must file an annual report with the Secretary of State ($75 fee) and maintain a registered agent. Corporations have similar annual report obligations plus additional requirements including holding annual shareholder and director meetings, maintaining corporate minutes, and issuing stock certificates. Chicago businesses may also need to renew city business licenses annually. We offer a compliance maintenance service that ensures you never miss a deadline.

Question 13

When should I have an attorney review a contract?

Accepted Answer

The short answer is: before you sign any contract with significant financial implications. As a practical matter, we recommend attorney review for any agreement involving more than $10,000 in value, any agreement lasting longer than one year, any agreement with non-compete or exclusivity provisions, any real estate lease, and any agreement involving intellectual property rights. The cost of a contract review ($500-$2,000 for most commercial agreements) is trivial compared to the potential cost of a problematic provision.

Question 14

How much does it cost to have a contract drafted?

Accepted Answer

Contract drafting costs vary significantly based on complexity. A basic NDA or simple service agreement can be drafted for $500-$1,500. Standard commercial contracts — such as master service agreements, vendor agreements, or partnership agreements — typically range from $2,000-$5,000. Complex agreements involving significant deal value, multiple parties, or unusual provisions may range from $5,000-$15,000. We always provide a detailed fee estimate before beginning work.

Question 15

What's the difference between a contract review and a contract negotiation?

Accepted Answer

A contract review involves our attorney reading the agreement, identifying risks and problematic provisions, and providing you with a written summary of recommended changes. This is a one-time deliverable. Contract negotiation goes further — it includes the review plus our active involvement in negotiating revised terms with the other party, drafting redline revisions, and managing the back-and-forth until a mutually acceptable agreement is reached. Most clients find that professional negotiation pays for itself through improved terms.

Question 16

Can I use a contract template I found online?

Accepted Answer

We strongly advise against relying on generic online templates for anything beyond the most basic agreements. Online templates are typically drafted to be one-size-fits-all, which means they're optimized for no one. They often fail to comply with Illinois-specific requirements, omit critical provisions relevant to your industry, and include terms that may actually harm your interests. That said, a quality template can sometimes serve as a useful starting point — but it should always be customized by an attorney who understands your specific business and objectives.

Question 17

What happens if the other party breaches our contract?

Accepted Answer

Your remedies for breach depend on the terms of the contract itself and applicable law. Common remedies include monetary damages (compensatory, consequential, and sometimes liquidated damages), specific performance (a court order requiring the other party to fulfill their obligations), injunctive relief (a court order preventing further breach), and contract termination with recovery of losses. The first step is always to send a formal demand letter, which resolves many disputes without litigation. If litigation becomes necessary, our commercial litigation team can pursue your claims aggressively.

Question 18

How long should I keep copies of expired contracts?

Accepted Answer

We recommend retaining all contracts for a minimum of 7 years after expiration or termination, and indefinitely for certain types of agreements including real estate documents, corporate governance documents, and intellectual property licenses. Illinois's statute of limitations for written contracts is 10 years, meaning a claim can potentially be brought up to a decade after the breach occurred. A robust document retention policy is essential — and we can help you create one tailored to your industry and risk profile.

Question 19

How long does a typical M&A transaction take?

Accepted Answer

Most M&A transactions take 3 to 9 months from initial engagement to closing, though the timeline varies significantly based on deal complexity, regulatory requirements, and financing arrangements. A straightforward asset purchase of a small business might close in 60-90 days. A complex merger involving multiple entities, regulatory approvals, or third-party consents can take 6-12 months. The due diligence phase typically takes 4-8 weeks, and the negotiation and documentation phase adds another 4-6 weeks.

Question 20

What's the difference between an asset purchase and a stock purchase?

Accepted Answer

In an asset purchase, the buyer acquires specific assets and assumes specific liabilities of the target business — the buyer can generally pick and choose what they want. In a stock (or membership interest) purchase, the buyer acquires the entire entity, including all assets and all liabilities — known and unknown. Asset purchases are generally preferred by buyers because they limit liability exposure and often allow for a stepped-up tax basis. Stock purchases are often preferred by sellers for tax reasons and simplicity. The right structure depends on the specific transaction.

Question 21

How do I determine what my business is worth?

Accepted Answer

Business valuation is both art and science. The most common methods are EBITDA multiples (applying an industry-specific multiple to your earnings), revenue multiples (for high-growth companies), and discounted cash flow analysis (projecting future cash flows and discounting to present value). The appropriate method depends on your industry, growth profile, and the purpose of the valuation. We recommend starting with our free Business Valuation Estimator tool for a preliminary range, then engaging a professional valuator for a formal opinion when you're ready to transact.

Question 22

What is due diligence and why is it important?

Accepted Answer

Due diligence is the comprehensive investigation of a target company conducted by a prospective buyer before closing a transaction. It covers financial records, legal compliance, contracts, intellectual property, employment matters, real estate, environmental issues, and technology systems. The purpose is to verify the seller's representations, identify undisclosed risks, and inform the deal structure and purchase price. Skipping or shortcutting due diligence is the single most common cause of post-acquisition disputes and buyer's remorse.

Question 23

Do I need an attorney for a small acquisition?

Accepted Answer

Yes — arguably even more so than for a large transaction. Large acquisitions involve institutional buyers with in-house legal teams and sophisticated advisors. Small business acquisitions often involve individual buyers with limited transaction experience, making professional guidance even more critical. Common issues in small acquisitions include unclear IP ownership, undisclosed liabilities, inadequate representations and warranties, and poorly structured earn-outs. Our M&A practice handles transactions from $1 million to $500 million with the same level of rigor.

Question 24

What is a letter of intent (LOI) and is it binding?

Accepted Answer

A letter of intent is a preliminary document that outlines the key terms of a proposed transaction before the parties invest in detailed due diligence and definitive agreements. Most LOIs are structured as non-binding with respect to the business terms (price, structure, conditions) but binding with respect to certain procedural provisions — specifically exclusivity (preventing the seller from negotiating with others), confidentiality, and expense allocation. Getting the LOI right is critical because it sets the framework for the entire negotiation.

Question 25

What are representations and warranties in an M&A deal?

Accepted Answer

Representations and warranties (R&W) are statements of fact made by the seller about the target company's condition — covering areas including financial statements, legal compliance, material contracts, intellectual property, employment matters, and tax obligations. They serve two purposes: allocating risk between buyer and seller, and providing the buyer with contractual recourse (indemnification) if the seller's statements prove false. Negotiating R&W is one of the most important aspects of M&A deal documentation.

Question 26

What compliance requirements apply to my business in Chicago?

Accepted Answer

Compliance requirements depend on your industry, size, and specific activities. All Chicago businesses must comply with federal regulations (employment, tax, data privacy), Illinois state requirements (business registration, workers' compensation, BIPA), Cook County regulations (minimum wage, paid leave), and City of Chicago requirements (business licensing, various industry-specific permits). Industry-specific regulations — such as HIPAA for healthcare, SOX for public companies, or state licensing for financial services — add additional layers. Our Compliance Checker tool can help identify your specific obligations.

Question 27

What is the Illinois Biometric Information Privacy Act (BIPA)?

Accepted Answer

BIPA is an Illinois law that regulates the collection, use, storage, and disclosure of biometric information — including fingerprints, facial geometry, voiceprints, and iris scans. If your business collects any biometric data (including through time clocks, security systems, or customer-facing technology), BIPA requires written notice and consent, a published data retention and destruction policy, and strict limitations on disclosure. BIPA provides a private right of action with statutory damages of $1,000-$5,000 per violation, making it one of the most actively litigated privacy laws in the country.

Question 28

How often should we conduct a compliance audit?

Accepted Answer

We recommend a comprehensive compliance audit at least annually, with more frequent reviews for companies in heavily regulated industries. Additionally, a targeted compliance review should be conducted whenever your business undergoes significant changes — such as entering a new market, launching a new product, significantly increasing headcount, or experiencing a change in ownership. Many of our clients engage us for ongoing compliance monitoring, which provides continuous oversight rather than periodic snapshots.

Question 29

What happens if my business is found to be non-compliant?

Accepted Answer

Consequences of non-compliance range from administrative penalties and fines to criminal prosecution, depending on the nature and severity of the violation. More immediately, non-compliance can result in business license revocation, contract defaults, loss of insurance coverage, and significant reputational damage. In many cases, voluntary disclosure and prompt remediation can significantly reduce penalties. If you've identified a compliance issue, contact us immediately — early intervention is almost always better than waiting to be discovered.

Question 30

Do I need a formal compliance program?

Accepted Answer

Any business with more than a handful of employees should have a documented compliance program. The complexity of the program should be proportional to your business's size, industry, and regulatory exposure. At minimum, a compliance program should include written policies and procedures, employee training, a reporting mechanism for potential violations, and regular monitoring and auditing. Having a documented program not only reduces the risk of violations but also demonstrates good faith to regulators, which can mitigate penalties if issues do arise.

Question 31

What data privacy laws affect Illinois businesses?

Accepted Answer

Illinois businesses must navigate a complex patchwork of data privacy regulations. Key laws include BIPA (biometric data), the Illinois Personal Information Protection Act (data breach notification), the Student Online Personal Protection Act (student data), and the Genetic Information Privacy Act. For businesses with customers in other states, the California Consumer Privacy Act (CCPA) and similar state laws may also apply. At the federal level, HIPAA, COPPA, GLBA, and the FTC Act create additional obligations depending on your industry. We help businesses develop comprehensive privacy frameworks that address all applicable requirements.

Question 32

How does your firm bill for legal services?

Accepted Answer

We offer several fee structures depending on the type of work: hourly billing for litigation and ongoing advisory work, flat fees for defined-scope projects like entity formation, contract drafting, and trademark registration, monthly retainers for outside general counsel arrangements, and success-based or hybrid structures for certain transactional work. We believe in transparent, predictable pricing and always provide detailed fee estimates before beginning work. There are never surprise charges.

Question 33

What are your hourly rates?

Accepted Answer

Our hourly rates reflect our attorneys' experience levels: partners bill at $350-$500 per hour and associates at $225-$325 per hour. These rates are significantly below the $500-$1,000+ hourly rates charged by large Chicago firms while delivering the same quality of work. We also staff matters efficiently — you won't pay partner rates for work that can be effectively handled by an associate, and we don't use the 'leverage model' of large firms where junior associates spend excessive hours learning on your matter.

Question 34

Do you require a retainer?

Accepted Answer

For most new matters, we request a retainer that is held in our client trust account and applied against fees as they are incurred. The retainer amount varies based on the nature and expected scope of the engagement — typically ranging from $2,500 to $15,000. For ongoing general counsel arrangements, we offer fixed monthly retainer packages that include a defined scope of services for a predictable monthly fee, with additional work billed at discounted hourly rates.

Question 35

Can you provide a fixed fee for my matter?

Accepted Answer

Yes, for many types of work. We offer flat-fee pricing for business formation ($1,500-$4,500 depending on complexity), contract drafting ($500-$5,000 depending on agreement type), trademark registration ($1,200-$2,500 per class), and several other defined-scope services. For matters where scope is less predictable — such as litigation or complex negotiations — we provide detailed budgets with phase-by-phase estimates and proactively communicate if the matter is trending above or below the estimate.

Question 36

What payment methods do you accept?

Accepted Answer

We accept payment by check, ACH bank transfer, wire transfer, and all major credit cards. For larger matters, we can arrange payment plans with monthly installments. We bill monthly and payment is due within 30 days of invoice. All billing details, including specific tasks performed and time spent, are documented in detailed monthly invoices that provide full transparency into the work performed on your behalf.

Question 37

Do you offer any free services?

Accepted Answer

We offer complimentary 30-minute initial consultations for all prospective clients. We also provide a suite of free online tools — including our Business Entity Selector, Contract Risk Analyzer, M&A Readiness Calculator, Compliance Checker, Business Valuation Estimator, and Legal Cost Estimator — that provide genuine value without any obligation. Additionally, we regularly publish free blog articles, guides, and resources on our website covering current legal topics relevant to Chicago businesses.

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