Common Legal Challenges for Businesses

I’ve provided legal counsel to 100+ CEOs over the last 5 years. Companies with $500K to $50M+ in ARR. 5 common issues I helped solve: 1. Contracts Issue: Too much time reviewing. Too many red-lines. Too much legal jargon. My approach: Define SLAs. One round of red-lines. Then a conversation. Summarize risk points. Place decision-makers in a position to decide. Minimize legalese. —— 2. Subcontractors Issue: Vendor didn’t perform. Vendor lied. Vendor poached. Vendor caused demand for indemnity. My approach: Review contracts. Update templates. Define insurance requirements. Perform better due diligence. Navigate disputes (see below). —— 3. Disputes Issue: Lawsuits. Demands for arbitration. Nastigrams. And, of course, “GOVERN YOURSELF ACCORDINGLY.” My approach: Review everything. Analyze exposure. Perform cost-benefit analysis. Root cause the issue. Address the immediate and plug the hole. —— 4. Compliance Issue: Lots of laws. Different states. Different agencies. New legislation. No oversight. My approach: Assume responsibility. Stand up compliance department. Outline requirements. Establish controls. Test. Report. Remediate. Test again. —— 5. Data Issue: Lack of documentation. And disclosures. Evolving regulations. New territories. My approach: Update privacy policies. Review disclosures. Establish internal policies and procedures. Negotiate with vendors. Draft licensing agreements. —— What common issues do you see in your legal practice? #inhousecounsel #law #ceo

Grow fast enough, and things start to break. It’s a good problem to have, but you need to address it quickly when it comes to compliance. Key challenges: 1. KEEPING UP WITH THE EVOLVING REGULATORY LANDSCAPE As regulations evolve, companies must adapt their practices to ensure compliance. This requires ongoing monitoring and interpretation of regulatory updates, which can be a resource-intensive task for growing organizations. 2. SCALING COMPLIANCE OPERATIONS WITH BUSINESS GROWTH As the organization grows, new business lines emerge, increasing the compliance burden. This necessitates efficient processes to manage and track compliance activities across the entire company. Simply using manual tools like spreadsheets can result in gaps, creating even bigger challenges for the business. 3. MANAGING MULTIPLE JURISDICTIONS AND COMPLEX REQUIREMENTS Expanding into new geographic regions introduces additional compliance challenges. Each jurisdiction has its own unique set of regulations and reporting requirements, making compliance management a complex and time-consuming task. For example, the GDPR and CCPA/CPRA have similar but not identical requirements. If you have EU citizens and California residents as customers (probably many businesses!), you’ll need to worry about both. 4. LACK OF BANDWIDTH TO MANAGE COMPLIANCE A growing company has a lot of areas to focus on, primarily scaling operations and meeting market demands. Amidst these challenges, allocating resources to manage compliance becomes a huge challenge for fast-growing companies. In most instances, lack of resources, not enough knowledge about compliance management, and shaky internal infrastructure can become primary bottlenecks. Even companies with established security teams shift their focus on managing compliance while they should be focusing on setting up proper security measures – which eventually leads to digging an even deeper hole. 5. MANAGING MULTIPLE FRAMEWORKS WITH DUPLICATIVE REQUIREMENTS Another challenge that fast-growing companies find themselves subjected to is multiple compliance frameworks, each with overlapping or duplicative requirements. ISO 27001 and SOC 2 are similar, but not identical, for example. This redundancy can create confusion and inefficiencies, as the company must allocate additional resources to address similar compliance demands across different sets of requirements. BOTTOM LINE As your rocket ship starts taking off, your compliance challenges will mount.🚀

What’s on the legal radar for the rest of 2025? Here are five big issues every business should be watching closely: 1. AI compliance and AI washing. The SEC is taking aim at companies exaggerating their AI capabilities to investors. Make sure your claims match your reality or risk getting burned. 2. Data privacy patchwork. Without a federal privacy law, states like California, Virginia, Colorado, Delaware, and Iowa are setting their own rules. If your data strategy doesn’t keep up, you’re playing with fire. 3. Worker classification. The Department of Labor recently pulled back from a stricter rule, giving businesses more flexibility in classifying workers as independent contractors. But beware: private litigation and state laws may still treat workers as employees in certain circumstances. Review your contracts and practices carefully. 4. Cybersecurity reporting. The SEC now requires public companies to report material cybersecurity incidents within four business days of determining they’re significant. Gone are the days of quietly handling a breach. You need a plan and a communications strategy ready to go. 5. ESG and greenwashing. The SEC is cracking down on misleading sustainability claims. If your marketing says you’re eco-friendly, you’d better be able to prove it. Bottom line, 2025 is shaping up to be a regulatory minefield. Staying proactive on these issues can make the difference between leading the pack and falling behind.