As we kick off 2026, many entrepreneurs and investors will look for and reevaluate who is the right lawyer for their business. Many are practicing “DIY” (“do it yourself”) lawyering with large-language models and free-to-consumers artificial intelligence engines (e.g., ChatGPT, Claude, CoPilot, Gemini, etc.). Despite the proliferation of AI, LLMs, and even proprietary datasets, choosing the right lawyer for your business “IRL” (“in real life”) remains one of the most important decisions entrepreneurs, investors, and executives can make. In 2026, legal risk now extends beyond doing business, negotiating contracts, granting equity, and engaging in litigation to include artificial intelligence, data governance, cybersecurity, cross‑border regulation, and reputational exposure in what has become a hyper‑transparent, “always-on” world, 24 hours a day, seven days a week.
Whether you are launching a new business venture, pivoting away from your old business model, scaling rapidly, or facing a “bet‑the‑company” opportunity or crisis, the lawyer you choose can materially influence your outcome. Consulting LLMs can certainly accelerate your learning on how to handle issues, the right legal representative will do more than identify and react to problems, they will anticipate them, align legal strategy consistent with corporate strategy, and help you responsibly grow your business.
In many cases, the best lawyer may be someone you have known for years, someone who returns calls promptly, understands your risk tolerance, and has your long‑term interests at heart. There will be other times when a trusted referral may be more appropriate. What matters most is fit. The lawyer who helped you form your startup may not be the same lawyer you need when you introduce AI into your product, expand internationally, or prepare for a liquidity event.
Ask yourself: Am I partnered with an attorney who can help my business grow to its next phase and manage the legal and ethical risks of emerging technology?
Am I using my attorney to proactively manage legal risk, or am I reactively using a lawyer when the rot has already set in?
Start Early and Ask the Right Questions
Your need for the right lawyer begins well before your idea is pitched to investors, customers, or partners. Early legal decisions you make can have consequences that are long-lasting, which is why asking yourself some key questions early in the game is important. For example:
• What legal entity best suits my business?
• Where should I incorporate this company?
• Should this company be an LLC, C‑Corporation, or S‑Corporation? Should it be a partnership?
• Who should get equity, and in what amounts, on what conditions, at what price, and what happens if one of us leaves or wants to exit?
• How will you protect the Company’s intellectual property?
• How will AI be integrated into the business model, and what are the regulatory frameworks that apply?
• Who will own the data collected, stored, or models developed with, and who owns it?
Capital Structure and Growth
Capitalization decisions matter more and more with every financing round. Dilution increases, governance becomes more complex, and mistakes made early can surface painfully at exit. Your lawyer will be someone to help you deal with these important and consequential decisions. For example:
• Equity vs. convertible instruments (notes, SAFEs, KISS)
• Founder and executive equity allocation
• Investor rights and preferences
• AI‑related representations, warranties, and disclosures
• Exit‑ready governance and compliance
Intellectual Property and AI Protection
Protecting intellectual property is foundational, particularly in an AI-driven economy where value is often embedded in code, data, and algorithms. Your early legal planning should clearly explain how inventions and processes are protected through patents, how brands and digital identities are secured through trademarks and domain strategy, and who owns the copyrights in software, AI models, and generated content. Equally critical are trade-secret safeguards, clear ownership lines, and compliance with open-source and third-party AI tools, all of which can materially affect valuation, defensibility, and exit readiness.
Key Criteria for Selecting the Right Lawyer in 2026
Just as you wouldn’t see a chiropractor for a heart condition, not every lawyer is the right choice to address every problem. Choose carefully, as if your business depended on it.
Bandwidth and Availability
Your lawyer should be responsive, accessible, have a wide network, and have a capable team. Early interactions are often predictive. Ask who will specifically handle your work, how to reach them, and whether they can work at a cadence aligned with your budget and cadence.
Experience
Look for a lawyer who has guided companies from formation through financing, scaling, and exit. Experience includes not only successes, but failures, valuable lessons that help you avoid common and costly mistakes. In 2026, this also means experience with AI regulation, data privacy, cybersecurity, and cross‑border compliance.
Industry and Technology Fluency
If your business leverages AI or emerging technology, your lawyer must be curious, informed, and forward-thinking. They should understand evolving regulatory frameworks, ethical aspects, and commercial risks, and help you turn compliance into a competitive advantage.
Network
No lawyer knows everything. The right lawyer brings a strong network of specialists: investors, accountants, technologists, cybersecurity experts, and regulatory advisors. They should understand your industry, geography, and stage of growth, and be able to offer meaningful introductions.
Reputation and Recognition
Your lawyer should be respected by peers, clients, and institutions you trust. Recognition signals credibility, judgment, and staying power.
Stage‑Appropriate Experience
• Startup Stage: You need efficient, practical advice often delivered in clear list items, not lengthy memos. Technology‑enabled tools and cost‑conscious strategies are significant.
• Financing Stage: Your lawyer should have a solid understanding of investor expectations, diligence processes, and fundraising technology platforms.
• Exit Stage: Your lawyer should anticipate buyer scrutiny, clean up complications proactively, and negotiate from experience.
Fees and Business Arrangements
Understanding billing structures upfront is key. Hourly, project‑based, alternative fee arrangements, and scaled pricing are increasingly common. Transparency matters more than cost alone. Always choose value, judgment, and alignment over price.
Selecting a lawyer will be one of the most consequential decisions your business will face. With the influence of AI, regulation, and constant change, your choice of an attorney partner can help you innovate with confidence, grow responsibly, and safeguard your highest priorities.