End-of-Year Enterprise Legal and Risk Check-In: How to Prepare Your Business for 2026
The end of the year is more than a calendar milestone — it’s a natural checkpoint to protect what you’ve built and prepare for what’s next.
For many organizations, legal and risk questions only surface when something goes wrong: a contract dispute, a regulatory inquiry, a data incident, a key employee departure, or a customer conflict. By the time those issues surface, options are narrower, costs are higher, and leadership is forced to respond under pressure instead of by design.
A structured year-end review does the opposite. It gives leadership room to step back, see the whole enterprise, and ask:
Are our legal, governance, and risk structures still built for the business we’re running now — and the one we intend to run in 2026?
This guide is designed to help business owners, executive teams, in‑house counsel, and risk leaders conduct a thoughtful year-end check-in that blends checklist discipline with strategic planning.
- Why Year-End Reviews Matter
Even well-run organizations quietly accumulate risk over time:
A “temporary” structure put in place three years ago is still running core operations.
A contract with one-sided indemnity or automatic renewal rolls forward unchecked.
New services or markets are added informally without revisiting regulatory or licensing requirements.
A data platform or vendor becomes business-critical, but no one has revisited the contract or security posture.
Individually, these feel like small, manageable gaps. Together, they can create outsized exposure — especially in a legal and regulatory environment that is:
More complex – multi-state operations, global vendors, privacy laws, employment rules, and industry-specific regulations intersect.
More transparent – public ratings, online reviews, investor due diligence, and media coverage make weaknesses visible quickly.
More interconnected – one incident can simultaneously trigger contractual disputes, regulatory reviews, reputational damage, and internal disruption.
A year-end legal and risk review helps you:
Confirm that your governance, contracts, and policies match your current reality, not an earlier chapter of your business.
Identify gaps, inconsistencies, and blind spots before they are discovered by counterparties, regulators, or plaintiffs.
Align legal and risk strategy with your 2026 business objectives—whether that is growth, consolidation, an exit event, or a major strategic pivot.
Done well, this isn’t just about “avoiding problems.” It’s about building a legal and risk infrastructure that allows leaders to make bolder, more confident decisions because they know the foundations will support them.
- Your Legal & Risk Management Checklist
Use the prompts below as a starting point. For many businesses, a productive year‑end session involves your CEO, COO, CFO, HR leader, internal or outside general counsel, and your risk/insurance advisor working through this list together.
A. Governance & Structure
Review governing documents
– Articles, bylaws, operating agreements, shareholder agreements.
– Do they accurately reflect your current owners, board structure, decision-making rules, and reserved matters?
– Are there ambiguities that could create friction in a crisis or transaction?
Confirm ownership and capitalization
– Have there been equity grants, redemptions, or transfers that aren’t fully documented?
– Are cap tables complete and consistent with your legal records?
Verify entity health
– Are all active entities in good standing in the jurisdictions where they operate or do business?
– Do you still need each entity, or is simplification appropriate before an audit, financing, or sale?
B. Contracts and Key Relationships
Map expiring and auto-renewing contracts
– Leases, major vendor agreements, customer contracts, tech & SaaS subscriptions, key professional services.
– For each: What is the term? Is there an automatic renewal? What is the notice period if you want to renegotiate or exit?
Revisit indemnity, limitation of liability, and insurance clauses
– Are you taking on more risk than you intend, especially in high-value contracts or those tied to regulated activities?
– Do contracts align with your insurance coverage and risk appetite?
Check signature authority
– Who is actually binding the company?
– Do board resolutions, delegations of authority, and practice match?
C. Insurance and Risk Transfer
Evaluate current insurance program
– General liability, professional liability, cyber, D&O, EPLI, property, auto, and any industry‑specific coverage.
– Are limits, deductibles, and retentions aligned with your size, risk profile, and appetite?
Compare coverage to current exposure
– Did you add products, locations, or lines of business this year? Acquire or divest entities? Enter new states or markets?
– Did your revenue, headcount, or international exposure change substantially?
Align incident and claims practices
– Do your internal teams understand when and how to report incidents to carriers?
– Are you capturing information early enough to support a strong defense or resolution strategy?
D. People, Policies and Culture
Update core employment and workplace policies
– Remote/hybrid work, use of personal devices, confidentiality, social media, use of AI tools, anti‑harassment, DEI, complaint reporting.
– Are policies current, practical, and actually implemented?
Evaluate hiring, onboarding, and training practices
– Do new hires understand key expectations, restrictions, and escalation paths from the outset?
– Are managers trained to document performance, address concerns early, and seek legal input when needed?
Review leadership succession and delegation
– For key roles, is there a clear plan if someone exits unexpectedly?
– Are responsibilities concentrated in one or two individuals, or distributed in a way that reduces risk?
E. Digital, Data and Cybersecurity
Assess data governance and privacy practices
– What data do you collect (customer, employee, patient, financial, proprietary)? Why, and for how long?
– Are retention, access, and disposal aligned with legal obligations and business needs?
Review cybersecurity safeguards
– Incident response plan (and tabletop exercises), backups, vendor access controls, phishing training.
– Are you aligned with any frameworks or standards expected in your industry?
Check contracts with key technology vendors
– Who owns the data? Who is responsible in the event of a breach or outage?
– Do you have clear exit and transition rights if you need to change systems?
F. Compliance and Regulatory Obligations
Confirm compliance with core requirements
– Licensing, registrations, reporting, advertising and marketing rules, sector-specific regulations (e.g., healthcare, financial services, senior living, insurance).
– Are there regulatory updates taking effect in 2025–2026 that you need to plan for now?
Document your compliance efforts
– Written policies, evidence of training, logs of audits and corrective actions.
– In many contexts, your ability to show “we took this seriously” can profoundly shape outcomes.
G. Disputes, Claims & Enterprise Risk
Review open matters and “near misses”
– Current litigation, threatened claims, demand letters, regulatory inquiries, internal complaints or investigations.
– What patterns or root causes are emerging?
Assess your dispute posture
– Are you always defaulting to full-scale defense, or do you have clear criteria for negotiation, mediation, or alternative resolution?
– Are there opportunities to address recurring issues through policy or process changes rather than case-by-case firefighting?
Revisit your enterprise risk map
– Strategic risks (market shifts, key competitors, concentration).
– Operational risks (supply chain, technology, workforce).
– Financial risks (liquidity, leverage, customer concentration).
– Legal/reputational risks (compliance, governance, brand).
– Are your top 5–7 enterprise risks explicitly owned, monitored, and linked to your 2026 plan?
- Pro Tips from the Field
After decades of working with clients in healthcare and beyond, certain patterns repeat themselves at year-end. A few practical lessons:
A. Governance and Reality Drift Apart Quietly
Many organizations form entities, adopt bylaws or operating agreements, and then move forward at high speed. Over the years:
- Ownership shifts subtly.
- Board composition changes.
- Decision-making happens informally via email or text.
When a major transaction, dispute, or leadership change hits, those early documents suddenly matter again — and mismatches between “paper” and reality can introduce friction, delay, or even litigation.
What helps:
Make governance review a standing agenda item every few years, or after any major event (investment, acquisition, leadership transition). Confirm that what’s written matches how you actually operate.
B. Contract Calendars Are Underrated
Some of the most preventable problems we see are linked to auto‑renewing contracts that no one tracked:
- Expensive software that renews on outdated pricing.
- Real estate leases that tie you up for additional terms unexpectedly.
- Vendor or service agreements with one‑sided indemnity or new pass‑through risks.
By the time someone notices, the window to renegotiate has passed.
What helps:
Maintain a simple contract calendar that includes:
- Renewal dates and notice deadlines.
- Internal review dates 60–120 days in advance.
- A short “risk snapshot” for major contracts (e.g., indemnity, data handling, termination)
C. Out-of-Date Registrations and “Zombie Entities” Cause Real Issues
Clients are often surprised to discover:
- An entity they thought was dormant is still technically active — or vice versa.
- A state where they do business, employ people, or own property doesn’t have an active registration.
- Multiple entities are performing overlapping functions, complicating banking, contracting, or tax reporting.
These issues may seem administrative until a regulator, counterparty, or buyer looks under the hood.
What helps:
Include a corporate housekeeping review in your year‑end process. Inventory your entities, confirm status and purpose, and decide whether to consolidate or clean up.
D. “Near Misses” Are Underused Learning Opportunities
Often, the most valuable insights come not from the case that turned into a lawsuit, but from the incident that almost did.
What helps:
Set aside time with your leaders and advisors to ask:
- Which situations this year could have become serious disputes, but didn’t?
- What did we do — or fail to do — in those moments?
- What can we standardize or formalize as a result?
Those conversations turn individual experiences into enterprise learning.
- Planning Forward for 2026
A strong year-end review doesn’t just look backward; it deliberately looks ahead.
As you plan for 2026, consider building legal and risk strategy into your broader business planning rather than treating it as a separate track.
A. Strategy and Risk Appetite
- Are you planning to expand (new markets, facilities, products, or service lines) or focus on depth and stability?
- Does your current legal and risk framework encourage smart risk‑taking, or does it unintentionally slow decision‑making?
- Are leadership and owners aligned on how much risk is acceptable in pursuit of growth?
A clear risk appetite can guide decisions about contracts, insurance levels, litigation strategy, and investments in compliance or technology.
B. Capital, Transactions, and Partnerships
If 2026 may involve capital events, strategic partnerships, or M&A:
- Are your books, records, and key documents diligence-ready?
- Are there legacy disputes, structural complexities, or governance issues that you’d prefer to resolve before inviting outside scrutiny?
- Do your current agreements allow you to pivot, exit, or restructure if needed?
Cleaning up now often yields a smoother process — and sometimes a better valuation — later.
C. Regulatory and Industry Trends
Ask your team and advisors:
- What are the top regulatory themes on the horizon for your industry?
- Are we anticipating change (and designing toward it), or waiting to react until a rule is final or a notice arrives?
- Do we need to adjust training, documentation, or technology to stay ahead?
Building early awareness into your 2026 planning can turn regulation from a surprise into a strategic consideration.
D. Culture, Communication and Dispute Prevention
Finally, consider the human side of risk:
- When something goes wrong, how does your organization communicate — with employees, customers, partners, regulators?
- Are your leaders trained and supported to have hard conversations early, when resolution is still possible?
- Do you have frameworks for service recovery, expectation-setting, and structured early resolution?
The way you handle conflict, complaints, and bad news is often as important as the underlying event. It can be the difference between a resolved issue and a multi‑year dispute.
- Partnering with Adelman Firm
At Adelman Firm, we view year-end as an opportunity to pause, regroup, and design the next chapter with intention.
We work with organizations as outside general counsel, strategic legal partners, and enterprise risk advisors to:
- Lead or support year-end legal and risk reviews.
- Identify and prioritize areas of exposure and opportunity.
- Align governance, contracts, insurance, and policies with your 2026 strategy.
- Develop practical action plans and support implementation as you move into the new year.
Our goal is not to generate a long list of theoretical risks, but to help you build a clear, actionable roadmap that protects your enterprise and gives leadership confidence.
Ready for a 2026 Reset?
If you’d like support structuring or facilitating your year-end review, we’re here to help.
Let’s start the new year prepared, not playing catch-up.
Contact Adelman Firm to schedule a year-end or Q1 strategic review conversation focused on your business, your risk profile, and your goals for 2026.