8 Most Challenging Contracts to Draft & Why They’re Complex

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8 Most Challenging Contracts to Draft & Why They're Complex

Drafting contracts is a nuanced art form in the legal world, requiring meticulous attention to detail, foresight, and a deep understanding of the parties involved. While some contracts may seem straightforward on the surface, many delve into complexities that can challenge even the most seasoned legal professionals. At Legal Consulting Pro, we recognize the intricate nature of contract drafting and understand the importance of identifying and navigating the most challenging types of contracts.

In this blog, we explore the eight most challenging contracts to draft and dissect the reasons behind their complexity. From intricate language requirements to multifaceted negotiation dynamics, each contract presents its own unique set of hurdles. By shedding light on these complexities, we aim to provide valuable insights into the nuances of contract drafting, helping legal professionals navigate these challenges with confidence and expertise.

Whether you’re a seasoned attorney looking to enhance your contract drafting skills or a business owner seeking clarity on complex contractual arrangements, this blog serves as a comprehensive guide to understanding the intricacies of the most challenging contracts. Join us as we delve into the world of contract drafting and uncover the reasons why these contracts pose such formidable challenges.

Commercial Leases

An initial commercial lease tailored to a client’s needs is one of the toughest contracts to draft because there are so many considerations to be taken into account. Drafting requires collaboration between business and legal parties to ensure the attorney understands the business goals, objectives, and risk tolerance levels. The provisions of a lease agreement can vary drastically, with any combination of pro-landlord, mutual, or pro-tenant clauses. The provisions are also tailored to the nature of the commercial property. For example, a lease for a warehouse requires different considerations than a shopping center. Attorneys and landlords must also understand negotiation points and be prepared to concede certain points during the lease negotiation process. These factors and others require careful consideration when drafting an initial commercial lease for a client.

Derek Colvin, Attorney, Waldrop & Colvin

Digital Asset Partnerships

In my role at MAH Advising PLLC, focusing on areas such as regulatory counsel, compliance services, and specifically contract review, I’ve encountered a wide array of complex contractual arrangements. However, one of the most challenging types of contracts to draft, in my experience, has been partnership agreements within the realm of emerging digital assets and cryptocurrencies. The complexity in these contracts arises not only from the rapidly evolving regulatory landscape but also from the intricacies of defining the operational mechanisms of digital assets within a legal framework.

The drafting complexity is further exacerbated by the need to anticipate and incorporate provisions that account for future technological advancements and regulatory changes. For example, in drafting a partnership agreement for a blockchain startup, it was crucial to incorporate flexible yet precise language to accommodate the potential for future blockchain protocol upgrades, changes in digital asset classifications, and evolving tax implications. This required a deep understanding of both the technology and the legal precedents, which are still in their formative stages.

Moreover, ensuring compliance with the Financial Industry Regulatory Authority (FINRA) and other relevant bodies adds another layer of complexity. In my experience, navigating the expectations of regulatory bodies while safeguarding the innovative spirit of a partnership in the digital asset space necessitates a delicate balance. A concrete instance of this was when working on an agreement that involved the creation of a digital asset fund; it was imperative to delineate the governance structure, investor rights, and regulatory compliance mechanisms in a way that was both pioneering and legally robust.

The value in crafting these complex agreements comes from not only mitigating risks but also in laying a strong foundation for future innovation and collaboration. Each contract becomes a case study in balancing legal compliance with the dynamic nature of digital asset ventures. In conclusion, the drafting of partnership agreements involving digital assets represents a unique intersection of law, technology, and innovation, demanding a forward-thinking approach and a willingness to navigate uncharted legal territories.

Michael Hurckes, Managing Partner, MAH Advising PLLC

Joint Venture Agreements

As someone deeply ingrained in the legal world, particularly with a focus on business litigation and drafting agreements, I’ve come across a myriad of complex contracts. However, Joint Venture Agreements often stand out as one of the most challenging documents to draft. My involvement in guiding clients through drafting clear, comprehensive, and enforceable legal documents, as detailed in my experiences with Moton Legal Group, underscores my capability to speak on this matter.

The complexity of Joint Venture Agreements stems from the need to intricately define the scope of the partnership, investment contributions, profit-sharing mechanisms, management structures, and dispute resolution procedures. Each party to a joint venture comes with its own set of expectations, objectives, and apprehensions, making it imperative to draft an agreement that not only aligns with all parties’ business interests but also mitigates potential disputes. For instance, drafting an agreement for a joint venture that involved multiple national and regional stakeholders required meticulous attention to the division of responsibilities and liabilities, showcasing the intricacy of these agreements.

Moreover, the dynamic nature of business necessitates that these agreements are both flexible enough to accommodate future business shifts and stringent enough to safeguard the interests of all parties involved. Navigating this delicate balance, while also ensuring compliance with applicable laws and minimizing risks, poses a significant challenge. My role in championing the drafting of business agreements, including the nuanced negotiations surrounding joint ventures, equips me with insights into the complexity of these legal documents. From my background, which includes extensive involvement in trial programs and a deep understanding of contract law, I’ve learned the importance of foresight, strategic negotiation, and the role of clear communication in drafting Joint Venture Agreements that withstand the test of time and change.

Denzell Moton, Esq, Owner, Moton Legal Group

Employment Termination Agreements

In my extensive experience as a managing partner and attorney with a focus on estate planning, elder law, and business succession planning, I’ve encountered a wide range of contracts and agreements. From my work, one of the most complex types to draft is the Employment Termination Agreement. This complexity arises from the need to meticulously balance legal compliance with protecting the business’s interests, alongside ensuring fair treatment of the exiting employee.

A key factor contributing to the complexity of these agreements is the necessity to incorporate provisions that comply with both federal and state employment laws. This often entails including specific language covering severance payments, confidentiality clauses, non-disparagement agreements, and sometimes, non-compete clauses. The balance is delicate; ensuring the business is safeguarded while not infringing on the employee’s rights or future employment opportunities requires a nuanced understanding of employment law.

From my experience, each Employment Termination Agreement poses a unique challenge due to the individual circumstances surrounding every termination. Crafting a document that addresses all potential legal repercussions, while also being tailored to the specific situation of the employee and the company, involves not just legal expertise but also strategic foresight. For instance, I’ve had to navigate negotiations where the inclusion of a comprehensive release of claims was critical in protecting a company from future lawsuits, balanced against the employee’s need for a favorable severance package to ensure their cooperation. These experiences underscore the importance of drafting these agreements with precision, foresight, and a keen understanding of human psychology.

Marty Burbank, Owner, OC Elder Law

Complex Trust Agreements

From my extensive experience as a full-service tax and trust and estate lawyer, particularly one with a specialization in estate planning, trust, and probate law, as certified by the State Bar of California Board of Legal Specialization, I’ve encountered various complex agreements. Among these, I find that trust agreements, especially those involving intricate family structures or substantial assets, present unique challenges. The complexity is often due to ensuring that all provisions comply with existing tax laws, which are perpetually in flux, and accurately reflect the trustor’s wishes without ambiguity.

One notable example involves drafting a trust agreement that aimed to distribute assets across multiple generations with specific stipulations on asset management and distribution. The challenge was not only in structuring the agreement to accommodate these multifaceted directives but also in ensuring that it provided the necessary flexibility to adapt to potential future changes in tax law and family circumstances. This required a deep dive into predicting possible legal and taxation scenarios and crafting language that was both precise and adaptable.

Moreover, navigating the emotional dynamics of involved parties adds another layer of complexity. While legal precision is paramount, understanding and mitigating potential family disputes, which could arise from perceived inequities, calls for a nuanced approach to drafting these agreements. Integrating mechanisms for conflict resolution and clearly defined steps for amendment or revocation of the trust requires a strategic and empathetic understanding of family dynamics, underscoring the intricate balance between legal requirements and human elements in these documents.

David Brillant, Founder, Brillant Law Firm

Partnership Agreements

In my experience as a legal professional deeply involved in drafting contracts and agreements, I find that partnership agreements pose some of the most significant challenges due to their inherent complexity. Partnership agreements govern the rights, responsibilities, and obligations of multiple parties entering into a business venture together, which introduces various factors that contribute to their complexity. These factors include structural considerations, profit-sharing and equity distribution, decision-making authority, exit strategies and dissolution provisions, as well as regulatory compliance and legal protections. Navigating these complexities requires a deep understanding of both legal principles and business dynamics, as well as effective communication and negotiation skills to balance the interests and expectations of all parties involved.

Jonathan Rosenfeld, Owner and Attorney, Injury Lawyers Chicago

International Joint Ventures

Drafting agreements for international joint ventures requires meticulous attention to detail due to differing legal systems, cultural nuances, and potential conflicts of law. Complex cross-jurisdictional problems involving ownership, management, profit-sharing, dispute resolution, and regulatory compliance necessitate knowledge of international law as well as commercial practices.

Timothy Allen, Director, Oberheiden P.C.

Partnership Agreement Complexities

One of the most challenging contracts to draft, in my opinion, is the partnership agreement. The complexity arises from the need to address various aspects such as profit-sharing, decision-making authority, dispute-resolution mechanisms, and exit strategies. Balancing the interests of multiple partners while ensuring clarity and fairness in the agreement requires meticulous attention to detail and a deep understanding of legal implications. Additionally, the need to anticipate potential future scenarios and incorporate comprehensive provisions adds to the intricacy of drafting a robust partnership agreement. Successfully navigating these complexities demands a nuanced approach that encompasses legal expertise, effective communication with the involved parties, and a thorough understanding of the specific dynamics and objectives of the partnership.

Lee Odierno, Personal Injury Lawyer, The Odierno Law Firm, P.C.


In the realm of legal consulting, mastering the art of contract drafting is an ongoing journey marked by continuous learning and adaptation. Through our exploration of the eight most challenging contracts to draft, we’ve uncovered the multifaceted nature of contractual complexities and the reasons behind their intricacies.

From navigating regulatory frameworks to managing dynamic negotiation dynamics, each contract presents its own unique set of challenges that demand careful consideration and expertise. However, by understanding the underlying reasons for their complexity, legal professionals can approach contract drafting with greater clarity and confidence.

At Legal Consulting Pro, we remain committed to providing invaluable insights and resources to support legal professionals in their journey toward mastering contract drafting. By staying informed, adaptable, and diligent in our approach, we can overcome even the most formidable contractual hurdles and ensure the creation of robust, effective agreements that stand the test of time.

As we continue to navigate the ever-evolving landscape of contract law, let us embrace the challenges ahead with determination and ingenuity. Together, we can elevate the standards of contract drafting and empower legal professionals to navigate complex contractual arrangements with precision and expertise.

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