Key Takeaways:
- There’s so much more to contracts than what any of us learned in law school.
- If you’re asked to review a contract for a complex or complicated project, don’t let pride get in your way.
- Sometimes the most important contract decision you’ll make is knowing when to walk away from a relationship that isn’t working.
After years of working with contracts and seeing the same mistakes repeated across organizations, I’ve learned that our profession is filled with conventional wisdom that often leads us in the wrong direction.
My Why This Not That
approach challenges these assumptions with practical alternatives that actually work in the real world.
In 2021, I wrote a series of 18 articles in my first online column called Why This Not That Contracts where I explored key topics in contract management, drafting, negotiation, and careers, and engaged in community dialogue through my LinkedIn posts. In this article, I revive the series in honor of the fifth anniversary of Contract Nerds–a community and media platform for all things contracts. Here are my expert contract tips that can truly transform how you manage contracts throughout their entire lifecycle.
Stop Treating Contract Life Cycle Management Systems (CLM) Like Self-Cleaning Ovens
Let me be direct about one of the biggest mistakes I see organizations make: thinking that someone on their team can manage a CLM system as a side project. The reality is that you need to hire a full-time contract operations manager instead of assigning this critical function to lawyers, paralegals, or IT professionals who already have full plates.
Lucy Bassli, a CLM expert and attorney I deeply respect, puts it perfectly when she says “your contract lifecycle management system is not a self-cleaning oven.” Just like that appliance in your kitchen, these sophisticated tools require dedicated attention and expertise to deliver real value.
I’ve seen too many organizations invest in expensive CLM technology only to wonder why they’re not seeing results. The answer is almost always the same: they’re expecting the system to manage itself. Success requires someone who understands contracts, technology, and business processes. This is a unique combination that deserves dedicated focus.
Build Your Contract Community (Trust Me on This One)
There’s so much more to contracts than what any of us learned in law school, which is exactly why ongoing contract training is absolutely essential. I used to think my legal education and experience were enough. I was wrong.
The solution isn’t cramming more individual study time into your already packed schedule. Instead, find a community of like-minded individuals who share a passion for all things contracts rather than trying to go it alone with outdated knowledge.
I’ve discovered that when you find a community of like-minded people who love what you love, your knowledge and expertise will increase proportionally with that community. It’s like having a brain trust at your fingertips. I’ve personally benefited enormously from events like How to Contract’s Annual ContractsCon conference, where I got practical, hands-on training that I simply could not anywhere else. And of course, the amazing contract expert content and webinars offered by Contract Nerds which has made contracting education accessible to everyone who works with contracts, not just lawyers.
And here’s a related truth: if you’re asked to review a contract for a complex or complicated project, don’t let pride get in your way—ask for help instead of going it alone and hoping for the best. Your client deserves the best legal representation possible, and sometimes what you’re asked to do is outside your expertise. It’s not possible to know everything. The Beatles had it right: “I get by with a little help from my friends.”
Create Contract Playbooks That Actually Work
If you’re in a high-volume contract environment, this one’s non-negotiable. You need to come to the negotiation table with a contract playbook in hand instead of escalating every single proposed template revision up for approval. I learned this lesson the hard way after watching too many deals stall in approval bottlenecks. If you have a high volume of contracts, having a playbook isn’t a nice-to-have—it’s a critical must-have for your organization.
Question Every Clause (Seriously, Every Single One)
This might be controversial, but I believe you can and should reject clauses that don’t add clarity to a contract, including redundant terms or unhelpful legalese. I know this goes against traditional practice, but hear me out.
When you include clauses without a specific reason, you may actually be introducing confusion rather than protection. I’ve seen contracts become unnecessarily complex simply because “that’s how we’ve always done it.”
David T. Daly’s guidance on problematic contract phrases has been eye-opening for me. Think about phrases like “Now, therefore, in consideration of the foregoing and the mutual promises and covenants herein contained” or “In witness whereof.” Do these actually clarify anything? My test is simple: if a clause doesn’t help make the parties’ rights and obligations clearer, it doesn’t belong in the contract.
Don’t Speed Through Those EULAs
I know it’s tempting, but you really need to read your end-user license agreements carefully instead of skimming or skipping over terms of service too quickly. You might miss important clauses—and some surprisingly amusing ones too.
Lindsey Dean highlighted a perfect example in Amazon’s terms of service, which includes a zombie apocalypse clause that voids restrictions on Lumberyard materials in the event of a widespread viral infection transmitted via bites that causes human corpses to reanimate. While that’s entertaining, the serious point is that legal obligations can be buried in routine language, and important rights may be waived inadvertently if you’re not paying attention.
Consider Relational Contracts for Complex Partnerships
Sometimes you need to be willing to abandon a traditional contractual agreement and consider a relational contract instead. When there’s a long-term, complex relationship at stake and trust is a problem, relational contracting may be exactly what you need.
When parties have a vested interest in each other’s success, formal relational contracting establishes a “what’s in it for we” partnership rather than an adversarial dynamic. These agreements include traditional contract components but also contain relationship-building elements like shared vision, guiding principles, and robust governance structures. The Dell and FedEx case study highlighted in Harvard Business Review shows how this approach can transform partnerships.
Write for Humans, Not Law School Professors
I’m passionate about this: contracts should be written in plain English so that the terms are clear to anyone who reads them, regardless of legal background or knowledge. But here’s where many people get it wrong—this isn’t just about eliminating legal jargon.
When reviewing a contract, I focus on both clarity of language and clarity of purpose and intent rather than exclusively hunting down legalese. I’ve encountered clauses where every single word was part of everyday speech, but when I read those words together, I couldn’t make heads or tails of what the clause actually meant. The problem wasn’t the vocabulary—it was how the words were structured.
Think Beyond Legal Terms When Drafting
When drafting a contract, you need to consider overall contract design instead of focusing exclusively on the terms within the contract itself. Your audience is usually made up of business people, not lawyers, who use the contract to memorialize expectations.
How do you best communicate with them? As simply and straightforwardly as possible, without unnecessary legalese. One practical approach is placing standard terms and conditions in one list at the back of the contract, since the only people who generally look at those provisions are lawyers anyway.
Align Your Contracts with Your Brand
Make sure your contract is drafted in a way that reflects your brand, values, and how you want to do business rather than drafting without consideration for your business approach.
If you want to be known as a business interested in establishing mutually beneficial arrangements, don’t skew the terms heavily in your favor. Remember, until the deal is signed, sealed, and delivered, it’s not done—and once it is done, you have to actually work with the other party. Don’t start off with a game of gotcha.
Use the Three-Pass Review Method
I’m a big believer in Sterling Miller’s three-pass review method rather than reviewing once and immediately redlining. Like most work for in-house counsel, the devil is in the details, so take time to do it correctly—everyone will be glad you did, especially you.
First pass: do a high-level scan without reading too carefully, just getting a sense of how the contract is structured and where everything is located.
Second pass: go through more carefully, starting with defined terms and reading carefully once through, then making your careful second pass. When a defined term uses another defined term, stop and flip to that definition.
Third pass: skim back through defined terms to see if your understanding has changed, then focus on termination, payment provisions, and the balance of the contract.
Don’t Walk Away When the Ink Dries
One of my biggest pet peeves is the assumption that contract management ends at signature. You need to be an active participant in contract management across the whole contract lifecycle instead of considering the job complete once the contract has been signed and safely tucked away in your repository.
The numbers are staggering. Craig Conte from Deloitte Legal shared research showing that companies, on average, lose 9.2% of annual contract value through poor management across the whole contract lifecycle, with most of that loss happening in the post-signature area. This loss occurs through revenue leakage from bad invoicing or change order management, which essentially means paying for the same thing twice or not holding partners accountable for what they promised to deliver.
Create a Business Case for What You Believe In
If you can’t afford a full CLM system yet, consider using templates and tools to track contracts and vendor relationships until your organization can invest in a complete solution, rather than lamenting the lack of automation and doing nothing.
Do you really want to be able to use a CLM? Don’t wait until you find money in your budget. Instead, encourage your internal partners to work with you to build a business case that demonstrates how CLM will improve operational efficiencies, reduce risk, and optimize profits throughout the contract lifecycle.
As research shows, manual systems contribute to extended cycle times that slow revenue flow, lack of audit trails necessary for compliance evidence, and disorganized storage that makes it difficult to find contracts and ensure compliance. CLM tools offer integrated clause libraries, configurable workflow engines, and automated metadata capture that address these pain points directly.
Plus, did you know that your CLM system can do so much more than cost reduction and risk mitigation? You can even use it to increase supply-chain diversity. For example, you can identify contracts with supplier-diversity commitments, ensure contract clauses support diversity initiatives, and utilize data to showcase supplier-diversity success. This approach transforms CLM from a defensive tool into a strategic advantage.
Here’s the truth: a CLM system isn’t an automatic fix to all contract management problems. Companies often experience issues not because they lack automation, but because they haven’t developed solid manual processes. If you create robust policies and procedures, develop templates, and maximize available manual tools, you’ll be perfectly positioned for successful CLM implementation when the time comes.
Make Compliance Actually Happen
Even the best-written contract won’t deliver value if people don’t understand their obligations. I recommend using contract summaries (which these days plenty of AI tools can help with) to push out contract terms to parties within the organization who are responsible for contract compliance rather than assuming some internal partner will magically extract and distribute the relevant terms.
Know Your Company’s Procurement Process
Understanding your organization’s procurement process is critical rather than assuming these processes aren’t relevant to contract review. Purchase management must be a shared responsibility, and when you know your company’s processes thoroughly, you’ll be in the best position to ensure contracts meet your company’s actual needs.
Here’s a practical example: if your company has a net 30-day payment rule but the vendor contract specifies net 10 days with penalties for late payment, your company may incur unnecessary fees by paying invoices on a 30-day cycle. Simply asking the vendor to revise the contract to net 30 days eliminates this mismatch entirely.
Know When to Walk Away (And Don’t Be Afraid to Do It)
Sometimes the most important contract decision you’ll make is knowing when to walk away from a contractual relationship that isn’t working instead of continuing to try and remediate the relationship and enforce contract terms indefinitely.
As Kenny Rogers wisely sang, “You’ve got to know when to hold ’em, know when to fold ’em, know when to walk away, and know when to run.” Enforcement is an expensive endeavor, and resources spent on problematic relationships might deliver better returns elsewhere.
The Bottom Line
These expert contract tips from my Why This Not That Contracts series for Contract Nerds represent lessons I’ve learned through real-world experience. Some of them the hard way. By challenging conventional practices and focusing on what actually works, we can create more value for our organizations while reducing risk and improving efficiency.
The legal profession often rewards following precedent, but in contract management, the most successful professionals are those willing to question assumptions and embrace evidence-based practices that truly serve business needs. That’s where the real creativity and problem-solving happens—and trust me, as lawyers, we’re more creative than we give ourselves credit for.
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