If It’s Hard to Buy, It’s Going to Be Hard to Sell: A Legal Perspective
Wednesday, August 20, 2025 - Filed in: General Interest
But this principle applies far beyond real estate or consumer goods. It’s a useful lens for thinking about legal matters, because the challenges you encounter at the beginning of a deal, contract, or dispute often foreshadow the challenges you’ll face at the end.
Contracts and Negotiations
If a provision is difficult to negotiate into a contract, that same provision is likely to be difficult to enforce later. Complexity or imbalance that makes the other party resist now will also make a judge, arbitrator, or mediator question it later. Good legal drafting keeps in mind not just the “buy-in” but also the eventual “exit.”
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Real Estate
When clients ask about buying properties with unusual zoning, title issues, or unconventional layouts, the saying fits naturally. If the purchase feels like an uphill battle, resale will too. The obstacles you overcome as a buyer are often the very ones that will narrow the pool of buyers when it’s your turn to sell.
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Business Transactions
In mergers, partnerships, or share purchases, convoluted ownership structures or shaky compliance don’t just create headaches at closing. They create ongoing difficulties in governance, refinancing, or sale. Barriers to entry often become barriers to exit.
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Arbitration and Mediation
The same lesson shows up in dispute resolution. Clauses or settlements that are vague or awkwardly worded often become the centrepiece of later grievances. What seemed workable enough at the table can turn into the very thing that requires arbitration to sort out.
Example: An agreement might say that overtime will be distributed “fairly.” At the time, that language allows everyone to move forward. But later, when each side interprets “fairly” differently, the ambiguity lands on an arbitrator’s desk. What was “hard to buy” in negotiation becomes just as “hard to sell” in dispute resolution.
In mediation, too, terms that are fragile or unclear at the outset often create renewed conflict down the road. Durable settlements tend to have balance and clarity—they don’t just resolve the immediate problem, but also stand up in practice once the parties return to their daily work.
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A Guiding Principle
Legal advice often comes down to helping clients and parties look a few steps ahead. The friction you face today is rarely an isolated problem—it’s a glimpse of what’s to come.
So the next time you encounter a deal, agreement, or dispute that feels unusually hard to “buy into,” pause and consider: will it be just as hard to sell, enforce, or resolve later?
In law, as in life, ease at the start is often a good sign of smoothness at the end. Years of experience as both counsel and arbitrator have shown me this truth time and again.