​The Opening Shot — Lawsuit vs. Demand Letter. Why You Should Usually Sue First and Talk Later.

02/25/2026

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Experienced litigators know this: silence is golden, and filing a lawsuit first is the smarter, safer, and more strategic path. In fact, it's the real power move! Read on to learn why.
 

1. The Role of a Demand Letter — A Specific Tool

In certain cases, a demand letter can be effective, but only if it’s appropriate. It's not a mandatory courtesy. It's a tactical option, and usually one that should be held back. The circumstances when a demand letter makes sense are far fewer than most people believe. A demand letter is typically appropriate only when the dispute is controlled, predictable, free from danger, and there’s a benefit to making a pre-suit demand. 

Outside these circumstances, it is usually ineffective and can do more harm than good. You may use a demand letter if: 

• the dispute is well-documented and not time-sensitive;
• you or the other side want to keep the dispute private; 
• the other side is rational;
• there is no danger in giving the other side advance warning; or
• the optics of “good faith” matter more than tactical surprise.

All other instances? File suit first and talk later.
 

2. The Rare Times to Use It

There are specific situations — usually rare — where a demand letter is productive. But remember, these are the exceptions. You send one when the facts are airtight, the harm is clear, and the other side is likely to respond rationally. In those situations, a firmly stated, well-written letter can open a path to resolution without litigation.

Over my career, I’ve used demand letters when I want to give the other side a peek at the evidence I have amassed, or to focus them on key contract terms or the governing law, all to support my client’s demand. It is a rational endeavor. Diplomacy. Not weakness. In short, I’ve used them to lay the cards on the table — to secure a resolution before costly, public litigation ensues. Sometimes, I may couple the letter with a draft complaint that will be filed shortly.

I’ve also used demand letters if the other side may value keeping the dispute confidential. Perhaps they may want to avoid alerting competitors of missteps. Or they simply would want to avoid bad press. In those cases, I will use the other side’s desire for privacy to my client’s advantage, essentially, as a premium.
 

3. If You Do Write, Make It Count 

When a demand letter truly is the smart move, the tone must be deliberate: calm, authoritative, and fully prepared for litigation. It should read like something a judge would respect — because one day, a judge may.

A demand letter should never sound emotional, speculative, or overheated. Precision and professionalism carry more weight than theatrics. You want the reader thinking, “This is serious, fact-driven, and not bluffing.” The tone and structure of the letter should be a disciplined preview of your case. Not a threat, not a rant — but a straightforward iteration of your position, with factual and legal support. 

In that regard, a demand letter typically should include: 

• the relevant facts, with a summary, chronology, and specific relevant evidence; 
• the legal support, citing key terms and governing law; 
• a specific, reasonable demand, with a deadline or timeframe; and
• a closing that leaves room for a professional resolution.

Again — this assumes that the decision to send the letter is sound. Think of a demand letter as a tool to use if parties want to resolve a dispute quietly, quickly, and relatively inexpensively, and without theatrics. But again — these situations are limited.
 

4. Why You Should Usually Sue First

However, most disputes and situations don’t fall into these narrow categories. And that’s where the demand letter becomes the wrong move. Many think it’s a power move; it’s not. Often, a demand letter will simply be a waste of time and resources, because they will simply ignore it, or give a low-ball proposal. For them, it's not a ripe litigation yet. Many simply will not act until a formal suit is filed in court. Frankly, may be a rational position. They will deal with it when they must. The rest may feel like noise, like spam, if you will.

So, one should be mindful of the downsides of sending a demand letter, in addition to the waste of time and energy (including lawyer's fees). They may include: 

• giving away your theory of the case;
• enabling the other side to prepare their defense;
• sparking a public relations fight before you’re ready;
• giving them time to move money or “rearrange” assets;
• they may destroy or manipulate evidence; or
• prompting them to file first in a friendlier forum.

If any of these are a real concern, the answer is simple: don’t send the letter. File the lawsuit first. In fact, the other side may view a demand letter in the opposite way you intend it — not as a sign of strength, but of weakness: a lack of desire for litigation, fearful, wanting to avoid the cost or time of suing. Or simply, your client doesn’t strongly believe in its case.
 

5. The True Power Move: Going to Court

Filing a lawsuit is not about aggression — it’s about control. In going to court, you choose the timing, the forum, the framing, and the level of pressure. You eliminate the dangers that come from warning the other side too soon. The conflict begins on your terms, not theirs.

Most importantly, you are not at the mercy of the other side’s desire to resolve things. That is, the lawsuit begins the formal legal process. Then, things start to happen, and they get real.
 

 A party can ignore a demand letter, but they cannot ignore a lawsuit! 

Filing an action in court brings you immediate, tangible benefits over sending a demand letter: 

• You set the jurisdiction and venue. Waiting invites the other side to choose the forum — often to your disadvantage. 
• You preserve the claims, tolling applicable statutes of limitations. 
• You establish the narrative, the legal theories, and the relief sought — from day one. 
• The court’s authority attaches. Everyone must follow procedures: court-ordered discovery (documentary, depositions, etc.) happens after the suit is filed. 
• You make the dispute governed by enforceable rules — not the other side’s voluntary cooperation. While a party need not answer a demand letter, it must answer a lawsuit. If it doesn’t, there are consequences, like a default and then, judgment enforcement proceedings!

These are not superficial flourishes. They are structural protections. In many disputes, filing a lawsuit first is the only way to protect assets, preserve evidence, secure jurisdiction, and move a dispute to resolution.
 

Takeaway from the Counsel’s Chair 

A demand letter is a specific tool for narrow circumstances. When the facts are settled, the risk is low, and you think the other side is rational and wants to avoid litigation, it can work. Outside of those circumstances, however, it can do the opposite of what it’s intended to do: it can educate the opponent, slow momentum, and shift leverage away from you, as the party trying to enforce its rights. Filing a lawsuit in court is different. It locks in jurisdiction. It preserves claims. It protects evidence. It forces engagement by the other side. It puts the dispute into a system where rules apply, deadlines matter, and consequences follow.

You can always send letters and negotiate. You can always talk settlement with the other side and then, once you reach a resolution, dismiss the lawsuit you filed. That’s why, almost always, the better move is to go legal…

When in doubt, sue first. Talk later.