Most demand letters about a restrictive covenant are written to be frightening and cost the sender very little. They quote the clause back at you, attach the signature page, set a deadline of five or seven days, and ask for a written undertaking that you will stop doing whatever you are doing. That is a cheap letter to produce. The expensive part, a motion for an interlocutory injunction, is a decision the employer has usually not yet made, and a careful reader can tell the difference by looking at what the letter asks for rather than how loudly it asks.
One. Read the ask, not the adjectives
Separate the sentences that describe consequences from the sentences that describe a specific demand. A letter seeking a signed undertaking, a list of clients you have contacted, and confirmation that you have deleted company files is asking for compliance without litigation. A letter that identifies particular accounts, names dates, and states that instructing counsel has already been retained to seek injunctive relief is further along. Note the deadline too. Seven days is a standard interval; forty-eight hours usually signals either a real motion in preparation or an attempt to prevent you from getting advice before you answer.
Two. Know the steps between a letter and a courtroom
Escalation in Canada tends to follow a recognizable sequence: the demand letter, a second letter after your reply or silence, a statement of claim, and then a motion for an interlocutory injunction supported by affidavit evidence. The injunction test, drawn from the Supreme Court's decision in RJR-MacDonald, requires a serious issue to be tried, irreparable harm, and a balance of convenience favoring the employer. Each of those steps costs the employer real money and exposes its own conduct to cross-examination. Many files stop after the second letter because the arithmetic stops working.
Three. Check whether the clause survives its own wording
Before you price out a reply, price out the clause. Courts read restrictive covenants against the drafter, and ambiguity is generally fatal rather than fixable. In Shafron, the Supreme Court declined to rewrite a geographic term that had no settled meaning, and Elsley remains the frame for asking whether a non-compete was necessary at all when a non-solicitation clause would have protected the same interest. Look for the four things that decide most of these cases: duration, geography, the definition of prohibited activity, and whether the clause names actual customers or sweeps in everyone. Note also who ended the employment.
Four. Understand what the legal fee actually buys
An employment lawyer reviewing a signed agreement and a demand letter is doing three separable things, and you can buy them separately. The first is an opinion on enforceability, usually a fixed fee for a defined scope: read the contract, read the letter, tell you where you stand. The second is a reply letter on firm letterhead, which is priced by the hour and depends on how much fact-gathering it needs. The third is litigation readiness, which is an open-ended commitment. Ask for the scope and the estimate in writing, and ask how many hours the reply is expected to take.
Five. Judge whether a formal reply earns its cost
A lawyer's letter does two useful things. It tells the employer that its weakest clause has been read closely by someone who will say so in an affidavit, and it creates a record that you acted reasonably, which matters when a judge weighs the balance of convenience. Weigh that against what is genuinely at risk: your new salary, your ability to keep a role you have already started, and the cost of a motion you would have to defend anyway. When the exposure is a year of income, a few hours of advice is cheap insurance. When the letter targets conduct you have already stopped, a short factual reply may be enough.
Six. Handle the facts as carefully as the law
Injunctions turn on affidavits, and affidavits turn on documents. Preserve your emails, return company property with a written inventory, and stop using anything you took with you, because confidentiality and fiduciary claims often outlive a struck non-compete. Keep your own timeline of who contacted whom and when. In the United States, the Federal Trade Commission is the agency responsible for non-compete policy at the federal level, a useful reminder that these clauses are treated as competition questions and not merely private promises. Canadian judges look at the same commercial reality.
The reader who does best with a letter like this treats it as a document to be checked rather than an instruction to be obeyed. Clause, dates, deadline, who terminated, what is actually being demanded. Then decide what to spend.