The case within the case
In New York, a legal malpractice claim generally requires showing that the lawyer's work fell below the skill commonly exercised in the profession, and that you would have done better in the underlying matter but for that failure. For a lost lawsuit, this often means proving the original case would have succeeded, in effect trying it again inside the new one. For transactional work, it means showing how the deal or the advice would have come out differently. A disappointing result on its own is not malpractice, since lawyers can make reasonable judgment calls that do not work out. The analysis starts with the file from the original matter.
Which losses count
Legal malpractice damages generally aim to put you where you would have been had the work been done properly. That can mean the recovery you would have obtained in the original case, or the added liability you took on because of bad advice. Whether a judgment in the original case could actually have been collected can become an issue in its own right. Fees paid for deficient work, and costs spent correcting the error, may be part of the claim in some circumstances. Emotional distress damages and punitive damages are generally not available in an ordinary malpractice case, and losses that are speculative are a frequent point of dispute.
Deadlines and the file
Legal malpractice claims have their own limitations period, and in New York it can sometimes be extended while the same lawyer continued representing you on the same matter. Ask for your complete file in writing; lawyers are generally required to turn over a client's file, though the details can vary. Keep engagement letters, bills, and correspondence. If the underlying matter is still open, correcting the error may come first, and that can affect the malpractice claim. In a first conversation we review the timeline and work out what the file needs to show.