You might get a bit of break on some aspects of pleading, but you will get no break at all on having to prove your case by proper evidence, having to comply with the rules of evidence in asking questions of witnesses, meeting deadlines, and putting together a sound legal argument in support of any contested position. And if you waste the judge's time because you do not know what you are doing, do not expect to be treated with patience.
I do not practice in IL and I am not sure what YOU mean by leniency--if you are asking whether judges will cut you slack on timelines, statutes of limitations, introduction of evidence, depositions, Bills of Particular, Answers, subpoena's and other procedural matters because you are not a lawyer--while holding your opponent to a higher standard--the answer in any jurisdiction I have heard of is 'NO'.
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You will be expected to follow the rules of the court. I would not expect leniency or a lot of patience if you make mistakes and waste the courts time.
Although pro se litigants are held to the same standard as attorneys, some judges do cut pro se parties a little slack. It depends upon the judge. It depends upon the area of law. It depends upon the demeanor of the parties and opposing counsel. Etc.
You have asked many procedural questions over the past day or so. Please understand that the lawyers here are volunteers who try to answer simple questions in a Q&A forum. We are not a subsitute for law school.
That is an unanswerable question. First because each judge has their own style. Second, because each division and courtroom has different rule. A much better question is will I obtain a better result acting pro se? The answer to that question is easy. No, generally a competent attorney will obtain better results 99 times out of 100. There are always exceptions, however, there is a saying "He who represents himself has a fool for a client." Hire an attorney.
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In general, pro se litigants are given leniency by judges in Cook County depending on the type of case. If you are handling a small claims case pro se, that is a normal occurrence. However, if you are handling break of contract, personal injury, medical malpractice or other complex litigation, the courts will quickly lose patience with a pro se litigant and hold you to the same procedural rules as any attorney. If you find yourself with one of the latter type cases, you should consult and probably hire an attorney for your case.
How are you defining leniency? Do you mean to ask if Judges will be less strict about procedure with pro se litigants? Or do you mean to ask if Judges will be less severe or harsh with the substance/outcomes of rulings against a pro se litigant (i.e. how much money you owe, how/when you lose ownership/possession of property)?
In either case, it would not be a quantifiable amount. Nor would it be a rule the Judge would have to follow. Judges generally try to be fair to both sides.
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As with many questions asked of lawyers, the answer is, "It depends." It depends not only upon what you mean by leniency but also upon the particular judge hearing the case and the issues involved. However, in general terms, it is not unusual at all for judges to give pro se litigants the benefit of the doubt when they request additional time to respond to pleadings or motions. This can be frustrating to the other side in the case when continuances are granted and the process of reaching a resolution of the matter is delayed. On the other hand, it has been my experience that Cook County judges in the Law Division and Chancery Division will hold a pro se litigant to the same standards as an attorney when it comes to questioning witnesses and establishing the foundation for evidence during hearings and trials.