When leaving an employer, should you sign a non-solicitation agreement?

No.  I wouldn't sign anything upon leaving an employer unless they were willing to pay me.  In the case of non-solicitation, it would have to be a lot of money, because I'm putting myself at legal risk by signing.

First, a quick but important clarification:  I’m not your lawyer and this answer doesn’t establish a lawyer-client relationship. I’m giving a generic answer to a generic question to educate the users of this site.  The information below is general in nature and should not be understood as a substitute for personal legal advice. I generally agree with Mike Prozan.  It's definitely not required that you sign anything and you should be getting something valuable to you in return if you agree to sign.  How valuable that has to be depends on how much the non-solicitation agreement is worth to you (and the company).  I'd be very surprised if this answer was different in any other common law jurisdiction, but I suppose there's always the possibility and I don't know for sure. I definitely endorse Mike's point about never, ever, ever taking any customer lists/files etc. with you when you leave.  That's all the more important if you will be working in competition with the company.  In that case, it's sometimes helpful to have someone from the company present in your office as you pack up your stuff (and, in extreme circumstances, sign off on an inventory), to avoid later accusations.  If you've recently downloaded or exported any company files or data (and assuming it was innocent), it's often worth bringing that up with the company before you leave so you can satisfy them that you're not hiding anything and that you've given back/destroyed all files.  Be cautious about this.  Don't stir up unnecessary trouble.  But bear in mind that log files are likely to show all of your downloads and exports, so think about it. As to the general question (how to think about these agreements), I'd make three general points: First, non-solicitation clauses (covering employees and customers) are often included in companies' form employment/consulting terms.  If you don't have a lot of bargaining power, you generally have to agree to these standard terms if you want the job/assignment.  On the other hand, it rarely hurts to ask (nicely) to remove them or add exceptions or clarifications, especially if you think the provision is likely to be especially problematic for you.  For example, if you're a freelancer, working for multiple clients, and your work isn't going to give you any special access to the company's customers, it would be very reasonable to ask to delete a non-solicitation of customers clause. If you're being asked to sign the provision on your way out (i.e. you don't have to do it and are thinking about whether it's worth it), there are two other general points: The more obvious is to think through what you're planning to do during the time period of the provision and consider whether it will prevent you from doing what you plan or make it harder.  If you're in doubt, ask.  Ask the company to clarify whether it thinks specific things you have in mind will violate the provision.  If the answer is "no," get that answer in writing (preferably in the contractual language itself).  Also consider asking other people.  Most obviously, if you're leaving for a new job and you're not sure if the non-solicitation provision will be a problem, make sure to ask your new employer. The second general point is that, in addition to thinking about what the actual constraints will mean to you, you should also think through (and, if in doubt, ask) whether anyone you're planning to deal with thinks it's a problem.  If you're going to a new job, that means talk to your new employer before you agree to anything.  If you're going out on your own, think about whether there's anyone in particular who might have an opinion you'll care about.  If so, again, ask before you sign. I hope that helps.  Good luck!