I am new to Upwork and have sent out several bids to no avail. I have had three bites but two of them insist that I get on Skype. Why Skype? Why are these people attempting to go around the procedures already in place on Upwork? As a new comer, this makes me highly suspicious of this entire thing.
They may be either unaware that Upwork has a video chat component or they're more comfortable with Skype. Video chats are not uncommon because clients want to see/ verify that the person who applied is actually the person who will be doing the work. I would just suggest to them that you can chat through Upwork before you're hired and you will glad to connect with them on Skype after a contract is in place.
Michael, in my opinion Skype requests alone aren't cause for suspicion, if a client seems otherwise legit, for example, is not a client with numerous posted jobs and little or no hires. Recently I submitted a proposal to a client who requested Skype in the job description, but after he read my proposal and some text we exchanged, he told me Skype was unnecessary because "your English is obviously flawless". Also, it's an unfortunate fact that there are a substantial number of freelancers who misstate their location, English proficiency, etc. so a client who requests Skype is as likely to be practicing due diligence versus attempting to evade Upwork regulations. Lastly, unless scammers have changed tactics, they seem to prefer Google hangout over Skype.