skype-call As Skype prepares to roll out five-way video calling this week — an addition the company plans to charge for at a later date — it’s also thinking of monetizing the now free user-to-user web calling serving with advertisements.

In an interview with The Telegraph, CEO Josh Silverman explains that the company — once again its own entity — is challenged by its desire to keep Skype-to-Skype calls free and to maintain the quality of service. As a result, the Skype team is “seriously considering” including ads from third parties in order to continue to operate the service free of charge.

On that note, Silverman shares that, “It’s challenging to get right as the way people use is Skype is very personal but we think our users expect us to do it so we can continue to support free. But it will be done in a tasteful way” [sic].

As it stands, Skype currently makes money from paid services that allow users to purchase credits to call landlines or mobiles, receive calls and manage a Skype voicemail account. Last week, Skype lowered calling plan rates and extended those rates to more countries.

Given that Skype has operated ad-free for so long, any introduction — regardless how tasteful — is bound to draw a strong reaction from users, especially those who have relied on the service to phone loved ones or opt for one-on-one video conferencing in lieu of face-to-face meetings.

How would you feel about ads in your Skype chats or calls?