When comparing Skype vs Flowdock, the Slant community recommends Flowdock for most people. In the question“What is the best team chat software?” Flowdock is ranked 4th while Skype is ranked 64th. The most important reason people chose Flowdock is:
An easy & simple interface to filter chat discussion into separate threads.
Specs
Ranked in these QuestionsQuestion Ranking
Pros
Pro Easily connect with others due to how popular the service is
There's a good chance that whoever you're trying to reach has Skype already set up and familiar with it, avoiding the hassle of installing and getting to know new software.
Pro Screen sharing
You can show your whole desktop, a select part of the screen or a specific window over Skype.
Pro Cross-platform
There's software for Windows, Mac & Linux and apps are available on iPhone, Android, and Windows Phone.
Pro Group video for free
You can hold video calls with up to 10 people.
Pro Available on Linux
A stripped down, minimalist version of Skype is available for Linux.
Pro File sharing
Skype allows you to send any files (MP3s, images, text, etc.) by simply dragging and dropping then in the chat window making it simple to share things with colleagues.
Pro Cheap fixed phone number
Starting at $5/mo you can get a Skype number.
Pro Send SMS and make regular calls
With Skype Credit bought or a subscription, you can send SMS and make direct calls.
Pro Group chat with archive / records
Pro Powerful 1:1 chat and also group chat

Pro Threaded discussions
An easy & simple interface to filter chat discussion into separate threads.
Pro Drag and drop file sharing
Files can be dragged and dropped in to the flow dock screen for upload.
Pro Multi-platform
Browser Based, as well as:
- iPhone and iPad App
- Android App
- Mac OS X App
Pro Stored chat history
Content and discussions are stored forever.
Pro Smart pastes & code syntax highlighting
Pro Private chat option
Able to speak privately/talk head-to-head.
Pro Notification system
A specific user or everyone in the channel can be notified via @user or @everyone respectively.
Pro A full developer API
Flowdock API allows developers the freedom to create custom integrations.
Pro Create and assign PRs from Flowdock
You can interact with Github directly from Flowdock to create PRs.
Pro Free for teams of five, non-profits and students
Pro Data exports
Back up conversations and files fully at any time.
Pro Add Tools
On top of our 50+ custom integrations, easily integrate any tool that sends emails or generates RSS feeds, as well as having the option to build a custom integration with Flowdock's API
Pro Status updating
Allows co-workers to know what you’re up to "/status I'm busy today!"
Pro Google Apps Integration
Google Apps get a Flowdock link to the Apps tool-bar and won't have to separately manage users
Pro Typo Fix-ups
Pro Able to host users external to your team
When working with stakeholders (clients or partners) you can add organizations to manage internal privacy
Cons
Con Plagued by bugs on all platforms
Crashes and other bugs are prevalent on Android, Windows and other platforms.
Con Subpar video quality with more than 5 users
Skype has significant problems with multiple users and video quality. Skype recommends that a max of 5 users group chat as video quality is severely affected. Even webcams tested with other chat services showed lower quality when used with Skype.
Con Not a feasible alternative as a professional team chat
Missing key feature such as centralized mgmt, centralized billing, data retention policies, ...
Con Poor quality when screensharing
It is not possible to manually set resolution or bitrate, and Skype often defaults to a resolution so low that text is unreadable. It is also not possible to transfer control over mouse and keyboard.
Con Slow filesharing speed

Con Owned by Microsoft
Con Obnoxiously large ads
Ads take up over 25% of the usable space.
Con Poor Linux support
The version available for linux users is quite outdated, and does not support some of the newer functionality, such as the free group video calling and screen sharing.
Con Requires both ends to be online (if neither end is using a cloud-enabled device)
Messages are sent and received only when both ends are online, if neither end is using a cloud-enabled device. In this case, if you are online 9-17 and your recipient is online 18-3, messages will never be delivered.
Con MIcrosoft (Skype's owner) actively assists eavesdroppers
On the other hand, if you lose your copy of one of your conversations, you may be able to get a copy of it from your government with a little bit of luck and a public records request.
Con Proprietary (non-free/libre)
Con No self-hosting available
If you are worried about third-parties getting access to your data you should consider self-hosting. With self-hosting you are in control over where your data is stored, who has access to it. You will also not be vulnerable to exploits of a third-party provider.
Con Buggy android app
Google sign up didn't work, then after going to the website to do the sign up, the invite team members screen was broken.
Con Free only for small teams, non-profits or students
Unless it's used by a team of less than five people, a non-profit or students, Flowdock will cost $3/mo per person.
