TL;DR: We’re sticking with Skype. Despite Skype’s chat weaknesses, having a single tool that does group voice, video and chat works better for us than using two overlapping tools.
The Skype Group Chat Anti-pattern
Skype doesn’t let you rejoin a group chat you’ve left without someone who’s still there inviting you back. As our team has grown, we have more and more group chats. No one ever leaves a group chat because of the barrier to rejoining. Over time, each of us has accumulated more group chats, and more notification noise. You can change your notification preferences, but Skype has no formal “mention” notifications, so there is no way for a sender to get a recipient’s attention without knowing the recipient’s notification preferences.
HipChat’s Promise & Delivery
HipChat lets you come and go from rooms as you please. I imagined that this would model face to face communication better, that I would show up to my team’s HipChat room in the morning, and that others could drop in on us if they needed something from the team.
HipChat largely delivered on that promise, and it exceeded my expectations with attention to subtle details that make a really nice user experience.
HipChat shows a list of all the people in the organization. No one needs to explicitly share their username with anyone else or go through the dance of connecting with each other.
HipChat search makes its chat logs a shared knowledge base. Skype’s decentralized roots have always made for a poor chat log search experience.
HipChat mention notifications are beautifully done. If I type “@” in a chat room, HipChat provides a list of users I can mention. If someone mentions me in a room, I get an invitation to join the room. If I’m offline, I get an email, a text message, or a push notification to my phone running the HipChat mobile app. The default notifications worked great, and it’s comforting to see that they’re all configurable in case the notifications get too noisy.
XMPP and the HipChat API make HipChat easy to automate. Within minutes of registering his HipChat account, one of my teammates had configured Jenkins to send build notifications to our team’s HipChat room.
But for now, Skype’s advantages are too significant to ignore.
Skype’s Surprising Advantage
I expected all along to continue using Skype for group voice and video. HipChat only has one-on-one voice and video. But I was surprised by the trial on two counts:
HipChat’s voice and video didn’t work.
Multiple people tried it, and most attempts yielded a black video window with no audio.
I discovered cases where I prefer Skype’s group chat model.
Skype shows offline group members, whereas HipChat hides you unless you are online or “away”. When I didn’t see a teammate in a HipChat room, I didn’t know whether that person was offline or just out of that room.
The barrier to leaving a Skype group chat makes it easy to contact a group like all of engineering, or all of the mobile developers. Of course, this is the other side of the notification noise coin. What’s easy for a sender risks noise for recipients. I think that means we should try some chat etiquette changes next rather than expecting a tool to fix the notification noise problem for us.
What Could HipChat Do To Win My Attention Again?
HipChat broadcasts a notification if you mention “@all”. I think this works for small teams, but it doesn’t scale. What I really want to do is mention an arbitrary named group, like “@webdevelopers” or ”@productmanagers”.
Group Voice & Video
HipChat could go toe to toe with Skype on Skype’s home turf. If HipChat added group voice and video, I’d definitely do another trial. Of course, HipChat will have to iron out the one-on-one voice and video kinks first.
Integrate With Skype
The simplest thing that could possibly give me the best of the HipChat world and the Skype world is a HipChat profile field for my Skype username and actions to start one-on-one and group Skype calls from within HipChat. I realize there are probably business barriers to that ever happening, but it could be a nice synergistic user experience.
Features I Hope They’ll Compete To Add
Screen Sharing & Remote Desktop Control
Skype has view only screen sharing. HipChat doesn’t have any screen sharing. We use join.me for ad hoc screen sharing, and GoToMeeting for larger groups and more organized presentations. I’d love a seamless experience incorporating chat, video conferencing, and screen sharing with the ability to control other participants’ desktops.
Voluntarily Joining Video Conferences
Daily standups routinely start with chat.
[one person] Ready?
[everyone else] Yep.
I’d much rather be able to say the meeting is at the same time, in the same virtual place, every day, and have everyone show up, just as they would in a physical office.
Anyone using Google Hangouts as a Skype alternative?
Bridging From A Telephone
Sometimes I’m not in front of a computer, but I’d still like to participate in a conversation happening on Skype. I’d like to dial into a conference phone number to join the Skype conversation.
- user directory 
- voluntarily joining a chat room
- chat log search
- mention notification regardless of presence
- automation via published APIs
 I think Skype for Business can do this, but it can’t associate existing Skype usernames with an organization. Instead, you have to create new Skype identities for everyone.
- voice and video
- screen sharing
- sender can pull people into a group chat
- voluntarily joining a group video conference
- conference bridge from a telephone
- remote desktop control
Group voice and video is the killer feature. We can’t eliminate Skype because HipChat’s voice and video doesn’t match up, and having two overlapping tools creates a paradox of choice that introduces more pain than it eliminates.