UX Review: Skype for Business

Gautam Krishnan
UX Reviews
Published in
7 min readFeb 20, 2018


Note: This article is about using Skype for Business on a Mac (Version 16.12.77). We at Vitech use Skype for Business for chat and internal collaboration. It has been three months since I’ve used this app, and a few of its features a hard time every day at work.

Here is the home screen and a few other screenshots with some of the issues I found:

The Skype for Business Interface (Sensitive details masked).

1. Spawning multiple threads:

Notice from (1) in the image above that Skype spawns new threads for conversations with the same person. If it had only 1 thread for every person I ever had a conversation with (Like Slack, iMessage, WhatsApp and countless other messaging apps out there), the list would contain only 12 items, making my life easier.

These threads also spawn randomly (Initially, I was expecting a reason for this behavior, like a thread expiring at the end of day), but was proved wrong. I started freaking out when Skype would spawn a new thread even during active, live conversations with my colleague’s latest message. During these times, I’m confused if I should be replying in the previous thread or the new one, not knowing how it would show up on the receiver’s end.

2. Unable to send a message:

Although this doesn’t happen all the time, but I have noticed that once in a while, Skype isn’t able to send messages as (2) in the image above. There is no visual cue to the user on what must be done now. Is Skype going to try sending this message again for me? Do I have to do something to make Skype try sending the message again? Or do I have to manually copy and paste the message and send it again? I’m confused here because I don’t want to copy-paste the message again only to realize that Skype might have sent it for me again, which would make me look like an idiot.

3. Attachments in the thread:

One simply cannot open a received/sent attachment by double-clicking on it. Being a designer, I send and receive a lot of quick screenshots to/from my colleagues. I need to find the ‘eye’ icon as shown in (3) above and click on it to open the image and view it. Although the ‘search’ icon to open the folder containing the file is a nice feature to have, I feel that the ‘search’ metaphor is a bit misleading here. At this point, I’m not sure if a ‘search’ or a ‘folder’ icon would be more appropriate. Also, the attachments only download to the Downloads folder and there seems to be no control over it, apart from users being able to turn the automatic downloads on/off. This means that I have a hard time finding stuff that was actually sent to me over Skype vs stuff I actually downloaded from the web.

4. Sharing one’s screen:

Each time I look at the screen sharing icon, I cringe. It looks totally out of place compared to the other icons there. Also, the diagonal arrow makes it look like its purpose is somewhere between fullscreen and maximizing the window. Skype seems to recognize that users might click on this for not the intended purpose and follows up with a confirmation (and with a preview of your screen) as below. Due to the confusion with the icon metaphor, I once accidentally clicked ‘Share Screen’ confirmation to send a false notification to my colleague.

Screen sharing confirmation.

This confirmation seems to be useful, as I get a preview of what the other person will be seeing, but does not give the flexibility to control what I share. I expected this confirmation to let me share the window/application that I wanted to, like other screen sharing apps. As I have been using the desktop version, I assume the developers would have access to a lot more native functionality/APIs to do better than web based screen sharing apps.

5. While sending attachments:

Consider these two images below: (5) is the typed message on the message composer box and (6) is the exact message after it is sent.

Adding images to the editor (Applies while uploading the file via the file dialog, as well as drag and drop.
After sending the message.

Skype treats the attachments as inline elements. One can add text before or after the attachments, although I’m not sure why anyone would want to do that. My point here is that the design should not give the affordance of doing this, which causes this problem. The messages from a person aren’t grouped, and it is hard to tell if the image reaches first or the text. Looks like the attachments are always sent first (as from the screenshot) but I’m unsure how it appears at the other end. I would expect all the messages to be grouped and attachments to appear after the text.

Concept: Separating attachments from the text.

The editor should have a separate section for the attachments so that the problem (as in 5) is avoided. Note that in the concept image that I made above, it suffers from drawbacks like not showing the preview, and doesn’t address issues like how multiple attachments will be displayed, or how different file types will be distinguished.

6. Emojis at the workplace:

The emoji name and shortcut are updated while hovering on each emoji.

The name and keyboard shortcut are shown on hovering every emoji. This is a very useful feature in my opinion, as one may not know what every emoji means. Making sure that I do not send an incorrect emoji (or an offensive one) is very thoughtful, especially for the audience for whom this app is built. My colleagues are from different countries and cultures, and this standardization of what each emoji means is much needed. It also helps to learn the emoji shortcodes so that I do not have to open up all the emoji every time.

No previews for emoji shortcodes.

Skype should have followed up with updating the shortcodes in the editor to the emoji itself. In the above screenshot, the text in the editor produces the result as shown in the last sent message. There’s a clear disconnect between the way you can insert emoji — shortcodes vs selecting from emoji box. In this case, a user innocuously typing one of the emoji shortcodes will not know that they will be turned to emoji until the message is sent.

Notice how I have been talking about emojis here and the screenshot says “emoticon”? I am not sure if the designers really understood the difference here as the words emoticon and emoji do not exactly mean the same. Here’s the explanation from the Unicode Consortium.

Are emoji the same thing as emoticons?
Not exactly. Emoticons (from “emotion” plus “icon”) are specifically intended to depict facial expression or body posture as a way of conveying emotion or attitude in e-mail and text messages. They originated as ASCII character combinations such as :-) to indicate a smile — and by extension, a joke — and :-( to indicate a frown. In East Asia, a number of more elaborate sequences have been developed, such as (“)(-_-)(“) showing an upset face with hands raised. Over time, many systems began replacing such sequences with images, and also began providing ways to input emoticon images directly, such as a menu or palette. The emoji sets used by Japanese cell phone carriers contain a large number of characters for `emoticon images, along with many other non-emoticon emoji.

I do not understand why the label should say “Emoji” or “Emoticon” there, or why there is a even a label there. They could have simply placed the emoji’s meaning there.

7. Lack of replies

This is one thing I wish the Skype team had prioritized earlier. When multiple messages about various issues are sent or received, there is no way to reply specifically for one particular message. This also means that it is tough to comprehend and associate replies to the multiple messages I have sent. To tackle this, I end up copy-pasting the sender’s message and replying to it inline and I have seen my colleagues follow suit. After using the replies feature in Slack and WhatsApp, it is hard to do without it.

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Gautam Krishnan
UX Reviews

Hacker | Product Designer at Vitech | Former UI/UX Designer at Zoho. I love solving problems and making people’s lives better. http://www.gautamkrishnan.com