It happens every time. Your company deploys some new software and tells everyone, “Okay, this is what we’re using now!”

Sometimes they give training. Sometimes they do not.

Inevitably, the change in technology causes trouble. People have trouble learning the new system, the training material gets lost…it’s a pain.

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Over the past few years, we’ve installed Skype for Business for hundreds of users. Many of those users called us afterward with their questions. “Where’s the Transfer button? It was right here on my old phone!”

What could we do? Well, after explaining where the Transfer button went, we took notes. Some of the issues were legitimate problems which needed troubleshooting. Others were “Pain Points” – changes in the technology that the users didn’t know about, or weren’t trained on.

Four Pain Points Many (Most?) New Skype for Business Users Have

If you’ve worked with Skype for Business at all, you know it’s a many-legged beast. It has lots of capabilities…and even more moving parts. When moving from another phone system, Pain Points are pretty much guaranteed.

The following are 4 such pain points. Common occurrences among new Skype for Business users that aren’t really issues, but they can cause plenty of frustration.

We’re listing them out for two reasons: One, to give solutions for them you can reference at any time. Two, to show you that you’re not the only one experiencing them!

1. Adjustment Period between Old Phones and New Ones

New VoIP desk phones offer features totally different from legacy phones. They’re organized differently too. When users know how to do things on one, and you give them another one? Expect some vehement feedback!

SOLUTION: Provide a reference guide for getting around the new phone. Many phone manufacturers like Polycom will supply a user guide, of course.   But sometimes users just need a quick run-down on how to do basic tasks.

We supply customers with short guides for their new phones that we call “QuickCards.” Here’s a screenshot of one QuickCard, where we explain how to present an application during a Skype Meeting.


Simple task-by-task instructions. It’s helped shorten the learning curve on new phones from weeks to hours.

2. Where did Skype Meeting Go?

As we know, Skype for Business adds “Skype Meeting” to Outlook’s New Items list. It allows quick & easy meeting scheduling.

However, from time to time, we’ve seen the Skype Meeting Option disappear from Outlook. Poof, gone, no warning. Of course this makes it difficult for users to schedule their meetings!

SOLUTION: Sometimes, the Skype Meeting Add-In within Outlook gets turned off. (Why is anyone’s guess.) The solution? Re-Enable the add-in. Microsoft has some simple instructions for doing exactly that. Just visit this page and follow them. (Works for Office 2013 and 2016.)

Skype Meeting control is not displayed on Outlook 2016 – Microsoft Support

3. I Need to Book This Conference Room!

One handy feature with Skype for Business is the ability to reserve conference rooms in Skype Meetings. If you reserve a room in your Skype Meeting invite, everyone’s Outlook calendar gets an update. Nobody else can reserve the room for that time period.

The problem is, some users don’t know how to do this properly. The steps involved aren’t complex, but often neglected in Skype for Business training.

SOLUTION: Make sure staff are trained on where the Rooms resource button is, and how to select the room they want.

(Hint: The Rooms button is to the right of the “Location” field in the Skype Meeting invite.)


4. Can You Hear Me? How About Now?

Skype for Business will always look for a default audio device. If you don’t have a headset or phone, it will default to your computer’s built-in mic and speakers.

Here’s the thing. Most of the time, the built-in mic and speakers are terrible!

You don’t want users hunching over their computers, shouting at the monitor, straining to hear the other person through tiny speakers. Not only does it create a bad user experience, but it will color both callers’ impression of Skype for Business overall.

SOLUTION: Introduce a headset or new desk phone alongside Skype for Business. If you’re looking for quality headsets at a good price point, we’d recommend the Jabra Evolve series or the Plantronics Blackwire series.

We Feel Your Pain (and We Help You Get Rid of It)

Skype for Business is a big change for most people. Anyone who’s worked in IT more than one hour knows that change comes with problems.

These Pain Points (as well as a few others!) turned up over & over for us. Which led us to adapt our deployment practices to address them, before they turned into problems. You can do the same, with a little preparation.


About PlanetMagpie

PlanetMagpie is a comprehensive IT services provider in the San Francisco Bay Area. The Magpie team assists businesses with all four “pillars” of business IT: Support, Consulting, Web Development, and Cloud Services. They are Certified Microsoft Partners for Skype for Business, Unified Communications, Exchange, and SharePoint. The transition to the cloud is not one to be taken lightly. There’s little question that organizations will be able to save money moving to Microsoft Office 365, but the planning and processes involved in transitioning from an established infrastructure to a cloud environment is a major undertaking.

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