Its surprising how many deployments I have seen that don't monitor their Skype\Lync environments. Its even more surprising how many monitor only the usual server type bits such as disk usage, processor, RAM utilization and services.
May I suggest that at the very least you monitor your environment by means of synthetic transaction.
Test of Skype\Lync modalities by utilizing Synthetic Transactions. Test results generate Event logs on the machine where the tool is being run, for easy identification by any monitoring platform.
All connectivity is over PSRemote Sessions to the Front End Pools. Automation is achieved by means of the schedule tab, this makes use of the Windows Task Scheduler.
Synthetic transactions are actions, run in real time, that are performed on monitored objects. In the case of Lync\Skype for Business, synthetic transaction allow you to emulate actions such as sending an IM, making an outbound call, delivering a voicemail message, and so on.
Of course if you are a Powershell Guru and you have scripted your own Synthetic Transactions that great. However, this tool does more than simply run a bunch of synthetic transactions.
220.127.116.11 First public release
18.104.22.168 Add PowerShell V4 compatibility
22.214.171.124 Added Email Reporting
126.96.36.199 Introduced Alert Emailing, Bug fixes
188.8.131.52 Added more Synthetic Transaction Test. Aesthetic changes to UI to accommodate new features. Added a Help file to replace the About Tab