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Skype for Business Deployment Checklist

IR Team

Written by IR Team


Many organizations are embracing the power of Skype for Business, whether it’s purely for internal Instant Messaging and presence or increasingly as the core unified communications platform for telephony, collaboration and audio/video/web conferencing.

If your organization is considering a Skype for Business deployment or is already using Skype for Business (or its predecessor Lync), this checklist will highlight critical areas to address to help ensure deployment success.

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Download a PDF copy of the Skype for Business deployment checklist

The one common thing with all successful deployments (or indeed, any large project) is that the overall project is broken down into manageable phases, with lessons learned from one phase applied iteratively in the next. Before you embark on the journey of moving to Skype for Business to know why are you doing it. At the beginning of any major investment in your organization’s infrastructure you must ask and answer the basic questions. Are you replacing an aging system? Are you looking to implement the productivity gains that Skype for Business provides? These answers will help you define what success looks like and help you plan where to begin, who to involve and how to measure success. It is also important to remember that all IT projects involve three key components; people, process and technology.

As IT professionals, it is natural to focus on the technology and the process but far too often we neglect the people aspect. It is very important to realize that people are going to make or break the success of the project. Understand the “why” of your decision and clearly articulate the vision. Communicate to your people early and often so that they are bought in and feel like active participants in the process. This will ultimately determine the success or failure of your project.

In July 2016, Microsoft released the Skype Operations Framework (SOF), a comprehensive guide and toolset for implementing and managing a reliable, cost-effective communications service based on Skype for Business Online. The SOF provides a standardized approach to successfully plan, deliver and operate Skype for Business (online & on-premises).

The SOF approach aligns with the critical areas of the project; considerations before you begin, during installation, and perhaps most importantly (and often overlooked) during sustained activity and normal usage.


Define Skype for Business goals.

  • State why you are making the investment:

    • To replace an outdated system?
    • To get additional functionality?
    • To make financial savings?
  • High Availability/Disaster Recovery:

    • State the level of criticality Skype for Business services will have in your organization.

    • State the impact of a Skype for Business outage on business operations.

    • Outline a contingency plan in the event of an outage.

    • Identify specific groups, sites or regions that would benefit from early access to Skype for Business.

  • Identify the business scenarios that will benefit the most from Skype for Business.

  • Note the Skype for Business features your organization will deploy and in which order.

  • Instant Messaging and Presence
  • Collaboration
  • Audio and Web Conferencing
  • Skype for Business voice features (e.g. voice chat and telephony)
  • Video
  • Fully federated voice and video
  • Identify what you will connect Skype for Business to:

  • Existing UC/VoIP/PBX/Room-based Video Conferencing systems.
  • The Public Switched Telephone Network (PSTN)
  • Does your country support PSTN calling?
  • SIP Trunk providers
  • Third Party applications and S4B/Lync customizations.
  • Outline your needs to support external user access (e.g. remote workers, guests, partners, etc.).

  • Outline the encryption approach will you use (IPSec VPN or SSL/TLS).

  • Consider and note whether you’ll enable Skype for Business federation with other enterprise organizations such as O365, Skype, etc.

  • Identify how your organization will support the (inevitable) requests for Skype for Business clients on mobile phones.

  • Identify how you will incorporate Skype for Business mobile into your mobile device management/security strategy.

  • Skype for Business Qualified Device validation/acquisition/roll out strategy:

  • Name the person/team who will provide the device needs segmentation.

  • Name the person/team who will select the devices, manage the acquisition, etc.

  • Identify the categories of devices your organization will require.

  • Video devices:

    • Personal

    • Conference Room

    • “Telepresence”

    • Room Systems

  • Standalone IP phones:

    • Common area

    • Reception/attendant/high call volume

    • Executive

    • Conference room

    • Knowledge worker

  • Headsets/Handsets:

    • USB

    • Bluetooth

    • DECT

  • Personal conference/speakerphone devices

  • Identify how you will promote and measure adoption.

  • Outline the training methods will you use to enable workers to learn about new features and capabilities.

  • State how success will be measured.


Test technical deployment and network architecture.

  • Note the tools and resources you require to set up a test environment.

  • Document the tools and techniques you will use to ensure the proper assessment and provisioning of the underlying network.

  • Create a strategy for assessing the ability of the wireless network to support Skype for Business.

  • ​Take baseline measurements of existing usage prior to deploying Skype for Business.

  • ​Assess whether the test environment is scalable to test larger or more complex deployments.

  • ​Record the existing systems (e.g. ticketing, monitoring, etc) that will need to be updated or reconfigured for Skype for Business.​

Evaluate Skype for Business as a viable solution to meet organization’s needs​.

  • ​​Name the person/team responsible for specifying the expected behavior or performance of the Skype for Business Proof of Concept (PoC).

  • ​​Validate that Skype for Business will meet the needs and demands of specific departments or groups, as well as enterprise-wide.​

  • ​​Write down the success criteria for the PoC.

  • ​​Expand the success criteria for the pilot and subsequent roll out phases. ​


Create service architecture.

  • ​​Divide and note which users will be using Skype for Business Online or Skype for Business Server on-premises.

  • ​​Identify how Skype for Business will be integrated into the telephony environment.

  • ​​Define firewall rules, SIP Trunks, accounts and certificates for each use case of Skype for Business.

  • ​​Separate clients who need to be migrated and which are already supported by Office 365.

  • ​​Identify what security, governance and rights management will be required to ensure data is secured in transit and at rest.

  • ​​Identify integration features required for on-premise and online versions of Skype for Business and other Microsoft products.

  • ​​If using Skype for Business for telephony, outline how you will manage the dial plan transition to Skype for Business.


Validate Skype for Business, resources and rollout plans with users in preparation for broad rollout.

  • Ensure your users are ready for the testing phase.

  • Ensure your users will provide you with the feedback you need.

  • Put in place a system (and timeline) for iterative feedback/user satisfaction surveys.

  • Name who will own the plan to address issues with end user satisfaction (which is the primary driver of user adoption/rollout success).

Deploy & Enable

Launch of Skype for Business across initial locations, departments and/or user groups.

  • Confirm lessons learned in the pilot (or previous rollout phases) have been applied.

  • Create an iterative feedback and evaluation process, which will allow your organization to adjust the rollout plan for each new site or group.

  • Review your scalability assumptions and High Availability and Disaster Relief (HA/DR) planning.

  • Determine whether the rollout plan is scalable for an enterprise-wide implementation.

  • Develop a user awareness and adoption strategy.

  • Define how you are measuring success.

Enhance & Adopt

Execute adoption plan to drive habitual user behavior and active usage of service.

  • Ensure your users have been properly trained and prepared for sustainability.

  • Give users guidance on available Skype for Business clients and device compatibility.

  • Identify and leverage internal influencers to encourage adoption of Skype for Business.

  • Ensure you have an easy way to obtain feedback and further enhance the deployment.

  • Check whether their additional features and benefits are required by users.

Run State

Follow operations plan for all key phases and focus areas to increase user-adoption.

  • Have support staff or help desk to answer questions and provide troubleshooting capabilities.

  • When problems arise, have the tools to quickly pinpoint and resolve them.

  • Have a performance monitoring solution, like Prognosis, that will enable you to pre-emptively avoid costly outages by providing alerts before problems occur.

  • Get tools, like Prognosis, in place to monitor, report and troubleshoot all aspects of Skype for Business to optimize overall performance.

Topics: Migration, deployment and adoption Microsoft Teams

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