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Building a strategy for a move from Exchange to cloud-based email

Here’s how two firms weighed the pros and cons of moving their Exchange email to the cloud and built a solid strategy for the present and future.

There is a lot of interest in hosted email services because of the benefits it offers, but there are also a number of risks to consider before moving from an on-premises Exchange environment to the cloud.

There needs to be a strong business case for moving to cloud-based email services, and there are many considerations to weigh. But where do you start? Let’s look at two companies (former clients of mine) that had reason to consider cloud email, the factors they considered and how they came up with their very different outcomes.

Weighing email services

Table 1 details the make-up of each company, its IT maturity and the attitude of executive toward IT and email.

  Company Size (in users) IT maturity Executive attitude
A Pharmaceutical 10,000 Immature – mostly use contractors
  • Bottom line is top priority (hence legacy system)
  • Highly cautious of data leaks


B Financial 50,000 Very mature
  • Cost conscious
  • Need to be flexible
  • Strong security policies (e.g., no VPN tunneling)

Table 1: Company profiles

The second table illustrates email issues and concerns facing IT at each firm.

Company Leading issues/concerns
  • Legacy environment – Exchange 2003
  • User and client complaints about email format compatibility
  • Overrun by .pst files
  • No archiving
  • Network sluggish with external domains
  • Already own Exchange 2010 and SharePoint 2007 licenses
  • Only own Office 2003 licenses
  • Approximately 2,500 BlackBerry users and growing rapidly; no ActiveSync
  • Short staffed for email support
  • Multiple domains due to mergers and acquisitions
  • Usability complaints about “email jail” and free/busy time problems
  • Network sluggish with external domains
  • No budget for new projects in study year
  • Third-party utilities and customizations need to be supported in the future
  • Flexibility for on-boarding new users due to mergers and acquisitions
  • In the process of completing an Active Directory consolidation
  • BlackBerry users, but no ActiveSync
  • A couple legacy Lotus Notes and Groupwise domains to migrate
  • Hosted email is not mature enough for their needs

Table 2. Company email profiles

Each company considered different paths for delivering email services, including continuing their on-premises Exchange environment, moving to Microsoft Office 365, Microsoft’s Business Productivity Office Suite (BPOS) or Google Apps Premier Edition (GAPE). 

They also considered business and technical requirements of email and performed detailed cost models that compared costs for mailbox services, collaboration, archiving services, perimeter security (antivirus/spam/malware and message encryption), and mobile services. It also included licensing and maintenance, support, staffing, hardware, network, storage, migration, and other costs associated with delivering email.

Company Studied Outcome Future considerations
  • Exchange 2010 and SharePoint 2007
  • O365-Standard
  • O365-Dedicated


  • Upgrade to on-premises Exchange 2010 and SharePoint 2007
  • Use native archiving tools plus third-party archiving and e-discovery
  • Hire enough staff to support growing environment
  • Write up user and service segmentation
  • Complete .pst migration to file serve project
  • Stay with BlackBerry
  • Consider hosted email solutions in future, especially for extranet purposes
  • Consider hosted messaging services (e.g., message encryption)
  • Current environment
  • Consolidate current environment on Exchange 2010
  • BPOS-Standard
  • BPOS-Dedicated
  • GAPE


  • Consolidate on current environment on Exchange 2010
  • Executives approved funding in study year for consolidation after cost model demonstrated significant cost savings with little investment
  • Write up user and service segmentation
  • Complete AD consolidation
  • Write up plans and policies for on-boarding mergers and acquisitions
  • Revisit hosted email solutions in 24 to 36 months for hybrid email environment (especially for mergers and acquisitions on-boarding)
  • Consider using hosted messaging services (e.g., perimeter security) in the future once networking and AD issues are sorted out.

Table 3. Study and outcomes

Regardless of the environment or the outcome, building the business case for cloud-hosted email and an email strategy put both firms in a better position to move forward. Documenting rationale, costs and data in the process of deciding which delivery option is best also puts IT in a stronger decision-making position and helps executive management understand the complexities of delivering mission critical email services.

In most cases, hosted email services are the most cost effective or efficient option, but companies have their reasons for putting off a move to the cloud. Many Exchange shops are simply waiting for cloud services to mature and for more options to emerge before making their move. At the end of the day, it’s really a question of the degree of services and flexibility the customer requires.

About the author:
Karen Hobert is an IT industry research analyst focused on communication, collaboration, content management and social software technologies. She offers over 20 years of hands-on and market expertise to enterprises planning, designing, and deploying shared information systems. You can read more of her thoughts at Karen's Connecting Dots blog.

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