Microsoft’s cloud focus has been both interesting and encouraging. In last few years, we have seen world wide adoption of Office 365 & Azure. Five years ago, Microsoft’s server products were much more powerful than their Office 365 counterparts. Today, those differences are shrinking, and Microsoft is increasingly offering Office 365 services that have no in-house counterparts. IT departments continue to struggle with understanding how Office 365 services interoperate with other Office 365 services, Microsoft server products and third-party solutions. The devil is in the details, and the details constantly change. And then there has been an interesting feedback from CIOs and IT Leaders, that they all prefer to start hybrid and continue to use in-house infrastructure and software in concert with Office 365.

As a CXO, you have had your leaders establish cloud first strategy, but have you defined your tolerance for SAAS and PAAS based applications in your cloud journey? Because once these pitfalls are understood and tolerance is defined, you are very close to commence your cloud journey.

There are unique challenges about several Microsoft cloud products that lead to failed implementations and thus reducing confidence in the cloud strategy. Some of them are

  1. The misconception about Azure as VM service: Azure is way bigger then spinning few VM. Its has full stack cloud portfolio that provides services and workloads across identity management, machine learning, big data, storage, API management, CDN and many more. You can see the directory of Azure Cloud Services here.  It is important to consider these services when building a cloud first strategy.
  2. Treating Office 365 as a quick fix: The time to market for Office 365 product line is quick but it needs detailed assessment and planning before jumping the bandwagon. The pre configuration for integrating with Active Directory for sync and single sign on takes time, effort and resources.
  3. Planning performance & delivery: Multinational organizations find that connecting to Office 365 has challenges with the individual services — the bandwidth required, the data and the quality of service. Under Microsoft’s current delivery model, customers must pick a region for the primary delivery and storage of the data for the services.
  4. Upgrades & New Functionality– Office 365 is ever evolving and dynamic with a new functionality being rolled out every quarter (or less).  Organizations can, at the most, delay the release, but not completely avoid it. Communication has to be frequent and consistent before, during and after new functionality has been rolled out.
  5. Deciding what to use when – Organizations face a very unique challenge. Over availability of solutions to address single problem.  You want your network drive that needs to be migrated to cloud, you have solutions ranging from OneDrive, SharePoint Team Sites,  Azure Storage, StorSimple to name a few. You want a digital media solution, you have Office 365 Stream, Videos, Azure Media Services and SharePoint sites. You want workflow based application and you have PowerApps + Flow, SharePoint Online, Azure App Services, etc to address these problems.

Most organization treat cloud as a single project. May it be Office 365 migration or Azure implementation. And this is generally followed by implementing all services at one go.  And then there are other organization that focus on single service model for Office 365 or Azure. They start with Exchange Online and then stop at everything.

In order to mitigate these challenges, it is imperative that organizations use methodology that allows them to tailor-make their deployments that are best suited to achieve their goals. As a consultant, I have come across instances where a cloud service is brought in for a proof of concept, then converted into production and finally end up building processes and metrics to support that deployment.

I consistently thrive to help organizations address these problems by following an approach that brings in agility to adopt cloud services based on their appetite to handle change.



This 4 step approach follows a service catalog methodology that helps define owners for each service and plan the migration accordingly. It involves different teams like cyber security, data center & network and firewall early to plan if hybrid deployment is needed and how to assess the readiness of on premise infrastructure to integration with cloud. Each Service would follow a swimming pool analogy with multiple lanes for swimming.

  • In some lanes, the organization will dive in and swim as fast as possible (for example, when implementing services such as Exchange Online).
  • In some lanes, the organization will stay in the shallow end of the pool. E.g Identity Management
  • In some lanes, the organization will merely dip a toe in the water. E.g PowerBI
  • Some lanes will not be entered at all.

If these challenges are well mitigated, your cloud journey can be as smooth as a summer trip to the beach with adequate sun tan and anti glares to keep you woes at bay. If you are interested in building your Microsoft Cloud strategy, reach out to me at and I would be happy to help.