2020 is going to be a big year for enterprise IT teams, with Windows 7 support having ended on January 14th. Even though the expense of paid extended support can easily be budgeted for by most enterprises, there is still a ticking clock counting down to the day when paid support runs out, not to mention other serious risk factors.

Enterprises trying to upgrade will find themselves running into brick walls, virtual or otherwise. But that’s not the only challenges enterprise IT teams will be facing. Let’s have a quick look at what we are facing today before we take a look at the expected obstacles for the next 12 months.

2020 IT Statistics & Trends

Before we get into each challenge in more detail, here are some quick statistics and trends in IT for 2020 to help put the challenges into a better context.

  • 76% of IT operations teams believe that the complexity of the IT landscape is the biggest barrier to productivity. Other major barriers are a reliance on manual processes (61%), a glut of tools (69%), the skills shortage (60%), and obsolete systems (62%). (Source: Fujitsu)
  • 83% of recruiters struggling to find suitable talent (Source: Business2Community)
  • 7% of budget will be spent on cybersecurity (Source: Spiceworks)
  • 9% of budget will be spent on server infrastructure (Source: Spiceworks)
  • Cybersecurity, lack of skilled talent, and cloud management are among the top worries, but budget is not an issue. (Source: INAP)

So, without further ado, here are our top candidates for this year:

#1 Infrastructure Is One Of The Biggest IT Hurdles You Will Face In 2020

When Windows 10 was released back in 2015, Microsoft stated that devices running Windows 7 would be able to upgrade to Windows 10 and wouldn’t become obsolete. In fact, when you look at the minimum system requirements for both operating systems, they are almost identical.

However, when you need to work efficiently in the real world and run multiple LOB critical apps, hardware becomes obsolete much faster.

For example, enterprises that use Virtual Desktop Infrastructure (VDI) will find themselves hitting a brick wall when migrating to Windows 10. The consolidation ratios change going from Windows 7 to Windows 10. A server was once able to host up to 40 machines, but now it can only handle 20-30. This is due to the much greater amount of processing power that Windows 10 requires, particularly for its UI and Edge.

Getting additional servers (or upgrading them) sounds easy, but it is definitely not the solution because it ignores the sheer amount of IT resources that is needed to refresh and maintain this infrastructure. As mentioned in the statistics above, the prospect for finding IT talent in 2020 looks bleak for most enterprises, so simply upgrading isn’t actually so simple.

Because IT talent is already stretched thin, the adding, upgrading, and maintaining of servers can become a hard-to-overcome bottleneck in a migration process, despite the fact that upgrading laptops and PCs to Windows 10 might seem like a routine task on its own.

#2 Internal Change Management To Evergreen IT

Whether or not resources is an issue, figuring out how to get your enterprise on board for continuous updates, or Evergreen IT, is key to not only 2020, but to the future of your IT environment. While the biggest concern for your IT environment might be migrating to and staying current with Windows 10, Office 365 can’t be overlooked in the process.

Office 2010 goes end-of-life on October 13, 2020, with no extended support, and while you can still upgrade to another on-premise version, Office 2019 will most likely be the last on-premise version made available. Additionally, because Office 365 continually gets new features, and because upgrading away from Office 2010 already requires significant rework to not have your macros and apps break, it becomes clear that migrating to Office 365 now will be far less disruptive than migrating down the road.

IT Automation is a huge part in making this Evergreen IT machine run:

  • With the help of Access AppScan, you can quickly re-certify your application portfolio and determine which applications might be suitable for a specific environment (e.g., when deciding if VDI is the right path forward).
  • Using Access Capture, you can automate the vast majority of your application discovery, packaging, and testing process while
  • Access Agent enables you to deploy fixes across your IT environment and provide you with the ability to offer self-service to your users.
  • Finally, with Access Sign-Off, you can train your users indirectly as they sign off on the new environment.

The focus of your rollout strategy should be to cause the least amount of disruption as possible. One way to go about this is to identify those users that aren’t running as many untested third-party apps, macros, add-ins, etc., that are line-of-business critical.

Figuring out your strategy and how many phases or waves of migration your company needs is critical for Evergreen IT success, as you will have to be successively and continually running these phases for Windows 10, Office 365, and the other as-a-service feature updates.

#3 Building The Right Security Stack Will Be Crucial, But Difficult

Along with all the new features that come with each iteration of Windows 10 and Office 365, there are also new security features. Although these features are well-intended, they can create a bottleneck in your migration or post-migration strategy.

While there are plenty of success stories on Microsoft’s site of organizations upgrading or migrating, our experience in a real-world enterprise environment has shown us that it never goes easily.

For example, a file from a trusted source, like Thompson Reuters, containing a macro gets blocked because the system doesn’t recognize it. Or an anti-virus software blocks certain parts of apps without forewarning, or VDI policies are changed to increase security, which can cause apps to be blocked as well, issues with Credential Guard, you get the picture.

In a Microsoft-shop, these issues are minimized as everything is built to work as one stack, but most enterprises are running a broad range of different products. This assortment of products and different policies on risk management cause issues that affect how locked down the IT department will have to make applications like Office 365, for example.

#4 IT Support And Contractors Will Be A Premium

As mentioned earlier, IT talent is a major concern for many organizations, which is why, for migration projects, enterprises would often hire independent contractors to quickly throw more hands onto a job. The benefits of hiring these contractors have always been straightforward: they have the expertise to get the job done, they don’t need to be onboarded like an employee, they don’t receive employee benefits (like healthcare, pension, etc.), and they are utilized for a limited amount of time.

Now, however, with countries and municipalities trying to find more ways to increase tax revenue, stringent laws are being passed, such as AB5 in California and IR35 in the UK, which make it harder to classify someone working for your firm as a contractor instead of an employee.

The impact of these laws can create a shortage of the skilled labor needed to migrate, update, and maintain devices and infrastructure. Contractors will be forced to move to an area with more favorable laws, or they will, more likely, take jobs at major IT firms, since more municipalities are sure to follow with similar laws. This will not only significantly increase the cost of your IT workforce, whether internal or external, but will also increase the time it will take to have a project completed, as there will be less choice in the market.

#5 App Complexity Hasn’t Gone Away

Everyone in the last five years thought that, with the adoption of cloud solutions, the complexity around application management would reduce significantly. However, that has not been the case. If anything, it has become more complex, and cloud adoption has become mainstream. Here are some statistics from Leftronic:

  • 90% of companies use some type of cloud service.
  • 80% of enterprises use Amazon Web Services as their primary cloud platform.
  • 77% of enterprises have at least one application or a portion of it in the cloud.
  • Enterprises use 1,427 distinct cloud services on average.
  • 60% of organizations use cloud technology to store confidential data.

One of the main reasons for such fast cloud adoption is that it flexibly provides data access everywhere — an action that is crucial for a shifting workforce that doesn’t report to the same office everyday, or may report to no office at all.

With all of these moving parts, such as employees working in remote offices, co-working spaces, or from home, and employees using company devices, BYOB, or a combination of both, knowing what apps you have, how many there are, which versions are actually in your IT environment, and which are LOB critical has become a nightmare.


In 2020, cyber attacks and breaches will certainly dominate the headlines as they happen, but the day-to-day management of an IT environment will be most affected by the lack of skilled talent. Enterprises that are able to implement effective IT Automation solutions will be better equipped to increase cybersecurity, handle migrations and updates faster and more efficiently, and improve their IT environment and infrastructure.


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