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About Windows 10

It’s time. Time to embrace Microsoft’s modern desktop operating system: Windows 10. Windows 10 Pro and Windows 10 Enterprise are faster, more secure, and easier to use than their predecessors. Users and organizations are overall very satisfied with Windows 10…but it takes a bit of work to get there!

While many organizations are already well on their way to deploying Windows 10, you are not alone if you are earlier in the upgrade process, even if you are just starting to think and plan now. This post focuses on Windows 10 for Business, as opposed to the Windows 10 Home edition.

Microsoft recognizes that desktop management hasn’t changed much in years and can be tedious and time-consuming businesses. Their approach to the modern desktop and the associated tools around analytics, app compatibility and upgrade/support flexibility are evidence of their intention to improve this situation for IT professionals. Microsoft promises that “the combination of Windows 10 and Office 365 ProPlus, referred to as Microsoft 365 delivers the most productive, most secure end-user computing experience available.” And many organization report that this is beginning to bear itself out.

As with all technical migrations, there are 2 important aspects that we need to evaluate and address: technology and users. The technology is, after all, there to support the organization’s goals and the team members who make it all happen.

End of Windows 7 Support

Windows 7 User with No Support

Windows 8 was not a huge hit with the IT crowd, so many businesses and organizations stuck with Windows 7. Windows 7 has been the most successful operating system in Microsoft history. While it has served many organizations well for the past decade, the reality is that it doesn’t offer the level of protection needed to deal with today’s new security threats.

January 2020 is the looming deadline. After January 14, 2020 Microsoft will no longer provide security updates or support for PCs running Windows 7 without additional yearly investment. For some sectors of the economy, such as Healthcare and Banking, this is a deal breaker: regulations require that these organizations use currently supported technology for security reasons.

Even if regulations don’t dictate a move to Windows 10, practicality does. The improved security is important to all organizations. (More about this below.)

Webroot, a prominent cyber security firm, reports that “devices that use Windows 10 are at least twice as secure as those running Windows 7.” They’ve seen a steady decline in malware on Windows 10 devices. Furthermore, new releases of software applications are already incompatible with Windows 7, and this will continue to snowball over time.

For those who are panicking, there is a relief valve, but it’ll cost you. For volume licensing organizations that need additional time to make the transition, you can purchase Extended Security Updates (ESU) for Windows 7 for up to 3 years; they are sold on a per-device basis and the price increases each year. For more information about Windows 7 ESU you can download this PDF from Microsoft.

Improved Security

Windows 10 is the most secure Windows desktop operating system to date, making it an appealing upgrade project, especially in the healthcare sector and the financial sector. Here is a small sampling of some of the great security features:

• Built-in two-factor authentication, referred to as Multifactor Authentication (MFA)

• Modular threat-resistant features that you can deploy as best fits your organization

• Useful new VPN profile options

• New tools to mitigate credential theft

And many more. See Microsoft’s Windows 10 Enterprise Security documentation to learn more about identity and access management technologies in Windows 10, how to secure document and other data across your organization, and using advanced threat protection (ATP).

Windows 10 Improved Computer Security

Windows 10 Migration Plan

In broad strokes, your migration plan needs to account for hardware, software, and users. Most successful migrations have a road map for each of these items. It takes some planning and preparation, all while keeping budget, timeline and staffing resources in mind.

Think about methodology, too: will you do an in-place upgrade or wipe-and-load or some combination? For existing computers running Windows 7, Windows 8, or Windows 8.1, the recommended upgrade path includes an in-place upgrade. This automatically preserves (almost) all data, settings, applications and drives. Microsoft also claims that it requires the least IT effort. For computers running anything older than that, you will likely need to rely on a traditional deployment method such as bare-metal or wipe-and-load (sometimes called a computer refresh.)

Business People Preparing for Windows 10 Migration

As far as migration timing, depending on the size of your organization you might want to stagger the upgrades by department or by job function. Some teams even stagger updates within job functions so that some team members can keep working in the older OS while other computers are upgraded. This can help to prevent productivity from stagnating during the migration.

Assess Your Readiness

Device Readiness

You’ll want to evaluate the inventory of devices across the organization, including virtual desktops, laptops, physical desktops, tablets and so on. Will they run Windows 10? In some cases, you might have support contracts that allow for upgrades to Windows 10 and you will need to allow time to work with the vendors to coordinate that. If you have hardware that’s not compatible, you will need to figure out a retirement plan for the old and a purchase plan for any new hardware that’s needed.

In addition to desktops and laptops, consider mobile devices, too. This analysis will vary depending on your organization’s policy around personal devices and company-issued devices. Do they need to be brought up to Windows 10 and can they support it?

Windows Analytics Upgrade Readiness service is a handy tool included with Azure subscriptions. It can inventory the computers, applications, and Office add-ins across your desktop environment for you.

Windows 10 User with Multiple Devices

Software Readiness

This is a biggie: are your applications compatible with a modern desktop? This is a key pain point during the deployment process, so be sure to plan time and resources around this as best you can.

The larger your organization, the more applications that you will need to evaluate and test. Prior to testing your own apps and workflows, you can get a head start by checking out the Microsoft directory that lists software solutions that are currently being used on machines running Windows 10.

Larger organizations often set up a test environment where apps can be exercised and evaluated against Windows 10. Microsoft provides virtual Windows 10 labs and others tools that IT pros can use to assist with this.

For each logical user group throughout the organization, sit down with a handful of users to understand their workflow. This will be much more effective than making your best guess from a distance. Find out what their work entails. At the very least you want the upgrade to not disrupt their workflow unnecessarily. But often we find ways that Windows 10 can actually improve workflows using simple tools like splitting windows with snap assist or the snipping tool with the delay feature. Keep these at the forefront and be sure to highlight them during training and support efforts (more to come on that).

Windows 10 Inter-Connected Software

You will find that many of the applications, drivers, and add-ins will work as-is as any application written in the last 10 years will run on Windows 10. Depending on the size and age of your organization, you may have some older apps that become roadblocks.

Here’s where your interpersonal skills will come in handy: working with cross-functional business stakeholders to determine the strategy in these cases where apps used by various job functions aren’t ready for the upgrade. If the apps are non-critical, can you work with users to retire or replace them? If they are critical, what are the vendor’s plans regarding Windows 10 compatibility, or will you need to extend Windows 7 support?

There may be pockets in your organization where older but still critical apps will delay your deployment and force you to consider the timeline extension options such as Windows Virtual Desktop which includes free Windows 7 Extended Security Updates, giving you more options to support legacy apps while you transition to Windows 10.

For example, one of our clients recently migrated most departments to Windows 10, but they had to leave the Radiology team on Windows 7 until a key imaging application and a custom, legacy hardware driver are either replaced or updated. But now, in the meantime, they are supporting a mixed environment which is more work and more hassle for everybody. They are actively working to resolve this within an aggressive timeline.

Communication & Training

Communicate, Communicate, Communicate

For each team that is set to be upgraded, be sure to foster communications with a main contact – a supervisor, influencer, or top performer – who can help before, during and after the upgrade.

Business Team Communicating

Involve these contacts as early as possible in the app analysis and testing as described previously. Prior to the upgrade, give them a demo or a mini training session and work with them to find a time to address their team. This often works well dovetailed with a regular staff meeting that they might have on their calendars. Once you have the end user’s attention, be sure to explain:

• What exactly is coming: how will this impact their daily work experience?

• Why it’s coming: what are the key benefits to the organization for upgrading?

• What to expect the day before the upgrade, the day of the upgrade, and the days following the upgrade.

Depending on the team culture, we have had good luck passing out a physical handout during the pre-upgrade briefing that team members can take back to their work and refer to on the big day.

In our experience, every time, with every user group that gets upgraded, there is something unexpected that happens and needs to be addressed. Even with great planning, you won’t catch everything. So be nimble, and make sure you have time and resources to address whatever crops up. For example, we’ve run into snags with Outlook auto signature, Firefox bookmarks, start menu issues, etc.

End Users Thrive on Training

Transition day training can make a huge difference in adoption and attitude, and, most importantly, productivity. Whether in-person or online, live or recorded, be sure user have something to assist them with the learning curve. And the cool thing about Windows 10 is that there are some great features that can get users genuinely excited. Training can bring them around from a “why-should-I-have-to-change” attitude to a “wow this is really handy!” attitude. We’re not just maintaining the status quo here; we’re moving the organization forward and building excitement!

If you take a user who has become comfortable using Windows 10 as part of their daily workflow and sit them down in front of a Windows 7 machine, they will quickly start to realize how dated it is. After getting used to the many new features of Windows 10, Windows 7 feels slow and inconvenient. If you focus on getting them over the hurdle of the initial transition, that will go a long way toward full acceptance and adoption.

There are Windows 10 users guides available, on-demand training videos, and many larger organizations will arrange for at-the-elbow support on transition day. Here are KnowledgeWave we have deep experience that provides all of these services at an affordable rate.

Younger audiences typically have some exposure to Windows 10 at home, or school, for example. So, depending on your demographic and your resources, you might wish to target more transition training efforts at your mature workers.

Business Team Discussing Training

Greatest Hits for Users

When we work with users who are making the transition to Windows 10, we often see users delighted over some of the productivity-enhancing features. Here are some of the highlights:

Task View

Task View allows you to efficiently work with multiple apps and quickly access previous activities on the timeline.

Snipping Tool

Sometimes a screenshot is worth a thousand words, and many users still don’t know how to do this. The delay feature is especially handy if you need to go pull down a menu or hover over something before the shot is taken.

The Start Menu

Apps, settings, files, all can easily be found on the Start menu. Less time spent finding stuff, more time spent getting good work done. Your organization can get huge value out of helping users customize the Start menu just right to support the workflow. Bear in mind that the out-of-the-box start menu can be overwhelming and confusing.

Splitting Windows with Snap Assist

With Windows 10, you can split and resize windows more efficiently than ever before. Snap assist makes it frankly kind of fun; it’s satisfying (and effective) when those windows slide into place and you can get on with your work.

Easily Add a Printer

Click the Start menu and type “printer.” Then follow the logical steps the rest of the way. It’s never been easier for a user to set up a printer.


Business Woman Considering Windows 10

In conclusion, upgrading your company’s software to Windows 10 is a great business decision. Windows 10 is now the default operating system and future updates are not likely to include past versions of the software. It is important to begin planning an upgrade strategy as soon as you can, the support deadline for past versions of Windows is rapidly approaching (January 14, 2020).

No matter what industry you are in, from healthcare and medicine to finance and banking, the choice to upgrade is a step in the right direction. The differences between Windows 10 and past versions of the software (like Windows 7) are well worth the investment. The switch will only increase business efficiency and collaboration efforts.

Windows 10 is easy to use and the software can be quickly learned by your employees. Providing them with additional training and information will only increase their learning potential while enhancing their skills sets and overall confidence with the system.

While this guide may not have covered every single application or tool available to your business in Windows 10, it includes some of the most basic and useful pieces of information to consider when planning to integrate the software within your organization. Give us a call today, or fill out the form below, for a consultation on how to integrate Windows 10 and its applications into your business and how to train your employees for success.

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