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Budgeting For Windows 7 End of Life: What’s Involved and How To Get Started

On January 14, 2020, several Microsoft products will be phased out, including Windows 7. If your organization still uses Windows 7 on any of your devices, including servers, you have some decisions to make. Updating to an entirely new operating system (OS) is a big deal — the more devices and apps that run on it, the bigger a deal it is.

Don’t procrastinate! Take a look at our six-step plan for how to budget a successful transition to Windows 10 and our rebuttal to the 11 most common reasons organizations put off upgrading their OS — do you recognize any of these?

The end of Windows 7 is nearer than it seems

Windows 7 End-of-Life (EOL) means the beloved OS Microsoft rolled out in 2009 will be vulnerable to intrusions in a few short months — Microsoft will no longer be patching the OS. No matter how great you think Windows 7 is and no matter how many millions of devices are using it, it’s a bad idea to run your organization on an unsecure system. Something will eventually go wrong.

Handling any EOL transition is a methodical process. The complexity, cost and speed of that process depend on your organization’s unique IT environment and the level of risk your organization faces. Your situation will be different, for example, if you have critical legacy apps running on Windows 7 or if your team is already using Virtual Desktop Infrastructure (VDI).

Microsoft provides information to help you along. It includes a Windows 7 EOL FAQ and articles on how to deploy and update Windows 10 and different Windows 10 deployment scenarios, among other resources. The Windows lifecycle fact sheet lists details for Windows 7, 8 and 10.

How much will it cost to migrate to Windows 10?

Your cost will depend on a slew of variables: The number of machines running Windows 7, if you need to transition legacy apps, if you need to buy new equipment or can choose cloud-based services, how much data you have, the size of the staff or outsourced team you’ll need to complete the migration, the level of risk you face — all of these circumstances and others determine your final costs.

A rushed migration can lead to uninformed or poor decisions that end up costing your organization more than it should. If you haven’t already begun to run the numbers, now is the time.

11 reasons organizations procrastinate and why it costs them more

  1. They haven’t budgeted for it. Many organizations and IT departments have prioritized other IT projects and dollars over a traditional PC refresh. Remember: Kicking the can down the road can create technical debt. Just like credit card debt, failing to pay off the balance can result in huge (and unnecessary) costs.
  1. They love Windows 7. Their entire business runs on it. With Windows XP EOL there was a lot of procrastinating so there’s likely to be as much or more with Windows 7 EOL. What’s different with Windows 7 EOL is that the upgrade option is much better. Remember: Windows 10 is not like Windows 8 — it’s a powerful, solid, fast OS that can improve productivity and open up new opportunities. And your employees can turn off the Windows 10 live (colorful) tiles if they want.
  1. Their computers aren’t old yet. For organizations that bought new computers within the last two or three years and are running them on Windows 7, it can seem like a waste of money to pay $100 to update each one and then replace it in the next year or two anyway. Staying the course with Windows 7 might seem to make fiscal sense. Remember: The cost of running vulnerable machines could be many times more than the cost of updating them.
  1. They think Microsoft will continue support anyway. Microsoft kept moving the goalpost after it officially stopped supporting Windows XP in 2014 so why won’t they do the same thing with Windows 7? There are millions of companies and people that will still be using it so Microsoft will feel the pressure to keep the patches coming, at least when there’s a significant piece of malware making the rounds. Remember: Cybersecurity risks — especially ransomware — are so much greater now than in 2014 that it’s increasingly difficult and more expensive for developers to keep up. It’s not likely Microsoft will continue to invest in supporting an 11-year-old OS when they offer a perfectly good, patched option with Windows 10.
  1. They believe they still have plenty of time. They know that testing app compatibility with a new OS can take a while and they may have extra hurdles to jump with legacy apps but 2020 is still far away — we still have the rest of 2018 and 2019 to get through. Remember: The time it takes to test a new OS, update devices, and move data should be overestimated, not underestimated. It can take a year or longer for large organizations just to do the initial testing. And you don’t know what unintended (and costly) consequences you’ll run up against.
  1. They don’t see the direct link between IT performance and business performance. If the pain won’t be immediate, what’s the rush if business won’t be affected? Their Windows 7 systems and apps won’t stop working exactly on January 14, 2020, so they have some wiggle room and will make the change once they start to notice an impact. Remember: An unsupported OS is not only risky, it will slow down your system and impact your ability to keep up and compete in the marketplace — and any OS-related red flags on compliance reports could cost you business.
  1. They don’t want to re-train their people yet. It’s not easy to teach people new things, especially when they’ve been doing tasks the same way for a long time and are busy doing their jobs. Postponing upgrading to Windows 10 means they get to postpone the pain that comes with re-training and the time it takes to acclimate. Remember: The sooner you know what’s involved in upgrading your network and apps, the sooner you can plan and start their training. Productive employees are happy employees who keep business flowing.
  1. They don’t have good lifecycle management processes in place. If developing strong lifecycle management procedures hasn’t been a priority, the task of planning an organization-wide OS update can be daunting – especially for fast-growing companies and companies with several locations. Remember: Taking the opportunity to get lifecycle management on track now will save you time, effort, and money – not only when transitioning to Windows 10 but for the long run. You will have to update every few years!
  1. They don’t think about the higher operational costs of not updating Windows 7. It costs money to update an OS so they rationalize that putting it off will save some money, at least for now. They think it will take a while to feel any ripple effects so why not save money in the meantime? Remember: Not only will keeping an outdated OS cost more in the long run, your employees will start using workarounds as software companies stop supporting Windows 7 in their new releases. Needing to quarantine unpatched machines to protect your network will slow down operations even more.
  1. They can’t decide on a strategy. Given the number of decisions and tasks involved, getting everyone on board with a single strategy can be a project in itself. Options can be confusing — devices to update or eliminate, apps to keep or move to the cloud, workers to assign or outsource — and have a slew of different price points. Different staff members have different ideas and priorities and different levels of urgency and risk tolerance, too. Even defining what is risky can be a point of contention. Remember: Aligning your IT strategy with your business strategy as soon as possible will keep your organization productive and help you win new business. An updated OS is key to business viability.
  1. They don’t care about security. Risk is not a big deal to some organizations. They’re more comfortable taking their chances than getting ahead of a problem. They’re not that concerned about hacking, bots, ransomware, or employees who fall for social engineering scams because they have backups and nothing bad has happened yet so what are the odds? Remember: Cybercriminals love low-hanging fruit. If they can exploit the holes left in your unpatched system, they will. Recovering from an IT disaster is harder than it sounds and staying at least as secure as the next guy can be what keeps you in business.

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How to budget for updating to Windows 10: a six-step plan

No company can afford to continue to maintain products forever and Microsoft is no exception. In fact, Microsoft is speeding up the product life cycle due to increasing security issues. It’s up to each organization to manage its own transition and keep its business securely on track. Here’s an outline for your team:

  1. Take inventory of what your organization needs to update.
    Develop a complete list of all devices and hardware running Windows 7, including the OS, Windows Server 2008, Microsoft apps (like some versions of Microsoft SQL and Microsoft Exchange), and other items.
  2. Confirm all of your apps will work with Windows 10.
    Test each app — chances are if it’s popular it will be Windows 10-compatible (Windows 10 has been out since July 2015) but be aware that some apps will not be compatible.
  3. Look at and evaluate cloud options.
    If you have apps that won’t work on Windows 10 or equipment that isn’t compatible with Windows 10 (or needs to be replaced soon anyway), look at what’s available as a service in the cloud. You could save money and other resources by ditching hardware and/or improve productivity as well.
  4. Do a risk assessment.
    Chances are you won’t be able to (or want to) update everything at the same time. Updating in phases is best to prevent disruption to your operations, so identify the risks related to migration in each area of your business.
  5. Create your budget based on risk.
    Figure out what percentage of your profit is associated with each of the risk areas you identified. You will want to allocate your IT dollars effectively and not outspend your risk.
  6. Prioritize the actions in your Windows 10 update plan.
    Cover the most likely risk scenarios first and the least likely ones last. If you can’t deal with certain risks before Windows 7 EOL, develop a risk treatment plan to minimize your exposure until you can update everything.

Leapfrog has been involved in countless OS migrations for our clients — that’s because we’ve been providing managed IT services since 1998 when Windows 95 and Windows NT4 were running. While migrations can be challenging, they’re much less so when you have a strong plan based on your business objectives and expert IT advice. You’ll get it done in risk-based priority order with as little productivity loss as possible. If you need help with your plan or allocating your Windows 10 migration budget effectively, please contact one of our representatives. We can do a network risk assessment to identify any computers, servers, and apps in your environment that are past their end of serviceable life.

And make sure to contact us soon! January 2020 is right around the corner.

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