We have all been there, we just finished upgrading our systems and software, and now we are being told it is time to do it again.  The question is, when does it stop?  Will I ever be able to stop upgrading? Upgrades are here to stay, but it is all in the value proposition when to upgrade and how often. Upgrades are driven by customer demands for new features and functionality, increased reporting functions, business intelligence enhancements, compliance issues, or compatibility with third-party applications. Since upgrades are here to stay, it is best not to regard them as negative or a nuisance but rather manage them, so the timing and the return on investment are worth the aggravation.


What is driving the dislike or fear of upgrading? The most significant reaction to upgrading is the unexpected changes in the look and feel of the software. Software developers sometimes make you feel the only reason for the changes is to make things harder or force a work process change internally. That is typically not the case, but customer feedback on how they use the software in the real world often dictates work process changes within the software. Another topic that often comes up is the time it takes to roll out the upgrade. We have all had implementations that took longer than expected, and it can be challenging to explain and support the reasons for those delays. Disruptions to the users are essential when planning the upgrade, and it is vital to publicize the positive aspects requiring the upgrade.


Change is bad because of habit; regardless of whether it is a good habit or a bad habit, words like change, new, different all strike fear into users and organizations because of the unknown.  Your staff has spent a considerable amount of time coming up with workarounds, short cuts, or spreadsheets to account for software shortcomings. The upgrade may cause those workarounds to become irrelevant or stop working altogether; however, the changes maybe for the better in some cases. It is essential that when upgrades happen, whether it is software or hardware, management understands there will be complaints and hesitations. In some cases, some employees' refusals regarding these changes, and it falls to them to be a positive voice in the chaos.


Replacing the panic or stress around upgrades with excitement can be challenging. Still, you have to remember that your company is one of many. Is it possible that the mass found a better, more streamlined way to do something or improve your business process besides the created workaround?  An important pre-upgrade planning step could be to work with your software vendor to see what information about the new system is available. Better yet, are there videos available to ease the upgrade's stress.  When employees see the improvements, they may decide that it will have little to no impact on them, or it might be a significant improvement over what they are doing now; either way, the stress and the unknown are going to have less of an impact.


Performing routine upgrades is essential; from a hardware perspective, there are new and faster CPUs, faster hard drives, and increased process power through additional processors. However, the most significant hardware upgrades driver is the software and the software's needs to operate on the hardware platform properly. Another primary driver for hardware upgrades is the age of your hardware; at some point, you could face a lack of warranty coverage or the lack of available parts. However, these can provide the end-users a more robust and reliable working environment, especially during 2020, when companies have increased employees working from home or are mobile.  New hardware or infrastructure can allow you to take advantage of new technologies that would not support the older hardware platforms. However, they might create compatibility issues with older software resulting in an unstable work environment. These upgrades could also open up the opportunity to take advantage of new and more reliable mobile technologies or software integration to have a more efficient work process and increase user productivity.


From the perspective of the technologist, it is critically essential to upgrade due to security reasons. The longer that an operating system is on the market, the more the weaknesses become known. The more those weaknesses are documented and made publicly known, the more they will be exploited by hackers, Malware, or other viruses. Ensuring that patch management is in place is critical to network security; routine patching is one of the best security measures you can take.  Software manufacturers don't release patches, hotfixes, or other upgrades because the software is perfect; they do it because the mass of users reports bugs, security holes, or other shortcomings within the software that have been discovered and need to be corrected. Improper patching or not performing routine software maintenance could create compatibility issues or leave security vulnerabilities exposed. Due to a lack of adequately upgrading, you could be missing out on the software's framework upgrade or the software developer's back-end code changes, which could contribute to poor software performance or security issues.  These framework and integration issues can extend to third-party applications or custom software; most manufacturers have a methodology for integrating their software with other software, not to create security leaks. However, most major software applications don’t typically consider custom applications or third-party apps when releasing a new version.  This incompatibility can create security issues or errors in one or both of the applications.


Before you start an upgrade, what are some of the checklist items you should consider?  Some software vendors want to do any upgrades themselves, which could be an excellent option for you because then the vendor is responsible for the upgrade's success.  Others will leave it up to paid consultants; others will allow your internal staff to perform the upgrade. However, this might be an area that would be money wisely spent to have a consultant perform the upgrade. These options have pros and cons, but you need to follow a process regardless of who is applying the upgrade. According to eLearning Industry, here are some of the steps you should follow to make sure you have covered before you start any application or operating system upgrade.


  • Publicize your intention to upgrade, engage ownership, end-users, trainers, administrators, other software vendors. This communication will allow you to work through any compatibility issues, discuss how the upgrade will affect them, and what might be required, such as testing and reporting issues.


  • Pick a change control planning team, and technical issues are only part of the issues that might arise during an application upgrade. Typically, the most significant gap in this process is communication to the people who are not directly involved in the process, creating many public relations issues on the upgrade's backside. There are often third-party consultants or developers who need to be in the loop on the upgrade's timing and testing.


  • Site and software review, doing a review, can document and track any customizations within the software or other applications that push or pull data from the software that will be upgraded—ensuring that you have everything documented. The specifications of hardware and software settings open a door of retreat if the upgrade goes sideways. The documentation will also allow any integrated third-party applications or hosted applications to connect and be tested entirely following the upgrade process properly.


  • Develop an upgrade plan and a roll-out plan; who is going to do the upgrade? Are you just upgrading one application, or are there other applications or add-ons that need to be upgraded at the same time? Does your current hardware and operating systems support the software upgrade? Then there is the timeline, when, how long, and what human resources you need to test the upgrade and any integrated software?  If the upgrade will require upgrading the workstations. Who is performing that task?  Are these upgrades something that can be pushed from the server?  Who is communicating with the end-users, and what the upgrade means to them?


  • Backup, I can't say it enough to backup your systems, software, and data. Unless you have the system capacity to ultimately build a new system and run the new and old in parallel, your only saving grace will be your backup. Don't just do a backup, but do a test restore; make sure that the backup is usable and there are no issues that will come back to bite you later.


When upgrading hardware, regardless of your servers, workstations, or even your phone system, there are some basic housekeeping tasks.  Completing these tasks will make things easier for you and remove some of the risks from the upgrade.  Uninstall any unnecessary software, we all download the app that looks cool, or we load test software, or we still have software that was in use for years but has been discontinued. It might be time to remove that software from the system, or at least from the production system unless you are keeping it for historical reasons. There are reasons that you might want to keep this software or databases around but move them to a separate system that operates independently of your production system. By isolating old software and operating systems, it will protect the historical data integrity and not compromise your production security or slow down the production system.


Scan your system for viruses, Malware, crypto, and ransomware, or other viruses. The last thing you need is to have a ransomware virus execute in the middle of your software or hardware upgrade, which will make a long night even longer and more frustrating.  If the inevitable happens, your backup could save you, so make sure you have a well-tested backup. Viruses now have become very intelligent and, in some cases, are more destructive now than ever before and can be triggered through events, so they will hide on your network and wait for a specific condition to exist, then they activate and spread.


Defragment your system, or do general disk management to ensure that you do not have a hard drive in the process of failing or compromising the upgrade process.  It is much easier to make sure that your system is in good shape before you upgrade.  I know that sounds contradictory to why you are upgrading, but systems in good health stand a higher chance of being in good health following the upgrade.


Another housekeeping item is cleaning up your users and active directory. Everyone faces staff changes, client cancellations, or adding or removing printers and copiers; sometimes, little things can become big things if not correctly address before the upgrade. However, cleaning up your active directory by removing old users helps in your security initiatives. Still, it also reduces the risk of corruption creeping into your active directory during an upgrade. This clean up might also include your Exchange server; removing old mailboxes and archiving old mail helps in the Exchange server's performance. Still, it also reduces the migration time if you are upgrading Exchange. Another area to focus on, especially if you have software applications that manage their own internal security, is to clean up those users and remove any users from those applications; this would include Office 365 if you are an Office 365 company.


During upgrade process is also an excellent time to harden your security throughout your network and server farms. Consider adding additional security devices such as DarkTrace, or Bandura Threat Intelligence Gateway to monitor and block internal and external internet threats. It is also an excellent time to run in-depth security scans. These in-depth scans will ensure that you don't have any unknown gaps in your security following the upgrade. The industry is starting to change its position on passwords and how often you should change them. It might be a good time to review passwords, force some password changes, or implement Multi-Factor Authentication, don’t forget about those service accounts.  I know what you are thinking; why would I want to add this on top of an extensive system or software upgrade?  Depending on the scope of your upgrade and the systems impacted, you may not want to, but the system will be offline anyway, so it is merely something to consider. However, worse case, you should run in-depth scans of your system to make sure the ship is tight and secure.


Now that we have discussed the role that computer system upgrades play within your business let’s talk about budgeting. Within small businesses, system upgrades are not part of the budgeting process; reoccurring technology charges might include copier leases, phone system leases, or hosted applications; however, system upgrades are evaluated and approved individually. Computers are now an intragyral part of your business, in today's competitive and data on-demand world, how would your business do without your computers? With that said, what percentage of your total revenue should go towards IT, systems, support, hosting, applications, copiers, phones, and the list goes on and on?  There are all kinds of surveys and suggestions around this question, but the real answer is, it depends on your reliance on technology, which, let us face it, increases every year. When you look at it that way, companies with a low reliance on technology could expect to spend 2% to 5%.  Businesses with a medium reliance on technology could expect to spend 2% to 6% on technology needs. However, companies with a high reliance on technology could spend 5% to 7% on technology. These guidelines don’t mean to be wasteful; you have to be smart and focused on what you are spending technology on and when, but be honest with yourself, and less is not always better. Still, neither is a lot, so these numbers are just a guideline but manage your expectations with what you are willing to invest in your business growth and reliance on technology.


When it comes to technology budgeting, it is crucial to categorize your needs, and this could be a long list.  However, I try to break it down into three major categories and then subcategorize under those significant categories.


  • Budgetary Items, these are reoccurring budget items, copier leases, payroll, consultants, end-user support, and software maintenance charges, as some examples. Still, these are the technology items you have to have to run your business, combined with fixed charges.


  • Growth Items, growth items are typically less critical than budgetary items. These are items that you need to improve work processes, streamline workflow, and improve efficiencies. These could be items such as add-ons to current software to increase data flow, reporting, or business analytics.


  • Transformational items, which could primarily focus on research and development issues, could include changing core software, increasing security, developing a new website or customer portal, and part of your longer-term business strategy.


However, when it comes to IT budgeting, ensure that those budget items are connected to business goals and objectives.  IT managers increase their budget needs beyond what they need, without tying that money to a specific business directive or need. In some cases, this can take money away from other areas of your business that have needs that should be addressed and improve your business. Having an IT audit that could drive a strategic plan related to your technology needs could give you invaluable insight into your actual needs, so you can focus on the areas that need to have money budgeted.  Having done hundreds of IT audits and strategic plans, it is sometimes interesting to find what IT managers are spending time and money on, with no to little business impact expectations. The basic rule of thumb is that the business should drive the technology needs, not IT driving the business. IT is a supporting and enabling role, which should drive the business forward by implementing relevant technology resources.


Through all of this, let’s not forget about the human factor. The goal of IT should be to empower your people to do more, solve problems, increase data flow, and streamline work processes. In some cases, this might feel like a hampering process because employees want to get their job done and go home, but with every job, there is paperwork, but make that streamline and put them in a position only to do it once. Soft cost dollars lost through ineffective software, work process, or documentation delays could be costing you money and creating moral issues within your staff. This brings us back to upgrading software and hardware; this entire process is an evolutionary process. With every new upgrade, speed improves, workflow improves, and the power of new technologies can drive your business to new highs.  However, although it feels comfortable, not upgrading can be hurting your business, and catching up is always more expensive.

By Scott M. Lewis, President / CEO Winning Technologies, Inc.

About the Author: Scott Lewis is the President and CEO of Winning Technologies Group of Companies, which includes Liberty One Software.  Scott has more than 36 years of experience in the technology industry and is a nationally recognized speaker and author on technology subjects. Scott has worked with hundreds of large and small businesses to empower them to use technology to improve work processes, increase productivity, and reduce costs. Scott has designed thousands of systems for large, medium, and small companies, and Winning Technologies' goal is to work with companies on the selection, implementation, management, and support of technology resources. Learn more about Winning Technologies by calling 877-379-8279. To learn more about Business Manager 365, visit businessmanager365.com.