We hoped things would return to normal, or at least stabilize around a “new normal,” after the pandemic. What we got is anything but. Continued supply chain disruptions, war, tariffs, inflation, disruptive new technologies, and an unstable global order have marked the post-pandemic era. Who could have predicted some of the events of the past few years? Unpredictable events aren’t all bad, but even “good” unpredictability can disrupt your business all the same if you’re not ready for it. For example, what if one of your products takes off unexpectedly, but you don’t have the capacity to meet the demand? You never know what’s just around the corner. If you can’t predict the future, then you should do the next best thing: build resilience into your business so you can adapt to any change, no matter how unexpected.

Strategic Foundation

The success of any business begins with strategy. Your strategy lays out who you are, what you do, and what makes you unique, and translates that unique selling point into a plan to reach a particular set of customers through actionable, measurable goals.

A strategy of resilience includes a growth mindset baked in at the level of strategy. People and organizations with a growth mindset understand that we can learn new things, master new concepts, and constantly grow and develop throughout our lives. Those with a fixed mindset, on the other hand, believe that they know what they know, they are who they are, and they can never change or grow. A growth mindset is adaptable, curious, and confident. A fixed mindset holds you back by telling you, “I can’t do that. That’s not me. That’s not how I work. I can’t learn something new. I have to stick to what I already know.” When a growth mindset is a part of your strategy, you will be ready to shift gears at a moment’s notice knowing you can learn and do whatever you have to in order to overcome any challenge.

Operational Resilience

Operations encompasses the production process, product development, process documentation, customer service, and everything that keeps your business running on a day-to-day basis, along with the technology your operations run on.

Successful operations departments are built on consistent and repeatable processes so that no matter who is completing the task, it can be done the same way, to the same standard. Process documentation is not something you can do once and forget about. The rapid changes in technology, the economy, and the workforce mean that processes must be continually improved. There should be a process in place for improving processes, as well, in which employees can suggest and test changes and then implement the most successful ones.

It’s hard to achieve operational excellence without the support of the right technology. But what do you do when that technology fails? This is where system redundancy and diversity have to be built into your operations. Do you have backups of your website? If your cloud storage service (Google Drive, Microsoft OneDrive, Dropbox) experiences an outage, how will you access your files? How will you process payments if PayPal goes down?

While these things don’t happen often, they do happen. In 2024, a bugged update to cybersecurity software CrowdStrike crashed over 8 million business and government computers running Windows, resulting in $10 billion in losses. 2025, meanwhile, saw web infrastructure provider Cloudflare suffer three major outages in a row in September, November, and December, outages that brought down services as diverse as LinkedIn, the graphic design platform Canva, and the multiplayer online video game Fortnite.

It's not just tech that needs redundancies. What will you do if a key piece of equipment breaks down or a key employee leaves? What if supply chain disruptions or changes to tariffs mean you no longer have access to a key supplier or manufacturer? Developing risk assessment and mitigation strategies lays the groundwork for a resilient business that is ready for these kinds of emergencies.

A growth mindset is key in operations. Sometimes, the only valid response to an unprecedented crisis is an unprecedented solution. A business built on a fixed mindset will say, “We can’t do that. It’s never been done before. I guess it’s over for us.” A business with a growth mindset will do what seems impossible while constantly monitoring and improving their processes as they sail uncharted waters.

Supportive Culture

Building a growth mindset into your strategy involves encouraging and providing opportunities for growth and learning in your employees. Just as you are constantly reviewing and improving your processes, your employees should be empowered to constantly improve their skills, becoming more knowledgeable, more confident, and more resilient along the way.

Culture goes beyond the office or shop floor. It encompasses all of your stakeholders and networks, from suppliers to customers. If you’ve built solid, mutually beneficial relationships with all of them, you’ll be able to help each other through times of stress and come out stronger on the other end.

Resilience is Foundational

In areas prone to earthquakes, old buildings have to undergo seismic retrofitting to make them more earthquake-resistant. One technique for making these buildings stronger is called “selective weakening,” a process that involves finding the most rigid parts of the building and making the building “weaker” by removing them. It seems counterintuitive, but when you’re facing something that can shake you to your foundations, rigidity and inflexibility is a weakness. To withstand earth-shaking economic and social changes, standing firm and fixed in place will only result in collapse. Being able to shift and wobble without toppling as the ground moves under you is how you not only survive but grow in an uncertain economy. 

Technology is always changing, and today it’s changing faster than ever. On top of the speed of change, it seems that new innovations are becoming more disruptive and more confusing than in the past. That speed can be anxiety-inducing, and with heightened anxiety comes decreased decision-making ability.

With all kinds of new software and tech products coming thick and fast, you need a framework for separating the ones that will work for you from the ones that don’t. A technology roadmap provides exactly that, giving you the bird’s eye view of your business that you need to take control and make sense of it all.

Planning Your Growth Road Trip

We’ve talked about the importance of the strategic roadmap before over on the StrategyWerx blog. You don’t want to take a road trip without first consulting a map. Maybe you’ve taken this trip before and you know the route by heart, but you still need to plan. You don’t know exactly how this trip is going to go. You don’t know how traffic patterns might have changed, if there is construction on the route, if a bridge or ferry is out of service, or if a new highway offering a quicker route has been built since you last made the trip.

A map also helps you consider the “best way” to get to your destination given the purpose of your trip. There is no “best way” in business strategy or in road trips, only the way that helps you achieve your goals. If it’s autumn and you want to see all of the pretty colors, then the best way is the most scenic route, even if it’s not the fastest. If you’re on a tight budget, the best way is the one that avoids the $15 turnpike and the $12 bridge toll. It’s all about knowing what you’re trying to achieve so you can make the decisions that are best for you, today and in the future.

Intentional Choices Informed by Strategy

A technology roadmap serves the same purpose. When you have a decision to make regarding the types of technology to integrate into your operations, it won’t help to simply seek out “the best,” because what’s best for a corporation with 20,000 employees and what’s best for a ten-person agency are two different things. Consider also your industry. What’s best for a city government, for instance, is not what’s best for a manufacturing enterprise, a lesson the city of Birmingham, UK, learned the hard way after a financially devastating failed ERP implementation, which we wrote about here. When you develop a technology roadmap, you’ll be able to put your business’s needs and goals first. You’ll better understand your business and your goals, and you’ll get a much clearer sense of the tech that will and won’t work for you.

Roadmaps aren’t just about where you are now, but where you want to be and how long you plan to take to get there. Your roadmap will also get you thinking about how a piece of technology will serve you in the future, whatever your growth goals. “The future” is a different thing for a company that plans to grow quickly and bring on dozens of new employees in the next year and for a company looking for slower, steadier organic growth.

For example, the spreadsheet you calculate budgets on might work for you today, but will it work for the accountant or CFO you eventually hire? You’ll need accounting software that can handle the intricacies of your business and can be easily shared among and edited by your team. And while you might be able to manually send out promotion emails to your mailing list today, is that method going to be scalable when you’re delivering personalized emails to segmented lists of thousands of customers? When you choose a new CRM to help automate those email tasks, how are you going to get employees to buy in and learn the software? How long will it take, and what resources can you devote to training?

A tech roadmap gives you clarity on these and other questions, giving you greater control over the technological aspects of your business’s growth. This is especially important in uncertain times. You’ll be better equipped to ask the right questions and choose technologies that can help you today, grow with you tomorrow, and keep you running smoothly over any potholes you might not have seen coming.

Find the Tech That’s Right for You

At ProsperWerx, we’re technology agnostic. That means we’re not here to get you to adopt a particular piece of software. We’re here to help you work through these strategic questions so you can see the big picture and help you find the technology that’s right for your business, both where you are now and where you want to be.

Recently, Forbes reported that hackers discovered an exploit in the code of Windows 10 and 11 as well as older versions of Windows Server that allows them to force a machine to open a URL with the less-secure Internet Explorer browser, which Microsoft has retired in favor of the safer Edge browser. The URL then gives the hackers control of the computer. As a result, the US government has warned Windows users to update their computers or stop using them. Vulnerabilities like this one are exposed and then patched by developers almost every day. Most users will remain safe if they update their software regularly.

If you’re using a legacy system, however, the developer may no longer be releasing updates, and your computers—and your business—will remain at risk. This kind of security exploit is just one of the many dangers of relying on legacy systems.

Sometimes, outdated software or hardware is so deeply entwined with your workflow that you can’t imagine working without it. Game of Thrones writer George R. R. Martin, for instance, still writes on WordStar, an MS-DOS word processing program first released in 1978. But when it comes to business applications, especially those that are cloud-based or connected to the internet, hanging onto a 40-year-old legacy system would do little more than keep an organization from reaching its potential. Stepping into the unknown comes with some risks, but with a clear strategy guiding the process, you can make your business more secure, efficient, and scalable.

What Is a Legacy System?

The term “legacy” denotes something with a long and storied history that has lost a bit of relevance. Legacy systems are those software applications or other technologies that have become obsolete, whether because the company has outgrown the tech’s usefulness or because newer tech can do what a legacy system does more efficiently. Legacy systems include outdated programs like Windows 7 or that Quickbooks program you’ve refused to update since 2014, the inventory management system you so proudly wrote in Filemaker Pro in 2011, websites still running on the long-since-abandoned Adobe Flash, and mainframe systems that nobody under the age of 73 knows how to support any longer.

The Dangers of Relying on Legacy Systems

Replacing legacy systems isn’t just about being on the cutting edge for the sake of it. Relying on outdated technology can pose a real threat to your business. First of all, old systems may no longer be supported by their developers, who prefer to put their resources into supporting their latest applications. If a piece of software is no longer supported, that means the developers are not releasing new updates to fix bugs or security workarounds known to hackers. This means that if you have a problem with the tech, you might not be able to get help for it. More importantly, company data and private customer information could be at risk.

Compatibility with newer technology is another issue you face with outdated programs. When you update to the newest version of your operating system, for example, you might find that the program designed for a twenty-year-old operating system no longer works correctly, if at all. If an unsupported program is the centerpiece of your tech stack, you might find that it does not support the ecommerce integrations or marketing automations so vital to the modern business.

Finally, old systems could simply be slowing you down. They might take forever to boot up, they might have unintuitive interfaces that take minutes rather than seconds to navigate, or they might be prone to crashing. All of these minor inconveniences add up over the course of months.

When Is It Time to Modernize?

If the above dangers seem all too familiar to you, it might be time to modernize your tech stack. It’s possible that you haven’t run into any issues relying on an ancient program, but with tech that is no longer supported, it’s less a question of “if” than “when” you will run into security or compliance issues.

An old system that you’ve been using for ages and know well is fine if you’re a one-person operation with just a handful of customers. But if you have any desire to grow, it’s better to start modernizing now. No matter the application, there is tech out there that can grow with you, especially today in this era of software as a service, where developers offer various tiers of service with features designed for businesses of different sizes.

Planning Your Modernization Strategy

Adopting a new technology is a major change for a business. Getting it right often requires working closely with vendors and experienced consultants who know what can go wrong and how to prevent it. Every company’s modernization strategy will look different, based as it is in each company’s industry, size, and growth goals, but there are a few broad steps most businesses will take when upgrading legacy systems.

If you want to know more about choosing the right technology solutions for your business, check out this article. 

Analyze Your Tech Stack

The first step is to evaluate your current systems according to the guidance above. Are you facing any of the dangers associated with legacy systems? If so, then it’s time to look for an upgrade.

When evaluating any new software, analyze it in terms of your current tech stack and your overall business strategy. You’ll want a system that can scale with you, that is affordable, and is within the capabilities of your staff. There are also regulatory and compliance issues to consider, depending on your industry. You can find a more in-depth guide to choosing the right technology here.

Evaluate Your Approach

You might find that you need to rebuild your tech stack from the ground up, or it may be the case that just a single part of it is outdated. However many systems need to be replaced, consider how the new tech will integrate with what you’ve decided to keep. If you are replacing several systems, there may be a single piece of software that can do what used to require multiple, separate applications.

Make an Implementation Plan

With your IT team, determine if it would be better to slowly phase out a legacy system piece by piece or all at once. Whether your plan is to modernize gradually or swiftly, you’ll need a data migration plan that will move your data securely and cleanly (that is, without errors) from the old system to the new one.

Provide Ongoing Training and Support

Your new system might not be running perfectly from day one. People need time to learn the software and acclimate to new workflows. Make this transitional period as smooth as possible by working with developers who provide all the documentation and support you’ll need.

Get the Right Help

Updating legacy systems is time-consuming but necessary for both keeping your systems secure and your business running efficiently. Avoid the common pitfalls and the often overwhelming decision-making process by working with people who have experience in implementation and expert knowledge in all manner of business software. ProsperWerx is here to help you get a handle on the tech that supports your business so you can get back to doing the work you love.

What is the best movie? The question is fodder for a passionately argued debate, the kind you might hope to avoid getting dragged into at a party, and the answer is entirely dependent on who you are asking. What are your criteria for “best”? A gripping plot, emotionally resonant acting, cutting-edge special effects, or artistic cinematography—or all of the above? Do you want to experience profound emotions and plumb the depths of your soul, or do you want to escape life and feel good for two hours?

It doesn’t take long to realize that “What is the best movie?” is the wrong question. It’s too subjective, requiring too much context. Perhaps instead we should ask, “What is the best movie for me?”

The same goes for technology solutions. That’s why we’re a technology-agnostic company. We’re not here to get you to adopt what we like to use, or what we think is “best” overall according to our own predetermined criteria. That’s because there’s no “best.” There is, however, a “best for you.”

A number of factors will influence what “the best” technology solutions are for your company: your industry, the number of employees who will be using the software, your current tech stack, the time you have to learn something new, and your budget, just to name a few. Whether you’re looking for CRM, ERP, or POS, making the right decision is about asking the right questions. Here are some questions to consider when choosing a new technology solution.

Does It Meet Your Needs?

Before you can answer this question, you have to have a clear idea of your business goals and your strategy for achieving them. Clearly articulated needs and goals make it possible to determine whether or not a technology solution meets your needs and will help achieve your goals.

Your strategic goals include your growth goals, so be sure to consider what you need now and what you will need in the future when choosing any tech solution. One solution might be full of features you don’t need now, but you might need them in the future. Another solution might look perfect for where your business is today but lacks the ability to scale up as you grow.

Does It Integrate With Your Tech Stack?

While it’s easier than ever to get different software to play nice together, you still have to consider any new software’s place in your tech stack. How will it communicate with other software? In which direction does the data flow? How easy will it be to move my offline spreadsheets into this new system? Also think about what your current tech stack is capable of and what a new solution adds to what you already have.

How Secure Is It?

You lock up your office or warehouse at the end of the day, install security cameras, and hire security. Cybersecurity is equally important to keep both business data and customer data out of the hands of criminals. Make sure your software uses two-factor authentication (2FA) for logging in, and ask developers about how often they release updates and how quickly they respond to bugs and security threats. 

2FA means that in addition to entering a password, users have to respond to login requests at a second access point, such as their phone. That way, even if someone steals your password, they won’t be able to access the program or app because the login code will be sent to your phone. There are ways around 2FA, but they are extremely rare cases, such as your phone being stolen or cloned. Hackers can clone your phone by stealing its unique identification code via unsecured public wifi (i.e. airport wifi). Again, this is an extremely rare case, so 2FA should be sufficiently secure.

In addition to login security, inquire about update frequency. Frequent updates help guard against both hackers and bugs. Bugs in critical software can cost your business money, so it’s important that any company you work with is quick to issue updates that patch bugs out. Look into other users’ experience with the software: is the company slow to respond to security weaknesses and bugs? If so, you might want to look elsewhere.

What’s the Learning Curve?

Every piece of software has a learning curve, some steeper than others. Realistically, how much time can you spend learning the new software? It might take an hour or it might take months for your team to feel like they are experts. It’s important to evaluate how much time you can give over to learning and fully integrating the system into your operations.

This is not to say that you should avoid software with a steep learning curve. If the right technology for you is something that will take time to learn, losing a little efficiency in the short term as everyone gets up to speed might be worth a big increase in efficiency in the future.

Will You Be Supported?

Availability of technical support, especially during the crucial implementation stage, is another factor to consider. Technical support should be there if something goes wrong, but you also want someone who can help you learn how to use the software and get the most out of its features. Good technical support requires both knowledge of the technology and the ability to teach it.

ProsperWerx Helps You Find Answers

Though they might lie outside of your area of expertise, these are some of the most important questions you will have to answer as a business owner. Our team of experts in technology implementation, integration, and administration is here to walk you through these decisions so you can spend more time on the business you’re passionate about and less time worrying about the technology behind your business.