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11 questions to ask when switching software

Last updated on 
January 18, 2021

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Riding on the back of the pandemic, 2020 was a year marked by rapid remote tech adoption. Adjusting to an overnight shift to remote work, businesses had to embrace digital transformation at an unprecedented rate. As we move into 2021, the importance of harnessing the right tech will only increase. According to Forrester Predictions, “2021 will be the year that every company doubles down on technology-fueled experiences, operations, products, and ecosystems.” But as well as adopting new tech, we need to consider the value of the stack we’re already sitting on.

Keeping vs switching software

As Forrester outlined in their 2021 predictions, the value of an organization hinges on how “resilient, creative, and adaptive you are in jumping to the next growth curve in your industry”. But of course, 2020 was also a year of economic crisis – so as much as companies will need to invest in new tech, not all of them will have the budget to do so.

What this means is that companies will also need to take full advantage of the tech they already have. It may be that they don’t fully realize the value of their existing software – in which case, switching software may not help. To help navigate the process, here are 11 key questions you should ask when switching to a new tool.

🙌🏽 Cultural fit

1. How does the new technology fit in with your wider business objectives?

This year, we’ve moved to a more human-centric way of working, and this is reflected in the tools we use. Now, we shouldn’t only take into consideration whether a tool is useful, we should also look into how it feeds into our business’ ethos, culture and objectives. That can be anything from software that automates unproductive work, improves compliance and boosts employee wellness, to tools that reduce remote work friction, simplify business-wide communication and support insight-driven decision making.

2. Does the tool benefit end-users?  

As the first question highlights, the right software won’t just “do the job” – it will directly improve the professional experience. For example, automating low-value work doesn’t only rid an employee of an annoying task; it also frees up more time so they can work on the tasks that are truly important to them, and allows employees to find a deeper meaning in their work. Many tools promising simple solutions actually end up introducing more daily admin into team workflows, so before investing in new tech ask yourself if will actually make employees’ days easier.

3. Does the tool protect employee privacy, or endanger it?

Another one of Forrester’s predictions is that in 2021, regulatory and legal activity regarding employee privacy will double. Breaching employee privacy is one of the quickest ways to destroy trust and company culture, which means extra care will need to be taken when choosing software. Companies should look for tools taking a “privacy by design” approach, and any new software will need to be compliant with your security regulations. You’ll also need to carefully assess how data is processed, secured and handled.

💡 Clarifying value

4. What’s wrong with your current solution?

To avoid software sprawl, you should also carefully consider what you believe your current software is lacking and establish key buying criteria for a new tool. To avoid being drawn in by pointless features, factor in what you don't need your new software to do.

5. What makes this tool different from your current solution?

It’s also important to consider whether the features of this new tool are worthy of upgrading from your current solution. Is it really a considerable step up, or is it essentially just a slightly more polished tool than the one you’re using now? If you decide to purchase it, what are you paying for that you didn’t have before?

6. What evidence is there of ROI?

It’s easy to check out software websites and be impressed with everything they say – but don’t just take a company’s spiel at face value. Instead, check out case studies, statistics, and reviews on third-party sites like G2 to determine whether investing in the software is really going to deliver a return.

💰 Long-term investment

7. Can the tool flex with you as your needs change?

During a time of rapid tech advancement and organizational change, you need to be sure that purchasing new software will be a long-term investment. Look into how much will it cost to add more people down the line – as well as the ease of scaling them back – and beware of expensive licensing restrictions.

8. How regularly is the software updated?

The whole point of moving software is to make things easier for yourself. Regular updates and development are an assurance of quality, so before buying any new tools look into how often new features and bug fixes are released. Will updates be automatic, or will they require time and effort from you? Is there a feature roadmap you can access? If new features are introduced down the line, will you be able to take advantage of them, or will they require spending more.

9. How will using the tool impact end-users?

It’s important to keep reminding yourself that tools exist to make life easier and the work process more enjoyable. So before committing to any new tech, consider whether it’s actually as smart as it says it is. For example, is it easy to use and intuitive, or will it create extra daily admin? To ensure buy-in, always trial new software with power users and involve them in the decision-making process.

💪🏿 Initial effort

10. How long will onboarding take?

In the same vein, if new software will take months to figure out and get used to, it’s probably not worth it. Find out what training materials are available, and whether you’ll have a dedicated account executive helping you set up. Investing in expensive new software only to find that most people can’t use it the way it’s intended is a huge waste of time and money.

11. Does the new tool integrate with your existing workflow?

In this day and age, any new software you use should seamlessly integrate with your existing workflow. Check whether your new software will be easily integrate with your existing tech infrastructure, or require hefty customization work to parse information with different tools. When the latter isn’t avoidable, make sure the output of your tool justifies the additional effort.

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