How to choose the right software for your business

By Catherine Pope

July 1, 2020

Even if you have a horror of technology, you’ve probably needed to swallow hard over the last few months. Many of us have shifted our businesses at least partially online, which has meant getting to grips with new software.  Although I’m very geeky, I don’t enjoy the process of choosing which software to use. This is especially annoying if the software is expensive - there’s a double cost of the time invested in learning it and the financial outlay.

In this post, I’ll share my 5 questions for choosing software.

1. Who developed it?

It’s always worth have a poke about on the website and clicking the ‘About Us’ page. If it’s just a stock image of an unfeasibly wholesome team, then look a bit further. Is this product part of a larger corporation? Do you have ethical objections to that corporation? Or do they have a bad reputation for customer support? You can also dig around to see what you can find out about the people involved. Is this a Silicon Valley rockstar with a proven track record of building a business, then blowing it up?

Big isn’t always best, either. Google are a menace for introducing new products with much fanfare, then dropping them (with slightly less fanfare) a couple of years later. I’m still smarting over the loss of Google Reader and their bookmarking tool. For Google, these products were just tiny specks on their business plan and there’s no long-term commitment. 

If a company makes just one product, they’re much more likely to keep it going - it’s their entire business, rather than only a part of it. This is why Evernote - a notetaking app - has been going for 20 years. While that might make a good choice over Google Keep, consider the next question …

2. How long has it been established?

The Lindy Effect is a theory that the life expectancy of a technology is proportional to its current age, i.e. every additional year of survival lowers its mortality rate. This isn’t always a helpful theory with software, though. If a solution has been around a long time, it’s certainly popular. However, are the developers going to move with the times? Big software companies struggle to adapt quickly and can get left behind. Evernote are currently in this position, with energetic startups like Notion and Roam biting at their ankles. Although Evernote have identified the need to modernise their software, they seem unable to actually realise this vision fast enough.

Conversely, though, you need to be wary of the Latest Big Thing. If a company is  less than a couple of years old, they’re probably still operating on initial funding and haven’t had to make their business financially viable. If they’ve passed this milestone, there’s a good chance they’re either generating a decent revenue or have won the endorsement of long-term financial support.

3. How is it funded?

Everyone knows by now that if you’re not paying for a product, you are the product. What value do you place on the privacy of your data? How much influence do you have over the future development of free software? And if the software is looking to move to a paid model in future, how much will it cost? You don’t want to invest your time in using something that you can’t afford next year. You should also watch out for the length of contract you’re committing to. Adobe are especially weasily with free trials and discounts which then lock you into a whole year at the full whack.

If you have the money, it’s always a good idea to pay for software, even if there’s a free option. You’re voting with your dollars to ensure the developers survive and it always helps them defeat some of the big players with their sharp practices.

Some apps, such as Notion, keep their products free or cheap for individual customers by charging a lot more to huge corporate clients. While this is seems like a win-win, it might mean they end up primarily serving the needs of those big beasts and perhaps not innovating as much. Generally, the smaller the userbase, the nimbler the developers.

4. How well is it supported?

Fortunately for us, customer service is an increasingly visible activity these days. Reviews on Trustpilot, for instance, will give you an idea as to the responsiveness of the developers. Of course, people who write reviews are often motivated by pique, but a high volume of complaints suggests something’s amiss, especially when they repeatedly use the word ‘pirates’.

If you’re buying very expensive software, is there a phone number you can call? Have a look on the website to see if you can fathom how quickly they respond to support tickets. Do they just use those pesky chatbots where you have to ask exactly the right question to yield a link to a half-arsed FAQ?

Even if the customer service isn’t top notch, perhaps there’s a helpful user community. 

5. Does it do what I need?

This question also relies on knowing what you need. If we’re stressed and need a solution quickly, we can assume that the product on offer will meet our requirements. It’s easy to make assumptions, such as “well, of course it’ll do X …”. Make a list of your absolute needs and check them systematically - contacting the developers, if necessary (this is also a good early test of their responsiveness). Word of mouth and fancy marketing can seduce us into thinking we should use a hot new app, even if it’s not yet fully formed.

For instance, if you’re looking for a webinar solution, do you need breakout rooms? The ability to accept payments? A replay feature? Maybe it doesn’t do everything, but is compatible with services such as Zapier which links apps together. How long will it take you to learn the interface? Is there a more basic product that does the job and will get you online faster?

Where possible, sign up for a free trial, making sure you've got time to really put the software through its paces. And if they've insisted on taking your credit card details, set a reminder to cancel before the first payment is snatched.

You can also ask whether the software does stuff you don't need. Are you paying for lots of extra features that look good but, realistically, you'll never have the time or the need to actually use them. Bundle deals like Adobe's Creative Cloud are only good value if you use multiple products.

The overarching question, especially for expensive software, is “Will this really make my life easier?” If so, it’s worth investing your time and money. Good software is an investment, as you’ll get a return in the form of increased productivity and hopefully profit. It can be like having another member on your team.

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