Business software is a big deal. Switching (that is, moving your data from one platform to another platform,) is a very big deal. It takes time, is rarely 100% accurate, and might come with a fee. Better that you should spend some time in the magical world of Free Trials before you end up with a system that hates you as much as you hate it. Watch the videos. Go on webinars and ask questions. Talk to your peers. (And your CPA.) Over these next few posts, I’ll discuss the various tasks you should consider finding software for.

But first, I’ll share my criteria for evaluating software.

Pretty much all the good stuff is in the cloud these days. This allows the developers to update and refine things more easily. Of course, this means they get to charge you for it over and over again… While most apps for business purposes can be purchased directly by the end user, check for discounts. Some things can be a little cheaper if you buy it through the software’s partner program (that is, someone who’s passed the certification for that particular software.) Some are cheaper if you pay a year at a time instead of monthly. Some accountants and bookkeepers package multiple apps into a really good deal. (We do!) So, first of all, look for the best deal.

Next, make sure it integrates smoothly with all the other things you are using. This is a very fluid area. Products are changing and making new alliances all the time.

Be careful about overlap and peripheral tasks. Some apps are going nuts adding new but unessential features that don’t really work all that well, and effectively make the initial product sort of clunky.

Make sure there is a help desk that speaks your language. As easy as these apps may be, problems nonetheless crop up, and it’s good to be able to call for help.

Finally, I expect software to be easy to use. If the software expects you to purchase a pile of training hours when you sign up, or it encourages you to attend the annual user conference where everyone gets together to share tips and tricks and learn all the new stuff, then maybe the software is a little too complicated. In this day and age, software should have plenty of free (F – R – E – E) videos easily available online. Nobody plows through user manuals anymore.

This brings me to a caution about bookkeeping software. If you think you can just enter a unique username and get to work, you are a fool. And if you think you can just take a class and immediately do it yourself, you have been deluded. Look at it this way: any software program that offers a class for 6 or 8 hours (or 2 days) to teach “the basics” has to be more involved than you have patience for. When I teach software, I spread it over a couple months, and only reveal something new after my students have had time to master the previous lesson. I want you to be good at doing it, not just intellectually aware that certain stuff can be done…somehow.

Yes, you’ll probably manage to enter some data, and you will undoubtedly figure out how to print the checks to pay your bills. But these programs are very B-I-G, and they provide so many ways to get it wrong. It pains me to see diligent entrepreneurs faithfully relying on numbers that actually make no sense. Please don’t get in over your head. Consider this: surely you are better at what you do than I might be, and my project would be handled and completed so much more efficiently and reliably when I hire you than if I insist on doing it myself. Nuff said.