Updated: Jul 2, 2021
In big law they hire an in-house director of technology whose job it is to source, evaluate, and implement the software for the firm and teach the firm's lawyers how to use it. As a solo lawyer you obviously can't afford that. There is the option to hire a legal-tech consultant to show you the different software options and suggest some that might work for you, but sometimes you just want to look for yourself. I mean... a google search is not that hard to do. Here are some tips:
1) Ask ASAP whether they have a pricing option suitable for solo lawyers: Some software providers (often the ones who don't list their price on their website) target specifically big law and set their prices so only they can afford it. Neither the sales person nor you want to waste your time if you are looking for software that is less than <$1000/month, so ask their chatbot on their website or call them and say "does your pricing cater to solo lawyers/small law firms"? Whether there is a free-trial on their website is also a good indication of what size of law firms they serve. If they have a free-trial they probably have pricing realistic for solo lawyers. Software providers that want to 'weed' out people who can't afford their software and just focus on a smaller number of well paying clients (i.e. enterprise sales) will remove their free-trial from their site and only offer access to it to clients after they have a demo call with them.
2) Use the following sites to browse legal software:
a) https://legaltechnologyhub.com/: Legaltech Hub Database and links to all the legal software companies available across the world.
Pros: Free and there are a LOT of companies listed on this site so if you like discovering new legal-tech companies you will have fun. Cons: Not efficient way to compare between providers. Must visit each site individually. Includes all vendors whether they serve small law firms or big law.
b) https://www.lumosemarketplace.com/: Lumose Marketplace
Centralized hub for solo lawyers to compare legal software using unbiased reviews from other lawyers.
Pros: Free. Only includes software suitable for small law firms. Easy side by side comparison of features/price/customer service without having visit each website URL, a.k.a. efficient. The reviews from other lawyers are especially useful because they are unbiased.
Cons: Only lists companies that are available in North America. You have to fill in form to get access to their marketplace.
c) https://techindex.law.stanford.edu/: CodeX Tech Index
Explore a curated list of 173 companies changing the way legal is done.
Pros: Free. Great categorization of legal software. Cons: Too many companies to sort through. Some companies are very early stage and not all companies specifically target the legal industry.
3) Ask other lawyers AND. The point here is that you want the opinion of other lawyers on whether they like a specific software (one that they use), but NOT on the overall decision of what software to invest in. This is because most lawyers don't know about the best software that exists unless they have heavily researched the space. There is software that can draft a good quality memo answering legal research questions for example that 99% of lawyers have not heard of. If you ONLY take the opinion of the lawyer you worked with previously, you will end up using only old, outdated software which means overpaying for software that takes a long time to learn how to use. However, and this applies especially to trust accounting software, asking your lawyer friends "have you ever actually used X software and if so what did you think of it?". But you should do more research over and above getting opinions from other lawyers because they likely only see the very top of the iceberg of the software they could be using to generate additional revenue while working the same amount of hours.
4) Ask your paralegal to book demos, attend them, and record them. While most sales people conducting demos would prefer it to be with the lawyer (because they are usually the decision maker), demos are not a good use of a lawyer's time, and you should attend more than one before settling on that software provider. Your paralegal should be your filter. They should book and attend about 4 demos and ask to record them to show others in the firm. If you have any other friends who are lawyers looking for software you can also ask them to record it for you. If the software provider has a problem with you recording it, try framing it as you want to tell your lawyer friends about their software. You can also sign up to a marketplace like Lumose (https://www.lumosemarketplace.com/) where there are short videos of what each software does all in one place without having to book a demo, or you can usually find a short video of what the software does on the software provider's website.