Business departments, teams or individuals work with software daily to do their work. Picking the right software can be the difference between being successful, struggle or even fail.
My experience showed me that even if you are an expert in your domain, it doesn't mean you know how to choose the right software for you to work with.
The first thing to realize is that you don't just choose the software you work with, you also choose the company that stands behind it. This are not necessarily the same thing and I will soon explain.
When choosing a software to work with, I recommend looking at 3 main factors: Technology, Commercials and Culture.
Technology - This is the most trivial factor. How does this software answer the needs I have. How much of these are must-haves vs. nice-to-have? An important point to remember here is to look into the product's Roadmap. When you choose a product you usually want to use it for a while and you want to make sure that it has a relevant and innovative roadmap.
Commercials - Another clear factor. How much does this product cost and is it in my budget? On top of additional considerations like payment terms, an important consideration to remember is the cost of growth. Everything might fit the budget today but what happens if you need to grow the license (users or features for example), you don't want to be surprised by the terms then.
Culture - This is the least looked at factor and to me it is a very important one. This is also where the difference between the product itself and the company that stands behind it, becomes clear and key. When you work with a product, in many cases you will need the help of the company behind it. Whether it is their support in case of issues or advise to answer a question. Ask yourself how this company's support looks like? How easy it is to get help, and how much would they try to help me? In a broader perspective, how much customer-obsessed is this company? In cases where there is an obvious size difference between your company and this vendor (you are a huge corporate and they are a small start up or vice versa), ask yourself if they can cater to an organization like yours and how important would you be to them as a customer? Lastly, my advise to you is not to ignore things like gut-feeling, red-flags or 'no culture fit'. These things usually pop-up during the sales cycle and the engagement between you, the vendor and its people. To me these things are fair-game to bring to the table in an evaluation of a product and a vendor.
Working in a systematic way and reviewing all 3 factors is important. Involving multiple people in the process for multiple point of views is always recommended.
