Questions you should ask when shopping for document automation software

15 February 2020

Five insider questions to ask when choosing document automation software

Five insider, secret questions to ask when choosing document automation software


Our CEO recently wrote a post on Medium describing what questions to ask document automation software vendors.

Spoiler alert: it gives away all the tricks that give power to consumers and takes power away from vendors! The idea is to acknowledge that you are extremely busy and identify the questions that cut through the fat as quickly as possible.

The Five Questions

The article recommends that you ask the following questions

  1. Can you please send me an example of a typical report or presentation the software generates?
  2. Can you please send me an example of a document that contains this chart type I frequently use, this type of table, and this paragraph?
  3. Can you please send me the how-to video or article on your website that tells me how to create my very first document?
  4. Can you please tell me what industry comprises the largest share of your users, and what percentage of your users are in my industry?
  5. Can you please send me an example file containing the data I could take with me if I left for another software provider?

The first question is important because it helps you start with your end goal. You should look at the final product — the output of the software — before taking any other steps. If the output you see (say, in report or presentation format) doesn't match your needs, you can stop considering that particular vendor right away.

The second is important for the same reason. In our experience, each team has their own chart and table styles, and you need to know if a particular piece of software will work with your team's style. Cut to the chase! Doing so will benefit both you and any potential vendor.

The third question is aimed at finding out one of the simplest, yet most overlooked things: the quality of online learning resources and in particular the quality of the resource that will help you get started with the software. From our experience, the single biggest hurdle for any user is the first step after opening it. At this point, the user is presented with a new and unfamiliar landscape of buttons and visuals. Once a user has learned how to do the most basic things in software, it's easy to learn more; but if those first steps are cumbersome, users rationally assume that the other steps are just as hard. We therefore think 'getting started' videos or written material that is simple and easy to follow are extremely important.

The fourth question is about the industry of specialization of the software vendor. It's worth asking because ideally the vendor specializes in your industry. When that's the case, you'll be the first to get new features and bug fixes. You won't be an afterthought!

Finally, the fifth question is about how easy it is for you to leave the software if it turns out it's not for you. It's easy to overlook this at the beginning of your search, but it's important that you don't. Vendors that make it easy for their customers to escape have to earn their keep every single day; vendors that make it hard for you to escape can rely on your inertia. Which do you think provides the better experience for you? You got it — you're far more likely to get the best experience with a software vendor that doesn't try to lock you in to prevent you from leaving.


When you're considering document automation software, ask the five key questions in this article of every vendor you're considering. If you do, you'll likely find a great solution for you and your team. If you don't, you may find that you accept a suboptimal solution that you and your team will regret for years to come.

If you're looking for document automation software, we invite you to contact us to start a proof of concept or a conversation. We’re here to help!