Document generation software can have an outsized impact on your organization – as long as it’s used properly. That’s easier said than done because many people start the process of understanding document generation after they’ve jumped in head first.

That’s a recipe for dashed expectations. Instead, it’s important to evaluate every step of the document automation journey objectively. This is before you ever consider a solution. For example, you’ll need to audit your processes, identify documents to be automated, get stakeholders on board, etc.

With this guide, we’re assuming you’ve already done the preliminary work and are ready to choose document generation software. Let’s look at the questions to ask before you choose a specific document generation or document automation platform.

What is document generation software?

Document generation software is the technology that makes automated document generation (document automation) possible. Document automation is the process of using technology to collect data, draft documents, and perform post-creation actions such as signing without human intervention.

Document generation tools can be broadly classified as document assembly tools and document automation tools.

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Document assembly software generally performs the core task of automatically generating a document. Document automation tools, on the other hand, go above and beyond. You can automatically create documents, get them signed, send them to third-party applications, and many other functions that automate most, if not all, of the document lifecycle

The tool you choose will depend on your needs but most of the questions you ask can be applied to both types of software.

Questions to ask about document generation software

Keep in mind that the following questions are not meant to be exhaustive. Instead, they’re designed to help you start thinking in the right direction. Ask the ones relevant to you, add your own, and remove them from the list as needed.

1.    Does it have the features I need?

This is an important question because almost all the tools you’ll vet have the core document generation features. Because of that, the deciding factor becomes whether or not it has the extra features you need.

Good question about document generation software meme

For example, does it have team management tools and if so, how robust are they? Can people be given different permission levels that restrict their access to sensitive documents?

Another thing you may want to consider is what type of documents it can handle? Does it convert PDF files into an editable format and does it handle other types of files that may not be as common but are important to you?

How robust is its document editor? Can you change fonts, can you add bullets, are quotes available, can you insert images? These things matter in the right situation so it’s important to know what you’re looking for and are able to confirm they’re available before making a choice.

2. How difficult or easy is it to use?

Ease of use is always an important thing to take into consideration. Oftentimes, you’re not the only person that will be using the document generation software. Whether your colleagues are well-versed in technology or not is irrelevant.

Some tools are just poorly made and will force you to do more work than is necessary. How do you find out if a platform is easy to use or not? You can read reviews but a more reliable way is to watch their explainer videos. Almost any piece of software has tutorial videos that explain how to use it.

Take note of how many steps are required to do things. How much effort is required to set up a document, access information, and otherwise automate your processes?  

3. What is the price and does it fit within our budget?

I could have put this first because it’s that important. If your budget is $500 a month and the software is $36,000 a year, it doesn’t matter if it has all the features you need.

Document generation software can range from anywhere between $29/m to $10,000/m. It’s not that some software is so much better than others. It’s designed for a different type of customer. The things an enterprise customer with 1,000 users needs is different from what a small business customer with 3 users needs.

For a small business, the sweet spot for document automation software is between $100 – $500 a month. Any less than that and the company may not be able to deliver quality support More than that and the costs may be too close to the savings you’ll get.

Of course, you know what your budget is and how leeway you have. The most important thing is to determine the budget beforehand and stick with it unless there’s a good reason not to.

4. Does it integrate with the other tools we’re using?

Before you ever considered document automation, you’ve likely got an entire ecosystem that you use to run your organization. Email marketing, CRM, payment processors, storage platforms, etc.

It would make no sense for the software you’re considering to not key into any of these. This is where the distinction between document automation and document assembly software happens. Document assembly software specializes in putting your documents together.

Document automation software specializes in putting your document together and the steps that occur after the document is created. Both of them are useful but document automation tools tend to have a deeper network of integrations for you to use.

5. Are we able to customize it to match our brand?

Customization comes in many shapes and forms. At a basic level, you’ll want to be able to match your colors and fonts. You may even want to be able to insert your logo somewhere.

More advanced customization is also available such as adding a domain that you own, hosting information on your domain, allowing your team to log in on your domain, removing the software branding from the app, etc.

The level of customization you’ll require will depend on what you’re using the document generation software for. If it’s client-facing, you may want to be able to add your logo. If you’re reselling or otherwise adding it as part of a solution you provide then total white labeling may be necessary.

6. What sharing settings does it have?

How can you provide drafts of documents and completed documents to others? This is separate from team management. With sharing settings, you should be able to provide access to documents (and limit what people can and cannot do) without inviting them to your account. Even within your team, how can you make specific documents available but not others?

Take a deep dive into this area because it’s important. You don’t want to hit hidden limits after you’ve already invested time into learning and money into paying.

7. What document storage and file organization options are available?

Over time, you’ll likely create a lot of documents. That’s kind of the point – right? One of the benefits of document automation is being able to cut down storage costs. That’s not relevant if you’re unable to find those documents when they’re needed.

There are two things to consider:

  • How can you search for documents?  
  • How can you organize documents?

Any document management solution needs to have a robust search function so the document you’re looking for can be found. Another thing it needs is an organization system that goes beyond a master list view.

For example, your document management system may have folders that mimic what’s available on your computer. You’re already used to it so it should be simple for most people in your organization to learn. Investigate the search function of the software you’re considering and the organization options.

8. Can we view form analytics as well?

This may not be something that comes to mind initially but it’s a nice-to-have feature that can help you make data-driven decisions. For document generation, users usually fill out a form that then populates the document.

That form can have multiple-choice questions which serve as the base for conditional logic. You can use the information gained from how people answer questions to make decisions in other areas of your business – but only if you have document form analytics.

Now, keep in mind that these analytics don’t need to be complex in the same way a true form builder has deep analytics. It just needs to show you the relevant information in an easy-to-digest format.


Document generation tools come in all shapes and sizes but they all have similarities. This guide has taken a closer look at the things you’ll need to consider to choose the right document generation software.

You can pick and choose the relevant questions as well as add your own to ensure you make the right decision. Let me know what you think in the comments and don’t forget to share.