I’ve been working in Legal Tech for a little over two years. More specifically, I’ve been working with a company that makes legal document automation (software-assisted document drafting) specifically for solo and small law firms, Woodpecker. 

During this time, I’ve had the opportunity to talk with and get to know many different lawyers across all sorts of practices. 

Our conversations always begin during the education stage of their document automation decision journey: they know the result they want, but are not yet sure which solution is the best fit. They are, understandably, committed to ensuring the very BEST possible fit, but aren’t always exactly sure what that actually means. 

It doesn’t help that there are a multitude of available options in the market with features that are often confounding, and differences in functionality and performance that are not easily understood. 

To get to the core of what they need and what will work best for them, we often discuss their specific practice area, the type of documents they frequently generate, the biggest pain points they have with document drafting, and the pressing problems they need to solve.  

Document automation technology can solve many different and complex problems BUT every platform has different capabilities. Having this conversation is crucial to ensure the right alignment and a successful business outcome for all parties.

If after these initial discussions, Woodpecker turns out to be the best solution for them, our conversations often continue into what their onboarding process will look like. I’ve collaborated with attorneys on custom training sessions, creating best practices, building project plans, estimating timelines, and providing demonstrations to senior leaders. Ultimately, my goal (and my job) is to help get the entire firm on board with document automation, a task that is unique to each and every firm. 


During the time I’ve spent with lawyers, I’ve heard countless stories about prior attempts to use document automation and suffice it to say, the regrets aren’t few. These stories center around badly designed user interfaces; unfair, lengthy, and one-sided contracts; complex, difficult to use software; non-existent or hard to reach support; challenges with low staff adoption; and other woeful tales of failed document automation initiatives.  

Fortunately, from despair comes hope and in this case hope comes in the form of invaluable insights from lawyers and the lessons they’ve learned with document automation. Their hard-won learnings can help prevent other attorneys from making the same mistakes, and I am paying it forward by sharing the wisdom that was generously shared with me.

Despite the disturbing stories I’ve heard, automating document drafting workflows can be a simple, smart, and straightforward endeavor, even for solo and small firms with smaller budgets and fewer resources. 

Being aware of the potential pitfalls drastically helps firms confidently navigate the process, realistically set expectations, create a practical plan for implementation, keep the project on track, and minimize any unwelcome surprises. 

Without further ado…

Reason #1 Why Document Automation Fails: Choosing the Wrong Software or Technology Partner

Many attorneys, certainly more than I would have anticipated, have already tried to use document automation when they find Woodpecker. 

In hindsight, I shouldn’t have been so surprised. Of course so many have tried it! Lawyers are very  well educated people and it makes perfect sense that they’d fully appreciate the value of automating the repeatable, predictable steps of a process. Not to mention, document automation has been around for an awfully long time and there’s been ample opportunity for adoption despite the consistently low adoption rate we continue to see across the industry. 

But being new to legal technology, I had incorrectly assumed that slow adoption and growth rates across the legal tech sector were primarily the result of lawyers carefully preserving the manual processes they had so thoughtfully designed over the years. Understandably, everyone gets a little anxious about the thought of deconstructing a well-running, tried and true machine. 

In my defense, inflexible mindsets and an industry steeped in precedent rather than innovation, certainly play a role; I just hadn’t considered that poorly designed technology, misalignment of problem/solution, and a horrible user experience could be equally responsible. 

Fast forward a couple of years, and I’ve a whole new perspective on the importance of selecting the right technology and the right technology partner for a document automation initiative. It is, without a doubt, the primary reason document automation projects fail to deliver on expectations.

Since there is no perfect, magical, one-size-fits-all solution when it comes to document automation (or any other category of software for that matter), it’s extremely important to think through your needs, resources, & priorities, and create concrete guidelines before you even begin shopping around. 

Here are some questions you’ll want to ask yourself to get started: 


  • Do you want to be able to populate documents in bulk

  • Would it be helpful to you and your team to be able to access your legal templates / documents from anywhere? 

  • Would you like to be able to use conditional logic, allowing you to consolidate multiple versions of a document into one? 

  • Would you want to leverage online client intake forms / questionnaires to allow your documents to be automatically generated externally? 


  • Do you work on PDF legal forms? Or do you work with Word documents? 

  • Do you have to use very specific Word formatting and auto-numbering? 

  • How often do you generate transactional documents where you are essentially replacing variable or boilerplate legal language? 


  • Is standardization a concern? Do you have multiple versions of the same legal documents / templates floating around, risking the chance of an outdated clause being used in error? 

  • Do you spend far too much time creating transactional legal documents, time that could be better spent on tasks that require your specialized expertise? 

  • Do you want to eliminate as many unnecessary and duplicate steps as possible, maximizing your productivity? 

  • Have you been stuck in an unfair contract and feeling underserved and undervalued as a customer?

  • Are you trying to get your team to commit to using document automation systematically and consistently? What do they need to do that? 

Software Attributes

  • Do you prefer intuitive features and user-centric design to more technically complex software?

  • Do you need a robust feature set to manage high-volume, complex documents? 

  • Is scalability a consideration? Will it grow as your practice grows? Can you add features as you need them? 

  • Does it do what it says it is going to do? 

IT Support

  • Do you have an IT department? How much bandwidth do they have? 

  • Will you need outside consultants for implementation and support?

  • Are you ok with having a dependency on someone else to make updates
    to your templates when you need them?  Or would you rather be able to make updates yourself?

  • Does it make more sense to go with a no-code / low-code solution with DIY template updates? 


  • Do you want to be able to access the software from any device? 

  • Would you prefer updates that automatically happen in the background, or do you want to install updates yourself? 

  • Do you want to be able to store templates and access them from anywhere? 


  • What additional productivity benefits would you get from being able to integrate with the other platforms you use? 

  • Do you work on a Mac or PC? 

  • Do you want something that snaps right onto the workflow you already have, or are you going to upend your entire workflow and start anew? 


  • Do you want the ability to pay month to month? 

  • Are you willing to sign a long term contract? 

  • Can you be certain that the price you pay today is the same price you’ll pay three years from now? 


  • Can you get responsive product support? 

  • What kind of support is offered? Email, chat, phone? 

  • What does the customer feedback loop look like? 

  • How often do you get substantive updates to the software?

  • What do others say about the vendor in reviews?  

By first answering some of these questions you can begin to create a simple plan, which honestly is enough for you to get going. Categorize features and attributes as “must have,” “nice to have,” and “don’t need” to help you identify which document automation solution will deliver the most value. Of course you can always modify your requirements as you refine your knowledge of what’s out there. 

If you prefer a more structured decision making approach, you can use a decision matrix to help you evaluate and prioritize your options. Here’s a quick walkthrough on how to set this up:

1. Create a matrix table (in Excel, Google Sheets, or even on paper). Organize the table into rows of software options and columns of criteria. Enter your options. 

For instance, for options, you might have Woodpecker, Company A, Company B, Company C, and Company D

2. Decide on your “must-have” criteria. These are the attributes the final decision must include. Add these to the matrix table. 

Criteria might include: responsive support, works in Word, cloud-based, supports populating multiple documents at once, fits the budget, connects to other tools, etc. 

3. Evaluate and weigh your criteria. 

Not all criteria will have the same level of priority, so you’ll need to assign a weight to each, using a scale of 1 – 5 (with 5 being the highest priority).

4. Score each option. 

Using the same scale of 1 – 5, with 5 being the best match / highest score for that option.  

5. Calculate each options’ final score. 

Multiply each option’s rank by each criterion’s weight, and enter the number in the cell. Add the totals in each row to get your final rank. 

Regardless of how you create your plan, giving some thought to what you need and what you want before you start shopping will not only help you narrow down your list of vendors, but will also help you stay focused on committing to  the technology you need. 

Otherwise, you risk buying a shiny new toy that doesn’t serve you, your team, or your practice well. If it doesn’t deliver the value and accessibility you need, you’ll end up with a failed document automation project, and the regrets aren’t few.