Josh Landsman is an attorney in South Florida with a focus on estate planning, tax, and probate & trust administration matters. Josh talked to Woodpecker’s Director of Customer Success about how using document automation to draft legal documents enhances the work relationship between him and his paralegal, ultimately improving the final work product.

Q. Tell me a bit about your practice. 

Landsman: I’m an estate planning and probate attorney in South Florida. I assist individuals and families with drafting their estate planning documents; for example,  wills, trusts, health care directives, and durable powers of attorney.

I also work with families to assist in the probate or trust administration process after a family member passes on. 

Q. Was there one particular problem you were trying to solve when you were looking at document automation tools? What made you decide that you needed it? 

Landsman: Over the years, regardless of the practice in which I was working, I noticed there was a natural workflow for every matter – a process that be copied and repeated for different clients, regardless of the different facts and circumstances. In particular, in my estate planning matters, I knew with the help of a certain level of automation, I could be far more efficient and accurate with my work.

The difficult task has always been finding the right system — a system that I could manage myself: easy to use, no coding required, with templates that I could build and maintain. I had been keeping an eye out for such a solution and Woodpecker was the first one I came across that fit the bill. 


Q. Did automation reduce your dependency on a paralegal? 

Landsman: For me, automation did not replace my need for paralegal assistance but it did change the dynamic between my paralegal and me. It’s enhanced the quality of the work we do together. We collaborate more effortlessly now. 

Solo practitioners who are considering hiring a paralegal may want to consider reviewing their current processes to first determine whether automation would reduce the need to add a full time staff member, however. For certain practices, automation alone could sufficiently increase attorney bandwidth. 


Q. How did automation enhance the work between you and your paralegal? 

Landsman:  First, it reduces the number of hands that touch a particular document, which can help reduce the introduction of errors into the final work product.

Second, automation helps take the guesswork out of the process: paralegals and other support staff do not need to try to guess what’s in my head and what needs to happen next for a client file.  

Q. Do you have any stories you can share about embarrassing errors? 

Landsman: Like other practitioners out there, misspellings of names or incorrect client contact information haunt your dreams from time to time.  Automating processes can help take these issues out of the equation.  

Q. What are other benefits of automation? 

Landsman: You’re able to offer more competitive pricing. Automation allows you to create work using a predictable, repeatable process. As you know, most lawyers bill hourly so if you’re saving two hours when creating an Estate Plan, that’s two fewer hours the client should have to pay for.  

It also frees up time to tend to the business side of your practice. You can work on projects that will secure future clients, such as business development, new service delivery models, and flat fee pricing structures.

You may even be able to reduce overhead by working with part-time staff instead of full-time staff. Or you can hire someone just to do the data entry for your documents, which you can do on a site like Upwork. 

That’s what’s nice about the Woodpecker questionnaire: you can use it for clients but you can also use it for internal data entry. Layering the questionnaire on top abstracts the legal information from the variable client data. This makes it easier to hire a Virtual Assistant, as it’s a straight data entry job at that point. 

The lawyer can then just focus on the accuracy of the client data, which is what catches the clients’ attention: whether their name is spelled correctly, their address is right, and so forth.  

Q. How does Woodpecker help solos and small firms compete?  

Landsman:  In law school, in my opinion, you’re trained to be an associate at a big law firm. Big law firms tend to utilize document assembly programs or research platforms that are cost prohibitive to smaller firms or solo practitioners.

I really believe Woodpecker offers a great solution for lawyers with a remote law firm, a small office, or who are solo practitioners. It’s easy to learn and affordable. Woodpecker works inline in Word so the technology is already familiar, and it’s very intuitive, so you don’t need an IT team or a consultant to build or maintain your templates. It really levels the playing field for solos and small firms.