Ask Me Anything · Wordsmith

Wordsmith on r/legaltech

Wordsmith's AMA on r/legaltech. Every question and answer below is verbatim from the live Reddit thread. Chapters are ordered by community upvotes on Wordsmith's reply.

AMA 29 Apr 2026 Chapters 27 Answers 34 Total upvotes 62
Top chapters by upvotes
01 Is there any discussion about a post-Microsoft Word world in your company ↑4

Asked by u/Wise_Taste3195 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Is there any discussion about a post-Microsoft Word world in your company? Is that a possibility at all in your opinion?

⚒️ falkenthal r · ↑3 · Reply on Reddit →

I personally find it hard to see a post-Microsoft Word world in the short term. But medium term yes I can see that. And yes it is something we think about and consider when we are building the platform

⚒️ wordsmith-ross · ↑5 · Reply on Reddit →

Honestly I think that’s where Anthropic is going, they want to replace Microsoft as the productivity layer 2.0. In the same way we presented our intelligence through word as a vector the same is likely going to be true of Anthropic once they start to seriously displace google and Microsoft. The surface areas will be commoditised and you will shop for AI in a similar way to how you shop for lawyers, based less on if they can use word, more down to what they do with it when they do.

⚒️ falkenthal r · ↑3 · Reply on Reddit →

And just to boast: We can already review and redline a doc in our platform without the user ever needing to open Word. I dont think that is true for all vendors

02 Can you riff on the need for legal-specific tools as opposed to foundation models adding legal-related skills ↑3

Asked by u/WashAndZoesDad · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Can you riff on the need for legal-specific tools as opposed to foundation models adding legal-related skills? Should lawyers have both and find the advantages from each or can we realistically have One Tool to Rule Them All?

⚒️ falkenthal r · ↑4 · Reply on Reddit →

I could riff all day about this. I think you can have One Tool to Rule Them All (btw I am going to steal that as a way of explaining it in the future 😄). I think you need legal specific because these tools are not just the AI models that power them. It is the software + the AI + the legal knoweldge. We have had to build a lot of software and put in a lot of legal knowledge to be able to deliver outcomes that are good enough for a lawyer (I was a tax lawyer in a past life). I personally dont think legal teams have the capacity and access to engineers to do that.

03 With Claude and OpenAI changing token pricing every now and then, do you foresee the price for your products to remain stable into the future ↑7

Asked by u/Wise_Taste3195 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

With Claude and OpenAI changing token pricing every now and then, do you foresee the price for your products to remain stable into the future?

⚒️ falkenthal r · ↑2 · Reply on Reddit →

It is hard to tell what the future will hold but we do not anticipate price changes due to token pricing currently. What I would flag is that if in a future world legal tech tools were charging more, than my expectation would be that the value being delivered would be higher.

⚒️ wordsmith-ross · ↑3 · Reply on Reddit →

Most providers are seat based today cause that’s what people currently understand. My best guess is that Eventually we are going to end up with a few pricing models. 1. Token plus (obvious) - mostly foundation providers. This is probably how AI companies will be taxed in the future on consumption here. 2. Outcome based - likely human, AI blended pricing models. Very heavily tuned AI that’s great at getting specific outcomes maybe with human in loop. Contract review is an early example. 3. Consultancy - effectively the forward deployed engineering model.

04 Which legal tech company is your fave (apart from your own) ↑4

Asked by u/context-missing · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Which legal tech company is your fave (apart from your own)?

⚒️ falkenthal r · ↑2 · Reply on Reddit →

Laurel AI because I hated doing timesheets in a past life!

⚒️ wordsmith-ross · ↑3 · Reply on Reddit →

I like spellbook cause I think Scott is the ultimate salt lord and I find his flamethrower campaigns on X a deep source of entertainment

05 We’ve all seen the Claude for Legal webinar and the interest it received ↑3

Asked by u/Verylawyerproblems · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

We’ve all seen the Claude for Legal webinar and the interest it received.

How would you answer the « Why Your Product VS Claude » question ? Particularly coming from in-house legal teams

⚒️ falkenthal r · ↑3 · Reply on Reddit →

our legal engineer elly wrote about this the other day. in short. why wordsmith vs. claude.

End-to-end workflows, embedded where you and the business live. End to end custom intake/triage and output (with full control along the way), bulk data analysis over 250k docs, automate your static templates into dynamic blueprint, contract review and redline

Governance. With Wordsmith you have full visibility into what the business is asking, what answers they're getting, or what they're doing with those answers. More than that, you have control. With Claude you risk creating shadow legal. For enterprises this is non-negotiable.

LLM Agnostic and no model lock-in. With Claude you're on one model. It goes down, you go down. We ensure you (a) use the best model for the task and (b) will ensure you're still up and running if an LLM goes down. also. the frontier shifts constantly. When it does, you're stuck with what you built on. Migrating your projects, data, workflows, training your team and getting buy in from the business is a huge task - you're not going to want to do that often...

06 Don’t you feel intimidated by Claude and ChatGPT ↑1

Asked by u/ghostsarerudest · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Don’t you feel intimidated by Claude and ChatGPT? How is your solution better?

⚒️ falkenthal r · ↑3 · Reply on Reddit →

I am Irish, we never feel intimidated 😉

⚒️ wordsmith-ross · ↑2 · Reply on Reddit →

Claude and open ai have been there since day 1, it was always an early conversation and it ebbs and flows as they make large releases.

The reality of any horizontal product is that when you are building for everyone you are constrained, you cannot give everyone the same quality or tier of product without over complicating your product or leaving huge sectors unserviced.

What we are seeing now is the foundation models expanding their surface area, making their AI available across more and more surface areas.

It’s a bit like we all started in the internet era before google launched chrome or Microsoft launched Ie. As they build those out we can focus more more on the quality of our AI and the outcomes it can deliver and far less on maintaining the chatbots, plugins etc.

I think there will be more companies than Anthropic in 5 years time.

We have seen this same pattern each time new platforms emerge. AWS didn’t kill every startup they unleashed a new generation of websites, same with chrome etc etc

07 Contract review is clearly where legal AI has found product-market fit first ↑7

Asked by u/Entire-Ask-3803 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Contract review is clearly where legal AI has found product-market fit first. Where does each of you see the natural next frontier for your platforms beyond contracts — and is there anything in broader legal workflows that you want to see more progress in?

⚒️ falkenthal r · ↑2 · Reply on Reddit →

Yeah for us Wordsmith has never just been about contract review. It has been about building a tool that the legal team can use to enable the rest of the business. We are buidling the comand centre for the in-house legal team. This is the place where they can manage all inbound requests. They can collaborate with the AI and the AI provides them with all the necessary company context for the task they are completing.

08 In hierarchical workspaces, who are your biggest users ↑3

Asked by u/Libralily · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

In hierarchical workspaces, who are your biggest users? Juniors who then deliver your product to seniors? Seniors who use the product instead of asking juniors to do it? Are partners using your profits?

⚒️ falkenthal r · ↑2 · Reply on Reddit →

we're serving in-house legal teams so less (unhealthy) hierarchy 😄 Interestingly we're seeing usage across all levels of the legal team, many of our power users are GCs and legalops leaders, senior contract lawyers, privacy lawyers etc. Every team member is basically getting value from the product with their own use cases (we also have some procurement and HR teams that bought themselves seats and can't get enough of it because they can self-serve while legal sets the guardrails)

09 As legal AI matures, do you believe the long term winner is the system of record that owns the full contract lifecycle, or the one that does it all that sits across tools and makes every workflow smarter ↑2

Asked by u/Big_Instruction2358 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

As legal AI matures, do you believe the long term winner is the system of record that owns the full contract lifecycle, or the one that does it all that sits across tools and makes every workflow smarter?

and where does your company deliberately choose not to compete in that stack

⚒️ falkenthal r · ↑2 · Reply on Reddit →

Don't see this as an either or tbh. I think the best in house lawyers are the ones who are deeply embedded throughout their business, not just within the legal department or an individual lawyer. Simply being a system of record for contracts won't be enough, it would be a dumb filing cabinet. The tools that can manage those contracts end-end, deeply understand company context and can provide legal throughout the entire business are where it's at

10 What’s the reason for failure you see most often when companies go live ↑2

Asked by u/JCL956 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

What’s the reason for failure you see most often when companies go live? e.g., playbook quality, change management, lack of context info/integrations, or something else?

⚒️ wordsmith-ross · ↑2 · Reply on Reddit →

We honestly don’t have many failed rollouts at wordsmith. A more common scenario is that it’s an under utilized rollout. They are just contracting when they could be hitting 50 more workflows.

They are just using it in single player mode when they should be deploying agents into slack and deflecting 50% of the volume.

They are just asking it to help with drafting when they should be creating a 22 step agentic workflow to eliminate the whole process.

Most people are in the early stages of adoption and it’s about moving them through the gears as much as building the tech that’s one our biggest focuses at wordsmith, enablement

11 Do you think the "Google" or "Microsoft" of legal tech is already here, or is that company yet to emerge ↑1

Asked by u/Severe_Post_2751 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Do you think the "Google" or "Microsoft" of legal tech is already here, or is that company yet to emerge? I sense the market is still in its early stages with a lot to explore!

⚒️ wordsmith-ross · ↑2 · Reply on Reddit →

Anthropic, OpenAi and google will be the new Google/microsoft.

We will need to build on and around the base line set of productivity tooling they offer enterprises

12 u/all In-house legal AI deployments may fail not because of the quality of your tools, but because the outputs don’t match how the legal teams actually assume risk, escalate exceptions, and coordinate w/ Sales, Finance, Corporate Security, Privacy, and other stakeholders ↑1

Asked by u/auslake · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

u/all In-house legal AI deployments may fail not because of the quality of your tools, but because the outputs don’t match how the legal teams actually assume risk, escalate exceptions, and coordinate w/ Sales, Finance, Corporate Security, Privacy, and other stakeholders.

When working with your customers, how do you help them address needs like these that sit outside the tool itself?

What are some of the biggest non-model/tool failures you’ve seen in deployments, and how have they changed your product or implementation approach?

Also, what would it take for your legal AI tools to complement document intelligence with a decision system of record?

⚒️ wordsmith-ross · ↑2 · Reply on Reddit →

Corporate data is not ready for AI.

They often don’t actually have a clear understanding or Common set of behaviours and view of their risk tolerance so this strange moment arrives when teams think they are just going to hit buy and magically their operation will instantly know this stuff.

The reality at wordsmith is that we spend time with a lot of our clients helping them to get their head around this.

We are so deep with in house legal it’s all we do and helping them to understand and see the best practices and templates other teams used was something I didn’t expect would have so much value up front.

This is as much about transforming how you work as deploying AI tooling.

13 You’ve all just mentioned internal evaluations, what metrics do you capture and how ↑6

Asked by u/context-missing · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

You’ve all just mentioned internal evaluations, what metrics do you capture and how?

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →
  1. We have “judge AIs” a few of them that cover different workflows. They retrospect on the output.
  2. We have a strong lawyer led human review laywhere where we sample and enrich our commentary on the output.
  3. Then we have a ton of stuff on reliability and latency.

We run these things constantly it lets us mix up the models and make sure it’s the best config for that specific workflow, this is an example of one subset that might run.

https://preview.redd.it/w4ddxdnfm6yg1.jpeg?width=831&format=pjpg&auto=webp&s=44e365099dca36c61c5cd222287b297546349bfe

14 Since you’re all operating in a fairly converged space, I’d be curious how you’d each articulate the real-world differences between your tools- what would make a user pick one over another in practice ↑5

Asked by u/raquelcunha · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Since you’re all operating in a fairly converged space, I’d be curious how you’d each articulate the real-world differences between your tools- what would make a user pick one over another in practice?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

Legal teams can use Wordsmith to truly enable the business. They can deploy Wordsmith agents where the business works (e.g. in Teams and Slack) and we integrate into their tech stack. We also really focus on pulling the company context into every interaction the users have with the AI. If you ask me, that is what makes a great in-house lawyer the person who has a huge amount of context on the comapny they work for. And with Wordsmith every lawyer on the team can have that context

15 What do you wish more people understood about your product but don't ↑3

Asked by u/nkim8972 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

What do you wish more people understood about your product but don't?

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

The rest of the business is actually the primary consumer, not the legal team.

That legal teams need precision and in house legal has a set of conflicting requirements to law firms.

They need something that is deeply built for their workflows and not just a rebranded version of something that was designed for big law.

16 How would you define your ICP ↑3

Asked by u/yungboi919 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

How would you define your ICP? At what point (company size, revenue, complexity) are legal budgets dictated by finance, vs. a state where the legal team is able to be more autonomous about their spend/procurement decisions?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

ICP is enterprise in-house legal teams, anywhere from a handful to 100s of lawyers. We deliberately made a decision early on to not serve law firms as their incentives are misaligned with the needs of in-house teams.

Legal, like any business function has AI budgets and business procurement processes they need ot go through. We see teams that are able to make decisions autonomously and since we can show high roi in all our trials it's not a difficult job convincing finance

17 Many legal teams would be reeling from failed CLM implementation /partial adoption from the CLM hype of about 5 years ago ↑3

Asked by u/Low_Walrus4683 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Many legal teams would be reeling from failed CLM implementation /partial adoption from the CLM hype of about 5 years ago. How do you build trust that your solution will be implemented into workflows and won't end up as another stalled tech project?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

yeah this is a great point

The time to value for CLMs is ridiculous The majority of our customers do a trial of Wordsmith before purchasing. This allows them to validate the expected value.

18 For small in-house legal teams (\~20 lawyers/contract managers; 7,000 total employees), what does implementation look like in terms of time and internal effort ↑2

Asked by u/LegalOpsandAdmin · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

For small in-house legal teams (\~20 lawyers/contract managers; 7,000 total employees), what does implementation look like in terms of time and internal effort? And what kind of ongoing maintenance is required after initial implementation?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

Good questions. It will depend on the use cases you are looking to deploy. The important thing to note is that you can enable the 20 lawyers so they can start getting value with a 1 hour session. Then depending on the use cases, you could be fully deployed within 2 months (we have customers who have done it in a week and those that have taken longer than 2 months). The amount of effort required from your side is dependent on how much you would like us to do vs you do. The ongoing maintenance is very light but we tend to find that you will have new use cases after a period because the tech is developing so quickly. And that is good because it means you are capturing more value

19 Having used one of your products, hallucination is still a problem, even if it has been minimized ↑2

Asked by u/Wise_Taste3195 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Having used one of your products, hallucination is still a problem, even if it has been minimized. What has your company done to reduce it that might give you an edge over other legal tools or generic tools, and do you think there will ever be a perfect solution?

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

There is an ongoing body of work I’m sure everyone is hammering out there.

The reality is you are always going to get a percentage that’s unacceptable.

Which is one of the reason legal AI is so heavily audited and cited. The consumer stuff won’t add this layer to see the references in as much detail because it’s largely useless for most non power users who don’t have the same requirements as legal.

20 For legal professionals managing documents across multiple entities or clients, how do your platforms handle that kind of multi-tenant complexity ↑2

Asked by u/Entire-Ask-3803 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

For legal professionals managing documents across multiple entities or clients, how do your platforms handle that kind of multi-tenant complexity?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

We allow teams to create and manage separate entity profiles, each with it's own world of context, from primary jurisdiction all the way down to nuanced negotiating styles

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

However this is actually an awesome example of where you are probably better off with a law firm product like Harvey or Legora.

They are actually build around external matter management and siloed data between those clients as a first class entity.

If you want to manage projects inside a company and leverage context between them it’s probably a better fit for in house gen ai

21 What data access issues are you still having ↑2

Asked by u/WashAndZoesDad · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

What data access issues are you still having? Things like local rules have a huge bearing on case activities but are really hard to get, for example. Same with ultra-niche regulations that sometimes aren’t even published, not to mention industry norms. To be a full solution for lawyers, what holy grail data is missing?

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

Great question, the biggest gap is the company itself.

On the law firms tech side this is more of an external data problem acquiring data sources.

In house it’s actually getting a clear view of policies and info that company probably doesn’t even have clear itself.

So a lot of your work is helping setup systems that will learn and improve over time to adapt to the guidance they share while they iron out those positions

22 If I only keep one of you in my stack, who should it be and why ↑2

Asked by u/NecessaryDull1124 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

If I only keep one of you in my stack, who should it be and why

⚒️ falkenthal r · ↑1 · Reply on Reddit →

Wordsmith. Because we will actually connect to the rest of your stack. We play nice with your other tools.

23 Which foundation models do your platforms use ↑1

Asked by u/_opensourcebryan · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Which foundation models do your platforms use? How do you ensure you are using the highest performing models?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

We use Anthropic, OPenAI, Gemini and some specific ones. We have a eval data set which allows us to test which are the best models for tasks and even specific sub-tasks.

24 What is one product feature that differentiates your product from others in the market ↑1

Asked by u/SortaConfusedHuman · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

What is one product feature that differentiates your product from others in the market?

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

We are “headless” which means you can anything in wordsmith from anywhere, be that our UI or Claude code or slack.

We are properly built for the agentic world.

Wordsmith has in-depth playbooks that let you specify guidance, redlines, fallbacks and gradual learnings.

Wordsmith also connects to and lets you service the rest of the business with deep integrations to slack, teams, Microsoft365 and hundreds of other tools.

It has advanced formatting and tempting products built for legal that allow for precision production of documents at scale without losing any fidelity or quality.

25 Does your system integrate directly with network drives, or do you require migration to Sharepoint or another cloud-based repository ↑1

Asked by u/LegalOpsandAdmin · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

Does your system integrate directly with network drives, or do you require migration to Sharepoint or another cloud-based repository?

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

We go very deep here at wordsmith, google drive sharepoint, imanage, notion (this one is uniquely powerful), there are dozens of them

26 When in‑house legal teams adopt legal AI for the first time, what expectations tend to be misaligned with reality ↑1

Asked by u/LegalOpsandAdmin · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

When in‑house legal teams adopt legal AI for the first time, what expectations tend to be misaligned with reality? Which use cases are commonly overestimated at the outset, and which areas end up delivering more value than teams initially expect once the tool is embedded into daily workflows?

⚒️ falkenthal r · ↑1 · Reply on Reddit →

Most common misalignment is assuming generic AI will do the job. Teams trial ChatGPT or Copilot, find it underwhelming. The gap isn't the model, it's the missing playbooks, governance, and workflow integration.

Related expectations we set with customers: don't expect it to be magic on the single most complex, bespoke contract your senior lawyer can't crack on day one. The teams that get the most out of it start somewhere achievable, get familiar with the tool, and watch it sharpen as they feed it more playbooks and patterns. Treat AI like a compounding system not something that's a silver bullet for all your jobs on day 1.

What surprises people on the upside is business enablement. People buy AI to make lawyers faster, then realise the bigger unlock is deflecting Sales, HR, and Procurement questions before they ever land in legal's inbox. External counsel spend tends to come down meaningfully too, one team we work with saved over $100k in external fees in the first phase alone.

⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

Great question.

Typically the multi turn contracting people struggle up front to appreciate just how much nuance there is in applying human judgement.

They think oh great this is going to be all but eliminated but the reality is that the messy middle of human interaction causes alot of noise and work.

Where we find most impact at wordsmith is when we sit down and help them adapt both their workflows and their technology. So they are actually changing how they work not just accelerating a existing workflows

27 Where in my workflow do you actually reduce time in a way I can charge more or work less ↑1

Asked by u/NecessaryDull1124 · H2H AMA Showdown · 29 Apr 2026 · Reply on Reddit → ·

  • Where in my workflow do you actually reduce time in a way I can charge more or work less?

What’s the highest-value use case you’ve seen for fractional GC work specifically?

*If I had 5 $8–10k/month clients, where would your tool materially change my margins?

  • What are people underpricing because they’re not using your tool properly?
⚒️ wordsmith-ross · ↑1 · Reply on Reddit →

I would literally strip out your entire first pass on any contract. Let them self serve it and pay you a fixed fee then only escalate to you if they need it. That first cut is almost 80-90% margin if you want it to be and you then give them Something sub par to your service and a reason to escalate

The wrap
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