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Featured Guest
Casey Flaherty

Casey Flaherty is an attorney originally from Los Angeles but now based in Austin, TX. He started his career...

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JoAnn Hathaway

JoAnn Hathaway is a practice management advisor for the State Bar of Michigan.  She previously worked as a legal...

Tish Vincent

Tish Vincent retired as the Director of Michigan’s LJAP. She is now the Chair of the ABA Commission on...

Episode Notes

Your firm has finally invested in new technology but that’s only half the battle. In order to actually save time and energy, you need to train your firm’s employees to use the technology correctly, whether it’s Microsoft Office, Adobe, or even an internal software service. In this episode of On Balance, hosts JoAnn Hathaway and Tish Vincent talk to Casey Flaherty about why investing in proper training is an essential part of investing in new technology. Casey recalls his own experiences working with firms’ adoption and productivity problems and discusses what beneficial training actually looks like in practice.

Casey Flaherty is well-known for creating the Legal Technology Audit (LTA), a test of basic technological proficiency for lawyers and in-house corporate departments.

Mentioned in This Episode

State Bar of Michigan: On Balance Podcast

Train Your Employees to Use Technology



Intro: Welcome to State Bar of Michigan’s On Balance Podcast, where we talk about practice management and lawyer wellness for a thriving law practice with your hosts JoAnn Hathaway and Tish Vincent, here on Legal Talk Network.

Take it away ladies.


JoAnn Hathaway: Hello and welcome to another edition of the State Bar of Michigan’s On Balance Podcast on Legal Talk Network. I am JoAnn Hathaway, Practice Management Advisor for the Practice Management Resource Center at the State Bar of Michigan.

Tish Vincent: And I am Tish Vincent, the Program Administrator for the Lawyers & Judges Assistance Program at the State Bar of Michigan. We are very please to have Casey Flaherty join us today as our podcast guest to talk about technology competency.

So welcome to the show Casey.

Casey Flaherty: Thank you for having me.

Tish Vincent: Would you share a little bit about yourself for our listeners.

Casey Flaherty: Sure. I am a lawyer turned consultant. I spent most of my time consulting with large law departments as well as with law firms around legal operations, process improvement, supply chain management, metrics, KPIs, et cetera. But I also own a legal tech startup focused on basic tech competence and that’s really my passion project, that’s my evangelism.

Tish Vincent: Casey, I know that you often compare Microsoft Word to Google. Could you begin by telling us more about that?

Casey Flaherty: Sure. And I make that comparison because people find it jarring, because for them Word and Google are at polar opposites of the usability spectrum. Google is quick, easy, intuitive, minimalist; Microsoft Word is big and clunky and intimidating. And I would submit that they are actually very much the same, we just don’t experience them the same.

So Google is minimalist and amazingly powerful. You type in some keywords, in less than one second it will rank 60 trillion webpages, something it does 3.5 billion times per day and less than 0.1% of us are ever desperate enough to go to the second page of results, it’s amazing. And yet people are very surprised to learn that Google offers two six-week courses on how to use Google, because the second you get past basic keyword searching to any kind of deeper functionality; filters, punctuation, safe search, jurisdiction specific, looking for specific file types, looking in particular date ranges, it becomes a lot more Boolean. It’s a lot less intuitive.

And certainly Google could cram much of that into a user interface; they have, just Google advanced search and you will go to Google Advanced Search and you will see what that user interface looks like, but all of a sudden it starts to look a lot more like Word, because at its simplest, Word is not a single purpose app. It’s an app ecosystem.

If you want to use it at its most basic, a typewriter with a glowing screen, it’s actually pretty intuitive. You open it up, you start typing, the words appear. It’s only when you want to start doing something more complex that it becomes difficult and you have to use all those little apps, which are up there in the ribbon and how many of those do we actually know how to use.

And the answer is far fewer than we should, given that lawyers in particular work in complex documents all the time; pleadings and contracts are complex documents. But in order to fully utilize Word or Excel or PDF or any of these powerful desktop softwares we have at our disposal, we actually have to learn. But we don’t. And we don’t impart because we don’t think we need to. We think it should be intuitive. We think it should be minimalist. We think that our technology should be self-driving, but like our cars, it isn’t, at least not yet. It can get us from point A to point B but it still demands precise user inputs.

And so that’s why I say that in many respects Google and Word are the same, where at their most minimal, they are very intuitive; at greater depths, you actually have to sit down and learn how to use them. I know it doesn’t strike you as that when you first see them, but that’s how it is.

We have very good empirical data from all over the world. The OECD did a study of over 200,000 participants in 30 countries. They tested precisely these kinds of skills, the basic skills doing a Google search versus a more advanced skill.


So a more advanced skill, even in the Google context would be, okay, we have now gotten to the page we want to and we are doing some kind of research, how do we find the place on the page that has the information we need? Do either of you know, if you went to a page and you were looking for some specific text, how would you find it?

JoAnn Hathaway: I know what I do is hit Ctrl+F and then I look for it that way.

Casey Flaherty: Ctrl+F, absolutely. But the thing about Ctrl+F is that’s a medium complexity task, it’s not obvious. It’s obvious once you know the answer but until then it’s not obvious at all.

JoAnn Hathaway: Somebody taught me that when I was in law school that used to be a legal secretary, that’s how I learned it. I didn’t know it before that.

Casey Flaherty: Google’s own search anthropologist studied Ctrl+F and found that more than 90% of the population does not know how to use it. And so we have these two competing things, we have the curse of ignorance, which is you don’t know what you don’t know. You don’t do things wrong on purpose, you do things wrong because you don’t know any better.

But we also have a curse of knowledge, which is once you know something it’s hard to imagine not knowing it. Once you know Ctrl+F, you start to assume that everybody else knows it too. And so there we have an impasse in training, because there is a bunch of people who need training, but don’t know it and then the people who might provide the training don’t realize that other people need it and so no one gets trained.

And you see the same kind of assumption runs throughout the chain. Law departments assume people get trained at law firms. Law firms assume they get trained in law school. Law schools assume they get trained in college, college high school, high school elementary school and the elementary school, they assume they somehow acquire it in utero.

We bought into this myth of the digital native and it really is — it is a myth, just because someone can use a single purpose app on their phone doesn’t mean they can use more complex software in a commercial environment. In fact, it tends to ingrain the opposite habit. There’s this expectation that everything is going to be easy and minimal and that you don’t need to learn.

Just because somebody can microwave a hot pocket doesn’t mean they know how to cook a gourmet meal. Now, they could cook a gourmet meal if you teach them, but the hot pocket doesn’t automatically translate into the gourmet skills without some form of deliberate practice and learning.

JoAnn Hathaway: That’s a fascinating way to think about it, how to get people to realize what they don’t know.

Tish Vincent: Well, I think it’s interesting too because I know when I consult with law firms and I hear a lot of consultants mention this, that law firms are notorious for not wanting to pay for training. And they will buy the software and they will spend hours and hours and hours to get the latest and the greatest and then they use it to 40% of its functionality, if that.

Casey Flaherty: 40% is rather generous.

Tish Vincent: Is it? I have to be nice when I am in there.

Casey Flaherty: The best studies we have on this topic come out of MIT and suggests that for every $1 you spend in technology acquisition, you may need to spend up to $10 on personnel, process, redesign and training. And we fail to make that complementary investment and so we fail to fully utilize the technology that we buy.

And again that goes back to this belief in robot magic. The idea that acquiring the technology is the last step instead of the first step and that’s tied into this assumption that things will be intuitive, belief in the digital native, et cetera. We believe in self-driving technology to our own detriment.

Tish Vincent: Another story I have too, talking about the digital native, it was interesting because I was providing some training to a relatively large law firm and the older partners in the firm actually asked for their own training sessions separate from the younger support staff, because they did not want to ask questions in front of support staff, assuming that support staff had all of the answers and they didn’t want to appear as though they did not.

JoAnn Hathaway: Interesting.

Casey Flaherty: So I actually, with my startup, I go out and I have reams of data on how people perform; support staff is the second lowest performing group.

Tish Vincent: Oh my word.

JoAnn Hathaway: Interesting.

Casey Flaherty: The only people worse than support staff are law students and slightly better than support staff are associates. And the highest performing group is partners.

Tish Vincent: Is that right?

JoAnn Hathaway: Is that right?

Tish Vincent: That surprises me.

JoAnn Hathaway: That surprises me too.

Casey Flaherty: Well, and since this doesn’t fit with your intuition, can you guess why that is, why my data has partners as the highest performing group?

JoAnn Hathaway: Because they engage so little so that that they engage in they do very well.

Casey Flaherty: Because partners make it mandatory for everyone else and voluntary for themselves.

Tish Vincent: Oh, interesting.

Casey Flaherty: The only ones who volunteer are the ones who have decided that they are tech savvy and so there is a lot of self-selection bias going on in the sample.

JoAnn Hathaway: Okay, so if they know they are not, they don’t do it, right?


Casey Flaherty: It skews. And of course then you can slice and dice the data where support staff on average scores below associates, but it tends to be a bimodal distribution, where you have one group who scores really, really poorly and then you have another group who scores much higher, and again, hearing that support staff doesn’t do well might surprise you, but then when you think about it as a bimodal distribution, with the people who are really terrible pulling down the average, now it probably makes more sense to you.

JoAnn Hathaway: Well, I think too sometimes in the law firms I have found or I think I make the assumption sometimes that support staff does not want to admit that they need help, even if they do realize something could be better because they think there may be the expectation that, okay, they came into this job, they should know how to do it, so I don’t know how real or imagined that is. Can you comment on that Casey?

Casey Flaherty: It’s very real and the Legal Technology Assessment, which is what I created and I will get into the history in a second, but it really is an assessment. It’s competence-based learning. It’s a test to figure out what you do and don’t know both matter; what you do know means you test out of training you don’t need. What you don’t know we can actually identify the gaps in your knowledge, again, because people don’t know what they don’t know.

Then you provide the training specific to those needs. Then you have a validating assessment to make sure the training was effective, because the point isn’t to get people into training, it’s to get them trained, and so you want to validate that the training actually worked.

And so with that again I have lots of data and lots of experience and one experience that keeps happening over and over again is that we will go into a law firm and this tends to be a small to medium size, where it has a few support staff, but not a large number and the lead person there, the head administrator will inform me, as so many people have in the past, that they are actually quite tech savvy and then they will not do nearly as well as they would think on the assessment, and then they will explain to me that they couldn’t possibly bring it into their firm because it would destroy moral.

So they would rather people walk around with a false sense of superiority, with illusory superiority, then deal with the fall out of anyone being told they are not as good as they think they are. And I see that over and over and over again. It’s the, we don’t need this, then you prove to them that they do need it, and then they explain to you, well, they couldn’t possibly handle it, precisely because they do need it.

JoAnn Hathaway: That’s very interesting, it’s very psychologically interesting. And Casey, I know you are going to be going into the Legal Technology Assessment in more detail so I hope I am not putting the cart before the horse here, but when I was introduced to it I always thought it would be wonderful for legal administrators, partners, whoever is interviewing support staff and/or associates to use it as a testing mechanism during the interview process for the candidates. Do you agree with that and do you find that people are using it for that purpose?

Casey Flaherty: Absolutely. There are firms and law departments that are using it for on boarding. The problem is, again, when you think about politics and politics being the art of the possible, there are a lot of people who want to have complete control over the hiring process. Meaning if they want to hire a friend or someone they personally like, they want to be free to do so, and once you start introducing objective measurements, all of a sudden they have to justify their hiring practices. So it is being used that way, but we run into the same kind of reluctance to introduce it that we would in introducing it to the firm as a whole.

JoAnn Hathaway: Interesting.

Tish Vincent: Very interesting. Yes, absolutely.

Casey Flaherty: As you can tell, I think a lot about adoption problems. While we have had nice adoption, it’s nowhere near where it should be given the need in the market.

Tish Vincent: Can you share with us and our listeners how you got interested in this, what’s your story, Casey?

Casey Flaherty: Absolutely. When I graduated law school the economy was still humming and I was able to go and work at a large firm and I was very happy about that and it took me about three days to look around and say this is nuts. And the main thing that was nuts was that clients were paying hundreds of dollars per hour for my time when I didn’t know anything. But the reason that there was so much time for me to bill is because we were massively inefficient.

A lot of things in the legal sphere get framed as a cost problem. I think that’s a mistake, following Professor Bill Henderson. I think it’s better to frame it as a productivity problem, because with the cost problem if you get a discount, you think you are solving it; with a productivity problem if you get a discount, you realize you are not actually solving the problem.


So I saw massive productivity problems and none of them had to do with how hard people worked or how smart they were or even how much they knew about the law. I worked with brilliant, brilliant people who genuinely cared about their clients and they worked so hard, but so much of the work was waste in the traditional sense of that which need not be done, that which was low value-add, and I was — I had a lot of low value-added tasks. And so, when I gotten in-house gig, I said, I don’t want to pay for that, and so, I had to figure out how not to pay for it. So, I imported a lot of practices from supply chain management.

In particular, I would go out and do site visits. I would take my bills, find the people who were billing me the most, figure out what they were billing me for, and sit down with them and ask them to show me how they were doing it, and then I would identify ways that that could be improved, and whenever I did this, and at the time it was called an Audit, a term I have jettisoned because it makes people really uncomfortable. But, when I would go in and do this audit of the firms doing work for me of the work that we were paying them for, I would walk into the relationship partner’s office and they would say, I know, we failed. Those morons in IT are not giving us what we need to do our job. Don’t worry about it, we have formed the technology committee. And I would always pushback, I’d say, look, your IT is not perfect but no one’s is, and that’s because IT moves too fast for you to ever be perfect. You could be completely up to date today. Six months from now you would be six months behind.

Certainly, your IT could be improved. I am not going to argue with you on that and there’s lots of technologies that have been around for a long time that you should incorporate document automation, e-signatures, et cetera. That said most of your people spend most of their time in the basics; Word, Excel, PDF, e-mail, their document management system, and they are terrible at it, and the partners didn’t, believe me, and we were at an impasse because we were having a normative conversation about an empirical issue. We were speaking about tech competence in the abstract, and so what I needed was data. Without data you are just another person with an opinion. And so, I created an assessment, based on work I was actually paying people to do, of here are tasks that we are sending out and being charged for, and I can get them done in about 20 minutes.

The average associate or paralegal who was billing me took 2.5 hours, and that was enough to get the law firms to change. And it wasn’t the only thing I was focused on, I was focused on knowledge management, document automation, staffing, delegation protocols, project management, process improvement, but it was the tech part that got the headlines. And if anyone’s interested in kind of the whole bundle of it, there is a free e-book I wrote for The Association of Corporate Counsel entitled Unless You Ask and it goes through all of these different areas. There’s a primer on it that I wrote for buying legal counsel. On service delivery reviews, you just type-in my name, service delivery review, you’ll find it.

So, I really am interested in all those things and that’s what I consult on this broader picture, but it’s the tech piece where I came up with the company, and so the first thing I did was gather a bunch of experts, trainers, in-house counsel, outside counsel, academics and refine the assessment and automate it. So, now people could take it and have a score and that score replace the mostly meaningless, a profession in Microsoft Word which ranks right up there with “I have read these terms and conditions”.

And so, instead, we score people individually on Word, Excel and PDF and we are starting to add more-and-more modules, but it’s one thing to diagnose the disease, it’s another thing to offer the cure. And it turned out that testing people was the best way to get them trained, because again, you could figure out what they knew and didn’t know and you could prove to them that training would be beneficial. Then you provide them the training and then the validating assessment and so we actually put together an end-to-end competence-based training platform. Right now we have introductory intermediate modules on Word, Excel and PDF, but we are working on a lot of additional content.

Tish Vincent: So, Casey, do you also do this kind of training with law schools?

Casey Flaherty: Absolutely, we’re in at over 20 law schools. In the beginning we were brought in simply by individual teachers. We would like our students in this class to take it, but now it’s being offered at certain schools to every student with teachers have the option of assigning modules in their particular class and I really do have a vision for a law school-specific curriculum that mirrors the traditional curriculum.

So, instead of saying, hey, use your electives to take a class on technology, it’s let’s weave practical training into the core curriculum. When you do your legal research in writing, this is how you format a memo in Microsoft Word. When you do your contracts class this is how you put together a contract in Microsoft Word.


One easy example from contracts, in the 1980s, Word introduced an automated cross-reference feature, so whenever it’s See Section 3.1 excluding Section 3.4.1 et cetera, right now, if you know how to use that feature and you update the contract, you press two buttons in every cross-reference updates. You don’t know how to use that feature, you have to do it manually and not only can it take you hours in a large contract but it introduces hundreds of opportunities for human error, and yet, less than 5% of legal professionals, lawyers, staff, law students know how to use that feature.

So, that’s one of many things you learn in your contracts class, in biz orgs or corporations you do some Excel, in civil procedure you learn how to put together a compliant e-filing, which would teach you a lot about manipulating PDFs, and then you’d have some kind of capstone, and then once you past all of those, you would get a certificate that would go on your résumé in place of profession in Microsoft Office.

As it happens, we do offer Micros Certifications with every single one of our assessments, so that if you get a qualifying or expert-level score, a third party issues you a badge and when someone clicks on that badge, whether it’s on your LinkedIn profile or your homepage, it takes them to this third party website and says, who earned the badge, when they earned it, what they did to earn it, and when if it all that expires?

Tish Vincent: That’s excellent.

JoAnn Hathaway: Casey, can you talk a little bit about the plug-in if I am referring to it with the right terminology for the assessment, and what I mean by that is, I know when I first looked at it, I am like, okay, well, with PDFing for instance, I use Adobe Acrobat Professional, but what if someone else is using a Nuance product, or there are so many different applications out here for PDFing if you will? I mean, this actually works in any application, is that correct? People can be tested?

Casey Flaherty: Yeah, we are both operating system and software agnostic.

JoAnn Hathaway: Okay.

Casey Flaherty: It doesn’t matter whether you are on Mac or PC, it doesn’t matter which version of Word you are using. You don’t even have to use Word, you could use Google Docs or one of the open-source softwares, it doesn’t matter which PDF software you have, as long as you can upload a compliant document. So, let’s say, about 3% of the market is still using WordPerfect. I understand why people love WordPerfect, but the people who use WordPerfect know they have to be able to send their clients and opposing counsel Microsoft Word documents that are formatted correctly.

We do expect you to upload a Microsoft Word document but we don’t care what you do to get there as long as it’s correct, as long as you are able to achieve the results. The only thing that having a different software like that will do, is that the training videos that we offer are not specific to it, you will actually have to go out to Google to figure out exactly how to do what you need to do, but by the way that’s not a terrible ancillary skill to develop. In fact, I have this dream, with a we wouldn’t offer training at all, that we would just offer the assessment and that people would learn how to find these answers on their own.

The market hates that particular idea, I found out, but it’s still my idea and we are actually putting it into place as we work specifically with State Bars to weave in some substantive content into our skills-based content.

So, for example, the first State Bar specific module will be launching is with Florida, as you may or may not know they have mandatory technology, CLE in Florida. I was actually brought down to address the Supreme Court on that particular issue. It will ask you something like, what is it sensitive information or personally identifying information that needs to be redacted, in full before filing a document with the Florida Courts, check all that apply, and then there will be 20 options about eight of which need to be checked, and just so you know there are about 16,000 answer combinations there so it would be really hard to game.

So, to the extent people don’t know it off the top of their head, what they are going to do is they are going to go and look it up. They are going to go to the resources at the Florida Bar and the Florida Courts already make available to them and figure out the correct answer. They are going to do what lawyers do, they are going to have a legal question posed to them, they are going to research it and they are going to come to the correct conclusion.

Then, in the next task, they are going to be given a document that has sensitive information that needs to be redacted and they are going to be asked to redact it. When they upload that document with the redacted text, our software reads it and can tell immediately whether or not it was properly redacted. And so, there we combine substantive legal issues with the practical skills that support them to create a brand-new kind of competence-based CLE of which I am a chief proponent. That doesn’t mean I am dismissive of standard CLE, there is a lot to be said for the traditional lecture format, it’s great for stimulating conversation and transmitting big ideas. It is not particularly well-suited to conveying specific information and even more so, specific technical skills.


Tish Vincent: I think that’s excellent because I think it’s hard to know — when you are practicing law it’s hard to know where you can find that kind of training and this offer is an avenue that people can access —

JoAnn Hathaway: And it’s on the spot training too, which I think is so attractive and it’s user-specific, which I think is so unique, and I would like to take this opportunity, you had mentioned the Florida Bar is working with you, the State Bar of Michigan is now also offering the legal technology assessment at a deep discount to our members. So, I am going to specify a URL here where our membership can go to our website to access that information and that’s  HYPERLINK “”

So, Casey, it looks like we have come to the end of our show, is there anything else you would like to share with our listeners?

Casey Flaherty: My overarching theme is continuous improvement. We can all do better, including me, so we should do better, and at the end of every year we should be able to look back and identify concrete things that we measurably improved on and that’s not true for a lot of us. And I understand why we are so insanely busy, there is so much pressure and so many deadlines, and it’s hard to carve out the time, and that’s why the State Bars are so important, and CLE is so important because they give us that opportunity and they give us a path that they help us identify what those things are, and so, I am grateful to you for all that you do.

Tish Vincent: Thank you, thank you.

JoAnn Hathaway: Okay, well, we would like to thank Casey Flaherty for a wonderful program today.

Tish Vincent: And Casey, if our guests would like to follow up with you, how can they reach you or find you?

Casey Flaherty: Our website is  HYPERLINK “” My email is  HYPERLINK “mailto:[email protected][email protected]. I am also very active on Twitter, LinkedIn, writing. I am pretty sure that if you Google “Casey Flaherty”, I will be the first two pages of results, so, I am not hard to find.

Tish Vincent: Okay, well, thank you, Casey.

Casey Flaherty: Thank you.

Tish Vincent: This has been another edition of the State Bar of Michigan’s On Balance Podcast.

JoAnn Hathaway: I am JoAnn Hathaway.

Tish Vincent: And I’m Tish Vincent. Until next time, thank you for listening.


Outro: Thank you for listening to the State Bar of Michigan: On Balance Podcast, brought to you by the State Bar of Michigan and produced by the broadcast professionals at Legal Talk Network.

If you would like more information about today’s show, please visit  HYPERLINK “”, subscribe via Apple Podcasts and RSS. Find the State Bar of Michigan and Legal Talk Network on Twitter, Facebook, and LinkedIn or download Legal Talk Network’s free app in Google Play and iTunes.

The views expressed by the participants of this program are their own and do not represent the views of, nor are they endorsed by Legal Talk Network or the State Bar of Michigan or their respective officers, directors, employees, agents, representatives, shareholders, and subsidiaries. None of the content should be considered legal advice. As always, consult a lawyer.



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Episode Details
Published: February 15, 2018
Podcast: State Bar of Michigan: On Balance Podcast
Category: Best Legal Practices , Legal Technology
State Bar of Michigan: On Balance Podcast
State Bar of Michigan: On Balance Podcast

The State Bar of Michigan podcast series focuses on the need for interplay between practice management and lawyer-wellness for a thriving law practice.

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