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The Human Edge in Legal Tech: Scaling Smarter with AI & Empathy – Dan Sharp & Neil Weitzman – S9E09

On today’s Legally Speaking Podcast, I’m delighted to be joined by Dan Sharp and Neil Weitzman.

Dan is the President and CEO of Infoware, Word LX, where he understands for law firms, time and reputation is everything. As CEO, Dan helps law firms automate and simplify document creation to protect their brand.

Neil is the CRO of Infoware, Word LX and the founder of Weitzman GTM, a GTM advisory building efficient GTM motions resulting in full pipelines and recurring revenue through people, processes and platforms. Neil brings 25 years off learning with B2B SaaS, technology and data business – helping lead companies through different growth stages.

 

So why should you be listening in? 

You can hear Rob, Dan and Neil discussing:

– Challenges in the SaaS Legal Market

– The Importance of Human Connection

– Effective Go-To-Market Strategies

– The Use of AI in Sales and Marketing

– Change Management in Law Firms

 

Connect with Dan here – https://www.linkedin.com/in/dansharp1


Connect with Neil here – https://www.linkedin.com/in/neilweitzman/

 

Transcript

Dan Sharp  0:00  

You try and find three things within your business, it will ultimately make your business unique relative to others.

 

Neil Weitzman  0:07  

Timing is everything. We are laser focused. Yes, we have a great product. Yes, we are extremely proud about it, but our superpower is our people and how we work with others to find the right client, to talk to them, to answer their questions, to be responsive.

 

Dan Sharp  0:23  

What you can’t do is replace the people we truly believe we listen and it makes us different. I love that, right? That’s the DNA of our organisation.

 

Robert Hanna  0:34  

On today’s legally speaking podcast, I’m delighted to be joined by Dan sharp and Neil Weitzman. Dan is the president and CEO of infoware word LX, where he understands for law firms, time and reputation is everything. As CEO, Dan helps law firms automate and simplify document creation to protect their brand. Neil is the CRO of infoware word LX and founder of whitesman go to market, a go to market advisory, building efficient go to market motions, resulting in full pipelines and recurring revenue through people, processes and platforms. Neil brings 25 years of learning with B to B SAS technology and data business, helping lead companies through different growth stages. So a very big, warm welcome to the show, Dan and Neil

 

Dan Sharp  1:17  

Thank you very much, Rob, for having us. Yeah, hi. Pleasure.

 

Robert Hanna  1:22  

have you both on the legally speaking podcast. And before we dive into all the amazing work that you’re getting up to in and around the world of legal we do have a customary icebreaker question here on the legally speaking podcast, where coming to you first, Dan, on the scale of one to 1010, being very real, what would you rate the hit TV series suits in terms of its reality of the law. If you’ve seen it, I have

 

Dan Sharp  1:44  

seen it a number of years ago. I would say five, five. There’s lots of parts that are what I would think are very legitimate, but I have a hard time getting past that someone could actually practice law without having gone through the appropriate tasks, right? There’s just something about that

 

Robert Hanna  2:06  

you’ve justified your five. And yes, Neil, do you want to give

 

Neil Weitzman  2:11  

to school? I’d probably agree that it’s not anywhere close to a 10, but my reason is going to be just because there’s not that many beautiful people in the world, and everyone in suits, other than, I forget his name, other than the one lawyer. Everyone else beautiful men and women. So I’m going to say that is not normal in most, at least in the world I live in.

 

Robert Hanna  2:34  

Well, there we go with that. We’re going to move swiftly on to talk all about you both in the work that you’re doing. So to begin with, Dan coming to you again, would you again, would you mind telling us a bit about your background and career journey? Sure. Yeah.

 

Dan Sharp  2:45  

So I, I’ve got a bit of a mixed bag of a background. I spent roughly 10 years in corporate Canada working for a large photocopier company canon. Worked in sales, predominantly moved into marketing. Loved it, learned some really good skills from there. I decided that I wanted to do something on my own, and bought and ran a logistics business for roughly another 10 years. And then roughly 10 years ago, I bought infoware with a partner, and we have both a managed service provider and a a software business, absolutely.

 

Robert Hanna  3:24  

And we’re going to get more into that a little bit later on. But Neil, would you mind telling us a bit about your journey and how you both

 

Neil Weitzman  3:30  

ended up here? Yeah, for sure. And thank you for the question. This is going to be fun. Yeah, I’m getting old these days, Rob, as if you couldn’t tell so I’ve gone around the block a few times, on different things. Grew up in the corporate world, large companies. Spent some time at like a large telco, big data company, Deloitte, for a little while, the last five or six years of my career and life have been maybe the most rewarding of all. I am generally what we now call kind of a fractional CRO, and spend a lot of time with a limited amount of incredible companies that I’m passionate about and really ingrained in. And word LX, which I’m sure we’ll talk about a little bit later, is one of them with Dan. And I love what I absolutely love what I do, and it’s really rewarding, and I get to add some value and learn from incredible CEOs like you, like Dan and people like you Rob. So love what I’m doing, and really big, important part of my career at the pop moment, yeah,

 

Robert Hanna  4:29  

and I’m right back at you, and I think that’s one of the beauties. You know, people say, Wow, you’ve done so many podcast episodes. You know, you’re not tired of it. So absolutely not. Every time I learn, I pick up some nuggets of wisdom. You get some inspiration. You learn a new strategy, you get inspired by a story, and it’s just amazing. But, you know, and one of the things we try to pride ourselves on the show is just just being real. And you know, the SaaS space right now is a tough market out there, maybe even tougher in the world of legal tech. So can you talk about what you’re seeing out there, very high level? And Neil, perhaps, let’s go back to you to start.

 

Neil Weitzman  5:03  

Uh, the basis, or the most important thing we might talk about today, because everything bases off of what’s going on in the marketplace. It’s, it’s one thing to talk about your individual business and product, but we all live, we don’t live in a silo. We all live in this, you know, quote, unquote, marketplace we’re in, which is the greater business world, the SaaS world, and more specifically, the legal tech SaaS world. And so yeah, it’s a really, really hard market. I would suggest it’s harder than it’s ever been in many ways. And while some things are easier because of the amazing technologies we have, it’s also led to this incredible noisy environment for and I don’t know it’s just, it’s not just legal tech, of course, but legal Tech’s a part of that. There’s, you know, even five years ago or 10 years ago, there was, you know, billions of emails being sent. We’d all get 80 or 90 emails in our email box. Just use emails as one example, and now it’s 1020, 30% more than it was even a few years ago because of the proliferation of emails. Again, just using that as an example. So of course, the hardest part for any company, but especially smaller ones, is, let’s call it the share of voice, or how do you even get noticed? Whether it’s an email or a cold call or an ad or a LinkedIn post or a podcast, whatever it may be. You know, when you’re the small guy or the smaller guy, you’ve got to do things to stand out and be creative and unique. And that’s easier, easier said than done, of course, because, you know, we all think we’re creative and unique. Who doesn’t think that? But of course, you got to find the ways to stand out in a noisy, noisy world. And

 

Robert Hanna  6:50  

I agree, and you know, we were in the attention economy, and I talk a lot about in some of my keynotes that I’ve given. You know, awareness times attention equals income. The more you can increase that visibility, the more that you can get that awareness as your top of funnel to then get that channelled attention from your ideal avatar, the more that eventually will lead to that. I’d love to come to you to pick up your thoughts from a sort of high level perspective as well, on the SAS space linking it to legal tech. Dan, what would you build on from what’s been shared there?

 

Dan Sharp  7:15  

It’s it’s a fascinating time, right? And I think you both touch on some really interesting points that it’s highly competitive. It’s more competitive now than it’s ever been. It’s shifting rapidly in terms of what works and what doesn’t work, things that you know, approaches that worked even 612, 18 months ago, not nearly as effective today as they as they were before. And so I guess there’s two ways to look at it. One is that, you know, for some people, they’d look at that and go, Man, that just makes it that much more challenging. The flip side, though, is if you can embrace the change, if you can look at new methodologies, look at different approaches. If you can use things like AI to assist with the different approaches that you’re taking, it can make a huge difference, and you can get out in front of that. So, you know, we’re certainly very excited. I talked to a lot of different peer members from various peer groups that I’m part of who are in the SAS space, not necessarily legal, but just other SaaS businesses. And I’d say the general consensus is that, yeah, it’s changing, but changing for the better. And

 

Robert Hanna  8:29  

look, the only constant in business is change. And you know, the word that I keep hearing a lot about is adaptability. You know, you need to be able to adapt and get that right fit. So I’d love to stay with you, Dan, because you touched on it a little bit high level around infoware. But you know, word LX is the ultimate legal document template management system that really includes powerful formatting tools. And I’m a big fan of this, as you know. But can you tell us a little bit more about info word LX and the story behind it, how it began, and then maybe Neil, you can come in to sort of how it’s all come about, and some of the things you’re getting up to. So we,

 

Dan Sharp  9:03  

we’ve been around more than 40 years. Infoware started back in 1981 so 4044, years now. And it’s a fact, I think it’s a fascinating story. You know, Neil alluded to the fact he’s a little bit older. I’m even older than Neil. I can relate to what I’m going to suggest here, and that is that the way that word Alex came about was back in the 80s and early 90s. A lot of law firms were struggling to migrate from Word Perfect to word I’ve heard it many, many times. Word is for amateurs, Word Perfect is for pros. And if you think about the legal industry, they are pros at what they do as it relates to this idea of drafting and editing documents. And word was not created for legal professionals. We can all agree on that word’s a great product, just not designed for for legal professionals, so that that literally is how. Infoware started, and the the founder his he had a family member who was at Ogilvy Renault, which is now part of Norton rose Fulbright, one of the largest law firms in the world. And they had a problem trying to get people to migrate from Word Perfect to Word and so he created some scripts to help lawyers and legal professionals use word more effectively, more efficiently, and then word spread went from one firm to another to another. Now hopefully it caught that I said the word script. It wasn’t software at that point in time, right? And so info has been on a long journey, as I’m sure many others have, where we moved away from this highly customised version of scripts to true enterprise software, and that’s where we are today. We’re true. We play. We deal exclusively with law firms. That’s that’s our bread and butter. We deal our ideal client profile is in that roughly 150 200 user on up to a couple 1000 or more users, but just in legal, that’s it. That’s where we play. And as I said, yeah, we’ve been around a long time and and we have a lot of experience where you have clients all around the world. We are incredibly we have a strong, strong, strong presence in Canada. We’re a Canadian based company. You could walk downtown Toronto and point at buildings and go, we’ve got 10 clients here. We’ve got 15 clients here. Type thing like, that’s, that’s the type of market presence we have in the Canadian market, yeah. And

 

Robert Hanna  11:35  

it’s hugely exciting. And I want to come to you, Neil, a bit about the sort of journey, because you touched on, obviously, your CRO across a few different organisations. But how did it come for you to sort of land with word LX, and what was it specifically that attracted you to what they’re doing?

 

Neil Weitzman  11:49  

Well, I mean, it goes without saying that Dan attracted me to come work with word LX, but no, I mean, listen, when I agree to work with companies. It’s not a it’s not me selling myself. It’s Is there a fit? And it’s my engagements with people like Dan. Is true? True relationship based. And the reason I bring that up is it’s similar to how word LX relates with their clients. We don’t, and I’ll say me versus word LX. When word LX goes to market with their clients and prospects to hopefully turn them into clients, it truly is a fit. It truly is. We’re not just throwing software on the wall and hoping someone wants to buy it. It is. Is there a good relationship here that this company can work well with us, that we can support them with all our abilities and do a good job. We’re not big enough to where we can just take on a million clients and think that some like we want it to be highly engaged, highly valuable, great customer service. And so I suggest we’re pickier than the clients are. We’re making sure that this customer sitting in front of me is a really good fit for our business, as much as they’re saying is this software that’s going to work for us. So that’s really important, and that’s how I work personally, when I find the clients that I work with, like Dan, and the beautiful thing, without trying to tear up here, is Dan and I have become friends, right? And that’s to me what an incredible relationship is. Like, I’ve got a job to do. He pays me to do a job, just like any employee, you know, but the relationship is wonderful, and that’s what makes it really, really special,

 

Robert Hanna  13:36  

yeah, and I’ve always taught very early on from a mentor that contacts are good, but it’s the relationships that pay. The more you can sprinkle value on those, the more you can go deeper into those organic relationships and grow together, the more that you get from that. It’s just profound, and I guess that leads nicely onto the journey. Dan, obviously you’ve done some smart recruiting. You’ve done some smart, you know, thinking in terms of legal, technology space, but, um, you know what makes your firm specifically so unique for the world of legal and what you most proud of in terms of the journey this thought, we

 

Dan Sharp  14:07  

use a system called the Entrepreneurial Operating System, Eos, yep. Okay, so you’re familiar with the Entrepreneurial Operating System and and one of the exercises you go through is you try and find three things within your business that will ultimately make your business unique relative to others. So let me share the first two, and you’d say, and rightfully so, that I don’t think that really makes you too unique, okay? And the first one is this idea that we have a profound knowledge in the legal space, okay? Fair enough. Like, that’s good. That’s what people would want. But that’s not a differentiator, in my mind. The second is that we provide peace of mind. So when we think about the firms that we work with, that’s incredibly important, they want peace of mind, right? You think about the change they need to go through, and. Order to work with someone like us, they need peace of mind. Again, I’m not sure that’s a differentiator, but the third one, in combination with the other two, I think, is really a differentiator for us, and that’s the idea that we listen. We listen. And what do I mean by that? When we work with clients, we truly listen to what it is that they need, what they’re looking for, how they’d like things done. If we can do it, we will do it. This is not something that started with me 10 years ago. This is in the DNA. This is in the fabric of infoware. I couldn’t get that out of our company if I wanted to. That’s how deeply rooted it is in the team. It literally has passed from person to person to person and it and what’s interesting about this is, when we first were going through the exercise, that was not one of the ones that we identified as a leadership team. This just happened organically about three or four years ago, where people on our team, Frontline, people brought it up and said, Hey, look, we truly believe we listen and it makes us different. I love that, right? I love that. That’s the DNA of our organisation, seen, heard

 

Robert Hanna  16:15  

and valued and truly valued, you know? And that deep learning and, yeah, absolutely. And I love that framework, and I’m running an event later this year with a great big legal offsite, and we’re partnering with strategic coach, and I’m a big fan of, you know, their headline sponsoring that, and I’m a big fan of Dan Sullivan as well, and his book 10 times easier than two times. And that level of thinking, I think that’s all really smart. And again, the way that you’re leading the organisation by really putting being client centred to another level, I think, is absolutely for the whim, particularly in the age of AI, when so much is going to be automated. And, you know, where is that human touch, where is that advisory lens, that trust being built? It’s going to be at the top of that pyramid where, obviously, technology is filling up a lot of that kind of process, that is exactly where you’re going to win. So I love that insight. Okay, we’d like to you, Neil, on the challenging side of cold outreach. You know, if we look at the market and sort of go to market strategies, you know, it’s getting harder. You know, AI is definitely making that more and more saturated. So you’re requiring more attempts, yielding fewer quality conversations, seeing a decline in responses. So what innovative go to market strategies are SaaS companies using to be successful, particularly in 2025

 

Neil Weitzman  17:26  

Yeah. I mean, geez, this is a question that’s going to get me talking for hours, and I know we don’t have hours, so I’m going to try. I’ll try to be sure. I won’t go too deep on AI right now, because I think maybe we’ll talk about it later. But AI is a topic unto itself, and how to use it effectively, and so on. But I do agree with you that cold outreach has become significantly harder. I still believe cold outreach can be effective. It is still and when we say cold outreach, I think it’s important to define it normally. I think most of us are talking about cold emails, cold calling, maybe some cold LinkedIn, DMS, things like that. There’s probably other examples, but those are the most common. I believe very, very strongly that those things can still work. Are they gonna work at the same effectiveness rates and open rates as we saw years ago? Likely not. And I know a lot of people, and there’s data out there that proves that point. But that doesn’t mean it can’t still work. It’s still cost effective to do emails. It’s just how do you make them really, really relevant? Timing is everything. How do you send an cold email to the right person at the right time when they have a problem in a way that they might notice it and resonate with the message, so that they reply, and that’s where technology and AI can come in to help you identify those times and the right type of messaging and so on. So I believe deeply in cold outreach still, but acknowledge it is 10 times harder than it ever was before. So therefore, where do you do? Well, there’s lots of things and just a list a few. Each of these needs experimenting, because every company is different, and what might work for Company A is not the same as might work for Company B, because of superpowers, ICP, etc. But there’s things like what I refer to as warm before cold is where? How do we focus on the things that are have a you know, well, that are warmer than they are colder, and that comes from things like customer referrals, relationships, connections that you already have, and this whole area of signals and triggers, which comes back to technology, how do I identify that Sally, the CEO of company X, you know, has done something in the digital world that makes me believe she may be warmer than a cold person, and it might identify that as an opportunity for me to reach out because she checked out my website or she read my link. In post about a certain topic, and so there’s certain ways to leverage this information to prioritise warm people over cold people. Maybe I’ll stop there, because I could go on forever on that,

 

Robert Hanna  20:12  

no, but you’re talking my language. You know, I always say work warm. Who do you know? Who can introduce you to someone you don’t know? That is my definition of working warm. And it’s just that it’s worked for the generations of time. And you’re right in terms of test, test, test. You know, you continually even us from like a podcast. And going back to your point, actually, I have a live example of getting into the minor details of knowing your avatar. So I have a legal recruiting business. A lot of listeners will know, I know one particular partner is a transactional lawyer. Is very busy. He doesn’t want to hear from me between the hours of nine till probably 7:30pm because he’s just got too much going on in his world. So I know if I need to hit them with some product and something that’s useful, then I need to hit them probably at like 8pm when they’re having a bit of downtime. They’re probably not had a chance to catch up with the news. So I can use things that are relative to them, that’s been going on in the world of affairs, that might be valuable for them, and hit them at a time point where they’re most likely going to be having that downtime, so it’s received. So to your point about understanding timing, understanding the quality, the content, and again, this links nicely to what I’m coming onto with you, Dan, and quality will still rise to the top, even in an AI world. So it sounds like you’re very focused Dan on this quality over quantity perspective. So how are you both making sure that you qualify the prospects effectively not to waste their time and indeed your precious time? Yeah, great

 

Dan Sharp  21:33  

question. So, so let’s start with the premise that you can only work on so many deals at any point in time. Yep, right. Like our, our team are responsible for generating opportunities and managing the opportunities. And we like to think in sort of 5050, ratios, 50% of your time generating opportunities, 50% working opportunities. The reality is, when you break it all down, that leaves you maybe 20 hours each week to be able to manage the opportunities Well, you got to be pretty selective in terms of who you’re working with, because, again, as I talked touched on, we deal with large law firms. Those are our clients. They do not come in and say, on a Monday, hey, we’re interested in your solution and buy on a Thursday. It can take months, and so we’re incredibly selective, and we do that by asking questions. And quite frankly, these are not difficult questions. It’s just being direct and asking the right questions, like, what are you looking for? Why are you looking now? What problem are you trying to solve? Like, pretty basic stuff, but asking the questions to make sure that if the Fit isn’t there, which Neil touched on earlier, if the fit’s not there, move on. Do them a favour. Do yourself a favour. Just move on. If it’s not a good fit, move on.

 

Robert Hanna  22:58  

Don’t waste energy on that. And I always know a lot about and I’ll come to you in a second, Neil as well. I second, Neil as well. I know you want to build 

 

Robert Hanna  23:07  

You know, I always coach people very early. And your first question was an open question. You think of questioning as a funnel. You’ve got your open question right at the top, you know, what are your thoughts or what are you looking for? Tell me, describe to me. Then you have your direct questions, which you naturally moved into. Then you have your closed yes or no. And anyone skilled will be very good at starting with those open questions, to get them talking to them, move to direct to then close them on whatever the next course of action would be. And like you said, it’s not going to be a sale there. And then it’s like maybe agreeing to a follow up. It might be agreeing to a demo, it might be agreeing to an introduction, whatever it may be. But yeah, I love that insight, and it’s exactly what I teach people. Neil would love to come to you to chime

 

Neil Weitzman  23:40 

Yeah, sorry. I was itching to get in on that one. That was a good one, and Dan said it, but I use three questions. I mean, we all talk about the word discovery and making sure there’s a fit. And every company should have their list of kind of fit or discovery questions that they need to go through without making it an interview. But it’s about talking and building a relationship and seeing if there’s a fit for me. And we have a list of a whole bunch of things we’d like to learn, but the three most important, and the three that sum it all up, are and Dan kind of alluded at this. Why anything? Why now? And why us? And if you do not have definitive, clear answers to that you shouldn’t be moving forward in any kind of deal or working thing. The second point I would just make on that is every, and I hope this comes off the right way, and Dan doesn’t fire me after this, every every company has great product right now, not every company, but many organisations in our industry have wonderful products, pros and cons to everything. Nobody’s product is perfect. It depends who you’re talking to and what they’re what they like and don’t like. Back to the word fit. To me, the biggest difference of where companies today and tomorrow will. Will thrive is being great at the go to market strategy. It’s being responsive, being awesome, being knowledgeable, being friendly, being someone who you want that the prospect wants to work with. Sadly, I think in this crazy, noisy world, media mediocrity has kind of taken over, and there’s so many companies out there not doing a great job at managing the sales process or responding or providing good customer service, we are laser focused on our superpower. Yes, we have a great product. Yes, we are extremely proud about it, but our superpower is our people and how we work with others, to find the right client, to talk to them, to answer their questions, to be responsive. Rob if you ask a question, we want to respond in minutes, ideally, and not make you wait for 48 hours. So anyway, I just wanted to mention that that’s where I think, is the difference maker in today’s market

 

Dan Sharp  26:03  

mind. If I chime in, yeah, go for it. So I was, I think you asked the question. I’m not sure I answered it previously, but it ties in beautifully with what Neil said there, and that is what I’m most proud of at infoware. Are people full stop. I’m a huge proponent of Patrick Lencioni and his work and talking about things like the ideal team player and The Five Dysfunctions of a Team and the mistakes that CEOs make, etc. And I think he nailed it. And that is that look, I can I can mimic your technology to a certain extent. I can mimic or we can mimic technology. We can mimic processes. We can do a lot of the things that you can do or others can do, and vice versa. What you can’t do is replace the people. It’s the people. And so with us, here’s what we subscribe to. We have this incredible culture of discipline mixed with a spirit of entrepreneurialism. So you’re disciplined, but you have the freedom to do things the way that you think they need to be done in order to have success. So we define what success is. We know where the goal posts are. We know what needs to be done, and then it’s incumbent upon the individual to use things like their critical thinking skills.

 

Robert Hanna  27:21  

Today’s episode is brought to you by Clio, the all in one legal practice management software designed to help solicitors like you save time, stay organised and deliver outstanding client experience. Clio is trusted by 1000s of legal professionals worldwide, offering a user friendly interface, seamless time recording, automated billing and secure cloud storage so you can manage your practice from anywhere. With Clio, you’ll get award winning support available 24, five by live chat, phone and email. So help is always there when you need it most. It’s no wonder Clio consistently receives five star ratings for its ease of use and top notch service. If you’re ready to experience a better way to manage your practice. Visit clio.com forward slash UK to learn more and see why Clio continues to be the go to choice for solicitors across the UK. Now, back to the show. I always say, you know, in this world and our listeners be sick of me saying it’s those vision and mission focused organisations that then give the power to the people to really feel their impact in line with that mission, so they can see they’re not just coming to do a job. They are helping go towards this North Star, and they seem seen, heard and value, and their efforts contribute to this flywheel and building the momentum. Now, I love that, and it’s so so true. All right, let’s talk about connecting with customers, because this builds nicely, and I say very regularly on the show, it’s not B to B anymore. It’s not B to C. It’s H to H. It’s that human to human connection people are craving. And even more so, to Dan’s point, it’s not, you know, in an AI world, let’s not underestimate the importance of pi. It’s that people intelligence echoing what you’re saying there, Dan. But what are the best ways Neil and to be human, to be creative, to truly connect with your customers. And how do you connect with them in the first place? And love some of your insights or strategies or hacks? Wow.

 

Neil Weitzman  29:13  

First of all, I’ll say, if I had the magic answer, then I’d probably be a billionaire, because that is the hardest part. And you know, it does come back to the old saying that timing is everything. And there’s data out there that any anyone could Google search that talks about, you know, on average, you know that how important timing is. And we try to get folk, we try to focus on that, but not get down on the fact that if we feel we wrote an incredible email, or did something creative to try to stand out, and the person, the lawyer, the IT, Director, what have you, on other side, didn’t respond. We’re trying to not to get down on that. It doesn’t mean we didn’t do a good job, and that’s hard. Sometimes we’re all human, like, Man, I’m working so hard. I’m doing such. Great stuff, but no one’s responding. We always have to remember that at any given time, only about 3% of the people we might reach out to have are looking for anything remotely close to what we have, and another 7% are even open to talking about it. So one in 10, you know, you even have a chance with realistically. So you got to keep that in mind number one, in terms of different creative ways. You know, I think we got to try different channels. I’m still a big fan of events, right? I’m still a big fan of doing things in person. If I’m standing there and Rob, Rob Hanna walks down the aisle at an event, I can walk up to rob and be human and say, Rob, I’ve been waiting to meet you. This is awesome. And if I’m a good person with a smile and something valuable to say, Rob is going to talk to me and remember me. And once he’s done that, then I can send him an email later and say, Hey, Rob, I met you. And he’ll probably respond then. So you know, I don’t think that’s anything unique or creative. Frankly, we’ve all been doing that for decades, but I think that remains as an incredibly effective way to do it. Sadly, it’s hard to scale that. I can’t be at 27 events for 1000s of people all the time, but we should be doing that as often as possible. And then you can get into different you know, let’s call it digital ways of standing out. Now, a regular an email is an email. I don’t care how well written a damn email is, it’s still just an email. But you can use a sense of humour. You can be human. You your email doesn’t have to be boring, stick in the mud. You can use cartoons tell jokes. I really believe and you need to understand your audience. But at the end of the day, I think we all worry too much about, well, this is a professional organisation we’re emailing, yeah, but they’re all human beings who go home at night and have either have kids or a partner and tell jokes and want to smile and want to laugh. I don’t care how professional, quote, unquote, they want to be in the office, I’m willing to bet nine out of 10 people, if I, if I could make them smile, they’re going to appreciate that. So maybe I’ll pause there. But there’s different ways to leverage humanity in a creative way, to stand out. And you know, being in a sea of sameness of I can help you solve problem x, and therefore you should email me back. That’s important, but that’s not the lead,

 

Robert Hanna  32:29 

And you can get me on my soapbox, talking for hours about this, and I’m gonna come to LinkedIn in a moment, but to reference that, but I think that the message I got from that is the event example is fortune is in the follow up, right? So you’ve met me at the event, and then you’ve gone that step further where you’ve probably then added something to that conversation. Hey, Rob, you mentioned you’re a Liverpool fan. I’ve seen those two tickets. Are you looking forward to that game, that the little touches are the big touches. Then you follow and you take that relationship to the next stage, and it moves forward and forward and look onto the point about everyone is human. I am a huge advocate for LinkedIn is the world’s largest professional networking site. If someone has said to you a decade ago, it’s going to move to an interactive site where there’s going to be a funny emoji if you can’t grasp at the work of World of Work is becoming more human. It’s becoming more let’s just bring our authentic selves to work. Because there’s been a mental health crisis, there’s been a burnout crisis, there’s been all of this stuff going on in the world, then you need to wake up. And I’m quite verbose about that, that I’m very much, let’s use Tech for Good, to actually improve our lives, to improve the overall well being of the workplace, and just drop the acts and bring our human selves and even off there we spoke. You said to me, how was my weekend? And you know, I said a very open thing about what’s happening to me personally, and personally and family wise, because I’m a big advocate for Let’s reduce the mask and just be our true self. So yeah, I’m gonna get off my soapbox, because, since you’re into you, but, um, it’s so true, and that’s why I’m a strong believer in community. But how coming to you, Dan, how should sales and go to market leaders, particularly in a SaaS approach like LinkedIn, create a real impact, and what are the best ways to build those authentic relationships and grow a community and turn those into meaningful opportunities?

 

Dan Sharp  34:09  

Yeah, great question. I’ll answer what I do, and then I’ll turn it over to Neil, and he can tell you maybe the right way to do it. I take, I take a slightly different approach than most people. I consider myself incredibly fortunate that I’ve had what I would deem to be a pretty diverse set of experiences in the working world and Rob, I gotta tell you, I’ve made more mistakes than you could possibly imagine, a lot of but, but what I do like to do is mimic, look at study other people, see what works, and learn from them. What I’m absolutely passionate about is this Go Giver mentality of trying to give back to others. So if you look at my LinkedIn posts, has nothing to do with selling zip, zero, zilch, never what I try and do. Share some of my experiences, what are some of the things that I have learned, that I have seen, the mistakes that I’ve made, and how I’ve tried to overcome them, and quite frankly, the end game there is if I can help one person avoid a pitfall that I went through that makes my day. I know that doesn’t really answer your question. And some people say, Well, how are you getting sales from that? And it’s like, that’s not my point. I’m not trying to do that full stop. As I always

 

Robert Hanna  35:26  

say to people when I’m coaching on LinkedIn, if you want to reach teach, right? And you’re sharing lessons there, you’re building a personal brand. And, you know, I run a legal recruiting business, I can guarantee you can go and look at the last four years of posts I’ve probably posted once that I’m hiring for a vacancies. It’s not my jam. It’s not, you know, hey, come and come and apply to this vacancy. I’m sharing thought leaders. I’m collaborating with people like yourself, solving problems to my end user at the end, but sharing stories, wisdom, building thought leadership and teaching, because then you build trust, and then you can convert it. So I love that insight. I absolutely love it. Neil, would love for you to come in and share some of your thoughts, particularly in legal as well, because, you know, we want to kind of double down on the fact that it is a tough space to stand out.

 

Neil Weitzman  36:11  

Yeah, I don’t. So I agree with everything you guys are saying on LinkedIn, so I’ll try not to repeat it. I’m equally, or just as much or more passionate about the power of LinkedIn to build your brand. And your brand is not just personally, but it’s related to your company, especially for a Dan sharp, who’s the CEO of the organisation, and so for not to turn this into a big LinkedIn learning session, I’m all on board. I truly believe in that. I don’t think legal is any different. I’ve talked to a lot of people, though, who are like, Well, my lawyers aren’t on LinkedIn as much, or if they are, they’re not paying any attention, or they’re and and I grant that, of course, let’s just say the average lawyer probably is not on LinkedIn, or is active on LinkedIn as much as you know, B to B sales person who is like spends half their life there. So granted, there’s differences based on personality. You know, job, personality industry. However, guess who is on LinkedIn? That lawyer’s best friend, that lawyer’s neighbour, that lawyer’s employee, any number of people, right? I think when you get caught up in the I’m not gonna spend time on LinkedIn, because the managing partner isn’t really active on there. You know, I think that’s a huge, huge mistake my job, or any of our jobs, is build our brand, add value, build relationships, and people are going to see it. It takes time. This is not a paid ad you’re running that is designed to fill out a form and get leads. This is brand. This is who am I? What do I stand for? What do I want to be known for? And if you do that in the right way, long term and consistently, it will start to pay off in a big way. I believe that deeply, almost irrelevant of what industry we’re talking about, almost

 

Robert Hanna  38:14  

Yeah, and look, I love that point, because you’re going to have your influences, and you’re going to have certain people that can make that decision maker, that end decision maker here and know about you through being visible, being out there like you say, people are going to see you. They’re going to build that trust. And then, hey, this, this, this is really interesting, actually, or they’ve been sharing insights for last three or four months. Maybe we might be worth to reach out to them. So just

 

Neil Weitzman  38:38  

one more quick thing Rob on that is, and you could start to see what, at least a proof point of what I’m saying. You’re starting to see more, because we’re starting to see posts and ads and sponsored posts in your feed from industries and companies that would never have thought about it even a year ago. Let’s call them like electrician companies, plumbers, things that, of course, you wouldn’t normally relate to a B to B Mark platform that is like SAS world, and they’re doing that because, yeah, I’m a CRO but guess what, I have a house. I need a plumber, I need an electrician, I need these things. And so all these industries that you wouldn’t normally have thought about are realising that what we’re talking about is true and it can make a difference for them.

 

Robert Hanna  39:31  

And so powerful. And you become top of mind. That person becomes top of mind when you need that plumber. And you know, and it comes back to what was saying before about being adaptable and changing to the environments and the way you go to market, the way you think about things. It’s not like it was years and years ago. You know, there’s not many plumbers necessarily going around leafleting like there would have been years ago. They’re going to digital. They’re understanding where their end consumers or potential consumers are. So I love that. Nick would love to stick to you around sort of AI driven sales taxes, because I do think AI use well. Is phenomenal, and I think it’s going to change the game for good. But obviously there’s going to increase automated messages emails, and they’re going to become more and more common, and there is going to be a spam part of it, so many people are going to be hugely turned off by that, if not already. Let’s be real. So how should SAS companies rethink their sales approach, and what strategy should they use to create real engagement with buyers?

 

Neil Weitzman  40:23  

Yeah, great. So first thing, I don’t think this is just SaaS companies, all kinds of companies, traditional industries, insurance companies, are all trying to figure out how to leverage AI to be smarter, better, faster. I think a couple quick comments, and we can either dive in or probably run out of time. So I’ll just keep it high level is quality over quantity. Just because we use AI doesn’t mean you should scale. You know, as I heard someone on LinkedIn Post this morning say, I love the line. Shout out to Jonathan Moss, be careful not to use your AI to scale garbage quicker. In other words, if you if you haven’t focused on the quality aspect of your brand your message, then all you’re doing using AI is moving quicker and faster and more efficiently with crap. And that’s not the purpose. So just because we use AI, we should never, ever, ever forget that Quality comes first. What is our message? What do we stand for? What do we say, and are we relevant? That cannot change no matter what technology we use. And there’s all kinds of past technologies that led to this. AI is just the new version of you know, I’m being very simplistic, but I used to use templates. I used to use sequencing. I used to use tools like outreach and sales loft to move do emails faster. These are all ways to scale garbage quicker. AI is the next one. If you haven’t focused on the quality aspect, that’s number one. And then number two is, I think we forget. And many people think AI is like a SaaS product. I buy it, I press a button, and wait a second. Why is this not working perfectly, and why does it have all these problems? And my analogy to this is it’s like my five year old kid. By the way, my kids are way older because I’m old. But the analogy of if I had a five year old kid, it’s like my five year old kid, they’re brand new. They’re just learning. He’s just walking, he’s just figuring out how to do things properly. That’s where we are with AI. The amazement and the power and the capability of my five year old kid is like, holy cow, just wait till this kid gets older and he’s gonna crush the world. And I believe that’s the same thing with AI, but if I don’t spend the time, I don’t care what AI product you’re buying or using. It could be an aisdr, a BDR system, a customer. I mean, there’s lots of use cases, but if I don’t spend the time the same way as I do with a human onboarding, the AI, training them, learning about its capabilities, the pros and cons, the watch outs, it’s not perfect. And respectfully, even the company selling AI are still learning about what to do and what not to do and its power. And so you gotta spend the time training the AI the same way as you would spend three four months training your new human. BDR, there’s no difference there. And if you skip that step, your expectations will be out of whack, and you will get pissed off and you will screw up. And I’ve been there and done that, and I’ve seen these mistakes happen, and still see them, and that’s because I didn’t know what I didn’t know either when I first started using these tools, but Dan and I as an example, are learning really, really fast, and it’s super exciting, but your mind has to be in the right place that this is a learning experience for everybody, and how do you leverage it to just to be a little bit smarter and better and faster with an eye to quality.

 

Robert Hanna  43:53  

So well said. And you know, I use, as a business owner, three Ds when I think of AI, it’s firstly due diligence, doing the due diligence like you’re referencing then, then it’s number two is the data. There’s quality of the data that it can build or not. And the third piece is, then, is discipline. So the more disciplined you can be with the implementation and ensuring, and if you can remember that three Ds, I think you can be, you know, super powerful, but you can’t shortcut any part of those processes today. And Dan would love to come to you before we close on terms of law firm barriers, there’s quite a few. But what are the barriers law firms face when adopting new technology, let alone what they’re currently using?

 

Dan Sharp  44:31  

Yeah, I think that the biggest one is the change management piece without question. You’re right. There’s lots of barriers. That’s the big one, right? You’re dealing with lots of people. They’re incredibly busy. The billable hour has not gone away. So what we find is you have to convey whatever your solution is, that it will be simple, easy and quick if you can’t do those three things, anyone. Of those three things, it makes it incredibly hard in order for them to make that transition.

 

Robert Hanna  45:05  

And again, I’d speak very openly on the show, if you confuse people, you lose people. And you know your your job is to try and reduce friction. You know there’s this friction and there’s pain points. The more that you can create fusion, rather than confusion. Actually reduce that friction, the more successful you would be. This has been an absolute masterclass, as I knew it was going to be. I’ve really, really enjoyed today. If our listeners want to learn more about either of yourselves or indeed, word Alex, where can they go to find out more? Feel free to share any websites or social media handles. We’ll also share them this episode. Do you want to give them a shout out? Neil, I would.

 

Neil Weitzman  45:39  

Yeah, sure. Thank you very much. And yes, thank you. I guess I would just say, to keep it simple, is as we heard and we talked about, Dan and I both are on LinkedIn. It might be the easiest place to remember. So please just look us up and connect with us and tell us you heard us on Rob’s show, and that’ll be an even more of an impetus for us to connect. So that would be one way, and that’s great, because then we can engage with you there. And if your post, if you post, we’ll like your posts, and we’ll comment and we’ll we’ll be friends there too, but from a website perspective, which, of course, is still, you know, our digital face, if you will, pretty straightforward. Www, infoware group.com, so please check us out there, or just send us a note and we’d love to chat.

 

Robert Hanna  46:23  

Awesome. Well, just leaves me to say, thanks so much. Once again, Dan and Neil, it’s been a pleasure having you on the legally speaking podcast sponsored by Clio. But from now, from all of us on the show, wishing you lots of continued success with indeed your current pursuit and indeed future ones. But for now, over and out, thank you for listening to this week’s episode, if you like the content here, why not check out our world leading content and Collaboration Hub, the legally speaking club, over on Discord. Go to our website, www.legallyspeakingpodcast.com. For the link to join our community there, over and out.

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