COVID-19 Resources for Lawyers
Featured Guest
Casey Cheshire

Casey is the founder and visionary of Cheshire Impact, as well as the creator and host of the Hard...

Your Hosts
Gyi Tsakalakis

Gyi Tsakalakis founded AttorneySync because lawyers deserve better from their marketing people. As a non-practicing lawyer, Gyi is familiar...

Kelly Street

Kelly Street is the Marketing Director at AttorneySync, a trusted legal digital marketing agency. With almost 10 years in...

Episode Notes

A lawyer only has so much time in the day and that time is best used in the service of clients, so why are lawyers instead stuck devoting so much time to marketing? Automation of marketing campaigns can lighten the load. Gyi Tsakalakis and Kelly Street talk with digital marketing expert Casey Cheshire about his three-pronged approach–capture, nurture, and automate–that shows lawyers how to simplify intake and develop client relationships through automated processes. They also discuss how marketing automation yields better reports, helping lawyers get a clear picture of which tactics are most profitable for their firms. 

Check out Casey’s new book, Marketing Automation Unleashed: The Strategic Path for B2B Growth

Casey is the founder of Cheshire Impact and the creator and host of the Hard Corps Marketing Show.

Special thanks to our sponsor Nexa.


Lunch Hour Legal Marketing

Marketing Automation: A Primer for Lawyers on Smarter, Simpler Marketing



Gyi Tsakalakis: Kelly.


Kelly Street: Hey Gyi.


Gyi Tsakalakis: What’s going on?


Kelly Street: You know, not too much, not too much.


Gyi Tsakalakis: Are you setting it on automatic?


Kelly Street: Wait, what? Are you talking about my Nest?


Gyi Tsakalakis: Oh, let’s talk about your Nest.


Kelly Street: Let’s talk about my Nest and how it doesn’t work and I am cold.


Gyi Tsakalakis: What is the temperature outside right now for you?


Kelly Street: It is 15 degrees, a balmy 15 degrees.


Gyi Tsakalakis: What’s the temperature inside?


Kelly Street: 65, which is too cold.


Gyi Tsakalakis: Is that — are you comfortable? Too cold?


Kelly Street: Yes. I know some people believe that 65 is a prime household temperature, but I am a 70-72 degree person.


Gyi Tsakalakis: That’s very efficient of you to keep it at 65.


Kelly Street: It’s not my choice. The Nest does not like me, it prefers my spouse.


Gyi Tsakalakis: I see.


Kelly Street: We all have our favorites and the Nest has their favorite.


Gyi Tsakalakis: So the Nest adjusts to your husband’s temperature preferences?


Kelly Street: It adjusts with his phone and when he leaves the house, it thinks that there is nobody here and so it automatically goes down to our daily temperature.


Gyi Tsakalakis: Which is very interesting and also topically relevant to today’s episode.


Kelly Street: Really? How does my Nest have anything to do with Lunch Hour Legal Marketing, Gyi?


Gyi Tsakalakis: Because we are talking automations and if you get your automations wrong, you might be sitting in the cold.


Kelly Street: Oh my gosh, that’s so good. You are one clever guy.


Gyi Tsakalakis: Boom.


Kelly Street: Well, after Gyi’s cleverness, let’s just roll into the episode. Here is our interview with Casey Cheshire.




Intro: Welcome to Lunch Hour Legal Marketing, with your hosts Gyi Tsakalakis and Kelly Street, teaching you how to promote, market, and make fat stacks for your legal practice, here on Legal Talk Network.




Kelly Street: And welcome to Lunch Hour Legal Marketing. Before we get started we want to thank our sponsor, Nexa, formerly known as Answer 1. It’s a leading virtual receptionist and answering service provider for law firms. Learn more by giving them a call at 800-267-9371 or online at


Gyi Tsakalakis: Kelly, how are you today?


Kelly Street: Hey Gyi. I am so good, ready to talk MA, not martial arts.


Gyi Tsakalakis: MA, mergers and acquisitions.


Kelly Street: Yes, yes sir, that is exactly correct.


Gyi Tsakalakis: We cover all of the serious stuff on this podcast, but seriously, we are actually not talking about anything. Well, it’s pretty serious.


Kelly Street: It’s kind of serious.


Gyi Tsakalakis: You think it’s serious? I think it’s serious.


Kelly Street: Yeah, serious business.


Gyi Tsakalakis: Without further ado, I will welcome our guest Casey Cheshire from Cheshire Impact.


Casey, tell these good people that are listening to this podcast a little about yourself.


Casey Cheshire: Oh my gosh. I am so happy to be here. All I could do not to laugh during that intro. I have loved listening to this show and talking to you all, so great to be here.


Like you were saying, my name is Casey, Casey Cheshire from Cheshire Impact and what we do is we help organizations with their marketing and sales automation, their marketing and sales technology.


Gyi Tsakalakis: Awesome, which many of our listeners, maybe some of them don’t, but many of our listeners I know, because they tell us, are in desperate need for some expertise in this area. So we are excited to dive in to today’s topic, Marketing Automation.


So I know we have some canned questions, but what the heck is Marketing Automation? I was at this conference recently and a lawyer stood up there and said, watch out, there is a new buzzword out there called Marketing Automation and I was like, number one, it’s not that new; and then number two, why are we so scared of it? They had a total misunderstanding about it.


So why don’t we hear from a true expert how would you describe or define Marketing Automation?


Casey Cheshire: Well, whoever said it wasn’t new; if that was you, you are correct, it’s not new; in fact, I have been working with it for about ten years now and it has changed the shape of marketing campaigns, companies, even careers by actually using this technology, so it’s not a new thing. But for a lot of folks who haven’t adopted it, it may seem new, and it’s definitely something to get on, especially before your competitors get on it.




And when it comes to talking about what is this thing, I like to start with just saying look, your time is important, whether it’s a billable hour or just the fact that you have limited hours in the day, human time, especially the boss, especially the high rollers, your time is limited and it’s valuable. And so you want to use that time as best as possible. And whenever possible, you want to use a computer, use automation to do those tasks that can take on the heavy lifting around marketing, around sales, around getting the messages out, around nurturing your potential buyers, your potential customers, potential clients, doing that work for you, so that you can free up your time to do what you are getting paid to do.


And so when it comes to what does Marketing Automation do, there are just a couple of simple words. I like to boil it down to capture, nurture, automate, and I added reporting in there. But that’s how it was first explained to me back in the day when I first bought the tool.


I like to use this tool called Pardot, but there is a lot of different ones out there. And the capture very simply is, you capture more leads, you capture more clients, potential clients off your website.


So you have got a site out there and sometimes that form is really long and no one likes to fill out a 12 field form. So if you have got one, there is things you can do to improve that. Every field you get rid of on your form increases your conversion rate from anywhere from half a percent to several percent points; that means more people filling that thing out just from asking less questions. And so these forms will dynamically adjust to be as small as possible, so you will get as many people filling them out as possible. That’s the capture side.


And then on the nurture side, I don’t know if you have ever had this where someone says, this sounds great, I think you can help me, I think we should work together, but something, right? I have got to do this. I have got to call this other person. I have got, I don’t know, some kind of excuse it sounds like and you are not sure are they being polite and brushing you off or do they really want to talk.


And so maybe you set a reminder to call them in six months like they asked, but sometimes, they call this the danger zone, sometimes people are ready to go three months later, even though they said six months, it’s three months later. And what happens? There is no obligation to call you back. They may do their research, find your competitor, call them back and start doing the shopping with them. And then you call them six months later and they say well, we already signed up with another group, sorry, right? So this is the danger zone.


So nurturing helps with this. Nurturing is simply maybe that email you would be sending out yourself manually, just checking in with someone; happy holidays, Thanksgiving is coming up or already past, whenever you are listening to this, just a quick little check-in. You can automate those check-ins. You can automate those little emails that are friendly. They are not salesy. You are not trying to pitch anything, but just little personal check-ins. You can automate that so you stay top of mind with people. So that’s the nurture side.


So we have got capture, nurture, automate; that’s the idea of well, do I need to hire a bunch of people to run around and move potential clients from one side to another and all these. Well, you can automate a lot of those processes and the computer doesn’t need to eat, doesn’t need to breathe, it can be assigning you new potential prospects at night, whenever they come in, and it’s constantly listening for people. And the whole goal is to engage, to spend your human time with people that are ready to go right now.


If they are not ready to go, let the computer continue to nurture them, but as soon as they are boiling, that teapot is kind of starting to whistle, then it’s like okay, quick, send them over to the attention of someone that can reach out to them and call them and actually get them in the door, and that’s the automate side.


And then finally, hope I haven’t been talking too long, finally is reporting and ROI, understanding that if you tried something new, you tried a radio ad, you tried a new program, you did some marketing and you spent 5k, 50k on some kind of thing, an event, AdWords, anything, how did it do? Is it working? Is it not working?


Things like Marketing Automation, these tools are built to be able to tell you that. They are built to be able to tell you, you spent 10 grand on that event, you met 80 people at that event and four of them turned into something like half a million dollars in revenue and hey, that sounds like a good event, let’s do that every year because it worked out.


And if the opposite happens, if you didn’t really get any one of quality at that event, let’s not do that event next year, let’s do a different thing, let’s repurpose those marketing funds.


That’s marketing automation; capture, nurture, automate and reporting.


Gyi Tsakalakis: I love it.


Kelly Street: Yes, love the way you boiled that down. So you typically are in the world of Salesforce and Pardot, which typically is larger businesses, but I know you know all sizes and types of businesses.




So when you are thinking about a small company, small business AKA small law firm in this case, where maybe they have just a few people on staff, what is the first step that a company can take to integrate Marketing Automation and put that into place and practice?


Casey Cheshire: Yeah, that’s a good question. And yeah, these tools are scalable so you do see the larger firms having them, but what’s cool is that the pricing on things like Salesforce and Pardot, it’s flexible. So you don’t need to — if you only have two people in the system, that’s okay, you are only paying for two people. You don’t have to necessarily invest a lot of money to be able to get into these systems, and they just track everything for you and it makes it very scalable.


So for the companies that don’t want to scale, for the firms that are kind of cool hanging out with the areas that they are at and they don’t necessarily want to grow, some other tools, some other smaller tools might be appropriate.


But for those groups that are really looking to grow and dominate a marketplace or really kind of expand and add more partners, those are the kind of firms that would look to something like a Salesforce and Pardot as well. Those two in conjunction really help you grow because then you can add different users. You just click a button and now you have added another person to the mix, and so it’s very scalable.


So to your question about the first step, where do you start, really what I like to tell people, thinking about who are the different types of groups, different types of people you would reach out to.


Do you have — there is a term in marketing called buyer personas, I don’t know if you have talked about that before, but the idea of who are the different types of people you would reach out to and what would you want to say to them, what kind of questions are they asking when they are either seeking you out or they don’t even know to seek you out because they don’t even realize there is an issue that they should be on the lookout for. So who are the groups you are looking to talk to and what do you want to say to them, those are really the prep work, if you will, the work you would want to do beforehand before necessarily jumping into the tech side.


Gyi Tsakalakis: Nice.


Kelly Street: Got it.


Gyi Tsakalakis: One of my things, and I loved how you outlined this topic and I want to kind of go deep, put you on the spot. So let’s start with capture. So I am starting to implement my Marketing Automation system, I listen to Casey and I have got to start with capture and you said some nuggets in there that I really wanted to go really deep on.


One is this idea of the ability to convert on forms based on the number of fields or the stuff that you request. So what are some of the things that lawyers should be thinking about? On the one hand, you could say well, one field, my hunch is it’s probably email, the essential field to be able to get them into something like this. But what kind of field should lawyers be thinking about in terms of doing intake to get people into their Marketing Automation system?


Casey Cheshire: Yeah, got a question for you. Are you a married man?


Gyi Tsakalakis: I am sir.


Casey Cheshire: Absolutely. And here is a question for you and for everyone listening too. How many dates did you go on before you popped the question or before you got married? And if you are listening to this and you are not married, imagine if you will, how many dates do you imagine you want to go on with someone before you maybe got married to them forever?


Gyi Tsakalakis: Do you want me to answer that question?


Casey Cheshire: Yeah, please.


Kelly Street: Oh, this is going to be good Casey.


Casey Cheshire: Kelly, you too, how many dates?


Gyi Tsakalakis: Seven years worth.


Casey Cheshire: Seven years worth?


Gyi Tsakalakis: Uncountable.


Casey Cheshire: Uncountable? So probably more than 50?


Gyi Tsakalakis: Yes.


Kelly Street: We can take an average between Gyi and I, because before I got engaged, I went on an average of three months worth of dates.


Casey Cheshire: Okay, three months, good.


Kelly Street: So mix the two of us together and that’s pretty normal.


Casey Cheshire: That’s fine.


Gyi Tsakalakis: Kelly is probably way more normal than I am by the way.


Casey Cheshire: No, I mean for me it was like three years too, it was three years and what are we doing. And all of those answers work.


Now, what I haven’t heard from anyone, at least I haven’t met anyone that’s gone to Vegas, I haven’t heard like one, right, and I don’t think anyone listening to this would imagine you would go on one date with someone and then get married.


Gyi Tsakalakis: Send us your emails if you have.


Casey Cheshire: Yeah, yeah, please do. So then why, the question is then why, why would we expect our future clients, the prospects, if you will, the people that maybe are interested in us, why would we expect anything different from them?


Oftentimes we are trying to get married with them on the first form. We are asking them to tell us everything about them; tell us your intimate details, maybe they are just wanting to get some information, maybe they are interested in that study paper that shows the top 10 reasons why you should look into this particular type of thing or how to protect yourself from a particular type of suit, maybe they are just kind of browsing information. They are just kind of looking to date, right, and then we are saying hey, let’s get married, right?




And so what we want to do is reverse this. Nobody wants to get married, maybe there’s a few percent of people, they go to Vegas, have a good time, they will fill out that big form. There is a lot of people on your site right now that don’t want to fill that out and so they won’t, but those would be great people for you to get on your list, to nurture them, to teach them, to give them some good content once a month, a podcast like this, maybe it’s content, maybe it’s white papers, maybe just a little blog post once a month, couple of times a week. They can learn from us, really grow to trust us and then sign up to work with us.


And so the whole goal of what we are trying to do is shift businesses and firms from thinking about the one-night stand with your future clients to getting in a relationship with them.


And so the idea is don’t ask everything upfront, right? I once saw a form that asked me my annual salary, what’s your gross take-home. I am like hello, we have just met, and it was a required field, I had to fill it out.


So when you get in that situation is people either reject the form completely and go away or they lie to you and that doesn’t help. Now you have asked information, you have started out your relationship with a lie. It’s like somebody putting the wrong photo in their dating profile at the very beginning, like that’s not off to a good start.


And so rather than forcing that what we say is look, have a short efficient form that maybe just says name, first name, last name, email, maybe a company if you work with corporate accounts, or what I always like to see is a drop-down at the end of that first form that kind of has a little categorization and it’s not a free text field where you are like, just tell me your life story. No, no, no, I want to know, and sometimes if it’s a company, ask your role, what’s your role in a question, are you in the sales side, are you an executive, are you IT, because I am going to talk to IT a lot different than I am going to talk to a sales rep or a sales VP, different persona.


So I want to know that right off the bat, who am I talking to, so I can give you a really good nurture tailored to you afterward. But that’s it. I don’t even ask phone number on the first form, because most people don’t want to do that. It’s like getting a phone number when you first meet someone. Do you ask them right away? No, maybe at the end of the night, or maybe email, you swap Instagrams these days or whatever it might be.


But thinking about how we could date the people we want to work with, consistent, long-term relationship, that’s where the great clients come from, the ones that are going to work with us for years.


Kelly Street: I love that analogy so much. I mean it’s just to break it into — I always say one of my kind of go-to analogies is or kind of mentalities for thinking about the sales process or the client development process is you do this every day, the client only does this for a family lawyer or a personal injury attorney, the client only does this maybe once in their life. And so you have to think about where they are coming to the relationship from versus where you are coming to it from.


Thank you.


Casey Cheshire: Absolutely.


Gyi Tsakalakis: No, it makes a ton of sense, and I think to translate for some of our lawyers out there that are listening to this and are maybe struggling with the context, you lawyers out there that are leading the relationship with your full intake form, that’s what Casey is talking about. When they come to your website for the first time and you are hitting them with the entire intake form, that includes all of this stuff that eventually you need after they have signed the retainer or after you have already developed a relationship with them.


So if you are at home listening to this, go check out your website, go check out your contact page, go check out your intake page, are you putting all — how many requests for information do you have of people that maybe the first time they have come to your site.


Casey Cheshire: Get them signed up. And maybe over time, and one of the things you can do with this capture side, this Pardot and these tools is called progressive profiling. So every time they come to the form, different forms, you can ask them different questions. So instead of having that — I love that you translated that too, that intake form of all of your questions, maybe the first time they come get some content, they fill out some things and then other times they come back, they fill out other things.


Now, it doesn’t mean you can’t have this form. For sure we always have the option. There is always a form on the site that says, here is the let’s get serious about this thing and you have something happening right now and you need some urgent response, by all means have that form, because they will fill out all of it.


But a lot of people are doing that prep work or they are doing the survey work, they are not even sure if they are dealing with something right now and they just want some counsel, some wisdom that they can rely on.


And I think of word of mouth, even if that person doesn’t become a client, but they are on your list and you are giving them good content continually, maybe they are forwarding that email to other people and maybe they don’t become a client, but they might introduce you to five other people that do. So I love to just capture people right away, get them on that list and then sort out the rest later.




Gyi Tsakalakis: Love it. All right, let’s move on to the next one, nurture, and this one I think is particularly problematic. I think there are — in the legal context my hunch is, and I can’t wait to hear your thoughts on this, but there is a real lack of patience out there. So people, you get them on your list or whatever you sign them up for and then you start hammering away on the emails, and so many of these emails that we see are these “nurturing campaigns”, and when I see them, they are so focused on the lawyer; how many years the lawyer has been practicing, where they went to law school, all these awards they have.


Tell us some of your thinking about how you start to build your nurture process.


Casey Cheshire: Yeah, absolutely, and I have a favorite radio station and I think the more modern equivalent is now my favorite Spotify playlist, though I am kind of getting partial to this particular podcast, because you guys are fantastic. So it’s called WIIFM, I don’t know if you have heard of that channel or that station.


Gyi Tsakalakis: I did not. It’s new.


Casey Cheshire: It’s What’s In It For Me. What’s In It For Me. A long time ago I had a marketing leader tell me about this radio station and said make sure you are tuned into this. And it’s a question that I always ask myself, it’s really the question, you are going to send a nurture email out or what you think is an email to nurture that relationship, just ask for a second, What’s In It For Me, put yourself in the recipient’s shoes and say, what’s in this particular email that’s going to be beneficial to them.


And I know, especially people listening to this, you are critical, you are good at the details, that’s why you are here, that’s why you have been successful, put yourself in their shoes and be just as critical and be just as like cynical and say, is this worth my time? We all know what you are billing. I know what you are billing, is this worth your time to read this email you are sending someone else right now? If the answer is no, don’t send it, because you are just hurting that relationship.


It’s like the needy person, back to that relationship example, they tell you to wait a couple of days before you harass that girl you just got a phone number from; are you going to text, how are you doing, like you have got to have some patience there.


And What’s In It For Me and here is a good example. You just redesigned your website, so what does everyone want to do, hey, let’s blast an email to our entire list to say, guess what, we have a brand-new website. Now, I am proud of you, you spent a lot of time and effort. I am sure you spent thousands of dollars on this thing and it’s internally a very cool accomplishment; maybe you emailed your internal team, you have them all check out your website But do I care about your website? No. Do you care about my website? No. Then why does everyone on your list care about your website? They don’t. So don’t send that.


Every email you send think of it as either a plus or a minus to that relationship. If it’s helpful, you get a plus. If it’s a minus, you get a negative, and you get a couple under 0 and you are getting an un-subscription. You are getting people dropping you, never going to utilize you, and if you get unsubscribed from any of these tools, you are gone, you are dead to me. It means you can’t ever email them again, even if you can call them, all these other things, you can’t email them. And so you have got to be very cautious about that.


And very exacting, is that thing, What’s In It For Me? Is this the station I want to turn into, and are you tuned into it when you are sending out that email, and if not, then don’t.


Kelly Street: Yeah. I mean that that mindset is so incredibly helpful, because in the legal field lawyers are noticing that it’s changing from having a person come in and sign a retainer and become a client right there, to a potential client going, actually I have three other lawyers that I am going to be meeting with and I will let you know if you are the one that I choose. And so the nurturing side of things is a whole new system that lawyers and law firms need to get used to that they haven’t had to do in the past.


Casey Cheshire: For sure. And nothing beats that personal touch. Someone comes in and you teach them something. Man, if I have someone teach me something; I had this other day on my podcast, where someone just actually taught me a couple of things, blew my mind and I thought, oh my gosh, I had never thought of that before. Man, they are good in my book, like what do you need, can I refer you to someone, can I work with you, like nothing beats that.


But the challenge is you can’t meet with everyone and you want to kind of use this system to figure out, and we will talk about automate, how you can kind of screen people out. But the same time on the nurturing, you could build your best nurturing, your best content, those aha moments, you can build them into emails. So maybe not everyone can come in right away, but you can give them those aha moments systematically, programmatically in an email and have the same kind of effect.


And one example I like to use is the newsletter. If you are sending a newsletter, you are in the old days, you are behind, and here is the challenge with newsletters. Most of the best newsletter content is done within the first three months, especially if you are sending every week. If you send every month, give it six months, all your best content is out the door, what do you have left?




And here is an example of that or a story. I was writing for — I am up in New Hampshire and I was writing for this New Hampshire travel magazine, like a tourism magazine, just for fun on the side, and you get to go to places, explore them and write about them in this travel magazine.


Well, New Hampshire is not the largest of states; we are not the tiniest, we are not Rhode Island, but we are also not Texas. So after about a year-and-a-half, two years of writing for this magazine, man, the topics got kind of hard to come by. I mean we started out writing about all these fun things and it came down to at the end model, railroad, museums in upstate New Hampshire, because we had already written about the best stuff.


And so what ends up happening is the same type of thing happens with your newsletter. Some of your best content happens when you first launch your newsletter, really good articles about those really need to know things, they happened. But the problem is what happens to someone that comes in seven months later or seven issues later, well, they don’t get to see your best stuff, and because it’s a newsletter, it’s like a newspaper, you are never going to recycle that because you don’t want to turn off the people that are continuing to read it, so they don’t get to see that.


Well, with nurturing, the idea is you create a series of emails with your best content and it’s evergreen content, it’s the stuff that — like a tree outside in the wintertime, it’s going to stay green. It’s always something that’s going to be valuable to the recipients.


So you have your first email with some killer aha moment content, your second email, your third, your fourth, your fifth. And what’s cool about nurturing is when someone gets added to that list, they receive the first one and then the second one and then the third one on their own schedule. Everyone else that comes in, if I come in like nine months later, I still get your first email, then your second email, then your third email. And you can really optimize this, your best email content, your best aha moments can be programmatically scheduled to go out, so that everyone that comes in gets your best newsletter content.


Kelly Street: Love it. Let’s take a quick break to hear from our sponsor and when we come back we will keep giving you guys some killer content.




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Gyi Tsakalakis: And we are back and we are talking Marketing Automation and we are moving into the automation portion of today’s program. And one of the things I hear a lot of resistance to about automation and I can’t wait to hear Casey’s thinking on this is well, okay, so we just used all this dating analogy, building relationship, nurturing, isn’t automation antithetical to that? Isn’t that going to create some inauthenticity or feel not real? How do we address these issues and how do we even think about like what things can be automated?


Casey, tell us what we need to know?


Casey Cheshire: Yeah, absolutely. I mean it’s a great criticism, it’s accurate, done right Marketing Automation can care at scale. Done wrong, it just simply does more of your bad marketing more. If you have got terrible emails that are all about you and your new practice and where you have got your law degree from, things that nobody cares about and you put into Marketing Automation, well, guess what, more people are going to get your bad marketing.


So for sure, it is not a cure-all just to have the technology, you have got to actually be sending good quality content, things that people want to read, things that are going to help them, that are going to answer their questions, give them a direction to go when they have a challenge.


So you still need to do it right, but if you do do it right, now, like with a newsletter, like with those nurtures, you are getting your best things in front of the right people. So 100% agree, you have got to have the right thing, but if you do have the right thing, then that automation takes the heavy lifting off of your hands.


A lot of times I bump into firms that they have that monthly campaign, maybe it’s a newsletter or maybe they have a one-off email every month, and again, their best ones were a year ago when they started doing this, now they are not really sure what to send and so they are sending weird things out like, about the Thanksgiving giveaway or something. But once a month they are spending time and they are getting things created and going through the motions. And do people actually read it or not, they are not sure, but there is a lot of busy work.


But if you take a step back and think, okay, let’s plan this in advance, how many emails, what kind of cool content do we have that’s really valuable to people, let’s schedule that out, let’s get it automated, then we can have this really good stuff and it can be personalized too.




We’re not talking about a spam message, we’re not talking about buy now or hire me now or become a client now, click here to give me a retainer, we’re not talking about that kind of thing, we’re talking about really helpful information that drives people to really trust us and want to get in an ongoing business relationship with us, sign up.


So, we’re saying these valuable things to people over time and then they’re just going to be like, yeah, get me some of that.


Gyi Tsakalakis: Right, and I think that’s the thing too that folks that are listening should at least take in consideration is the more value that you’re adding, the more latitude you’re going to be given on the automation side of things. So I think people — when we signed up for something, we’ve already captured — there’s a certain expectation today that there’s going to be some nurturing and some automation going on, and I think people are generally okay with that assuming that you’re delivering on the value and assuming you’re personalizing something that matters to them.


Casey Cheshire: For sure, and I think part of automation is a two-way street. You don’t want to talk to everyone and they’re the people that maybe they are tire kickers, maybe they are overselling themselves or they’re just not your ideal client, they’re just not a good fit, and hopefully you’ve identified what that person might be or organization if you work with those.


So you can build that into the automation as well again, it’s almost like having your own marketing coordinator. I remember when I first got Marketing Automation right before getting it, I was like telling the CEO I need, I need support in marketing, I can’t do this all alone, I need a marketing coordinator, I need someone, need someone, then we got the tool and I stopped asking because actually it was good.


I started automating things and I was able to free my time up to do more strategic marketing things like where else could we find potential new clients, where else could we go and test out new sources instead of letting me do the busy work all the time? I think old-school marketing is all about the activity, all about the busy work, how many emails did we send this month?


The new marketing is all about how many people are getting nurtured automatically, where are we going to try to find new sources of leads and new sources of clients?


Kelly Street: Yes, it’s the bad automations that are giving automations a bad name and the good ones are giving people more time to do other work that that is important and matters more.


And so I listened to a whole bunch of other podcasts but I was listening to one with a CEO of a t-shirt company the other day, and he was talking about how they’ve gained so much PR for their email automations and he was talking about how they’re a simple thing of their confirmation email for when someone makes a purchase is it just sets them apart from every other competitor out there.


And so I would say as a challenge to all of our listeners, when someone fills out a form take a look at that automated email that you send to them thanking them for signing up for your email list or thanking them for submitting the information, take a look at that automated email that gets sent out and see how you can add a bit of your buyer persona into that.


What are the kinds of things that are — what’s in it for them that you could add to even though it’s an automated email, make it a little bit more personal for your law firm. Challenge accepted?


Casey Cheshire: I love it.


Gyi Tsakalakis: Cool, now, potentially for some people the most important part of all of this and I’ve been on it, so I’m going to be a little — we’re talking reporting here, now I think there’s huge opportunity for improvement on reporting and understanding attribution and I want to get into some of the things that how that actually works.


But one of the things that’s been kind of like in my craw recently and I think that this is maybe we’re at the front end of this problem, but that people are in this like direct-response mindset where it’s like they want to see in our context here, they want to see capture, nurture, nurture, nurture emails, we’ve automated some things and then up direct response and so we’ve got a straight line.


But it seems to me especially for legal services’ consumers, their journey is so all over the place. Google’s talks, micro-moments and all this stuff, so talk to us about some of the things that we should include it in our reports and I don’t know maybe I’m leading it too much here, but it seems to me also that we’re so stuck in this attribution direct-response mindset that we forgot that we’re trying to build this relationship.


So how do we build a report that kind of does both those things, shows us our return on investment but also doesn’t give us such like blinders to just be like up this didn’t work because I sent four emails and they didn’t sign up?


Casey Cheshire: For sure. I think I would take a step back and before we even get to the reporting side, I mentioned earlier the activity mindset, so I think whether you’re a firm, a company, a marketer or related to this, I think a lot of times the old mentality was more of that.




I don’t want say B2C almost like you’re selling sneakers. I was working at a company and I remember bumping into the CEO this back in the day little Casey day and I was just a marketing manager and the CEO I think he swung by lunchtime and he said, hey Casey, because that’s how CEOs talk.


Gyi Tsakalakis: That’s how he talks, right.


Casey Cheshire: — and he’s like how many emails did we send this month?


And I don’t always know the details but I thankfully knew that detail and I said, well, actually it’s about a million this month. And he was like, oh, that’s great. Next month let’s send a million-and-a-half, and we weren’t selling sneakers, we weren’t selling ice cream, we were selling this complicated IT software that takes months to purchase and it’s not like another half a million emails to the same people is going to do anything.


I get and sometimes with some brand recognition and depending on what kind of firm you are, maybe need a little bit that brand recognition but it’s got to be a positive recognition, just scent blasting another half-a-million emails out to the same people, all can do is annoy them, annoy them like, oh, this email is useless, my Inbox is busy enough now, get out of here, you are blocked now. I don’t want you in my Inbox anymore.


And so that was that activity mindset and so the cool thing was when I shifted overnight I adopted Marketing Automation, I was able to start showing some ROI. So I would say first things first is to get off of activity metrics right or if your firm has someone doing some marketing, let’s get beyond how much they’re doing. It really doesn’t matter how many emails you’re sending that doesn’t really have any direct correlation.


You’re not selling Adidas, so it doesn’t have any direct correlation to the results, and so with Marketing Automation you can start to show these things and so to get it your question, Gyi, about it isn’t a straight path from start to finish and how do we look at these things.


I really divide it into that first touch ROI and the multi-touch ROI and so what I’d like to say is the first things first, first touch ROI, that’s your source. Where did I meet these people that became clients, and that’s a little bit more of that direct response and it’s not always clear, and sometimes it might take longer than you think, longer than selling shoes, establishing a client relationship.


But at least be able to show that I met all these people in this networking event or from the podcast or wherever it was from and the systems keeping track, you don’t have to keep looking at it but eventually when down the line, people become clients, you can look back and say where do they come from?


Because I think that the key question in marketing and for your marketing efforts is always, well, what’s working and what’s not working, so that we can improve and we can grow and optimize and expand and just stop wasting money but also start growing by taking that wasted money, put it in the stuff that’s actually working.


So what’s working, where do I meet more of the people that are great clients? If you look to your top 20 clients, where do they come from? How did I meet them and then you invest more into that. So I love just focusing on just saying be able to say, okay, if you invested money or time be able to show where did these top clients come from.


And your point that multi-choice understanding, well, what kind of activities happen in the middle that maybe threw them over the cliff to eventually want to work with me, that’s a lot more of a gray area like you at least know where you met someone. If you’re tracking it right, if you’re using Marketing Automation, you can actually see that and it’s clear as day, black and white in numerical format, you spent this much money, it became this amazing client and maybe you can even show as well if you enter that to your system. You can show how much money on return you made from that small investment in that event or that AdWords campaign.


The multi-touch stuff understanding all the different touches in between, that’s a little bit more advanced and I only want people and we only advise our clients to do that once they’ve done everything else with Marketing Automation.


So you’ve got all these different nurtures happening, all these different marketing things happening, you’re really robust. We have a roadmap for Marketing Automation and there’s ten steps to it. When you’ve done all nine before that then you hop into that multi-touch because you’re right, it isn’t very clear. And so to try to measure that internal stuff gets very sketchy. So that only happens when you’re done all the baseline, the foundation work.


Gyi Tsakalakis: Right, and then the other thing that comes up a lot is because in these systems they start to churn out all sorts of data or through all of these different metrics, beyond ROI, are there any ones that you like to advise clients on that kind of keep on your short list of your eye on to just kind of tell that you’re moving in the right direction?


Casey Cheshire: Yeah, I’d like to look at the key moments that happened and so the first – just think of like all the different touches that happen, all the different transitions, what are the different key moments and really create a little marketing funnel to understand, okay, well, how did I first meet these people so that first meeting is very important.




Not the first meeting in person but like how did we first get their information, and it’s that source so that source is critical. And also that last touch which is when did they sign up and what drove that? That’s important as well.


In between there, there might be some steps to keep track of. There’s this sort of term they use the MQL, the (Marketing Qualified Lead) and there’s this sort of middle touch where what was the point when this person who’d signed up maybe for the newsletter or filled out a partial form, partial intake, at what point did they sign up to schedule something? That’s usually that others step where it’s transitioned from the digital world to that physical world.


The humans getting involved, what was that part like keeping track of the number of people we’ve transitioned from ethereal, digital, bits and bytes of a person to now they are on the phone with us or now they are in our office, those are the numbers I’d like to keep track of, how many — it could be appointments, it could be scheduled phone calls, that next step where it got into the real world. That’s one that I like to look at a lot, the beginning, the end and that middle where we became real.


Gyi Tsakalakis: Makes sense to me.


Kelly Street: Yeah, so this is kind of in line with what you’re talking about there for getting data in those particular things to look at, but I am wondering about segmentation. So law firms are typically using kind of on the edge of a CRM more of a case management system but it has a lot of the same information listed.


Are there kind of tips that you have for thinking about how to segment your leads and in that automation process to get a little bit more of the personal touch to lead to better data, those types of things?


Casey Cheshire: Yeah, for me it’s been over this past year work around buyer personas and I think this kind of practice extends across all industries just understanding our buyers better, and I think this is something that has had a lot of confusion even for me. I mean, I’ve been in marketing for years, I guess a decade, I don’t even want to claim that or more because it makes me feel old, but it’s one of those topics that I think we’ve avoided in marketing as well as we’ve avoided just in general practice.


And it’s understanding the process and understanding a little bit more about the buyer, not just their case, not just what they’re bringing to us and their particular situation, but what was the process they went through to find us? And I had the luxury of interviewing a couple amazing people on this topic and one was Adele Revella, she wrote the book ‘Buyer Personas’ and she literally schooled me on the podcast because it’s kind of embarrassing you can hear me being incorrect and as I’m learning from her and she actually corrects in like it gets me to an aha moment while we’re chatting.


But I’d kind of just always thought, okay, clients — almost like a demographic, like a profile, like a most wanted profile, this type of clients, they are between 30 and 50 and they usually have pets and they like traveling to the islands and it’s like that sort of general type information.


Well, when you really think about it, none of us do that too much because it’s not very actionable. Okay, knowing that you may or may not more likely have a pet or not, I may send you a pet Christmas present, but doesn’t really tell me how much to get like to get more of you or to help smooth out the process to get more clients like that.


And so the persona is actually different, the persona actually starts with interviewing your clients and asking them questions and it doesn’t have to necessarily be the attorney doing this, it could be the marketer on the team, it could be someone on the team just taking the time to ask the question of when you first began this process to look for someone, this is usually the first question — when you first began the process to look for someone, what was on your mind and where did you go to look for it? And just describe for me that process and just describe for me your experience, what did you do, you had this thing happen and what was in your thought process?


And you start asking these common questions of people and the follow-ups are amazing. I mean, it’s like a cross-examination but a little friendlier and you’re just wanting to know in their minds how did they shop really is how you’re getting to it, how did you go about the process of finding me?


And I think a lot of us simplify that, you have it on a form, how did you hear about us? And then it was like radio ad and a couple generic things or people type-in their friend or something but to actually take a little more time, you need to do this to hundreds of people literally 20 is enough.


When you start doing that and you see some trends, and I remember an example that Adele shared with me is that she did this process for particular John Deere subsidiary or a subsidiary where it was — this was in like multiple geographies, they sold to multiple geographies, languages, currencies, it was a key product they had in this particular company and thousands of buyers.




Thousand different — many different industries would purchase this equipment and she did some interviews with different people and she started to see some patterns and Gyi, in company like this, how many personas do you think they had when she interviewed many different people, they had multiple geographies and buyers and industries.


Gyi Tsakalakis: A 100.


Casey Cheshire: Right, you would think something would be crazy like that and as a marketing team you’d be thinking, oh my gosh, do I have to do a 100 nurtures? Come to find out they are only 2 buyer personas.


Kelly Street: What?


Casey Cheshire: Only two, there are only two different ways that people purchased and to kind of oversimplify what she was saying, it was essentially there was a newbie buyer who had never bought this type of equipment before that really wanted to see some examples of how you use this to create new business and new opportunities, these businesses and then they definitely want to talk to someone right-away to kind of get that sense and then there was the experience buyer, who’d bought this equipment before, they wanted to see a comparison chart, that was like the common trend. I need to see comparison chart and I do not want to talk to someone, do not call me, that’ll piss me off, don’t call me.


And so you could see how these two buyers bought in such a different way, they shopped in a different way, they acted in a different way, and then if you just had a single approach to marketing, you would tick off half the people on that list with whatever you did but by dividing them up then they were able to use some advanced dynamic content and Pardot and these kind of things. They could show different countries and languages and they could attack industry, which is a simple picture just to show that, yes, we relate to your industry, but in the messaging, they only had to create two different nurture campaigns because there’s only two different ways people are buying.


So to kind of take this into the modern day and to like the present conversation, it’s like how are the different ways that clients come to you and there are different kinds and probably people thinking right now, yeah, there are some different categories of people that come to me and this is without even asking them these specific questions and giving them a little bit of investigation, you may find there’s only two or three different ways that people are coming and buying from you.


And as soon as you can identify which one they fall into, you can get on them on that nurture track that treats them the way they would love to be treated, love to be shopped, and no one else is going to be doing that. So you’re going to stand out is speaking their language and they’re going to want to sign up with you.


Kelly Street: Wow. I mean, honestly, Casey, my mind is actually blown that is because I was going to say one of my critiques of buyer personas is that I think it’s one of those things where I say it and I think it’s important, but I also internally kind of roll my eyes and cringe a little bit and it’s because, it’s this sort of if you’re thinking about, oh, 25 to 35, they have a dog, they live in the suburbs, that’s sort of an ethereal thing and then when you have someone who doesn’t fit that mold, you’re kind of like, oh, my buyer persona, it all goes up in smoke.


But when you think about how they are essentially making a purchase or for lawyers how you are retaining them as a client or what that client retention process looks like that just flips it on its head and that’s really at the essence of buyer.


Casey Cheshire: Totally it’s step number one and in the quote from Adele was something defective. Most of what passes for a buyer persona these days is actually a profile and profiles aren’t very actionable and that’s why we sort of haven’t really done them is because to your point, yeah, you’ve done a profile, you have a picture of a fake customer or a client, you’re like, okay, well, what do I do with that? I don’t know.


But you could see how, when we do the real persona, you’re like, oh, well, they want to talk to people or they don’t want to talk to people and they want to see a comparison chart, do we don’t have a comparison chart? We need to make one. So all of a sudden, these — all these different thoughts come to mind and part of this buyer persona research is choose like what resources do you trust when you were shopping for me, when you were looking around and evaluating firms, what do you trust in that process? Oh, I hate the comparison things or I never look at reviews or I always look at reviews and then now you know where to invest your time and money. Okay, two of my buyer personas are all about reviews. Well, let me double down and some review marketing get some of my clients to be up on there and get some five-star ratings or not, if it doesn’t actually matter.


In that way, you’re not just blindly spending your time and money, you’re actually going for the paths that were already walked already by the clients you want.


Kelly Street: Yeah, this is so great. I mean, I know it’s going to be hard for lawyers the first time or your intake specialist the first time you ask those questions of our reviews and when you were searching for a lawyer, how important are reviews in your process, but if you think about what you just said, you only have to ask 20 people to figure out those personas.




It’ll get easier by the 20th and then you can continue to ask always or then you’ve got your data right there. Love it.


Casey Cheshire: Totally, totally and one thing to sort of add to that just another aha moment, Ellen Naylor, amazing, amazing woman has a book called ‘Win Loss’ and what she actually does is not just interview the 20 or so people that chose you but she will actually go and interview for you the people that did not choose you that chose someone else.


And what’s funny is she’s this amazing lady, she’s so kind, people just tell her everything. She’s the person at the grocery store, you just can’t help but tell about your day and so when she talks to people, she’s asking them the same question when you were evaluating people, what sources did you trust, what process did you like and why did you choose those people?


And now, if you ask them that they may be shy, not going to tell you or certainly if you were the one they talk to they don’t want to disappoint you and tell you bad things usually unless they’re from New York, but everyone else they’ll tell Ellen and they’ll tell people.


So consider having someone reach out to those that didn’t sign and say, hey, no problem we understand, we’re not the source for you now but we’d love to learn more about why you made this decision and sometimes, you learn more from the failures. We’ve all experienced this, you learn more from the failures than you did from the ones you won.


So just taking a little bit of time to ask them and not even kind of putting something forward by suggesting a particular source, just tell us about the process and they start going down a path and then you kind of key in on some of the things they’ve said and ask the follow-up questions and start discovering the paths that you want to address.


Kelly Street: One thing I wonder about this is your opinion on if you can do that — if you think you can be successful asking those with a sort of auto survey, Google Form kind of a thing?


Casey Cheshire: Yeah, the answer is no and this is what everyone who’s an expert on this topic has told me and the reason why is it’s the follow-up question and this kind of ties into — tied into cross-examinations, tied into all the different types of interviews you’ve probably had professionally. It’s not so much that first question but it’s you hear something and it strikes and it’s like interesting.


They got really excited when they said X or they got really angry like in asking, well, tell me more about that and that’s what a survey can’t do, and the other thing with surveys is you can toot your own horn. I mean, we’ve all taken these surveys where it says what did you think of this experience? It was a fantastic opportunity, it really helped in my education, it really helped in my career or it was just plain old fun.


Well, what if you don’t fit any of that? Sometimes, by even just having the bullets themselves, you can shade everything, you can bias it, a lot of the marketing testing experts I’ve talked to, you have to be aware of your own biases, you may be just trying to point people in the direction of, oh, let’s do more of this marketing.


So instead, you’re saying take me back and you can hear Adele say this to me, she says, Casey, take me back to when you first decided you wanted to get Marketing Automation, why? What was going on through your mind? Take me back to that time. What was going on and what were challenges you were facing?


And I just started talking and talking, and I mentioned, oh, I just started a new job and I wanted to really turn things around the company, she goes, oh, so you just started at that company and I was like, yeah, and so what she identified was their particular persona for Marketing Automation was the new employee coming in wanting to fix things up and that might be a persona that if you’re selling Marketing Automation, you could go after.


But she wouldn’t have necessarily known that from a survey she had to hear me say it and then it was that follow-up she dug into it, so it does require a little bit of that effort, a little bit of that expertise to get in there, but I mean the rewards are so much better than just like a cut and dry survey.


Kelly Street: Gyi, any remaining questions?


Gyi Tsakalakis: No, I think we have nailed this topic. I’ve been writing some notes down, I’ve learned some new things, I’ve had a great time. Do you have any final questions for Casey?


Kelly Street: No, I mean, I think we could go on and on and on, we joked before we started recording that we could talk for three hours and I think we actually could, but I think, Casey, you as a podcaster have just are able to get your message across so clear and people are going to learn so much about Marketing Automation from this episode. I am super-pumped for people to hear it.


Casey Cheshire: Well, it’s been awesome coming on here. Obviously, it’s something I’m passionate about and if you don’t mind, I actually, my book just went live on Amazon.


Kelly Street: Yes.


Gyi Tsakalakis: Congratulations.


Casey Cheshire: And I would love to tell you about it. It’s all about what we’re talking about today, it’s all about Marketing Automation and it was just me just pouring out my passion and talking about the capture, the nurture, the automate, and just getting that into written format.




Gyi Tsakalakis: Tell us how to get more Casey in our lives?


Casey Cheshire: Yes, more Casey, so you can go to Amazon, you can just look for, search for my name “Casey Cheshire’, choose the easiest way to get it. I’ve only got one book on there so it pops up at the top. There’s also a URL it’s, and that’s actually — that’s a link on Pardot, on Marketing Automation, so if you click through that link, it actually tracks you in Pardot.


So it’s like using Marketing Automation for all sorts of different things and that’s the same kind of way you track direct response, the same way you track did people want to call me, did people want to click on my link?


So it’s those kind of things, we’re trying to show you not just teach you about these things but show you how the Marketing Automation works so you can copy it, straight up copy you take the best of what works and use that in your own practice.


Kelly Street: Yes, this is awesome. I wish you the best of luck with your book. I’m looking at it now, it’s got an amazing rocket ship on there, and I also want everyone to check out your podcast that Gyi and I have actually both been on the hardcore marketing show, that’s a great one and it’s how we got connected with you. And I am going to right after this start listening to that episode about buyer personas.


Casey Cheshire: Yes, episode like 3, I believe, so it was amazing that she talked to me so really on when I didn’t even know what I was doing back then. So, yeah, definitely check her out, and yeah, I really appreciate being on here. I had so much fun chatting with you and I remember when I first heard your episode, you guys have such a great chemistry together and it’s so much fun to listen to. So I’m happy to be a part of it.


Gyi Tsakalakis: Too kind.


Kelly Street: Too kind.


Gyi Tsakalakis: Thank you sir and thank you to all of our dear listeners, whether new or regular subscribers, for those of you just stumbled upon this podcast, congratulations. Please don’t forget to subscribe on Spotify, Apple Podcasts, Google Play, wherever you like to get podcasts, and please don’t hesitate to leave a review, good or bad, positive/negative, we want to hear your feedback.


Thank you so much. Lunch Hour Legal Marketing, we are out.




Outro: Thank you for listening to Lunch Hour Legal Marketing. If you would like more information about what you heard today, please visit Subscribe via Apple Podcasts and RSS. Follow Legal Talk Network on Twitter, Facebook, LinkedIn and Instagram, and/or download the free app from Legal Talk Network 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, its officers, directors, employees, agents, representatives, shareholders, or subsidiaries. None of the content should be considered legal advice. As always, consult a lawyer.




Kelly Street: Well, after Gyi’s cleverness, let’s just roll into the episode. Here is our interview with Casey Cheshire. Here is our interview with Casey Cheshire.


Gyi Tsakalakis: Now, leave that one, that’s the one. Do the one with the F thumb.


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Episode Details
Published: December 20, 2019
Podcast: Lunch Hour Legal Marketing
Category: Legal Marketing
Lunch Hour Legal Marketing
Lunch Hour Legal Marketing

The podcast version of this free webinar featuring nationally known legal experts discussing a variety of marketing topics.

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