Technology can often be a double-edged sword for small business owners. At its best, automated technology can significantly reduce your overhead and improve both the speed and efficiency of your daily operations. However, if your interface is too difficult for your customers to navigate, you may end up losing more money than if you had stuck to traditional live support. So, how can you ensure that your technology is actually helping you and not hurting you? In this episode, Jon Aidukonis and Gene Marks discuss how small business owners can take advantage of automated technology without compromising the customer experience.

Podcast Key Highlights

  • What Are The Disadvantages of Incorporating Automated Systems into Your Business?
    • Technology can overcomplicate simple processes for your customers.
    • Small problems can easily snowball when AI (artificial intelligence) fails to recognize its own errors.
    • Automated systems are not always equipped to address more complex problems or questions.
    • If your staff isn’t technologically savvy, your business will require additional tech support to help resolve your customers’ problems.
  • Why Do Some Customers Prefer Less Automated Small Businesses?
    • There are rarely any surprises. Clients know what to expect when they interact with another human being.
    • Live support can handle a broader range of problems than any automated system.
    • Speaking with a real person makes your clients feel like your business genuinely cares about their experience.
    • Having a live support team who can actually build relationships with your customers will help foster brand loyalty.
  • How Do I Ensure That My Business Will Actually Benefit From Automated Technology?
    • Always consider whether automating a particular system will really improve the customer experience or whether you’re just trying to cut overhead.
    • Make sure your automated systems aren’t being used as a crutch or substitute for proper employee training; all your employees need to understand the piece of the business that they’re operating in.
    • You need to check the security of every automated system to prevent any theft or data breaches.
  • What Are Some Good Examples of Automated Technology That Can Help Your Business?
    • AI Chats
    • Automated Point of Sales Systems with Separate Screens for Tips
    • Self-Service Creative Platforms
    • Text Reminders



The views and opinions expressed on this podcast are for informational purposes only, and solely those of the podcast participants, contributors, and guests, and do not constitute an endorsement by or necessarily represent the views of The Hartford or its affiliates.

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Jon: Welcome back to another episode of Small Biz Ahead, the small business podcast presented by The Hartford. I am Jon Aidukonis, joined with Gene Marks, and we are here to talk about technology today.

Gene: Technology. And Jon, you’re going a little negative on technology, aren’t you?

Jon: This is a polarizing conversation. As most of you know, Gene works in CRM-

Gene: Tech, yes.

Jon:… in tech, and talks about it weekly, and the technology.

Gene: Write about it.

Jon: I am a consumer who has been intercepted by automated technology for companies over the past week, and I’m at the breaking point, I think, of one more mild inconvenience causing a full-on breakdown.

Gene: What happened?

Jon: So long, long story short. I was dealing with a prescription issue where the tech platform that the company uses redirected my prescription to another pharmacy. And after about I’d say 16 hours of phone calls, four hours of driving back and forth across different counties in New England for holiday and weekend hours to get this corrected because I needed to talk to a person, because the options were not available in the platforms that were available, we were able to get this corrected. But after many, many phone calls with things that did not understand what I was saying or gave me the opportunity.

Gene: And the reason why your situation happened, which was for some drug that you were ordering, you know, some prescription, was it was bad AI. Some type of automated process intercepted your request for a prescription and basically misunderstood it. And that caused a chain reaction of events that really caused you headaches as a customer for like weeks after that.

Jon: It did. And what was interesting is that none of the humans who were able to kind of discuss the issue on the service side had the ability to fix it. And it was like a shared frustration. Who creates the system and how do you fix it and how does it learn better, right?

Gene: If you’re running a business, all you hear is the messaging from the Googles and the Microsofts and the Amazons and the Apples. It’s tech, tech, tech, tech, tech. Everything is technology, technology, technology. And do you think it’s too much for a small business? I mean, is there a tipping point where more technology is providing less value to a small business?

Jon: I think for any size business. I mean, I think about my interaction in the different roles I play in life. I think a lot of things have been automated over the past 15, 20 years where it feels unnecessary. And I’m guilty of being convinced of this, right? I think that I need something or I think that I need a safeguard or I’m communicating some kind of benefit that I think is important that I never use, but now I add in a whole bunch of steps that I blindly trust to complete a pretty simple and human task.

Gene: Yes.

Jon: And I think in the long run it ends up costing more time, money and frustration for me. I do think there was a benefit to automating and routinizing and making things kind of simple. But I also think that sometimes a simple user interface is actually a very complex interaction where the true benefit is not ever realized and it ends up causing a lot of frustration.

Gene: I think one of the reasons why people like to do business with smaller businesses is because of that human interaction.

Jon: Oh, 100%. I mean, I am at the point where for a lot of those day to days… And I’ve always tried to support small and local.

Gene: Sure.

Jon: You know what I mean? It’s in my DNA. I travel a lot. There are some things that are chain…

Gene: Yeah, you get it from the chain the same way.

Jon:… make it easier.

Gene: Right.

Jon: I don’t believe that that ease is really there in a lot of instances. So when you have one person to call and someone’s ultimately accountable, not because you want to call them and complain about them, but you know what to expect.

Gene: Yes.

Jon: You know that you can get resolution. And I think that sometimes the trade-off of an automated interaction is that their only resolutions that are there are the normal or expected. And I would say typically when someone’s really frustrated, it’s not because of a normal or expected problem, but that’s all that the kind of solution is able to accommodate.

Gene: We sell Microsoft products and this is not… And Microsoft’s great company, so this is nothing bad on Microsoft, but we when we implement a CRM system, I assigned… There’s a small team to it, but it’s generally led by one person. We’re a small business. We sell to small business. So that one person, our clients have that person’s email, mobile phone number, office phone number as well. And when they have questions or an issue, they know they can reach out to that person and they have a relationship with that person in our company and that person is responding back to them and helping them and all that kind of stuff. If that same client were to rely on a company a larger corporation… And I see larger companies than mine, even competitors, that over automate. Like, oh, well, go online and fill out this form or have a chat or whatever. There’s this disconnect that happens that you’re used to when you’re dealing with a larger corporation that nobody seems to like. They don’t like the lack of personalization. There are some cases where people… you can get the information fast and move on. But in a service business in particular, sometimes I see small clients trying to over automate themselves when their biggest benefit being a smaller company is humans in their business. You know?

Jon: I think it’s the shine, right?

Gene: It is the shiny new thing and…

Jon: It’s really easy. And again, as someone who’s bought into it… And I’m pretty skeptical as a human, but there’s been lots of times where I’m like, oh, this would be great or we can automate this and then all these things work together. I’m like, should they? And then I feel oftentimes that comes with an investment.

Gene: Yes.

Jon: So the long tail cost might be cheaper than a human investment or you think so because you’re not kind of considering for all the problem solving that comes along with it. But what ends up happening is now you have to build 100 more processes to operationalize and routinize. And I think about even workflow management systems, right? So I feel like that’s kind of been the… maybe at the end of their peak the past couple of years. It was like everybody needed one. It’s like, well, why?

Gene: Overkill.

Jon:… and it’s going to tie into your chat system. Do I need it to? And there was something about single sign on or single portals. But they never, in my experience… They might work the way they’re supposed to. I don’t feel like they work the way they’re expected by the users to, if that makes any sense.

Gene: Yes.

Jon: It might do everything it claims to do, but the way that that claim is somehow presented makes it seem like the solution is going to be a lot more streamlined than it is. I’ve never to this day, even when you… And then in terms of the product, well, if I buy this product and then I buy the platforms that work on this product, you buy everything, because in your mind you’re going to have a one button solution to life. It’s going to wake up for me, it’s going to cook my breakfast, it’s going to pay my bills on my phone. Like, all that stuff. They never really… There’s still the level of manual intervention you need to set up, to manage, to kind of conduct, which now you have all these other layers of complexity around it which prevent you from maybe the human interaction that solves it. Right? I find myself more often… I’ve been going to the bank more. I make more phone calls. I want a human to be able to talk to.

Gene: How old are you?

Jon: I know.

Gene: You’re talking an old man.

Jon: Yeah, I…

Gene: I should be the one saying this, not you.

Jon: I live in 1994 still.

Gene: Yeah, and I have clients… I have one client I’m thinking of in particular. They’re outside of Philadelphia. They’re actually in South Jersey. The guy refused to have an automated phone system where you know, choose one for customer service and choose two for whatever. He employs a receptionist to pick up the phone because he’s like, “My customers when they call us, they want to speak to a person.”

Jon: He’s my hero. I called some… It was for dinner the other day.

Jon: I called on the way home because I wanted to get takeout from someplace. But I do try… This is one thing I will always take the extra step to do when I’m ordering takeout from a restaurant, to order from the restaurant versus a delivery service, so they get the most money for the purchase, and it tends to be the same price.

Gene: But you call the restaurant, I’m hearing. You didn’t even do it online?

Jon: Yeah, so this place didn’t have an online option.

Gene: Okay.

Jon: So I call the restaurant because the online option was like…

Gene: Right.

Jon: So I call the restaurant and it’s the first time ever… Or for this one, they went to the same thing like an IVR… And then it’s like, “To place an order, you can either go online or hit three.”

Gene: And it’s like a small business, right?

Jon: Right. So it took me like seven minutes to get in touch with the person to take my order. I was already halfway there, right? And you expect to navigate a little bit, but it was kind of like… And the frustration from that just was one level. I could’ve been on hold the same amount of time and not care because someone… Like, I know that they’re busy, they’re doing something, whatever. But the fact that you couldn’t even talk to the person made me want to give up halfway through. I’m like, just… Or you say operator, you try and hit zero on these…

Gene: Oh, that’s what I do. I just start hitting zero a million times to get to… Because that’s what you expect. You expect that kind of thing from a big company and you dread it, you know? I have a problem with my bank and I’m like, oh my God, I got to call the bank now and go through their rabbit hole, their Alice in Wonderland maze of automated systems to finally get to speak… In the end, we just want to pick up the phone and call somebody to just get a solution to our problem, right?

Jon: And I think that goes back to business strategy and customer experience. Three things I think of. If I’m calling you, it’s probably because I need something.

Gene: Yes.

Jon: If I need something-

Gene: You’re not just checking in to say hi.

Jon: Right. It’s probably because something irritating happened… Like, there’s something that prompted you-

Jon: So I don’t want to deal with an irritation beforehand.

Gene: Yes.

Jon: That’s one. Two, if you’re spending on technology to solve for that I don’t think you should be able to limit yourself with that. But like, you should solve for the most frictionless. So if I’m calling and I’m a regular customer and you can pick up my number and all this, like, that should be somehow ported in.

Gene: Yes.

Jon: Which that is not a digger comment on the people using it, but the people who develop these platforms, it’s doable and it’s happening more often.

Gene: Yes.

Jon: That to me should be table stakes.

Gene: Yes.

Jon: Because if you are a company that…

Gene: They should know you and they should know not only your number, but also your history.

Jon: Right.

Gene: Like, oh, “Mr. Aidukonis, good to speak with you. I see you bought this product from us. Is everything okay?” Just like… Right? Like they know you.

Jon: And if you can’t for some reason or you have to tier… So this comment’s more to the vendors who provide the technology solutions. The new standard should be, like, frictionless.

Gene: And by the way, that’s so easily done by any small business with most mainstream CRM systems. They all have phone add-ons that you can integrate with your phone system really easily so whoever’s picking up the phone, they get a screen pop showing that it’s Jon calling and there’s a little bit of history about Jon. Do you know what I mean? It’s super important to do.

Jon: I have a bank that I’ve used personally, and for them, you can go through… It’s a one step and they’re I’d say from my experience the best with automated and human. So if you download their app, you can validate your phone through the app. So you do go through a one-time thing where you say your name. Whatever they do to secure that it’s you calling. So if you then call through the app, so you log in, then you hit the contact us, you call and the first thing it says your name. It understands your number. And I’ve never waited more than three rings to talk to a person.

Gene: That’s awesome.

Jon: And I’ve never had to give a reason why until I talk to the person. They’ve also never had to redirect or transfer me once I talked to the person.

Gene: Huge.

Jon: So the customer service person had been empowered

Gene: Yes.

Jon:… and given the access and resources information to solve the problem.

Gene: Yes.

Jon: So…

Gene: Because normally you give the problem and then they redirect you to somebody and then you have to give the whole problem.

Gene: You have to start from square one.

Jon: So when you think about kind of the notion… And actually, my cell phone company do. I would say they do a really good job, which two things. You typically don’t call a telecom provider or a bank-

Gene: Unless there is a problem.

Jon:… unless there’s something like, hey, I got a question here. There’s something not working right. And both of them I think understand that.

Gene: Yes.

Jon: Or at least in my experience I feel like they’ve understood, which is what matters as a customer. I think you understand me, whether you do or not, but you convinced me that you do. And I think that that’s the part that gets missing. And I think sometimes even when you’re talking about people who are… you know, whether the project management or the HR space, you have these companies who are coming out and trying to sell small business owners these tools ’cause it’s going to make their life easier. Is it? Yep. Because if I’m going to make the person who now has to use the system really hard. Because you’re probably not thinking about automating or simplifying unless you’re trying to outsource it or you don’t feel like you’re trying to do it or something. There’s a trigger there that they’re pulling on that emotional strain.

Gene: There’s a real thing that has to be considered here is that if you’re going to automate, it’s not about you. It’s about the customer.

Jon: Right. And that could be an internal customer. It could be your employees-

Gene: But a lot of people, a lot of my clients, they want to automate because they want to save costs or cut overhead or be more productive. It’s always about me, me, me. Like, how can we be more efficient through automation? And that’s fine. But to me, I think if you want to automate, it’s because you want to make the experience for your customer better, not necessarily to cut your costs.

Jon: And I think that the trade-off there too… And this is a supposition. I’m making a pretty broad statement on the state of the world. People need the expertise in the industries that they work in.

Gene: Yes.

Jon: So if your frontline employees don’t actually understand the pieces of the business that they operate in, they’re not equipped to really serve the customer. And I think that sometimes these automated tools, especially for the next generation of workers or coming… someone new in a job, if all they have to do is click a button and connect things, that’s great when you have the background to understand what you’re connecting.

Gene: Sure.

Jon: But if the responses you’re constantly getting on the phone as a customer, “Well, I don’t know. The system says this,” or… That’s not an acceptable answer even if that’s a reality.

Gene: Sure.

Jon: Right? So you think about… Again, I guess I’m in 1994. With an intern, you’d start an intern and work their way up. Even as a junior employee, you got to see the way different things worked within an industry or business. I think that sometimes automation actually kind of loses that. So if you’re an HR professional but your only job is to click, send, or copy a document and you don’t actually understand what’s behind it.

Gene: You don’t understand the big picture. Sure.

Jon: I think that’s something that actually gets lost and we as probably a culture and then economy needs to start solving for is how do you teach the expertise if you’re taking out the practicing craft.

Gene: Right. Okay. So as a customer yourself and as a person who works for small businesses all the time, can you give me an example of some type of automation, new technology that a small business has? Could be a restaurant or something like that that you’re like, “This is really good. This is a good technology.” I mean, I’ve got some examples that I can… While you’re thinking of it, I can throw out one or two. So let me throw out one or two.

Jon: Sure, okay.

Gene: One of them is Google just recently released, if you have a Google business profile, they have an automated chat and it’s AI chat. So if somebody goes and they have a question or they need something, they can do that right there and then, and then you can be notified right there and then that they’ve got a question or a problem and you can follow up right there. That’s a simple little bit of automation, right from the… And it’s completely free to set up that will alert you of either a prospect or a customer that has an issue. And that’s that’s one thing that I think is really important.

Gene: The second thing, and I know this sounds maybe… Point of sales systems, right? There is where I live in Philadelphia across the street is a bakery. It’s a pretty iconic whatever. And they’re great and you go in there and they just resisted getting a point of sales system and it was a chaos to pay. It was a mess. So they finally got wow, wizardry, two handheld point of sale devices, which not only sped up the ability to take their orders and getting payments and all that. But they also included a really important I think for these business is that when you go to make a payment… And I recommend this for anybody who has a point of sale system regardless of your business. They have the extra screen if you want to leave a tip for the employees. And I talked to the owner of the business because I interviewed her for another article I was writing. She said it has increased the… They used to have a tip jar out front. Who carries cash to put a dollar into a tip jar nowadays?

Jon: I have comments on that too.

Gene: Okay. Well, there… Yeah, right? And that was an example of she bought this point of sales system. It was a minor investment really overall. It not only sped up and increased their customer experience going through the store, but it also… You automatically, yeah, get 20% or an extra dollar throwing it on the card or whatever. Their employees… It reduced turnover and helped compensate their employees that much more. So again, there’s some technology that can really help not only with your customer experience, but also with your internal people as well. Those are good examples of technology in my opinion. Go ahead. Your turn.

Jon: Yeah, so mine’s actually… I’m going to give a shout-out to a big streaming audio brand who launched a small business self-service platform when it comes to creating audio ads to use on their platform. So when you think about the cost that comes with marketing, especially when you’re thinking more kind of brand level marketing-

Gene: Sure.

Jon:… they made it really easy to buy media directly, to produce that media in a way that makes sense on their platform and to create creative services without having to work through three or four agencies. And you can essentially do it live, right?

Gene: Huge. It’s huge.

Gene: So it’s a self-service platform for doing that.

Jon: It’s a self-service creative production, but it’s backed by humans.

Gene: Got it.

Jon: So you’re putting in essentially a creative brief, and your spend and things like that, but you can turn it around relatively instantly, especially when you’re thinking about kind of advertising. So say you’re coming up on a local promotion or kind of a sale item where maybe you want to give a little bit more oomph to.

Gene: Good.

Jon: They make it really easy for someone to kind of get the benefit of broad reach marketing without having to sort of…

Gene: Hire all these expensive agencies and involve a whole team of people.

Jon: Right. And they make it simple and the output’s really good. So that’s one I think-

Gene: I like that a lot.

Jon: That’s one I think has done a nice job. I think the other technology-

Gene: You mentioned self-service and while you’re thinking about that, there’s a… There’s a lot conversation going on right now about the good and the bad of self-service. For example, there’s a supermarket… In fact, again, this is public news. Wegmans which is a supermarket chain in the mid-Atlantic and Philly and up to New York state, they’re getting rid of their self-service app. They had an app that you can go around and buy stuff, scan it, record it and walk out the door. It’s just payment, whatever, which to me is a no-brainer. But they were losing a lot of money, people stealing stuff from them, and so they had to take their… You have to be careful using self-service. But I stayed… I was in a hotel in Vegas a month or so ago and they used to have a dozen people behind the check-in desk and now they have one person. They have like a dozen self-service kiosks and you put in the confirm number. Have you done this yet? You put in the confirm number, you slide in your driver’s license and it spits out your room key. It was awesome.

Jon: Yeah, I-

Gene: It was a great customer experience.

Jon: I’ve never done that at hotel. I’ve done that with the airport check-ins.

Gene: Yeah. It was awesome.

Jon: And I think it’s a balance, though, right? So if you’re an industry where… I mean, convenience is probably rules everywhere. But some transactions are just about convenience and there’s very low risk or the issues that are likely to arise are pretty minimal. Then I think, yeah, automation makes a lot of sense. I think that we’ve erred on the side of simplicity, of execution versus kind of the expertise that comes from good problem-solving. And to me that’s where we start to get into a little bit of a…Because then you’re causing more problems that now you have to solve for, so now these people are selling the new solutions-

Gene: Agreed.

Jon: Because people just don’t understand the nature of what they… are they’re not empowered or able to solve for it because they’re kind of now barriered by the technology to make them.

Gene: Final comment, and then I know we got to cut this short, but one other good experience I’ve had, CVS Pharmacy. I’ll give you an example. We had a dog who passed away two years ago. She was a pretty sickly dog. And we had a… You should see the pharmaceuticals that we had for this dog. But I would get texts from CVS saying, “Do you want a… Lavender’s…” I didn’t name the dog Lavender. It’s my wife’s name. But Lavender’s prescription’s coming due. Do you want to renew it?” And I would just respond “yes.” And then it would say, “Oh, we need to call for renewal from your vet. Is that okay?” “Yes.” And then it alerted me when it was ready. You mentioned convenience. Whatever… Again, the customer experience. That was convenient for me. It’s convenient when I go to my dentist which is a small business and they send me a week in advance a confirmation of my appointment that’s a reminder to me, and also helping them in case people don’t show up for an appointment. And then you got to say yes or no, I’ll be showing up. Any technology that you can have that improves that customer experience I think is really, really important to do. I think it is more of a priority than cutting costs. That’s my thought.

Jon: I agree.

Gene: My final thought.

Jon: And I think that’s a good…. It’s a nice line to kind of snap it on. Because I think if you can make the low risk and high demand tasks-

Gene: Yes.

Jon: Easier to handle-

Gene: Yes.

Jon: Then you’re probably creating the capacity for the human side to handle the more serious relative or kind of unique situations. But I think especially when it comes to communication, you need to be able to give people the option quickly to identify and get that remedied. Because I think that’s what gets lost in a lot of the circle.

Gene: Good. Good stuff.

Jon: Awesome. Well, Gene, thanks again for the conversation. We will pick this back up.

Gene: Yeah, lots more in technology to talk about.

Jon: Maybe I will come around and find the brighter side of it.

Gene: Yeah, you’re in a bad mood for this conversation. Jeez.

Jon: But hopefully it wasn’t too much of a bummer for the people out there. We will catch you on the next one. In the meantime, you can check us out at or, and we will see you soon.

Gene: Take care, everyone.

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