Dean Curtis - When to Chat, Text And/Or Email - PODCAST TRANSCRIPT

Editor's note: The following is the transcript of a live interview with Dean Curtis of Ingage. You can read the interview below or listen to the podcast.

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Hello, everyone. My name's Megan Ellsworth here at rooferscoffeeshop.com, and you are listening to a Roofing Road Trip. I'm so excited. Today, we're talking with Dean Curtis from Ingage. Hi, friend. How are you?

Dean Curtis: I'm great. How are you?

Megan Ellsworth: I'm doing good. I'm excited to talk about Ingage and when to chat, text or email, all the different things with all the different generations coming up into the workforce. So let's get started just by you telling us a little bit about yourself.

Dean Curtis: Yeah, no, I appreciate it. This is, I think, my second time on the podcast, so I appreciate you having me on again. It's great to be back with you. So I've been at Ingage coming up on eight years now. It's kind of crazy to think-

Megan Ellsworth: Wow!

Dean Curtis: ... it's been that long. My tech journey, believe it or not, my first job was as a classroom teacher and then I got into tech by way of a big company, Oracle. Went to Palm, went to spend some time at Apple.

Megan Ellsworth: Wow.

Dean Curtis: And I was looking for a place to go to really try my hand at a startup and something much smaller. So here, eight years later, we have tackled the home improvement industry with Ingage, so it's been a great journey.

Megan Ellsworth: Wow, amazing. That's incredible. Apple, those are some big names you mentioned, Oracle. So can you tell us a little bit about what you're seeing around communication struggles with the four very different generations in the workforce currently?

Dean Curtis: Yeah, sure. I mean, we're a team of just about 40 people here at Ingage and you wouldn't think with just that few people there would be the gaps, but it's pretty amazing when you see... So I'm 53 years old, so I default to certain things and then the newer team members that we have on and then we've had interns on as well who are still in college. It is pretty crazy to see, right?

Megan Ellsworth: Yeah.

Dean Curtis: First and foremost, everybody has tech and platform preferences, right?

Megan Ellsworth: Yes.

Dean Curtis: Whereas I might have defaulted to email, maybe other people are defaulting to Slack. So each generation has its preferred tech and way of communicating, and sometimes this can cause friction when certain tools are favored by one, they're like, "Hey, did you see my message on this thing?" And you're like, "No, because I don't look at that thing."

The other thing that we see is formal versus informal communication. Different generations might be a little more informal on some communication methods or don't see the value of formality, or maybe older generations don't see the of informality, right?

Megan Ellsworth: Mm-hmm.

Dean Curtis: So, that balance between being formal and informal. I think also another one to think about is speed of communication. Right?

Megan Ellsworth: Yeah.

Dean Curtis: So different generations might be... It's funny, I just had somebody start at the company. I always give this advice. The speed at which you respond to someone at the beginning of your time at a company is what they're going to expect for the rest of time. And when you start somewhere, you're not very busy, so you're maybe a little faster to respond.

But I think also this is a generational thing too, where some people are just totally plugged into their devices all the time. Well, guess what? I turn all my notifications off on things, so maybe my communication speed's going to be a little different. Is it because I'm older? Is it because I'm maybe more mature to say, "Hey, I'm going to put that away for now"? So, I think that communication speed's one.

And then last but not least, that face-to-face communication versus digital. We think about technology and all of this communication stuff, but there still is the old-fashioned, "Let's go take a walk," or, "let's grab a coffee," right?

Megan Ellsworth: Yeah.

Dean Curtis: So I think there is definitely something there when we talk about face-to-face versus digital as well.

Megan Ellsworth: Yeah, for sure. It's really interesting too. I actually have a follow-up question. Is Ingage completely remote? What's your office style? Do you have an office?

Dean Curtis: We do. So we have an office here in Pennsylvania, so the northeast suburbs of Philadelphia and we primarily have that. There's a few of us in this office. We are primarily a distributed... I call it a distributed company because I think of the word remote as there's us and then everybody else, and I never want to think that way about our company because it creates a, "Oh, I'm not there, I'm missing out from headquarters."

So we've created a headquarters location and the goal is to provide a place for local people to come and work if they want to, but most importantly, provide a place where our team can come and gather and on a consistent basis. We typically try and have teams come together twice a year where they can plan and strategize and meet each other eyeball to eyeball. And that was the goal of taking this space last January, actually.

Megan Ellsworth: Really cool. That's awesome. Yeah, RoofersCoffeeShop, we are completely online. We have a couple offices, but we have people spread across the country, so I can totally relate to that aspect of it. It's really interesting.

So can you talk a little bit on the different communication methods that are available today and how that has changed from a [inaudible 00:05:40] decades ago?

Dean Curtis: Yeah, totally. I mean, I think the obvious statement, technology is ever-evolving. Right?

Megan Ellsworth: Right.

Dean Curtis: I remember back in the day... It's so funny. When I heard we were going to talk about this, I just pictured myself on the corded phone from the kitchen and the innovation at that time was a long cord. So I could take the phone out of the kitchen, still connected, but down the steps into another room where I could shut the door and talk to my friends without having everyone listening to what I was saying because there was only one phone in the kitchen, right?

Megan Ellsworth: Yeah.

Dean Curtis: So it's interesting because when you think about it, there's that traditional communication of face to face. Another traditional was written. I actually received a really great follow-up, I have it right here at my desk-

Megan Ellsworth: Aw.

Dean Curtis: ... from a conference I was at last week where I met somebody for the first time in person. They sent me a handwritten note. While that seems like maybe a traditional way, it's still a very impactful way-

Megan Ellsworth: So impactful.

Dean Curtis: ... to communicate with people. And then phone calls. I have a Calendly link, and originally, I only put my Zoom on the Calendly link because, like, "Oh, we're going to meet video face to face," right?

Megan Ellsworth: Yeah.

Dean Curtis: I actually changed it so I have multiple options. One is a 15-minute phone call. Just give me a call. It's okay. We can still talk without being on video.

Megan Ellsworth: I like that.

Dean Curtis: So you have those traditional ones, which maybe some people think are going the way of the Dodo bird, but I think they're actually still super relevant, right?

Megan Ellsworth: I agree.

Dean Curtis: And then you have those digital ones, email, instant messaging or chat, text messaging. But I also think social media is a communication method today because one, it's another inbox. I don't know, how many inboxes do you think you check a day, right? It's kind of nuts.

Megan Ellsworth: At least two.

Dean Curtis: Oh my gosh. Think about it.

Megan Ellsworth: Maybe more.

Dean Curtis: Your text message inbox, your email inbox-

Megan Ellsworth: Oh.

Dean Curtis: ... your Slack inbox, your Facebook inbox, Twitter direct messages, Snapchat, TikTok, Instagram. It's nuts, the amount of inboxes. So I think those social media platforms are person-to-person communication, but they're also business-to-consumer communication as well.

Video conferencing, before the pandemic, getting on video on Zoom was something that not a lot of people did. Now it seems to be the default of what people are doing. So Zoom, Teams, Google Meet, whatever your thing is. I'm doing a lot more FaceTime calls with people as well.

Megan Ellsworth: Interesting.

Dean Curtis: So rather than just a phone call, we'll just jump on FaceTime where I'm going for a walk and I'm FaceTiming with someone. And then you have the future. You have AR, VR, AI.

Megan Ellsworth: Oh, yeah.

Dean Curtis: You have certain ways that you can... I went to a session a couple weeks ago, it was fantastic. It was the use of AI avatars to do video communication. So basically, I could record a message to a customer and the platform can, basically like a mail merge in an email or a letter, it can mail-merge in, "Hey, RoofersCoffeeShop. It was great to meet you at Las Vegas," and you fill them in. And it's so good because when I first saw this, I'm like, "It's going to be terrible. It's going to be like, 'Hi, RoofersCoffeeShop. It was great to see you in Las Vegas,'" like this... It's not. It's really amazing.

Megan Ellsworth: Whoa.

Dean Curtis: So personally, you asked me what are the different communication methods? There's a bazillion different choices that you have, and I think there's a place for everything depending on a lot of different factors.

Megan Ellsworth: Yeah, yeah. No, that's so true. I didn't even think about, when you first said, "Inboxes," I didn't think about text. I didn't think about social media platforms. I just thought about my email and my Teams, and there's so many, no wonder we're all overwhelmed.

Dean Curtis: Well, and it's a choice, right?

Megan Ellsworth: Right.

Dean Curtis: You have to really think through of where am I going to interact with people?

Megan Ellsworth: Put my time.

Dean Curtis: Because you get multiple perspectives here. Inside the company is one thing, outside the company's completely different, right?

Megan Ellsworth: Yeah, totally. So because there are so many ways to communicate with consumers, with each other now, how do you determine which is best in each situation?

Dean Curtis: Yeah. I mean, I think there's a number of factors that come into this. Number one, what's the purpose? Why am I communicating? Is it to inform? Is it to ask? Is it to just connect?

I have a habit of when it's someone's birthday, I'm not perfect at this so someone's going to watch it and be like, "You didn't send me one," but one of the things I like to do is record a little video and send it to them in a text message.

Megan Ellsworth: That's sweet.

Dean Curtis: Because it's a little bit more purposeful and a little more personal connection, right?

Megan Ellsworth: Yeah.

Dean Curtis: So I think the first thing is understanding when you're communicating what is the purpose of the communication? You have to be intentional about that.

The second piece is the complexity of what you want to say. If it's just a simple informing, a text message might be a perfect way to communicate with someone. If it's educating someone on a topic, well, maybe there's video or maybe you got to go a little above and beyond on the method that you use to communicate. So that purpose of the communication, the complexity of the message.

And then I think another factor is the urgency. How quickly do I need... I don't know. What do you check faster, your text messages or your email?

Megan Ellsworth: Text messages and Teams, always.

Dean Curtis: Totally, right?

Megan Ellsworth: Mm-hmm.

Dean Curtis: So there's a hierarchy of where you're going to reach people. People in our company know we have Slack as our... You use Teams, we use Slack. I don't look at Slack all the time. If you need to get me, you need to send me a text. It's the one, that is the number one way to get me is through text message. So understanding the urgency of the message also, whether it's internal or to a customer, that can also determine the means by which you communicate.

Something I'm not sure people really spend a lot of time on is the tone of the communication as well. Is it a familiar tone? Is it a questioning tone? I'm a big fan of this guy, Jeremy Miner. He's a sales "guru." You can take that for what it's worth, but he talks a lot about tonality in sales and how you communicate with your tone is really important.

And then lastly, who's your audience? If I'm texting my kids, it's very different than if I'm texting the CEO of a company that I want to do business with or sending a communication to them. So having real understanding of who your audience is and what they would expect is pretty important.

Megan Ellsworth: Yeah, and I think especially having all these younger generations coming into the workforce and being in the workforce now, some of that mentorship from older generations is really helpful and useful. And also, the back and forth between the two is helpful.

Dean Curtis: Well, I think the other way is important too, right?

Megan Ellsworth: Yeah.

Dean Curtis: It's important for people who are in an older generation who are maybe a little more stuck in their ways, it's an assumption, but I think it's a pretty safe one, to be open to coaching from the younger generation to say, "Hey, it's okay to throw a couple emojis in every in a while." Some people really like that, right?

Megan Ellsworth: Yeah.

Dean Curtis: Or, "Choose the emojis well," or, "here's some..." It's not just emojis, but it's a simple example of how there's really stuff to learn from one generation to another, whether that's up, down or in the middle, there's a lot of different things that we can learn from each other.

Megan Ellsworth: Yeah, yeah. I think something that I have been really appreciating too about the business world as I've been entering it over the last six years is it's okay to be fun. You don't have to be so businessy all the time, and I think that's something that's maybe even happened since the pandemic, a more relaxed vibe and feeling like sending gifts in the whole crew chat or something or sharing more personal stories and just calling someone and being like, "Hey, I have a quick question," because it'll be the fastest way to reach them or stuff like that. Being more relaxed has happened, increased since I've joined the business world.

Dean Curtis: Yeah, I think the other thing to consider when you're looking at that mentorship, whether it's from young people to more experienced or older people or older people, an older generation to a younger generation, is vulnerability. It does take some vulnerability to admit, "Hey, maybe I'm not 100% great with this. Maybe there are things that I can learn."

And being humble enough to say, "I'd love your coaching on this," even though it's someone who's two years into the workforce and you have 22 years in the workforce, it's totally fine. There's so much that we can learn from each other.

Megan Ellsworth: There's so much, and like you said earlier, it's vice versa. Older generations learning from younger generations, but also, so the older generation has to have that vulnerability and open-mindedness, the younger generation needs to be a little introspective and say, "Yeah, maybe I could work on my communication skills," and, "maybe I do send too many emojis," or something like that. So definitely that open communication is important.

Dean Curtis: Totally.

Megan Ellsworth: So this communication challenge extends further than the office, like you mentioned, it's in multiple areas of life, so it affects customers as well. How do we approach having successful communication with our customers?

Dean Curtis: Yeah, I think it's almost a repeat, right?

Megan Ellsworth: Yeah.

Dean Curtis: Because if you're going to choose to communicate well within your company, it's the purpose of the communication, it's the complexity of the message, it's understanding the urgency, it's the tone of what you're saying, it's knowing your audience. It's all of those things are equally important as you're communicating outside of your company as they are inside. And as soon as you're practicing one thing inside your company and another thing outside your company, you're actually not practicing the same skills, which are very, very important for your success.

It's your success internally and building rapport and communicating with your own teammates, but it's those same skills that translate out to the market as well. And if you're hitting your customers up only with email and they're not responding... We do this within our sales process. One of the most golden things we can get for a customer or a prospect is a cell phone number because we can text them because we know that texting people, they're going to answer faster and it's good for everybody. We can help them faster, and also, our sales team can be more efficient in their process, not just our sales team, our customer success team, our customer support team, all of them. So the communication challenges that are inside the office, it works with the customers as well.

But the key one, I think if I had to pick one that's most important, know who you're talking to. If you're talking to someone in a generation that doesn't use text, don't use text. Don't expect them to adapt to you. You have to adapt and have communication methods that are meaningful for them and hit them where they are most likely to feel comfortable in that communication stream.

Megan Ellsworth: Totally. Yeah, absolutely. I love that. And I mean, I didn't even actually think about text because a lot of times when a customer isn't responding via email, I just go straight to calling. But maybe it would be better to shoot them a text first and say, "Hey, can I chat with you?" Or something like that. That's a really good point.

Dean Curtis: Yeah. Because I mean, let me ask you a question. If your phone rings and you don't know who it is...

Megan Ellsworth: I'm not answering it.

Dean Curtis: I think most people are like that these days, right?

Megan Ellsworth: Mm-hmm.

Dean Curtis: With all the robocalls and all that stuff-

Megan Ellsworth: I know.

Dean Curtis: ... it's really tough. So versus a text, you can respond and say... Because you can give them context.

Megan Ellsworth: Context.

Dean Curtis: We're always training our team on. So I'm going to send you a text and be like, "Hey, Megan, this is Dean from Ingage. I've been trying to reach you. Let me know when it's a good time to give you a call." And now they have your number, so when you call, they're actually going to answer. It's definitely... It's better for everyone. Right?

Megan Ellsworth: Yeah. I love this conversation. Okay. So is there a way to establish best practices throughout a company to maintain branding and keep the messaging, you just talked about you work on this with your sales teams, to ensure the right communication style is being used in the right circumstance?

Dean Curtis: Yeah, absolutely. I mean, branding is a huge thing for us and our company, but I'll start with this. I think creating clear guidelines and processes is really important. We use the term at our company is playbooks. So if we're doing a specific thing, if it's a customer success sequence or if it's a sales sequence or if it's customer support thing, we have clear guidelines and processes that we call playbooks that are run to accomplish the task that we want. So it's really important to have clear communication to your team on when you're communicating to customers about this, that and the other thing, here are the methods that we use. We templatize a lot of things, so we have a lot of email templates and text templates that people can use in order to have clear communication. It also helps us understand what's working and what's not working.

So if we're standardizing our ways, means that we're using to communicate, text, email, voice, whatever it happens to be and we're standardizing the things that we say in those communications, we can now test, A/B test and say, "Hey, I know I got Megan on the phone more quickly because I did email, text, phone call, rather than email, email, email, phone call," or whatever the... Silly example, but that's the point of having that real consistent playbook.

Megan Ellsworth: That's huge.

Dean Curtis: Absolutely. So the other thing just internally is talking about what we call platform usage guidelines. So if you are trying to communicate with your teammates internally, we use Slack. So if you just need a quick answer to a question, we use Slack. If it's a piece of information that needs to last longer and is more of an education piece or a training piece, we use a system internally called Notion. So it's a Wiki, it's a database of stuff or maybe you have set rules for email.

So having those usage guidelines, like my thing I said earlier, you want to get in touch with me in a pinch, you better send me a text. Right?

Megan Ellsworth: Mm-hmm.

Dean Curtis: So those guidelines for people internally also is super important. It just gives you a way so that people know the most effective ways to communicate, both internally and externally.

Megan Ellsworth: Yeah. I love what you said about keeping a record on how a customer responds to a certain communication style. Maybe, like you said, email, text, phone call. If that's the best pipeline, then stick with that pipeline for that customer. Don't switch it up.

Dean Curtis: That's right.

Megan Ellsworth: Someone should be taking notes here. That's good.
You touched on this, but how does Ingage address different communication styles within and without the company? Like you said, Slack, Notion. What if someone, like you said with text, what if someone keeps trying to get a hold of you on Slack? What [inaudible 00:22:15] do in that instance?

Dean Curtis: Yeah. I mean, so internally, it's just the constant reminder. A, it's good onboarding. So when people join, and I onboarded someone this week and we set up all their systems on their computer and we're like, "Okay." He's like, "Okay, you just installed 10 things. What is the purpose of each of these pieces of software?" "All right. Well, we typically use email for this and we use Slack for this and we use text message." We don't text message each other very much. That way, it becomes the most important one.

So it's really those platform usage guidelines of where do I go to find certain information? And I think as you're communicating with customers as well, it's building those best practices around what the expectation is and then holding people accountable to it.
The other thing that I think is important though is if you have a new team member, or if you have somebody on the team who's having great success, what are they doing? Right?

Megan Ellsworth: Mm-hmm.

Dean Curtis: Ask them, what are they doing that's bringing that success? One of the things within our Ingage software platform that we talk about all the time is our analytics for data-driven decision-making. And so if your sales team is out there and they're delivering presentations, and now you can look at the analytics behind the scenes of what's going well and what's not or how people are using the content, a lot of people when they go and deploy these presentations and start looking at the analytics for their team, they have an idea of how they believe someone should be presenting in the home. Almost everyone who's listening has a sales process and they expect you to go from A to B to C to D, whatever it is, five steps, seven steps, whatever it is.

Our software gives people the ability to see how well the presentation is being delivered to the training that they may have been given, but maybe Megan's doing really, really well and is not 100% on the script that she was taught on because she figured out a new way. Using those analytics for that as well is super important. It's not just punitive. It's not just Big Brother. It's, "Wow, Megan's closing at a 5% higher rate than the rest of the team, and she's spending more time on section three of the presentation. Let's bring Megan in or have her share some best practice with the team."

So we're talking about communication, but there's also the idea of using technology to support consistency in your environment and reporting back. I mean, almost every platform that people deploy in their tech stack has some kind of analytics in it. So how can you use those analytics to assess the communication that's happening? Are people opening text messages? Are they responding to emails? Are they clicking on links? All of this is there, but if you're not using those analytics, it's kind of pointless.

So what we do, so you asked me the question how do we address it, not perfectly by any stretch, there's no question that we could do a better job, but we try to look at the analytics within the different platforms we use for communication to understand how effective it's working.

Megan Ellsworth: Amazing. Wow. Yeah. And like you said, keeping that process again, "What's Megan doing different? Let's document this." That's great.

So how would you suggest a roofing contractor implement some of these processes into their business, and maybe can implement starting with Ingage as well?

Dean Curtis: Yeah. Our product aside, the key is don't take on too much. I think we talk to a lot of contractors who are in the middle of a big tech refresh or implementing a bunch of technology, and many, many times, they get overwhelmed because there's so many different things that they could implement and there's so many great pieces of technology out there.

But the idea that I like to share is prioritize your tech stack. Which of the things are going to have the most impact with the shortest amount of integration time? Get those things up and running so that way you can get your people enabled on the technology because one of the things that people underestimate in the deployment of technology is the adoption piece of it.

We can all go out and spend tons of money on technology, but if we don't have a plan around the integration, the deployment and the teaching of how to use it and why it's important to the workflow of the person in your company, that's going to lead to failure. And none of us want to fail. We're all well-intentioned in purchasing these solutions.

So I think that piece of it is so important and often overlooked of how much time is it going to take to really get people to understand and adopt, activate the software in a great way? And how do you do it from a communication standpoint? You start simple. You start small. The bigger your project, I think the more likely it is to not have success. So if it's, "We're going to now, we're going to, just this month, we're going to focus on our email and we're going to look at how well our email is performing and then next month, maybe we'll add some text messaging to it so we'll see if texting has the ability." Remember, back to science in high school, you're taking it, you can't change too many variables at once, otherwise you don't know what actually impacted the experiment.

So as much as we'd love everyone to take our software, and I'm sure all of our partners would love everyone to just jump in headfirst into all this technology, I think it's important to take a measured approach and really add things layered on to see what's really having an impact in your business.

Megan Ellsworth: Yeah, that's great advice. I think that can also be used in your way of communicating as well.

Dean Curtis: Totally.

Megan Ellsworth: If your communication style isn't working with someone, change one thing and see if that works. If it doesn't work, change the next thing. Try a different style.

Dean Curtis: I remember really vividly a conversation with a sales rep one time, and it was like, "Oh, we have this big deal in the pipeline. We think it's going to close." I was like, "Well, how are you..." They're like, "They haven't called me back." I was like, "Well, how many times have you called them?" They're like, "Well, I haven't really called them, but I've emailed them like 12 times." I'm like, "Buddy, you can't just email. You need to rely on multiple ways of communicating. Maybe your email's going to spam at this point, maybe. How do you know? Have you texted them? Have you called them? Have you sent them a letter?" I was like, "Try, please, try something different."

The definition of insanity is trying the same thing over and over, expecting a different result and finally, he picked up the phone and called them and sent them a text and it was amazing how they got back to him because that customer was more likely to respond to personal connection. They found email to be impersonal. Great. What a learning.

Megan Ellsworth: What a learning experience. Exactly. Send a carrier pigeon if you have to.

Dean Curtis: Whatever, send them a basket of cookies. I don't know, something. Get their attention.

Megan Ellsworth: That's a great idea. Well, Dean, we blazed through all of these questions. Do you have any other tips or tricks for roofing contractors or anyone out there listening to this that wants to improve their communication skills through technology?

Dean Curtis: Yeah, I mean, I would say try something new, right? It's the summary of what I just said is it's okay to try something new. There's tons of great AI stuff out there as well that might help you improve the message or make a very consistent way to automate some of these processes as well.

I had a meeting this morning with someone I used to work with a long time ago who just started a company doing AI chatbots for websites, and we were just talking about how something as simple as that can offer a totally improved experience on your website and that's another communication method. Your website is a communication method.

Megan Ellsworth: It is.

Dean Curtis: How can you convert more leads that come to your website, and he was talking to me about the AI technology that they're using when people come to websites in order to have a better conversation with them. It's AI, it's a bot, it's not a real person, but they can be trained really, really well to answer the most common questions and potentially get a lead in your funnel. I think contractors that I talked to recently, leads are at a premium right now, so any way to get better leads to communicate with those leads, to educate those leads before they even talk to your team, maybe there's some AI technology that can be used as well.

Megan Ellsworth: Yeah. Dean, thank you so much. This has been so informative and really fun, so thank you for chatting with me and I hope to see you again on another Roofing Road Trip.

Dean Curtis: Yeah, no, I appreciate you having us on.

Outro: Absolutely. For everyone out there listening, you can go to rooferscoffeeshop.com to the Ingage Directory to learn more and we'll see you next time on the next Roofing Road Trip.

If you've enjoyed the ride, don't forget to hit that subscribe button and join us on every roofing adventure. Make sure to visit rooferscoffeeshop.com to learn more. Thanks for tuning in, and we'll catch you on the next Roofing Road Trip.