In this episode, we talk about digital disruption – specifically the disruption of a process as old as humanity itself: finding a mate – and what lessons you can learn from it about boosting efficiency at work. This podcast features an interview with Online Dating Consultant and Digital Nomad, Steve Dean.


Podcast Transcript

Heather Taylor

Hi, I’m Heather Taylor, and you’re listening to the Simplicity 2.0 podcast, devoted to exploring how executives can tap some of today’s most disruptive technologies to gain a competitive edge. Today, we’re talking about digital disruption, specifically the disruption of a process as old as humanity itself – finding a mate – and what lessons you can apply to boost efficiency at work.

While there used to be a stigma against admitting you met someone online, today, 59 percent of adults say that online dating is a good way to meet people compared with 44 percent in 2005.

It probably helps that going digital has an attractive upside.
Business Insider reported that the average time for traditional dating to marriage for couples who met offline was about 42 months, while couples who met online averaged only 18.5 months of dating before walking down the aisle.

Is it time for businesses to take a cue from the online dating world to boost efficiency? Find out now.

Simplicity 2.0 is brought to you by Laserfiche, the world’s leading enterprise content management software, which manages and controls information so you can empower employees to work faster, smarter, and better.

[Music playing]

So, I’m here today with Steve Dean, an online dating consultant from Dateworking. Hello, Steve. Welcome to the show.

Steve Dean

It’s great to be here.

Heather Taylor

So, I’m going to jump right into questions. Steve, what made dating so susceptible to digital disruption? And what business processes are similarly susceptible?

Steve Dean

So in the case of dating, it started out, I mean, dozens of years ago, where people were trying to meet face-to-face. But there’s a lot of problems with just trying to find out whether this person across from you is interested.

And if you don’t have a person across from you, you have to go and, like, find out where those people live. You go into a new city. You don’t know what’s around. You don’t know who’s around, who to actually find.

And then suddenly, online dating comes along and says, “Oh, not only are all of the different people with their profile photos right here, ready to be displayed, but also here is information about their background, about what they actually want.”

So, you don’t have to fish around for hours and hours. And every endless conversation, trying to find out whether or not you’re actually compatible. We have algorithms that can say, “Okay, here’s the information you already wanted that would have otherwise taken you hours, days, or even months or years to actually come across all of those deal breakers that you don’t find out about until months later.”

Online dating says, “Hey, let’s just put them right to the front so that you know exactly what you’re going to be dealing with.” And in terms of business processes that are susceptible here, I like to think about – like, anything that can be touched by algorithms and big data is going to hit business really hard in a good way, potentially.

So, I’m thinking something like housing. When you’re looking in the housing market, trying to find a way to get access – like, well think of how much data it takes for you, as an individual who wants to understand where you should find your next apartment.

And try doing that. And you look through classifieds. You look through – like, there’s just so many little things you have to, like, go – well, before Airbnb. Before, you know, big data came along and said, “Hey, we can just crunch all the numbers on every preference, every different thing that’s available, and immediately show it to you in a very easy interface.”

Before that, you know, people would – you would have to ask your friends, maybe post on Facebook, go to different Facebook groups. There’s just so much you have to go through and do in order to find out, like, “Where do I stay for tonight?”

And suddenly, Airbnb just says, “Oh, you know what, like, that data is available. Let’s just either – let’s create the repository, where everyone can find out exactly where to stay next.”

Heather Taylor

Fantastic. So if we’re looking at taking that and to make things more efficient – so, I read a 2014 study by a marketing strategist at Convergex Group. It’s a New York based global brokerage company.

And it found that online dating can actually save individuals thousands of dollars. So, what lessons does this offer executives looking to make their firms more efficient?

Steve Dean

So, I think it’s interesting that online dating has barely even touched into AI, so far. They’ve been really focused on a little bit of machine learning, but mostly just making flows easier. So when I say, “flows”, I mean like if I want to get from point A to point Z, it may take a lot of steps.

I may have to go out to a bar, start talking to people, do all those different things. And one of the things that dating was able to do is actually reduce the number of total steps required, by letting you do most of them online and in seconds, rather than taking hours or days in order to actually accomplish it.

So, I would say let the AI do the work for you. There’s so much work that can be done through AI and machine learning. And most businesses are either not capitalizing on it. Or they end up paying people who are.

So, think about Salesforce. How much money do people spend just to use Salesforce? And what is it that Salesforce does? It allows you to handle your lead generation a lot more seamlessly. So rather than having to make sure you remember to message the last 15 people you’ve called and write down all of their contact info, Salesforce says, “You know what, let’s just – we will handle that for you. You know, we’ll collect the info. We’ll put it in a massive database. We’ll make it easier to access. We’ll send you reminders when you need to follow up with people.”

And it’s not just Salesforce that does that. There’s a number of other companies. And this is like across the startup world; you see every couple days a new startup launching that tries to handle some more of this.

But the main thing is, if you’re not – either build it yourself. Like, take advantage of the machine learning and the AI that can allow you to save so much time and energy in your internal processes. Or, I mean, you’ll end up, probably more often than not, just outsourcing to a service that already has specialized in that specific category.

Heather Taylor

So, really for the efficiency to take place, you really need to have that data and have that information. So, we recently – Pew Research found that a third of people who’ve logged onto a dating platform online, have never actually gone on a date with someone from those sites.

So, what can executives do to ensure a better adopt trade of new technology among employees so they can continue to become more efficient?

Steve Dean

So, it’s fun to think about why people fail to actually go on dates from dating sites. And then, how that directly translates into why people might fail to adopt a new technology that a business proposes.

And a lot of it comes down to user experience – design user experience, which you would call UX. The biggest challenge is that if you don’t account for your users being confused, being busy, having their attention divided or attention elsewhere, then you’ll end up launching things that either piss them off or make them just get really confused about what they’re supposed to be doing here.

So a lot of dating sites, you know – even think of something as popular as Tinder. One of the things that it does is leave users really stranded. So like, they match. Okay, that was really easy. They made the UX super easy to get in, to make a profile.

It takes two seconds, two swipes. And then suddenly, you have a profile and you’re matching people. But the next step is where the critical failure is, where they didn’t think it through. Like, what do users do once they’ve matched?

They don’t know what to do. Now, they say like, “Hey, hi? What’s up?” And so, one of the things that businesses need to realize is that you can get people maybe even using a product if you tell them like, “You’ll get fired if you don’t.”

But they’re not going to use it well, unless you’ve really put the effort into the UX portion, where you actually think through how many steps does a user have to go through in order to make sure that they get from point A to point Z.

And it’s probably going to be, ideally, fewer than 26 steps. You don’t there to be a point Z. How can you reduce the total cognitive burden on each of your users, each of your employees? Because the more work you make them do, the more you make them transition out of what they’re comfortable with, the harder it is for each individual employee or user to actually adopt the new product.

Heather Taylor

And if we’re looking at the idea of choice – so obviously, dating apps – there is tons of choice now. I’m sure there’s hundreds and hundreds of apps and ways to get that date. So, you know, I think it’s a little bit overwhelming.

So, how do you engage employees in choosing new technology solutions while avoiding this sense of option overwhelm?

Steve Dean

I have a funny anecdote related to this. My previous startup, we went through over seven different product management apps. So, we would choose one.

Heather Taylor


Steve Dean

And then, we’d realize, “It’s missing a little bit.” And so, we’d then try another. And then, someone else would say, “Hey, how about this one? I got a membership to this one.” And so, we’d try that too.

Now, we’re using two of them at once, and that’s terrible.


Steve Dean

So yeah, option overwhelm is very real. I think the thing that I would bring over from the dating industry that’s actually worked really well is the Tinder example, once again, in this case, something they’ve done super well.

I don’t know if you’re familiar with GIF messaging, which is when you send those moving photos to people, rather than sending text. Tinder – most dating apps had never even heard of or implemented GIF messaging.

And then, Tinder started taking a page out of the most popular smartphone apps on the market. So like, what’s happening in Snapchat? What’s happening in Facebook Messenger, which is one of the most popular apps in the entire app ecosystem worldwide?

And even WhatsApp – the big players – they’re all using GIF messaging. And so, Tinder said, “Hey, you know, why don’t we do that?” And so, the thing that is crucial to remember there is, like, users were familiar with this.

This is something that – you know, if on every other one of your apps when you’re talking to your friends you’re sending GIFs and then you go to dating apps and you don’t get to send GIFs, there’s a problem there because something you’re familiar with is not being implemented in an industry.

And as soon as they started launching that feature, suddenly people immediately – I mean they immediately began using it because, you know, it’s something that users are familiar with. So, I’d say start with where your users are already familiar with certain features or certain flows.

And then, use those as the bridge to implement something new. So, you really want to start with what they’re familiar with. And start with something that, you know, they can get their heads around. Because sometimes when you introduce something new, it can be a little bit scary or frustrating.

And if you pull in, you know, some of the nicer, easier things that they’ve already been familiarized with, it makes your life a lot easier.

Heather Taylor

So, if we think about – you know, we’re talking a lot about being online and in this kind of a progressive future. But Pew Research also points out that even among people who have been with their partners five years or less, 88 percent said they met their partners offline without the help of dating sites or apps.

So, what can CIOs do to encourage a digital transformation when the rest of the C-Suite in their company is maybe sticking to tradition and isn’t ready to take that next step?

Steve Dean

I have an example from my personal life here, where I tried to teach my mother how to use texting. And this was something she was very unfamiliar with. And so, I figured, “Okay, what do I actually have to do to get” – like, I – she had a phone, but she wasn’t using it.

She would still e-mail me. And I don’t like checking my e-mail. So, what I actually starting doing – I stopped validating the behavior of e-mail checking. And instead, I just said, “If you want to know about life, you’re going to have to read your texts. If you want to ask me questions, you’re going to have to learn to text.”

So, I basically aligned her incentive. She wants to know what’s going on in my life with the necessary reward. So if she wants to actually get more information from me, she has to check her phone and she has to start texting.

And interestingly, she now is at the point where she can start sending emojis. So, she’s actually gone above and beyond the call of duty there. And from the dating industry, there’s actually a really cool thing.

I don’t know if you’ve been following just the meteoric trajectory of Tinder since it launched. One of the things that they did was they recognized that users were not really ready for the dating industry.

You know, still, you know, I think only 20 some percentage of people have actually used online dating. And so, it’s something that, you know, it’s still new. There’s still a lot of stigma around, you know, “You don’t want to date online. Can’t you just get a date in real life?”

But Tinder killed it. Tinder killed the stigma. And the way they did it was by not calling themselves a dating app, at any point. They said, “We are a social networking app. We’re here so you can meet people. Meet awesome people nearby.”

And by doing that – and even branding the actual flows in the app as a game, as a swiping game where you can learn about other people – they made it so it wasn’t this creepy, weird thing where you had to do it to get a date or the type of people on this app were only there because they couldn’t get a date offline.

It said like, “Meet your next friend. Go to a new country. Swipe there. See who you can meet while you’re in that country.” They really hit the branding in a way that allowed for that stigma to roll away.

Because you could be on Tinder and your friends wouldn’t say, “Ugh, what are you doing on Tinder?” No, they’d be on it with you. And you’d be like standing side-by-side, swiping through, laughing together.

And that’s something that, you know, by sweeping away the stigma, that really paved the way for the dating industry to become much more mainstream. And so, I credit Tinder with that.

Heather Taylor

Fantastic. Well, that’s it for us for our questions. I’d like to thank Steve Dean from Dateworking that kind of came and spoke to us today. So, don’t forget to add Simplicity 2.0 to your favorite RSS Feed or iTunes.

Thanks to Laserfiche for sponsoring today’s episode. Learn more about Laserfiche at or follow us on Twitter @laserfiche.

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