Digital Journeys Can Be Human

Clicking “buy now” shouldn’t feel like shouting into the void. In this episode, we explore how digital retail can feel more human by pairing smart personalization with trust-building micromoments. Instead of proving what we know, we focus on what customers need next: clear fit guidance, delivery transparency, and friction-removing policies that build confidence before checkout.

We share practical moves you can use this week—from confirmations that speak to the shopper (not the order number) to shipping updates in plain language, short stylist videos, and behind-the-scenes warehouse moments. We also cover how to use chat well: being upfront about bots, designing warm handoffs to humans, and giving AI a role that feels helpful, not blocking.

Reassurance is the real conversion multiplier. We talk about sizing honesty, responsible return signals, clear expectations on duties and timelines, and how to keep the warmth going after checkout. The simple test we return to again and again: would this message feel kind and useful if you sent it to a friend?

If these ideas help, subscribe for more customer experience strategies, share this episode with your team, and leave a quick review so others can find us. Your feedback shapes what we explore next.

Resources Mentioned:
Order your copy of Experience Is Everything -- http://experienceiseverythingbook.com
Experience Investigators Website -- https://experienceinvestigators.com

Want to ask a question? Visit askjeannie.vip to leave Jeannie a voicemail! (And don't forget to follow Jeannie on LinkedIn! www.linkedin.com/in/jeanniewalters/)

Chapters

• 0:00 Framing The Digital Human Gap
• 1:39 Helpful Not Creepy Personalization
• 2:34 Micro Moments That Build Trust
• 5:16 Humans, Bots, And Transparency
• 7:40 Reassurance On Color, Fit, And Returns
• 10:20 Celebrate Purchases And Keep It Warm
• 12:15 Choose Channels Customers Prefer
• 13:45 Close The Loop Like A Human

Transcript

Jeannie Walters: 0:00

Let's face it, we live in a digital world. Let's dive into it in this edition of Experience Action.

Listener Question: 0:09

Hi Jeannie. I work for a retail brand where the buying journey is mostly digital, but customers still expect that personal human touch. I'm struggling to figure out how to make an online experience feel as warm and engaging as an in-store interaction. What are some ways to bring that emotional connection into the digital shopping experience without it feeling forced? Thank you.

Jeannie Walters: 0:37

Such a fantastic question because really, when we are talking about digital journeys, we aren't really translating what the customer is experiencing. The customer is simply going for something. They are going to purchase something. They are trying to rectify something online. They are simply having an experience. So we, So it's up to us as customer experience leaders to really understand what is it they're trying to do and how can we bring the human experience to them. Because really, they're not comparing this experience that they're having against other digital experiences. They're comparing this to all the experiences they have: human, face-to-face, on mobile, on the digital desktop, whatever it is. So the first thing we have to think about is how can we weave in some ways to treat them just like we would treat them face to face? Now, one way to do this is personalization, but we have to walk that line. We have to understand this is personalization that feels helpful and not creepy. We don't want to say, wow, it's been a while since we've seen you, right? That would be creepy. But we might say, you know what? You were looking for those types of sweater. Can I make a suggestion? Can I share something that goes with that? When we ask those questions in a digital channel, a lot of times people do feel like it's helpful. We are predicting what they might need next, just like a really great salesperson in a store would do that. So think about the actual experience that they have and how to personalize that as they go through your digital experience, but focus on their benefit. What can they get out of it instead of really thinking about, you know, we just want to sell more. The other thing we want to do is really think about those micromoments that I love to talk about. I define micromoments as the moments that can either build or erode trust, but are often neglected. They are sometimes the in-between moments or what I call the meh moments. These can be things like a confirmation email or something like, you know what, if if you're about to send out something saying your order is being shipped, those little moments along the customer journey that are pretty transactional. What can we do to warm those up? There are some great ways I've seen this done. One is instead of saying something like, your order has been placed, uh, say something more about them, about how excited you are for them. You're going to love this thing that you ordered. Here's what other people have said about it. I would love to know your feedback once you receive this item. Just really making it a one-to-one conversation. Now, the other thing is how do we really weave this in in those neglected moments? Those neglected moments are important to look for in your journey as well. Now, when we talk about customer journey mapping, this is one of the things we look for. We want to look for those micromoments. What are those moments that, yeah, they're fine, but they're not great. They're not personal, they're not warm, they're not human feeling. So as you look at your own customer journey, I encourage you to think about where are those micromoments where we could turn up the warmth a little bit. We could make them feel seen and understood. We could suggest the next step for them before they have to ask for it. So all of that would be a great way to warm up the digital experience. Now, the other thing to remember is that we like humans. We like to see people, we like to see faces. So let's use humans proactively. When we are talking with a human being, it feels different. We like knowing that there's somebody who is really looking out for us. So if you have something like a chat bot on your site where maybe you have people some of the time and maybe it's AI some of the time, be very, very transparent about that. And then also, I've seen some really creative ways that brands are starting to use photos of the real team members there or an avatar, a fun avatar. So if you are talking to an AI bot, you know who you're talking to, essentially. So look into ways that you can warm up those types of purely digital transactions so that people feel like they know who they're speaking to. Uh, the other things that I've seen sometimes are around really showcasing the team that is putting your order together. Look, this is this is uh Mirabella, and she is packing your package for you. One of my favorite examples, which I've shared in my keynotes and other places, is when I ordered some Halloween costumes for my kids online, and I got an amazing confirmation email, and they sent a video where they showed people actually getting really excited that I had ordered. They had everybody in the warehouse kind of cheering, and then they went through a little journey of saying, look, we're gonna get it from here and we're going to package it up, and it's on, it's going to be on its way to you very shortly. Now, of course, this was not a custom video for me as a customer, but every customer who ordered got that amazing, warm personal touch that made us feel like, oh, this is a real team. This is not a faceless organization. So anytime you can add that, that can be very helpful. Nordstrom is doing something interesting. They've been doing this for the last couple of years, where they actually show their in-store stylist in a little video explaining why an item is popular, how to wear it, how to style it, all of those things. So sometimes they even say this item was selected as our item of the week by the stylist in Minneapolis or in, you know, California, wherever they are. It's just a little human touch to help that digital experience. And then, of course, you've heard me talk about this before: reassurance, reassurance, reassurance. We have to be proactive about answering the questions that our customers have before they have them. So if you are shopping digitally on a retail site, you might have questions like, is this really the color? Because we've all had those experiences where we order something and it comes to us and we're like, whoa, that color was really off when in the picture. Um, we want to see how it would look on ourselves like clothes or in a room. We want to ask questions like, okay, well, you know, this says this is a certain size, but is it really? So all of those questions, the more that we can proactively answer those for folks and let them know they're not alone with those questions, that can be really good too. One of the things that some of the digital retailers do is also share this item is returned often, or this item is is not. That gives you reassurance as well. The other way to reassure folks is to say, this is exactly how you can return this easily. So it takes away that barrier of, oh my gosh, I don't want to get something, and if it doesn't fit, I don't know what to do with it. So anyway, you can break down those barriers, those points of friction, so they don't have to ask those questions. They get that reassurance along the way. This is also especially important with shipping. Right now, today, we are hearing about customers getting surprised by uh having to pay duties or tariffs or things like that. So make sure that however you're shipping things, you are setting the right expectations around the timing and the cost and anything else. For instance, going back to the returns, will they have to pay extra to send something back in today's market? These are questions you have to look into for where you are and how you're shipping things out. But it's very, very important that you are being very direct and transparent and honest with customers throughout this. So any way you can provide that clear, empathetic guideline around what will happen next, what could happen, and how to help the customer proactively, that reassurance will reduce the anxiety and really create a sense of we are valuing you, we are caring for you. And then the other thing I would say is let's make sure that we celebrate the moments, right? Like if somebody's making up their mind on something, and it could be a small purchase, it could be a large one. People order cars online now, they order furniture. So if they're making a purchase like that, that's a big deal. And we want to celebrate that. Like, congratulations on your new car. That's amazing. But we could also do that for the small things. Oh my gosh, you're gonna love this tea kettle. All of our customers love this tea kettle because it's fast and it looks great. It's going to look great in your kitchen. You know, really humanizing in the way that we would if they were right in front of us. That can be really fun. You can also make some thank you videos, I've seen that, um, progress updates that feel very human. So things like, hey, I'm so-and-so in the warehouse and we're packing it up right now, and it will be shipped to you in two to three days. So just making sure that we are keeping them connected and communicating in that really human way. Now, the other consideration is that we have to understand how our customers like to be communicated with. A lot of organizations now have different options. And so you want to see is an email better? Would you rather have text updates? What works for you? And with those text updates, you can be even more creative. You can use those emojis, you can use different fun things. Don't be afraid to do that. If you were talking to a friend, how would you reassure them? How would you add some humor? How would you add some happiness? That's what I want you to think about as you design these experiences. And then finally, you know, I think sometimes the transaction leading up to the sale can be very warm. And then a lot of times afterwards, it feels very transactional. We get those ugly emails that say, you know, confirmation. We might get something after saying, here's a survey. But what if we warmed that part up? What if we kind of close the loop more like a human? And we said, how did everything go? Right? Like, what can we do next time? If we start the conversation that way, it feels very different than, hey, customer, fill out this survey. So there is so much opportunity here with digital journeys to really warm things up, to make them more human, and to do it at scale. And I think that we aren't taking advantage of all of these things in the way that we could. We are kind of staying in that transactional lane sometimes. So shake it up, try things out, see what messages resonate, see what your customers want and how they want to be communicated with, and then go for it. Be human. It's okay. So I hope that as you approach your digital journeys, you will take note too when you are a customer and it feels warm. Make little notes about that because that's how we can all learn from each other as well. So thank you for asking this question. Always a good one. And I just want to say this year has been phenomenal. We are at the end of 2025 here, and I am so proud of each of you. I really am. The questions that you ask, the way that you are leading right now, it is impressive. So give yourself a pat on the back. You have made it through 2025, which, you know, we've had a lot of ups and downs, haven't we? But you've you've done it. And you've done it with grace and empathy and compassion. And you've also done it as a leader. And so as we look to the future of 2026, I really encourage you to think about how you can lead in an even more empathetic and strategic way. How can you deliver those results that your organizations want based on delivering exceptional customer experiences? Because that's what we all want. So next year, I'm going to be, you know, sharing a lot more about my book, Experience is Everything. We have a lot of great things in store for you. So I hope you will check that out and visit us at experienceinvestigators.com. And hey, if you've loved this podcast, please do us a solid and leave a rating. Make sure you leave us a little review. That really helps others find this podcast, and it helps us a lot too. So thank you for everything you do. I can't wait to talk to you soon. And I can't wait to hear your next question on the Experience Action Podcast.