Omnichannel - The Psychology of Outsourcing Difficult Conversations to AI (Perfect Words and Human Avoidance)

Episode Date: September 8, 2026

Send us Fan MailIn this wonderfully improvised couch recorded episode, you will learn about the newly present phenomenon most of us are facing at every single level.AI text messages breaking up with you.AI firing you or downgrading you.AI coming as a buffer between a difficult conversation to replace contact.And while there is nothing wrong with using a tool to organize your thoughts, the issue is the mismatch between the modality and the language used for such conversations to take place.Learn More about the Human to Human programs here: https://www.dominikalegrand.com/programs-1

Hello, my dear entrepreneur friends. Welcome back to another episode. And this is audio only because this is one of those moments where I'm chilling in the couch. I am fresh out of a conversation with an expert in relationships. And we just had almost two hours conversation on human connections and AI and all of that beauty. Now, there's just something that I have been observing that I needed to. to mention today. And if you have been observing the same phenomenon, welcome to the fucking club. We are in this together. But there has been this increasing outsourcing for AI for difficult conversations. I actually had this conversation with the girls on the pole dance class where one of the girls said, well, people are getting broken up with by AI right now. And, through text message. You know how we used to get mad when people texted us and they break out with us through text message?

Now it's going to be AI, please write me a compassionate text message in which I, you know, how do I break up with this person basically? Like how do I do this? Please tell me. Because I don't want to take that confrontation that comes with having imperfect words and just like not knowing what to say or even cracking my. brain on how the fuck am I going to phrase this. And so AI is beautiful because it gives you that synthetic empathy, that illusion of care when you're using it because the words are super nice,

but really they are not your words. They are just something that AI written. And I feel like when we get those messages and now it's not just breaking up in business, that could be a negotiation of a retainer that now is AI writing those emails or messages, that could be an outrage that's important. It feels personalized, but it's not really personalized. It's AI. That could be someone firing. You know, like you fire someone and you send them a nice AI email

instead of giving them dignity of seeing them in person. So our problems that were used to be around the medium itself, is like, why is this a text message? Remember, like, I used to get mad that my mom was texting me happy birthday instead of calling me and then calling me for something silly. Like, okay, how is it that you're going to call me for that and not text me for this? Like, that's just such a mismatch. And I feel like it's so interesting because now we've a use of AI, our language is getting

more sharper in a way, but also easier, right? And it's not so much that you can get mad that, okay, why aren't you having this on a call with me? Why are you texting this to me when you could just call me or see me in person and tie into my face? You know, I feel like that to me is where the mismatch is. The added layer of AI makes human relationship even more complicated because it can't sound like care like I said before. And it can have zero fucking care and only can. carries that you're prompting it well and you copy-pasting the message. That's where we are at. And I feel like what has been the pain and the hurt inside of these interactions, whether yes,

even if, even when there was no AI, the modality would still hit you if you get a, if you get text messaging which someone is breaking up with you, it could still hurt you. But you would be like, okay, this is just an asshole, right? But now with AI, the words can sound really nice and it can still, the person can hide behind it and not get into contact with you and actually have a conversation with you or actually taking the time to reach out

and just, you know, finding a modality that works for both of you. And so what has been now interesting and what I have been experiencing in the business interpersonally that a use of AI becomes this crutch in which people rely on to make sure that they sound good. And so it's no longer about what to say. Like it's no longer about the words themselves. It's more so like, okay, I can already have the words, I can polish them into perfection. I can make them sound very compassionate and sweet. It's like the psychopaths, you know,

trying to mimic the facial expressions of empathy and, you know, it's so funny. It's just like using AI for that is now something that has been happening. And so what has been interesting to me is just recognizing that's what's happening, like that's the pattern that we are dealing with and seeing what are conversations that actually still need to happen in person. and if that's the case, especially in the age of AI, how can we better equip humans to be able to tolerate the discomfort that comes with contact, right?

Because what you are saying is essentially is that especially in human-to-human contact, there's nowhere to hide. You cannot hide behind an AI message. You actually need to speak to someone, right? And while there's still opportunities to hide, if it's a text message when it should be a phone call. I feel like just having to tolerate that discomfort that comes with this imperfection of a human

who is not going to give you the most optimized response and you're dealing with that. I feel like more than ever feel, people feel disconnected because you go to AI to talk about your business problems. You're using therapy, AI, right? it helps you organize your thoughts and almost like you get instant gratification because now you know the answer and you don't have the sitting ambiguity because you don't know like it gives you this shield of oh no it's okay i can i can talk to AI and it's going to be okay right but the problem is it's not replacing that ability to actually come into the trenches with the human and encounter whatever

reaction they're going to give you even if you don't like it and how do we build a capacity to hold space for that reaction and for ourselves at the same time. And much of that work is very, very human to human in the body of work I'm building into helping leaders to be equipped with the capacity that it requires to stay present in complexity, to stay grounded in moments when the other person cannot, in helping you, equip you to empathize well and to also know when to put those boundaries down at the same time and know when to speak up and dare to speak up. Much of the program self-expressed that I ran in June was around speaking up and learning the consequences and bearing the consequences of

that happening and letting people witness you in those moments. in which you're still in, you're attempting to do something that's difficult for you because you're not perfect at it yet. And much of the, the interesting revelation that I have gained or teaching those programs live is that still there are many fields and areas in which you have to be in contact with human. If you are working with humans and I had a physical therapist in one of our programs and her holistic approach, and that to be presented to people and her not wanting to speak up when she saw something that was off.

And it was difficult for her to bear the reactions of people ridiculing her approach or even mocking it. And how can we just not want to control that so much as see how we show up and how we respond to what's happening? Because that's still in our control, right? and it's so interesting to me how those all go back to contact like how am I in contact can I hold a conversation can I hold and stay with complexity I remember my cousin's daughter passed away in December it was very tragic and just having to sit with the father in his pain and just sit through

that discomfort of, okay, this is really difficult for you. And just sitting with someone who is occasionally speaking and bursting out to crying and is speaking and bursting out to crying and just staying in that depth and complexity without being crushed by it is such a huge gift and human nervous system help that you can put. provide if you do this and learn this capacity really, really well. To me, it's, it's everything. And on the flip side, I completely understand the courage that it takes to actually stand up and say, hey, you know what? Here's how I feel. Or, hey, you know what? I'm sorry. Unfortunately, that's what's happening. And then we need to let you go, right? Like, I wonder with firings that were

happening everywhere people are being let let go of like I wonder how many of them was getting that through a fucking email vision by AI and you know I think that is just like the dignity of just giving them the dignity of speaking to them in person and not AI writing an email right it sounds compassionate so I feel like that's where we are headed where how can we equip people better to be good in contact. How can we equip people better to be to be able to stay with complexity and being able to support and guide people through those complexities? How can we raise awareness on issues that are AI distorting because it has apparently written a fucking sales page about exploiting people without you noticing that's what's happening because you don't even, you don't, you

don't even audit the output that extensively. Human to human guides and the people who are in this practice and I have yet to build that infrastructure of you guys. But the way I see this play out is almost like having human to human leaders next to leaders who show that side to them, who help that be that compass on what the decisions that are making and how they impact other people and how do we do better? And our messaging and how does that impact people? Our marketing, how is that impacting people? How what we say and how we sell and are we like fucking capitalizing people or are we

being cognizant of how things are on the receiving end? And my obsession with how people receive you has been with me. since Art of Approach, which I was doing in February. Because to me, what I have gotten is a lot of really shitty messages and attempts and outreach. And while you can empathize endlessly with such things, and oh, yeah, poor human doesn't know, they really need money, they want opportunities. It doesn't change from the receiver side of things like, okay, but that didn't quite land with me, right?

it doesn't make you want to move closer to someone who's bombing their approach towards you. It doesn't make you, I mean, you can give second chances if you want to, but that obsession with how do I land with people? Like what I say, how does that impact people? And impact awareness was something I talked about it before, but to me is like, how do I even, like, when I show up, like, what do I leave behind? Like what is the response in someone's nervous system when they hear from me? And just having that understanding because I've been on the receiving end of things like that

where there was no consideration whatsoever on how this lands with me. And turning that back to other people and be like, hey, just be careful because if you're sending grandma passed away over a text message to your daughter, maybe that impact, it's almost like you're dropping a grenade, an emotional grenade on them, and you walk away from the explosion. And like, I can't be bothered with how this affects you. I can't give you the dignity of a phone call because, yeah, you know, I'm just telling you the information as is.

And I think the more we can give consideration on the impact that we have on people, okay? because on the other side of a text message, there's an actual human. On the other side of a Slack message, there's an actual human. On the other side of a dating app, there's an actual human. On the other side of a Vibor, WhatsApp, DM, there's an actual human. And the more we can be cognizant of that, just because it's a text message or a Slack or an email, the more equipped we are in being the person who's actually received well. And this has downstream effects in not just business, but in business as well.

I've seen people bomb collaborations because they are just, they lack the consideration on how a late invoice is affecting a collaboration. They lack the consideration on how, if you don't say thank you, but you will want to extract from the collaboration, it's no longer mutually beneficial. You lack the consideration if someone wants to raise prices on you because the value has increased and you shut them down, that will affect the relationship quality itself. More than ever, and most of us in business of relationships, even if you don't think you are, you are, because your buyers have a relationship with you and an experience with you,

your customers, your clients, your collaborators, your investors, they are all in relationship with you. And the more we can be cognizant of what that looks like and how to attend to it well and how to be showing up in them well, the more we can retain them longer or let them go if they don't make sense, but at least we can let them go with dignity. We can let them go with goodwill. that you know this mattered and just because this doesn't make sense right now or anymore it doesn't mean I don't value you or I don't care about what happens to you next or I cannot think about okay you know if I no longer need to hire you because AI is not replacing what you do how can I make sure that I can give

you a reference or I can send you to someone that or that I know who might needs what you are doing like those tiny things matter so much that's all I have for you I have art of repair coming up, I have no idea when. I feel like it's brewing and every single conversation is bringing me closer to its creation and life and everything is teaching me all of that in real time. But this is coming soon. And I like you know when those come and it is something you care about, you care about relationships and you care about collaborations. and retention and impact and how to build capacities around those arenas as well. So you can handle these conversations in person.

Auto-prepare is going to be an amazing, awesome program for you. All right. Thank you so much for listening to the contemplations on the couch. I'm going to go eat something because I'm super hungry. Bye, guys.