Wedding Business Solutions

Allison Shapira - AI for the Authentic Leader

• Alan Berg, CSP, Global Speaking Fellow

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Can AI make you sound more human? Can you use technology to connect authentically—without turning into a robot? In this episode, I share lessons from Allison Shapira’s new book and our conversation about striking the right balance between efficiency and genuine connection. Are you using AI to amplify your authentic voice, or are you leaving the human touch behind? What are the boundaries we need to draw so our communications—whether wedding vows or emails—stay personal and impactful in the age of AI?

Listen to this new episode for practical ways to make AI work for you without losing authenticity, and hints on how small businesses can use tech to build stronger, more empathetic client relationships.

Allison Shapira is an executive advisor, Harvard lecturer, keynote speaker, and bestselling author who helps senior leaders communicate with confidence, clarity, and authenticity in high-stakes moments. Since 2003, she has advised leaders from prime ministers to Fortune 50 executives, designing communication programs that build trust and drive results. An adjunct lecturer at the Harvard Kennedy School, her work has been featured in The Wall Street Journal, Bloomberg, The New York Times, and Harvard Business Review. She is the author of Speak with Impact and AI for the Authentic Leader.

Contact Allison Shapira, Keynote Speaker

Website: www.allisonshapira.com 

LinkedIn: https://www.linkedin.com/in/allisonshapira/

YouTube: https://www.youtube.com/user/AllisonShapira

Instagram: @AllisonShapira

X: @AllisonShapira

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I'm Alan Berg. Thanks for listening. If you have any questions about this or if you'd like to suggest other topics for "The Wedding Business Solutions Podcast" please let me know. My email is Alan@WeddingBusinessSolutions.com. Look forward to seeing you on the next episode. Thanks.

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©2025 Wedding Business Solutions LLC & AlanBerg.com

To approve AI for the authentic leader. You're going to want to hear this one. Hey, it's Alan Berg. Welcome back to another episode of the Wedding Business Solutions podcast. I am so happy to have my good friend Allison Shapira on to talk about her new book. Allison, welcome.

Thank you. And I have the book here as a prop.

Yes. And those of you that are listening, she held up her book. There you go. We get about five times more people listening than watching in. So we're going to describe that. So I want you to know yours is the second physical book that I have read in years. And the first one, I was on a cruise last summer and I actually had time to read a real book. I usually do audiobooks, but your book, first of all, it's nice and short.

I love that it was nice and short and such a timely topic. So tell everybody just real quick about yourself, what you do.

Certainly. I trained as an opera singer. That's the background I bring to the work that I do. And for over 20 years, I've been helping leaders build their confidence to speak with impact, so to be more effective speakers so that they can more effectively lead their organizations.

And Alice and I have had the pleasure of making music together many, many, many times at National Speakers association and hopefully coming up again. So my audience are wedding and event professionals, many of them very small businesses, some of them bigger businesses. But there was so many things in here that really applied, and one of them is something that people are worried about is sounding robotic. Right? You have AI and you're sounding robotic, and you address that a lot, talking about authenticity. So tell us about that.

Certainly the reason I wrote the book is not because a lot of people were asking me about AI and communication, but because they should have been and weren't. And so I wrote the book as a guide, not just to my clients, but to anyone who needs to speak as part of their role. So you're speaking to clients, you're speaking to people who are very emotional about the event. This is not necessarily a dry business topic. This is something that viscerally is part of people's memory for the rest of their lives.

And so for such an authentic event, for such an authentic type of communication, how do you use AI without losing your authentic voice? That's the question that I sought to answer with the book, because you can very easily just use AI to write your vows, use AI to write an email, use AI to write, you know, letter to your child. My mother did that.

When ChatGPT first came out she sent me this really long, beautiful email, and at the end she wrote, it's from ChatGPT, but it's all true. And I have to say, I know she meant it in a loving way. And I love my mother. I did not love the fact that she used ChatGPT to write a letter about me. So we really have to be careful when we're using it, that we're using it in a way that brings out who we are. Because at the end of the day, we're humans relating to other humans. We have business relationships, we have personal relationships.

And so the premise of the book is you can use AI and be more human in the process.

Right? Now, speaking of that, there was interesting thing in there about how AI can sometimes sound more empathetic than real people. Right.

That's a great point. And I would love to talk about that.

Please, please. Because I thought that was great. I'm like, right, so.

A point that I make in the book, and I make it in my keynotes as well, when I talk about the power of authenticity, is that authenticity is not always a good thing. You can be authentically lazy. You can be authentically unprepared. And a point I make in my keynotes is that I am authentically impatient. It is not a good quality. It doesn't make me a good leader, doesn't make me a good friend sometimes.

And so when people tell you to be authentic, we have to remember that there's good authenticity and there's bad authenticity. And I think of them as a Venn diagram. So you have authenticity on one circle, and then the other circle is the effectiveness of the event, the person you're speaking to. And my goal is for people to find the overlap, which is what I call strategic authenticity.

And sometimes we need some help finding it. So the point you brought up about empathy is really important because we have seen through research and through surveys and studies that AI is really good at simulating empathy. And even a study from a few years ago comparing doctors responses to patient questions to AI responses to those same patient questions found that patients overwhelmingly preferred the AI response to the doctors and rated them higher for both quality of answers and empathy.

And the reason is doctors are busy. They're running around from one patient to the next. They don't have time to say things like, I understand how that makes you feel, but the AI had been trained to be endlessly patient. And so that's something we can learn.

But wasn't it also that humans are trying to make our writings more perfect, which makes them feel sometimes less empathetic. And the AI is injecting these human qualities. Right, that the AI can sound more human. Right?

Yes, we see that with filler words. So I've. The reason I've been studying AI is eight years ago, well before ChatGPT, app developers would come to me to test their public speaking apps. And I started to see how you could use AI to keep track of your fillers and help you remove the ums and ahs. And you knows, now my book is more about how do we use AI on a deeper level. But even then we were using AI to reduce our filler words.

Well, now what we're seeing is these AI voices are starting to strategically add filler words to sound more human.

And that paradox is mind blowing.

Like, like Notebook. Notebook. Lm. That makes these fake podcasts. Right. I don't know if you've seen those yet.

That's right.

They make these fake podcasts and those voices overlap each other and they have these filler words again, which we as professional speakers try to teach ourselves not to have these filler words. And I was reading something recently about Gen Y and Gen Z, about how things that a Gen X or a baby boomer was told not to do, such as, like, it's like, you know, Alison, like, it's. It's like, you know, we should, like, we should like, it doesn't seem odd to them when someone speaks that way, whereas to me it's like nails on a chalkboard. Because as a professional speaker, we're trying not to do those things. And it doesn't seem unprofessional when somebody hears somebody do that. And to me it's like, please stop.

That's right. That's right. And in fact, I remember an employee who was younger worked for me once, and she said, I think you're spending too much time on uptalk and filler words, and I don't think it's necessary. And I asked her why is that? And she said, well, because only people your age and older notice it.

I didn't think that was the most empathetic way of giving feedback to your boss, but I never forgot that comment. But it does bring up a point of communication is generational. And in our work, when we're communicating with someone of a different generation, AI can actually be helpful as a mirror to us in how we're communicating, how we're crafting an email or even a difficult message in order to understand how might I make this message more relatable to someone who doesn't come from my background, who doesn't think like me, who doesn't speak like me.

And I'm not saying that the AI advice is going to be better than a human with that lived experience, but you might not have a human available, and then the AI can help save you from yourself.

And that brings up an interesting point going back to your mother's letter where you said, when is it okay to use AI? When not. And then the question was, would I be okay if a person did this? Would I be okay if a virtual assistant did this? Would I be okay if I had an assistant in another country or whatever do this? And I was. As soon as you said this with your mother, with the letter, I'm thinking, no, you would not have been okay if your mother had somebody write a letter for you.

I mean, can you imagine you're a busy executive and you have your assistant write in your child's birthday card. That's not okay, you know, so that it doesn't pass the test that I set.

Right. But there are times when it does. And as soon as I read that in the book, I'm thinking, yes, there are things that I'm doing I would be perfectly fine handing off to someone else.

And then there are some things like writing content and writing speeches and stuff. I'm okay with crafting the titles of the presentation, the descriptions of things like that, but when I'm on stage, everything I'm saying is mine. All right? I'm okay with it doing research for me as long as I can follow up and do the attribution.

So what are some besides the birthday cards and the letters, what are some other it's not okay. What would you think? What comes to mind?

There are so many examples of what not to do. Our mutual colleague Terry Brock likes to say, copy, paste, customize. And that customization component is really important.

What I do in the book is I provide a framework for people to use when they're crafting a message, whether they're delivering a speech or they're sending an email or preparing for a difficult conversation. And it starts and ends with the human crafting the message, delivering the message.

In the middle, you bring in AI to give you feedback on the message, especially if you have information about your target audience. And then you can use AI to practice the message.

So I like to use the voice function of AI to role play difficult conversations or different situations that I'm preparing for and talking through that scenario. I would certainly do that with another human. And I do.

And when those humans aren't available or because I'm an overthinker, I want to practice the conversation 20 times. The human after a couple times is going to say enough already, just do it. And the AI will say, sure, let's practice again, let's do it again.

So a great idea that I heard the other day was a wedding professional and we were talking about blogging because blogging is very important for SEO. Getting more content on your website, fresh content and all. And so few people are doing it because not everybody reads the blog. I don't care. Google's reading it, right? And AI is reading it.

So the idea was when they leave the wedding at night, their mind is still going. So they turn on ChatGPT and they turn on the talk to it function and just tell it about the wedding, just tell it the story. And this was a wedding of Chris and Chris and it was fantastic. Chris's mother, man, she danced, she was out there boogieing and whatever. And they had their dog and their dog was Fido and whatever and just telling everything.

Well then the next day you can use AI to craft that into a blog post. You can use AI to break that into social posts. But it started with you.

And I think that's the thing. So Terry Brock, who you mentioned, so Terry and RK3 Robert Kennedy III did a presentation January of 2024 at one of our speaker conferences.

And I was resisting AI because I thought it was for creating content from scratch, you know, says a guy with 360 podcasts and 13 books, I can do this like I don't need help.

You check the box. You're good at creating content.

I can create content. Not hard, right? So they talked about using AI with your own content. And that took me from being a resistor to eventually being an evangelist.

And I try to show people what kind of content do you have? Well, your content is your website, your content is your brochures, your content is your social posts. Your content is anything you've ever written in terms of a blog and article or whatever. And if you start with that, you can make it better.

And I love what you brought up about who is this for generationally. Because my audience people listening, you're mostly dealing with Gen Y and Gen Z these days, right? If it's for weddings, if it's for Bar Mitzvahs, Quinceaneras, Sweet 16s, it's the parents who are likely Gen X or older Gen Ys.

But a friend of ours asked me to help her edit her book, and her audience is baby boomers and Gen Xers. So we told it that before we started because it needed to put that hat on.

When I speak in Ireland, in the UK, I tell it that so that the English is not our English. Certain words that we say, like we talk about putting your pants on. Well, to us, that's your trousers over there. Your pants are your underwear. So you don't want to talk about your pants.

But AI can help you with that. Just making it right for the audience.

Yes. Yes.

And another quote that you had in there. The employees who embrace AI as a way to improve their individual performance are the ones who will make themselves indispensable in the future.

So a lot of people listening don't have employees. They are the employee. But there are other people who are employees there. So as a small business person, where it might just be you and a couple of people, how do you make yourself indispensable using AI?

It's recognizing that AI provides the ability for you to augment your own capabilities. So I'm a small business owner as well, and I'm constantly feeling understaffed, even with nine people.

The correct answer for how many people do you need to be fully staffed? The correct answer is always just one more. Just one more.

And so when you have this situation where you feel like there's more to be done, there are ways in which you can use AI or AI agents to augment those capabilities.

The way in which we translate that comment from the book to a smaller team is recognizing that the people, your competitors, who are the same size as you but are using AI are going to start to run circles around you in terms of efficiency and customization for the client.

And so that's why we want to make sure that we're utilizing these tools, because otherwise we're going to lose our competitive edge.

And I know I froze for a minute, but the people who hear the recording won't see the freeze and the people watching it will. Forgive me, please.

So it's recognizing that the competition is changing, and if in any industry, it's up to us to stay ahead of the trends and the tools.

And so this is a new tool that has exponential impact on our industry, on your industry. And so it's up to us to figure out how to use it. Because the people who do figure that out will have the competitive advantage and we'll still be drowning in paperwork and form emails because we're trying to customize it manually for each person.

Right. And it's also understanding that AI isn't a thing. There are different tools.

So one of the things I do in my presentation, besides have slides of your book up there with some of your quotes, which I think is the best thing to do in a presentation.

Absolutely.

But I also did a strengths and weaknesses of different AI tools. I show ChatGPT versus Perplexity versus Claude versus Copilot.

And I showed, listen, they're not all great at everything. Each one of them is good at something. Some of them are really, really good at something and really not that good at other things.

So my Ask Alan Anything chatbot right now is powered by Claude. But I constantly look to see there's a new version of Claude. Well, I might update to that.

Perplexity I do my research with because it's so much better than ChatGPT. It has current information, which chat doesn't have.

I did something crazy the other day. We needed something, we couldn't find it. I actually drew a picture of it and took a picture of that, uploaded it, described what I was looking for, and then I found the links to go buy it.

So yes, that kind of creativity is such a wonderful example of something we could have never done before.

And so when you embrace this, it's almost like an additional limb that we have that we can use. And it's a limb that can be repurposed for all sorts of different creative and efficiency focused tasks.

So I love that you shared that example and I love what you're doing because you're teaching people how to use these tools in non obvious and wonderful ways.

And that's the thing is, I'm sure you've done the same thing. There are so many things that I've used AI for that will never see the light of day. You throw something at it and again, it doesn't complain. It doesn't go, really, Allison, you want me to do that? It doesn't do that. It just does it.

And I've done some stuff and go, okay, I can't do anything with that. And it's okay because you tried.

I guess it's just like life. We tried and it didn't work out.

But each of the tools, it's like I go to my garage, there's 17 saws in my garage. There's little ones, big ones, power ones, whatever.

But if I need to cut a little tiny piece of wood, like my wife the other day for our grandson's birthday, she bought these Lego, it was a Star Wars theme, bought these LEGO characters, wanted to put them on the cake.

She handed me chopsticks and said, cut these down so I can put them on the cake.

Well, a power saw would have been overkill for that.

So it's the right tool for the right job. And a lot of people are just stuck in their ChatGPT or they're stuck in their Gemini or whatever.

Expand your horizon a little bit.

But please pay those platforms. You know you want people to pay you. I think you should be paying for those as well.

So let's go back to why you talk about why. Like why you. Why do you care? And how does AI play into that? Because that goes back to authenticity again.

That's right. Whenever I'm working with someone, whether they're individuals or I'm working with an audience through a keynote, I always ask them the question why you? As a way to bring out their authentic sense of purpose around why they do what they do.

And why you doesn't mean why are you qualified, what's your title, how many years of experience. Why you means why do you care about the work you do and the impact you have. And when was a moment in your life that made you care.

And when people take the time to answer that question, it brings out this rich history and story.

And then once you answer that question, the very next message you write is more authentic because of it.

When I work with large clients at publicly traded companies, I say nobody answers why you to increase shareholder value. It's more personal than that.

And the why you works regardless of whether you're a company of one or 215,000, especially the smaller the company.

When it's your company, you're on a small team, people take risks by joining those small teams. And so their motivation is usually much more purpose driven.

And that becomes your competitive advantage if you're talking to clients. It becomes the way in which you form relationships with the people you serve, and then they refer you to others and they come back to you again.

And so AI can help with that, because if you can share your why you with a chatbot and then say, here's the message I'm trying to deliver, how can I make it more me?

Yeah.

And that also goes to training your chatbot or your ChatGPT, whichever platform you're using.

So one of the things I put in my presentation is I show people go to the personalization settings in ChatGPT and tell it who you are.

And mine is not two sentences. Mine is paragraphs.

And then I showed you the back end of my Ask Alan Anything. Those instructions are very, very long, very, very detailed. And they didn't happen all at once.

We kept adding to them and adding to them. And if it wasn't doing what we wanted, we trained it again. Just like we would a person.

But mine writes like me. Mine understands me.

My ChatGPT, it didn't say exactly this, but it was scary. I uploaded a transcript of a presentation, and it said something to the effect of, oh, that's so you, Alan. Or that's quintessential you or something.

I was like, whoa, that is cool and creepy at the same time. But it knows me. It knows me.

And that's, I think, the important thing. Again, why I resisted is because I didn't want it to sound like anybody else. I wanted it to sound like me.

And that was the theme through your book. Here is, again, it's a tool. Help you do more.

But you know, when you said that AI can sound more empathetic, yeah. I see a lot of messages from people that are so transactional. It just feels transactional. Can we make this feel more relational?

And again, I could do that.

That's right. AI can remind us when we're not being relational. Because the point I make is we don't always bring our best selves to every situation.

So AI can serve as this gentle, patient reminder of who you are and who you want to be at your best and then show you even when you're at your worst.

And one feature that I would love to see in Gmail, if you write the word attachment but you don't attach something, there's a pop up that says, are you sure you want to send this, you used the word attachment.

I'd like to see a pop up that says, you mentioned wanting to be more empathetic. How about we add this sentence.

Or even on a personal front, there's an 87% chance you'll be sleeping on the couch if you send this email as is. How about we reword it?

So marriage helps.

I would certainly say there's a benefit there if we can use it in the right way that isn't, as you mentioned, increasing the creepiness factor.

We want to reduce the creepiness factor and increase the utility factor.

And we're still figuring out as a society where those boundaries are.

And everyone draws those boundaries in a new way because in order to customize these tools for you, you have to tell it who you are.

And so there are privacy concerns and data concerns about how this data is being used.

So that's why I wrote the book. Because these are the conversations we're having now, and together we're deciding where the boundaries are. And I wanted to be part of that conversation.

Yeah. And I think the other thing is if we're signaling that we're using AI, a lot of people are like, oh, that was AI. That can't be good.

And that's why one of the things I did, I did a podcast that said, please stop using the green square check mark and the red X because you're just signaling that.

As soon as I see it, I'm like, oh, did they really read this? Did they really know what this is?

And when I'm using ChatGPT and others, I will specifically say, no icons. Don't use any icons.

You can use a check mark or whatever on a grid or something, but no icons.

Because I want you to know this is good content, but I don't want you to automatically discount it.

Every day somebody sends me an email with those things. It doesn't mean it's bad. Because again, it's a tool.

But I think we have to stop signaling that as well, because people might not give us as much credit or might think we're less professional or something.

That's right. And there's research, recent research, showing that when a leader uses AI in a way that's obvious in their communication, their employees find them less genuine.

And that doesn't matter what company size you have and who you're talking to. Nobody wants that.

So that's a common challenge we have to overcome.

And unfortunately, because AI was trained on this large corpus of data, traditional tools we use like the em dash.

I've been using the em dash for 30 years.

I finally found the keyboard shortcut for the em dash and now it's become an AI telltale.

And so we have to, it's optics as much as fact or reality.

And that's something that we have to be aware of.

Yeah, I've noticed that.

I was at another conference somebody was speaking about that and said the em dash.

Although they did teach me something I did not know why it's called an em dash is because it's as wide as the letter M.

And the en dash is narrower because it's only as wide as the letter N.

I learned something new.

I did too. And there you go.

So we're teaching today. This is Reading Rainbow.

We're teaching today over here. I want some construction paper when we're done.

That's right. Conjunction junction.

But you could teach your AI never use an em dash, never use an en dash or just use an N dash.

I will do find replace on those things.

But I also think again going back to seeming more authentic, don't make it perfect.

I use Grammarly to check my books and I don't accept a lot of what it wants me to do because it's going to make my writing sound less like me.

It's going to make my ninth grade English teacher look over my shoulder and say, excuse me young man, that's not proper grammar.

I know. I know. I don't use proper grammar.

So well, we could go on forever.

So how can people find out more? Because you mentioned a tool. You have a chatbot there.

How can people find out more about that?

So you can learn more about the book and download a one page resource guide which has this experimental chatbot authenticity chatbot that people can play around with.

They can go to allisonshapira.com/ai.

And I know that will be written in the show notes so you'll know how to spell my name right.

And then I welcome people connecting with me on LinkedIn. I write a lot of content on LinkedIn and I'm happy to answer questions and connect with people directly.

Excellent. Well, thank you so much for joining. We could go on forever here, but I will see you next time with your guitar and my keyboard, and we'll make some more music.

Looking forward to it. Thanks, Alan. Thanks.


I’m Alan Berg. Thanks for listening. If you have any questions about this or if you’d like to suggest other topics for “The Wedding Business Solutions Podcast” please let me know. My email is Alan@WeddingBusinessSolutions.com or you can  text, use the short form on this page, or call +1.732.422.6362, international 001 732 422 6362. I look forward to seeing you on the next episode. Thanks.

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Alan Berg, CSP, Global Speaking Fellow

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