TL;DR:

AI can help us work faster, organize information, and automate repetitive tasks, but Angie Callen believes businesses need to be intentional about what they hand over to technology. As AI creates more content and more automation, human connection, personal outreach, referrals, empathy, imperfection, and trust become increasingly valuable. Use AI to give yourself time back, then consider spending some of that time connecting with actual humans.

Human Connection in the Age of AI: How to Out-Human the Robots

AI has given us some pretty amazing shortcuts.

I can automate parts of my weekly show prep that used to eat up most of a Thursday. I can organize research, find patterns in piles of information, and take care of repetitive tasks that I really don’t need to be doing manually every week.

I love that stuff.

But there’s a question I’ve been thinking about more lately:

What are we doing with the time AI gives back to us?

Are we using it to be more creative? Build better relationships? Maybe even rest?

Or are we filling every newly available hour with another 29 things AI told us we could be doing?

That’s one of the things Kira Pogge and I talked about with Angie Callen, founder of The Modern Coach and author of Scary Good. Angie is a former engineer turned executive coach, which means she brings a systems-thinking brain to something considerably messier than engineering: people.

Her philosophy comes down to five words:

Work has changed. Humans haven’t.

Angie isn’t anti-AI. She describes herself as pro-human and believes we should become what she calls

“AI-enabled humans on purpose.”

I really like that distinction.

Because as businesses rush to automate, create more, and try every shiny new AI tool that shows up before lunch, Angie thinks there’s an opportunity hiding in plain sight.

Be more human.

And yes, that sounds ridiculously simple. Putting it into practice takes a little more thought.

How Do You Know If You’re Overusing AI?

Angie believes we’re still in the “Wild Wild West” of AI adoption. Her prediction is that we probably have another 18 to 24 months before some of the dust settles and we begin finding healthier, more sustainable ways for humans and technology to work together.

In the meantime, how do you know when you’ve gone too far?

Pay attention to when AI starts making your work harder.

Angie described what she calls the “sycophantic loop.” You keep prompting, correcting, and arguing with an AI model, trying to force it to give you what you want.

Another prompt.

Another correction.

“No, that’s not what I meant.”

“Try again.”

Before you know it, you’ve spent an hour accomplishing something you probably could have done yourself in 20 minutes.

Angie suggested asking yourself a simple question before automatically opening Claude or ChatGPT:

Can I use my human brain, work this muscle, and get the same result in roughly the same amount of time?

AI can be incredibly useful for repeatable processes that already work in your business. But if you weren’t doing something before AI showed up, it’s worth asking why you’re suddenly doing it now.

“Look what I can automate!” isn’t always a compelling business reason.

What Happens When AI Makes Everything Sound the Same?

One of the biggest warning signs Angie sees is what she calls the sea of sameness.

You’ve probably noticed it.

You scroll through LinkedIn and start recognizing a certain cadence. The structure feels familiar. The sentences feel familiar. Sometimes you can almost see the prompt sitting behind the post.

AI is great at helping organize ideas, identify patterns, summarize information, and get you moving when you’re staring at a blank page.

Angie gets more cautious with the final output.

Copying and pasting whatever AI hands you can slowly remove the quirks, opinions, experiences, and sentence structures that make your content yours.

And please don’t outsource your comments to an AI bot.

As Angie basically put it, why would anyone want to have a comment war with a robot?

Fair point.

Why Imperfect Content Can Build Human Connection

Angie shared a fantastic story about accidentally sending one of the ugliest emails imaginable.

She had an automated sequence set up in ActiveCampaign. One placeholder email never got finished but, unfortunately, did remain connected to the automation.

So out it went.

Weird beige background. Generic stock images. Placeholder copy. Even the scheduling button was broken.

Basically, all the things you hope your email platform never sends at once.

And people responded.

Angie received around a dozen messages letting her know the scheduling button didn’t work.

Of all the things wrong with the email, that was what they wanted fixed. 

Her takeaway was simple: Spend a lot less time thinking everything needs to be perfect.

The mistake was obviously human, and people reacted to it like humans.

I’ve experienced the same thing with my own email list. Sometimes I’ll send something I think is fantastic and hear crickets.

Then I mess up a send time or tell a personal story, and suddenly everybody wants to email me.

Apparently my mistakes have excellent engagement rates. So if you’ve been holding off on email because you’re a perfectionist…maybe don’t do that.

How Can You “Out-Human” the Robots?

I asked Angie a very practical question.

If someone had one hour on Monday morning, what’s the single best thing they could do to “out-human” the robots?

Her answer came immediately:

Reach out individually to other humans.

That could mean:

→ Texting someone you haven’t talked to lately
→ Sending a few personal messages
→ Following up with a prospective client
→ Leaving someone a voice memo
→ Reconnecting with someone you met at an event

None of those requires a fancy new tool.

You’re showing another person that you thought specifically about them and took the time to reach out.

In a world where personalization can increasingly be faked at massive scale, actual personal attention becomes pretty darn noticeable.

What Does Human-Centered Leadership Look Like With AI?

Angie has a line about leadership that I highlighted:

“Strategy without empathy is a plan no one follows, and empathy without strategy is just good conversation.”

Good leadership needs both.

That becomes especially important when bringing AI into a team.

Angie suggests thinking about AI agents almost like non-human coworkers entering an existing culture.

If you’re introducing new AI tools, talk to your team.

Explain what you’re testing. Get their input. Establish guardrails. Listen to their concerns.

Because imagine sitting at your desk while management quietly rolls out a fleet of AI agents and nobody explains what they’re for.

I’m sure everyone will feel super relaxed about that.

Angie believes leadership is about the people whose care has been entrusted to you. New technology doesn’t change that responsibility.

Work Has Changed, Humans Haven’t

We’re going to spend the next few years figuring out exactly where AI belongs in our businesses.

We’ll automate some things we probably shouldn’t have.

We’ll also discover uses that give creators and small businesses abilities we could only dream about a few years ago.

I’m excited about that part.

But Angie’s five words are a pretty good compass:

Work has changed. Humans haven’t.

We still want to be heard.

We still want to trust people.

We still respond to stories, humor, imperfection, empathy, and someone taking the time to reach out personally.

So use AI. Automate the repetitive stuff. Get some of those hours back. (And resist the urge to immediately fill them with more tasks).

Send the voice memo.

Answer the email yourself.

Go meet somebody for coffee.

Make something.

Heck, take a nap.

If AI is going to give us more time, using some of it to be human seems like a pretty good return on investment.

What Marketing Is Still Working in the AI Era?

Angie saw a noticeable shift in her own business during 2025.

LinkedIn had been an important source of authority for years. SEO and inbound marketing reliably brought in leads. Then things started changing.

Her advice isn’t to panic and abandon everything you’ve built.

Keep using the channels that still make sense while testing new ones, and don’t depend too heavily on any single source of leads.

Algorithms change. Search changes. Platforms change.

Interestingly, Angie is seeing some very human approaches become even more valuable.

Referrals are a big one.

As Angie put it,

People shop around, but referrals often don’t.

Someone who comes to you through a person they already trust begins that relationship differently than someone comparing five strangers they found online.

She’s also seeing success with her weekly newsletter, Combating the Sunday Scaries, which she says continues to get around 40 to 50% open rates.

Email gives people a quieter way to intentionally hear from someone they trust without digging through a feed full of ads, memes, sponsored posts, and AI-generated content.

And when somebody replies?

Answer them yourself.

That’s exactly the kind of interaction we shouldn’t be rushing to automate.

Connect With Angie!

The Modern Coach: https://themoderncoach.co/

Scary Good by Angie Callen

No More Mondays Podcast

SHOW TRANSCRIPT

This transcript is automatically generated by Descript.  Any errors or omissions are unintentional.

[00:00:00] Angie Callen: I just think that we still have another 18 to 24 months before the dust kind of settles

[00:00:04] Angie Callen: And then we’re gonna go into something that I think is more, long-term maintainable, to the point that we’re gonna understand how humans work alongside technology in a healthy, sustainable way instead of this very chaotic, sometimes scary, you know, adoption process we’re in the crosshairs of.

[00:00:24] Jeff Sieh: Hello, folks. Welcome to Creator News Live. I’m Jeff Sieh, and you’re not

[00:00:27] Kira Pogge: And I’m Kiera Pulga-Breivik, and this is the show that keeps you up to date on the creator economy and so much more

[00:00:32] Jeff Sieh: You ever been doing everything they told you to do using AI, posting more, automating more, and somehow it’s all landing softer than it used to? Maybe you feel like you’re shouting into a feed where everything already sounds the same. And have you ever wondered whether the thing that actually sets you apart is the one thing that you keep polishing right out of your work?

[00:00:51] Jeff Sieh: If that sounds familiar, well, you’re in the right place

[00:00:53] Kira Pogge: Our guest today is Angie Callen. She’s a former engineer turned people person and award-winning executive coach, author, and [00:01:00] speaker who helps people find and use their voice with purpose, confidence, and intention. She’s the founder of The Modern Coach, the author of Scary Good, and she is known for blending strategy, humor, and humanity to help leaders navigate change, influence authentically, and makes values aligned decisions without losing themselves in the process.

[00:01:19] Kira Pogge: She’s built her whole practice around five words, which I love this so much. Work has changed, humans haven’t. Today she’s showing us what’s actually working now that we all have the same tools and how to lead real people on the other side of it

[00:01:32] Jeff Sieh: So sit back, clear your schedule, clear your mind to get ready for this week’s episode of Creator News Live There we go. So that was cool [00:02:00] to

[00:02:00] Angie Callen: I need that.

[00:02:02] Jeff Sieh: Oh, I will send it to you. So it’s really fun that we were able to do that now. So, this is gonna be a good show. one other thing I wanna talk about, and you kinda mentioned this in your talk, I think, in Wichita, was, and Kira mentioned it, you know, your, your whole brand is built on these five words, kind of your, your focus words that you have, kind of build everything around.

[00:02:18] Jeff Sieh: You know, work has changed, humans haven’t. So unpack that for us. What has specifically changed about work in your opinion, and what is the part that ha- you know, that you’re convinced has not?

[00:02:30] Angie Callen: So I wanna preface those five words with making sure no one thinks it means I’m anti-AI, because I definitely am not. I’m just pro-human, right? So I like to think of us as being AI-enabled humans on purpose in this day and age that we’re living in. And what, and we need to remember the humans on purpose component, because that’s what hasn’t changed.

[00:02:51] Angie Callen: While work has gotten more and more complicated, our lives have gotten more and more complicated than they’ve ever been, and that’s kind of been building over [00:03:00] the last 20 to 30 years as technology has continually seeped into our lives in increasing amounts of presence. And in a way, I think AI is bringing a lot of the challenges that has created to light.

[00:03:14] Angie Callen: And so we’re more disconnected than we’ve ever been, and I think AI is making people realize that. We’ve kind of over-automated, over-technologied a lot of work systems. Hiring is the easiest way to think about this, where fundamentally humans still hire humans. That has never changed. We still hire people the way that we did 40 years ago before you could ever apply to a job on monster.com.

[00:03:39] Angie Callen: However, we’ve put all of these, hoops and technological pieces in between that very fundamental, very simple process that now makes it feel like a very inhuman or un-human, act. And so it’s, it’s just a really specific, almost granular example of how we see, humans [00:04:00] fundamentally still doing things the same way we always have.

[00:04:02] Angie Callen: We are still curious creatures. We’re still connected creatures who wanna be in community and collaboration, yet we have created all of these systems to almost remove those strengths, and the, the environment from our daily lives and our work

[00:04:20] Jeff Sieh: Very true. Very true.

[00:04:22] Kira Pogge: you know, I think the, the claim and the thought that, like, we’re kind of swinging back towards this kind of human-centered approach is something that sounds really good and it feels really refreshing, but I also think it’s something that’s hard for a lot of people to take in and kind of believe just because everything you see is more tech, more AI, more tech, more AI.

[00:04:43] Kira Pogge: And so you have some data to back that up, that we’re kind of swinging to the other side. So what are you actually seeing in the data? ‘Cause I think it’d be great for people to kind of hear you talk through that when all they’re seeing in the news is kind of just AI everywhere.

[00:04:57] Angie Callen: Yeah, and the first thing we have to think about [00:05:00] is, you know, there’s this graph of adoption of new things. It happened, with the internet. It happened with the, the Ford Model T that everyone thought was going to kill them when a car came on the scene, right? And there’s about 15% of the population who becomes early adopters.

[00:05:15] Angie Callen: We are in an echo chamber of those people right now, right? The three of us. but it’s only 10 to 15% of the population, and then, there starts to be this escalation of people adopting whatever the thing is before all of a sudden the bottom falls out of that, and, like, the antitrust starts, and then it comes back up to whatever, let’s say long-term, maintainable, sustainable level of adoption and incorporation, th- society feels we can maintain.

[00:05:42] Angie Callen: So I think right now we are actually still on the ramp-up of early adoption because of the overall low percentage of the accessible population who’s using AI, right? So even if we remove the fact that, like, third world countries have high populations that don’t have internet access, [00:06:00] the people who h- have access to internet and AI ha- are still low percentage adoption.

[00:06:05] Angie Callen: So I think we’re still on this ramp-up into, how the heck does this look in, in society? And because of that, I think all of us are experiencing what is basically the Wild Wild West, right? It is, unroll AI, automate, build a- agents, and do everything we possibly can to use this stuff to, you know, cut time, cut money, cut whatever, whatever, whatever.

[00:06:28] Angie Callen: and it, and if you are on the late side of those, this early adoption, that feels super, super chaotic. Now, what’s ironic is if we look at some, like, granular stuff that’s been happening even in the last year, we’re already seeing super early adopters start to realize we over-indexed on things. So there have been companies, like, even a year ago, Taco Bell, Klarna, there’s a couple other companies, recognizable names you would know, who when AI hit the scene, they’re like, “Sweet, we’re gonna replace all of our [00:07:00] customer service with AI,” and then they went, “Whoops.”

[00:07:03] Angie Callen: And they have, unrolled it, right? That’s a huge cost, by the way. But we’re already seeing examples of, where we’ve over-indexed on a broad scope rollout and realizing it isn’t the way. I just think that we still have another 18 to 24 months before the dust kind of settles on this, like, before all the land in the Wild Wild West has been claimed with its little white flags, right?

[00:07:25] Angie Callen: And then we’re gonna go into something that I think is more, long-term maintainable, to the point that we’re gonna understand how humans work alongside technology in a healthy, sustainable way instead of this very chaotic, sometimes scary, you know, adoption process we’re in the crosshairs of.

[00:07:42] Jeff Sieh: Yeah. it’s interesting because I think, I mean, a lot of the news, at least this news cycle, is, like, the negative, you know, people are not… It, it’s, it’s frustrating people. It’s scary. I think one of the, the things that’s why it’s so scary is it’s moving so fast. Like, I’ve been in technology for a long time.[00:08:00]

[00:08:00] Jeff Sieh: I have never ever, ever seen something this fast, and even the AI, like, gurus or influencers, even our pal Dustin Stout, who is the, uh, founder and CEO, big cheese, head dude over at, Magai, that’s… I mean, I know. Like, it’s, it’s a constant battle to stay up to date on this stuff because these models roll out.

[00:08:17] Jeff Sieh: They get updated almost daily, and it’s, I’m, I, I do not envy his job because even me trying to stay up, you know, up to date on this stuff, it’s just, it can be overwhelming. So you have written that we are using it more but trusting it less, and I think the news cycle shows that people are trusting it less.

[00:08:32] Jeff Sieh: So that’s a really weird, kind of uncomfortable place for a, a whole market to be sitting in. So what happens to a business, you mentioned Taco Bell and some of the other ones, who are on the wrong side of that gap? And so how would somebody, like a small business, a solopreneur kind of people in our audience, how would you know if you are on the wrong side?

[00:08:51] Jeff Sieh: Like, what are some warning signs that you wanna get in front of before your customers start deserting you or you’re having issues?

[00:08:58] Angie Callen: Yeah, I was actually having this conversation [00:09:00] with somebody yesterday about just how in the last few days, like, Claude’s language models changed, and I’m like, “I don’t need a preachy academic giving me five pages of stuff. I just need somebody to help me, like, collate information and pull out the tidbits,” right?

[00:09:13] Angie Callen: So I would say from an individual perspective, if you feel frustrated or you feel like you’re caught in the sycophantic loop is the big thing, it’s time to get human intervention, right? Either your own human intervention or, intervention from a, for, from a third human. I was talking to a client who is literally starting a business, and we’ve talked about the fact that she stays in AI too long, and then she gets really frustrated and can toil on this one tiny thing trying to force ChatGPT to acquiesce to, uh, her request, and at some point you’re just not gonna do it.

[00:09:46] Angie Callen: And so I would say one thing to be cautious of just as you figure out how to use it is to make sure it remains efficient and productive and doesn’t slip into actually creating more work, and more frustration for yourself. So you kind of have to [00:10:00] find that limit. And, and the, the signs of that are, you know, frustration, spending an hour trying to force it to do something it’s just not gonna do, and, and, and bring a human into that process.

[00:10:10] Angie Callen: Now, from a business perspective, to me, you know, again, I fully believe in being an AI-enabled human on purpose, but, but AI and enablement are, key words to making sure that you’re a purposeful human and that you remain so intentionally, right? And so for instance, one thing that’s really easy to do is get into the copy-paste content strategy, and that is what Jeff referred to at the very beginning as basically this, like, sea of sameness that we’re seeing, where, you know, you see a post and you’re like, “Oh, wow, copy paste.”

[00:10:43] Angie Callen: And it’s not because of em dashes, people. Em dashes existed way before ChatGPT, and I had to embrace that fact in my book because I wrote and released my book at the height of the if there is one em dash, it was written by

[00:10:57] Jeff Sieh: Right, right, right

[00:10:58] Angie Callen: however, it’s like a [00:11:00] conversational book, and there was just no way to write it or else there were gonna be 9,000 Oxford commas in it, right?

[00:11:04] Angie Callen: So it, it … Like, you can’t just copy paste because there is a tone, a cadence, a sentence structure that we feel when we read content created by AI, and it’s starting to become more noticeable, and I think that’s where the trust slip starts to happen, where we, we’re using AI more but scrutinizing it more because we’re seeing it everywhere and, and if we’re not careful, it’s gonna become the norm.

[00:11:30] Angie Callen: and so to me, you can, you can outsource, time to AI, but you can’t outsource what fundaly- fundamentally makes a brand you, right? So you can’t just broad scope copy paste without reading it and giving it your own. you certainly please do not- Outsource commenting to an AI bot because I am not gonna engage with you because why do I want to co- have a comment war with a co- a robot, right?

[00:11:58] Angie Callen: And so, like, there’s a bi- there’s this, [00:12:00] especially at a solopreneurial and a creator level of making sure you maintain your human skills and presence in the ecosystem while you’re enabled by AI

[00:12:09] Jeff Sieh: I think that’s great. One of the things, and we talked about this last week, and even my friend Paul Gowder made a little video based off of what we said with, Michael, King Jr., was that I f- I’m finding a lot more time. Like, I’m able to automate things before, like even show prep and stuff, like little minutiae stuff e- like, you know, putting a show and doing all this stuff, like that took a lot of time.

[00:12:28] Jeff Sieh: The problem that I see, and it’s, it’s actually a lot of articles have been written about it, is that the time that we’re saving, we’re filling it with more work. We’re not becoming more creative. We’re not doing, you know, that kind of stuff. And I think we have to, as creators and business owners, is, okay, we’re getting maybe an hour or two back.

[00:12:45] Jeff Sieh: Okay, don’t just stuff it with more admin things. Use it to grow and be more creative, and maybe take a r- a break and rest because that makes you more creative in the long run. So, anyway, I just, when you were talking about that, we can’t, [00:13:00] we can’t use the time we’re, we’re saving and these tools are giving us to just pack it full again.

[00:13:05] Jeff Sieh: That’s just not… And we as

[00:13:07] Angie Callen: And it’s really easy to do that because the tools allow you to sit and develop never-ending strategies and implementation plans that all of a sudden you’re like, “Oh, wow, I just gave myself 29 things to do.” That’s something I did and then had to, like, back off because it was like, how many different strategy conversations can you have across Fortune?

[00:13:24] Angie Callen: But generative AIs, right? And I want to, the one, the one point I wanna make on the, on the end of that, this, this little piece, Jeff, is that in my opinion, we should not be doing anything with AI that we wouldn’t have done as a human without AI. And if you’re going to automate processes and build agents, the best and most effective way to do it is to build that to replace a repeatable, already proven, vetted human process that’s existed in your business, instead of saying, “Hey, look at this AI process I can bring in,” and then either adding something new or trying to [00:14:00] force your humans to follow an AI process that didn’t already exist in the ecosystem.

[00:14:05] Angie Callen: So again, use it as enablement to either replace or augment things that already exist and are already being done by a human before you try to add more

[00:14:15] Jeff Sieh: One of the things is that I love being able to do things that I’ve always wanted to do but I haven’t been able to do before, and an example of that is a, this is a blatant, you know, I’m, I’m you should go sign up for this. JeffSieh.com/cheatsheet. That gives you these cheat sheet, they’re really cool documents that kind of wrap up the thing.

[00:14:33] Jeff Sieh: This will, the one for Angie’s will wrap up today about 3:00, and then it, it’s automatically going to your email inbox, all that cool stuff, JeffSieh.com/cheatsheet. I had always wanted to do that. I saw Amy Porterfield do it y- years ago, and I thought, “That’s so cool.” And now I can do it automatically because of the time that I’m, I’m getting back with some of these AI tools.

[00:14:50] Jeff Sieh: But anyway, blatant, promotion there. So anyway go, Kira, take your question.

[00:14:56] Kira Pogge: I was just gonna say I love, I love what, you know, you were [00:15:00] just talking about, about, you know, we fill, we fill more of our time, what you said, Jeff. And I just, I do feel like that is, like, an American corporate way. It’s hard to, like, unlearn that. B- then all of a sudden when you’re not busy you’re like, ” I should really be busy.”

[00:15:13] Kira Pogge: and what you just said, y- you’re right. You’re sitting there thinking about something that you should be doing rather than e- existing as a human. and what you said, Angie, when you mentioned, like, you kind of did a deep dive on strategy over across four or five LLMs and kind of got lost in that process, and I don’t think you’re alone in that.

[00:15:30] Kira Pogge: I think probably all of us have done that at one point or another. Can you dive a little bit deeper into, like, what that was like and how, how did you recognize that was happening and then take the step back? Because I think, yeah, I don’t think you’re alone in it, and I think a lot of us struggle with, oh, b- but we could do all these things, so how

[00:15:47] Angie Callen: But should you? Just because you can doesn’t mean you should. Also, side note, side note on the shameless plug, I have an entire chapter in my book about how rest is a requirement, not a, a reward, [00:16:00] ’cause that is a hu- And that, AI or not, I am a huge proponent of the fact that we are not supposed to be on 100% of the time.

[00:16:06] Angie Callen: So there’s our little shared, uh, human message for all of you throughout the day. But to answer your question, Kira, you know, for me, what I realized is that I was spending more time in AI than I wasn’t. And I’m a natural, I am a, a natural idea generator. like, I, you, I can’t … You give me an idea, I’m gonna tell you 97 ways to make money on it, and I just can’t help but do that.

[00:16:26] Angie Callen: And so all of a sudden, AI is a blessing and a curse, because it can help take those ideas and actually flesh them out into something you could do with it, but 97 plans on how to make money with something are a whole lot of things to implement, in a small business. And then at the same time, it can also take somebody who’s already an idea generator, 3X that, and create the exact same, level of kind of overwhelming compulsion to do, right?

[00:16:51] Angie Callen: So for me, what I realized is I, I had too many different conversations happening in too many different places. I couldn’t remember where it [00:17:00] was, and even fundamentally I also knew that all those conversations probably had a common thread that really should be in one place. And so at that point it was like, “Okay, we’re gonna back off of this, and I need to just very logistically create myself one dump, one, one conversation where I can dump ideas so that it’s all in one place,” but I also have guardrails on the fact that, one chat is only gonna allow me to do one thing at a time versus 12 chats allowing me to do 24.

[00:17:27] Angie Callen: So for me, it was really my own accountability and realizing I was, enjoying having a strategy partner a little too much. and, and also then you get in the loop, and I realized I needed to intervene with my own humanness

[00:17:39] Jeff Sieh: Yeah, I agree. just back to, and Dusty even said, he says so, he sees so many people just adding a bunch of work with AI that they would, you know, never have done otherwise because it’s unnecessary, but sounded cool, but why not? So I, I really am trying to like, like Angie was saying before, it’s like, okay, what tasks am I doing that I repeat every week, and can I automate them?

[00:17:59] Jeff Sieh: I [00:18:00] mean, it’s very systems thinking, which is something as a creative a lot of us struggle with. We are very much the ooh, ahh, ahh, squirrel kind of thing. A new tool, and like, oh, there’s a new model. I gotta go try that new model, of AI. And so I think that being focused on real outcomes and putting the human back, like I’m not gonna, I’m not gonna fake, you know, my Tuesday, Wednesday emails.

[00:18:21] Jeff Sieh: Those are something I write to my, the people I want to have a message to, and we interact back and forth. That stuff’s not gonna be automated. But, you’re a leadership coach, which means y- basic- the way I see it is you kinda make your living off things that don’t automate, right? Like you, th- you can’t send somebody to the Angie AI w- I mean, I guess you could, but, what is…

[00:18:42] Jeff Sieh: When you look at your

[00:18:43] Angie Callen: one day soon I will be able to. Wink, wink, nudge, nudge.

[00:18:46] Jeff Sieh: There, there, it’s, it’s getting kinda scary. Um, but when you look at your own work, like, what is the piece AI can generally take from you, and what is the piece you’re never, ever, ever, ever gonna let it touch?

[00:18:56] Angie Callen: Hmm. Are you talking about me personally or the royal

[00:18:59] Jeff Sieh: business, [00:19:00] like your business, like as a leadership coach

[00:19:02] Angie Callen: Yeah. So I, and this is something that, i- ironically maybe AI helped me to put, put words to something I naturally do and did not know. I did, I knew I did, but didn’t know how to say it. You know, I, naturally, I am a systems thinker, by the way.

[00:19:17] Angie Callen: So former engineer who loves people, the best and most exciting problem I can solve is a human one, right? It is the most interesting, complex, and fascinating. It’s way more than designing pipes to flow shit downhill, right? and so for me, that systems thinking and pattern recognition are two things that, I’m naturally wired for, and then having an engineering education exacerbated it.

[00:19:39] Angie Callen: Now, AI can do pattern recognition, but what it can’t do is recognize the patterns for a group of 20 people sitting in a room together. And so for me, it’s really about what container do we need to create for those humans to connect in the way they need to connect in order to get to the goal we’re trying to go to?

[00:19:55] Angie Callen: And AI can’t walk in that room and understand it doesn’t have empathy for that [00:20:00] room. It might be able to recognize patterns based on what it’s told, but it doesn’t know what isn’t being said. And so for that reason, there’s like, that’s where, you know, I really think about engineering human potential, because we have infinite capability to, maximize inhuman or non-human potential is probably the right word, right?

[00:20:19] Angie Callen: So for me, it’s really about making sure that human skills, human connection, and the fact that humans haven’t changed in the curiosity and need to be connected to things is really the, the, the root and the foundation of a group of people and a team, so that as AI comes in, there’s a strong foundation to adopt it instead of it blowing up because that foundation was not created, and that’s something we’re seeing a lot right now

[00:20:44] Jeff Sieh: Mm-hmm. I totally agree. As it moves so fast, it’s easy just to kinda roll with the tide, and I think we need to stop and like, “Okay, what can I make human?” You know? Or not give up. Like, let’s … And I think it’s a slow death. I, I like with, like a thousand cuts.

[00:20:59] Jeff Sieh: I don’t think [00:21:00] people like, “I’m just gonna not be human and give it all to AI.” I think it’s like, “Oh, this is easy,” and you mentioned the easy button and, and people are copy and pasting. same thing when Canva came out. Like, you could go through like Pinterest and go, “Oh, there’s a Canva template. Oh, there’s another Canva template.

[00:21:13] Jeff Sieh: There’s…” You know, like it’s, it’s almost like that like 10X, right? Because it’s so easy anymore. And so I think we, we have to all pause and take those breaks and go like, “Okay, did I really need to do that that way with AI? Maybe I should’ve just fired off an email instead of like, oh, what can chat do for me?”

[00:21:30] Jeff Sieh: kind of a thing.

[00:21:30] Angie Callen: Yeah. I think there’s the, you know, you bring up a good point, and this is, this is an idyllic thing to say, I recognize the fact, that myself included, we all should pause before we open Claude and say, “Do I actually need this to accomplish what I’m accomplishing? Or can I use my human brain to make sure the muscle continues to be worked to get the same result on the same amount of time?”

[00:21:54] Jeff Sieh: Good, good stuff

[00:21:56] Kira Pogge: I love that. I think that’s definitely a process that… I’m gonna write that on a [00:22:00] sticky note and just put it on the wall in front of

[00:22:01] Angie Callen: I think I am too, Kira.

[00:22:02] Jeff Sieh: that’s

[00:22:02] Kira Pogge: constantly looking at it while I’m doing work, ’cause I do think that’s a, it’s a beautiful question to ask ourselves, and like you said, it’s a muscle.

[00:22:09] Kira Pogge: Like, our creativity, ideation, strategy, like, all of those are muscles, and we don’t e- use them if we overuse AI. what about, you know, you talk about authenticity, so authenticity in leadership, authenticity in, in being the human that we are. How do we move forward, and what are you seeing between people online?

[00:22:28] Kira Pogge: Like, what’s the difference between actually being your authentic self and performing authenticity? Like, this is what I think an authentic person in this specific industry would look like or sound like. what’s that difference that you’re seeing when you’re going through coaching people?

[00:22:42] Angie Callen: Oh, that’s a loaded question. I actually have a couple… Oh, I get to shameless plug for a hot second. I have a couple, No More Mondays episodes of my podcast where we dig into this. Because I think authenticity has actually become a buzzword that has diluted and almost ironically changed [00:23:00] what people think authenticity means.

[00:23:02] Angie Callen: And unfortunately, performative authenticity, and the complete irony of those two words together, is almost more normal than j- than, like, genuine, confidence in who you are inside so that that person and that being and purpose and values can go exist outside of yourself. And so to me, authenticity is kind of that, like, self-actualization.

[00:23:28] Angie Callen: now we go woo-woo coach for a minute, right? There is this, it’s a, it’s, it, to me, it’s a sense of knowing and comfort in the knowing of who you are, what you stand for, and what your purpose is in this world, so that you can leverage that internal confidence in order to go out and relate to other people.

[00:23:43] Angie Callen: Now, this is the key, because it is in taking that authenticity and relating to other people that sometimes we have to shift context slightly. Because as a, an authentic human, I am gonna show up slightly differently, in my living [00:24:00] room with friends than I do when I go to a stage. But that doesn’t mean it’s a different person or that either is performative.

[00:24:07] Angie Callen: It means that I am taking my authenticity and putting in context of the container. And I think that’s an important thing to know, because we can very easily slip into abandoning that authenticity in order to shape-shift to fit the container instead of remaining the same with context to who else is in it.

[00:24:24] Angie Callen: That’s where the performative authenticity or the what we call authenticity comes up. You’re not authentic if you’re trying to think about how you need to be to get people to relate to you. Because if you are who you are, you put your ideas out there in context of the audience, they will naturally grav- gravitate towards you.

[00:24:41] Angie Callen: However, when you try too hard, now you’ve stepped outside of it

[00:24:44] Jeff Sieh: Yeah, I think that’s great. one of the things, and I wanna go back ’cause I think this relates to being authentic, is, that some of the time saved that, like, I was talking about, like, it took me, like, all day Thursday to get ready for the show on Friday. Now I can do it in about an hour because of all the tools that I [00:25:00] have to help me get things set up and put it to Ecamm, all the, all the different stuff.

[00:25:04] Jeff Sieh: so what I’m doing for that time I get back is I’m trying to be very, very specific and, you know, think about it, and actually leaving voice messages for people instead of comments. Like, I’m taking that time so I can go back and go like, “Hey, I hadn’t seen you around s- it was so great to see you, you know, comment on my Instagram Reel.

[00:25:23] Jeff Sieh: How are you doing? Tell me about your…” And actually leaving a voice memo instead of just typing it out, and it’s been a change of habits and thinking, and I still have to remind myself to do it, but I’m seeing it pay off because I think if we are very specific on how we’re thinking about, okay, time saved with AI to be more human, that’s the best of both worlds, in my opinion

[00:25:43] Angie Callen: Yes. Ooh, that’s a good way to think about it. And, you know, Jeff, what you just said was actually a part of my answer to Kira’s question I wanted to, but I got on my woo-woo soapbox and forgot, is that what I’m seeing from a practical perspective out there, and I’d be curious to hear what you two are seeing as, as [00:26:00] creators, is people gravitating towards content and types of communication that are genuinely, authentically, no question human.

[00:26:10] Angie Callen: So we’re seeing, you know, unedited videos g- are more popular than something that’s produced. podcasts are a great way. Even email marketing, I think, is seeing a resurgence because people know they can subscribe to something they specifically get from a single human, and they don’t have to scroll through a newsfeed of cat memes and AI slop in order to find it.

[00:26:33] Angie Callen: And, and I experienced this because there was a point where I was like, “Okay, we’re gonna get smarter about content. I’m gonna load all these transcripts from meetings, you know, into Claude, and it’s gonna give me some posts.” Guess what those five posts did? Meanwhile, let’s talk about how I flipped upside down on my mountain bike last week, and I’ll have 12,000 impressions

[00:26:50] Jeff Sieh: Right. Exactly. Yeah. our friend Paul Gowder is, is, he’s like the king of short form video. and he’s been doing, like he’ll do travel stuff, he’ll just do a hot take kind of thing, but [00:27:00] it’s very, you know, what they call those yap type videos where you’re yap- yapping into a thing. And he’s seeing tons of success, and he’s teaching it to other people.

[00:27:07] Jeff Sieh: And like even Sean from But Mostly Disney is, is doing that stuff, and it’s just killing it on these platforms by being authentic and just talking about stuff. In fact, I want to bring up, comment. He goes, “AI seems to be,” I think it means, he m- doesn’t mean pooping, but, “popping in for me, as a skeleton for me to add my own stuff.

[00:27:24] Jeff Sieh: It, it gets me moving through first step or when I am lacking motivation.” And, Paula says, ” AI has hijacked authenticity, and I’ve noticed it’s draining my confidence and self-esteem in ways I never considered.” So that’s, I mean, that’s the kind of the downside of it, as well. So hopefully, like you were talking about, the pendulum will swing back to the other human way.

[00:27:44] Jeff Sieh: I just, this happens over and over again, and, and everyone gets all upset, and then, you know, it comes back. And so I’m … It’s moving so fast, that’s what’s scary, but I think, I think we’re in, for the long haul. We’re gonna get more, more human.

[00:27:57] Angie Callen: I wanna, I wanna say something to what Paula just said [00:28:00] because, one, Paula, thank you for admitting that level of vulnerability, because I believe other people are feeling that and don’t think they should. Because we have access to this, quote-unquote, all-knowing being who knows all things historical data, and I think it feels as if we should be able to have a con- a conversation with it and feel confident in the output it creates or what it helps us do.

[00:28:21] Angie Callen: But because it isn’t human, we have just this little kernel of mistrust in it that actually makes us start questioning ourselves and our sanity. So it’s really, it’s just really interesting, can be a little bit dangerous, and again, ironic, that you can be inside a sycophant and still have, questionable self-confidence because of it.

[00:28:42] Angie Callen: And that is something we need to be watching out for and making sure that we’re still surrounded by humans who can be our sounding boards, validate or, debunk things that, you know, we might be pulling out of it

[00:28:54] Jeff Sieh: Yeah. Totally too. And we, we were talking about, like, the distrust of m- AI and, and we’ve ta- and Kira and I have talked about this in, in the [00:29:00] mastermind group as well, is like, you know, you have to be careful even saying that you’re using AI for your clients. We’re talking about in w- the, kind of the, the small business, solopreneur, area, because in some areas of the culture, it’s like, like young people, they hate it.

[00:29:14] Jeff Sieh: Like they just hate it. And it’s just really interesting ’cause my daughter is kind of on the, the verge of that, and we have some interesting discussions about all the things. and it, and even Michelle says, we were talking about being authentic, she goes, “This makes me more confident on my content.

[00:29:30] Jeff Sieh: It doesn’t need to be perfect. It just needs to be me and relatable.” That is so, so good. Yeah. And then, a great point how to, how to use things is, Tech Trou- Troublemaker says, “I love dumping all the context and content into AI to organize it and sort it out and find patterns, but you are right. This can dehumanize my content.”

[00:29:50] Jeff Sieh: So it’s that

[00:29:51] Angie Callen: That’s the right way to use it, right? Like, r- right? Use it to filter content, take large batches and, and distill it down [00:30:00] into, like, individual sound bites, recognize patterns. Don’t use it for the final output

[00:30:05] Jeff Sieh: Yeah. And speaking of ways to be authentic, well, you know what? You could go live, and the best way to do that is by our friends over at Ecamm. You can find out more about them at Ecamm.com/jeff. You can save 15% on your first purchase by using the code JEFF15. And I was so flustered at the beginning of the show, and I was so excited to have Angie on, I forgot to mention them.

[00:30:24] Jeff Sieh: But no worries, we do have a word from our sponsor So hopefully that you wouldn’t think that is AI slop, but that is something I’ve always wanted to be able to do, and I can do it now with AI, and it’s kind of fun. So

[00:30:53] Angie Callen: Was literally sitting here going, “And that is the perfect use case for AI.”

[00:30:58] Jeff Sieh: It’s, so it’s fun, [00:31:00] it’s novel. I, I enjoy doing that. But, let’s move on to our next section where we’re gonna be talking about, you know, how can we out-human the robots? We’ve been talking about that a little bit already. and I kinda wanna get to, like, the uncomfortable, practical part, and I’m gonna put you on the spot a little bit, Angie, because you have written something publicly that nobody of, at your level kinda says.

[00:31:20] Jeff Sieh: And you, you actually did a, you know, you mentioned your marketing stopped working, your LinkedIn went sideways, SEO leads went quiet or got junky. so if, if this broke for you, then it’s definitely broke for other people. and you wrote that, like, online content is up 57%, since generative AI showed up, and that standing out in that sea of sameness is harder than it’s ever been.

[00:31:44] Jeff Sieh: So in your business, what broke first that you noticed? Was it, you know, what did you see and how long did you take to admit, like, it wasn’t just a slow q- quarter, it was broken. Like, something happened in your business

[00:31:56] Angie Callen: Yeah, it, it it took probably close to a year to realize it, [00:32:00] and, and, and part of that is because i- there’s a, a convergence of things happening right now, a lot like happened, between about 2005 and 2010, where there are, like, multiple factors that are really snowballing, and that’s why it took a little while for me to realize what was happening, and AI is a big contributor to that.

[00:32:18] Angie Callen: But, you know, 2025 in particular was a really challenging year for coaching and knowledge-based businesses because, you know, AI really came in and exacerbated economic factors that were at play, social political stuff that- that’s happening out there that’s creating uncertainty and, and keeping people from investing in themselves.

[00:32:38] Angie Callen: And now you add AI to that, and there is the perception that it can do the things that we do. Now, it can do some of the things that, like, coaching and knowledge professionals do, but in a very limited, a, a limited capacity that we’ve gotta keep guardrails on, right? And so but we also know that in the market, perception is [00:33:00] reality.

[00:33:01] Angie Callen: And so it took a little while to figure out kind of how people were perceiving like, human coaches and human knowledge professionals versus what AI could do, and also to figure out how people were just buying in an economic market that had shifted. And so there were multiple variables there that I didn’t, I couldn’t identify right away, let alone start to solve for until I had both, you know, several months of data to look at and some peers who were s- telling me they were seeing the same thing.

[00:33:33] Angie Callen: And so, you know, it was, it was a really a, a challenge because, you know, I believe from a marketing perspective, we have, we are starting to see the shift away from, like, okay, so we had traditional marketing forever, right? Billboards and phone books and TV. And then we moved into the digital age, and now I believe we are shifting away from the digital age to whatever the new thing is gonna be, and I still think we’re in the, [00:34:00] the messy middle of figuring out what that is about to be.

[00:34:03] Angie Callen: But for years and years and years, a lot of us in knowledge-based businesses got really spoiled by exceptional inbound marketing thanks to digital presence, and that’s the thing that ultimately I star- I started realizing we have to get out from behind a computer and back in front of humans

[00:34:20] Jeff Sieh: Totally agree. Totally agree

[00:34:22] Kira Pogge: I think that’s a great point. And for, I think, you know, for people who are listening who have kind of depended on digital marketing and inbound marketing over the last, like, decade or so, and then some, what would you say is working right now? Because I love how you said the messy middle, ’cause it definitely feels like that, um, still, where people are like, “Don’t be on social, but be on social.

[00:34:42] Kira Pogge: Should you use email? Email is dead.” Like ev- you know, they’re all the headlines exist at the same time.

[00:34:47] Angie Callen: And you can confirm any one of them you would like

[00:34:49] Kira Pogge: Yeah, 100%. So for people listening who are in that space and they’re trying to build their small businesses, what’s working right now as we’re, like, in that transitional period? What would you [00:35:00] tell them?

[00:35:00] Kira Pogge: And do you still think that, like, newsletters and referrals are, are a way to go, at the moment?

[00:35:07] Angie Callen: Oh, there’s a, there’s, there’s many things there I wanna make sure I remember to, I remember to say at a high level, I think it’s don’t react. And what I mean by that is, like, don’t burn your boats, don’t shut down LinkedIn, don’t shut off Google business, don’t stop posting content. Because what I believe, what I believe is that the ecosystem that has al- already been a multifaceted SEO ecosystem has just gotten some new family members, right?

[00:35:30] Angie Callen: And so we wanna keep doing everything that we were doing that was working before, and figure out how to adapt, add, or modify based on the new family members that are generative search. OpenAI now has ads. So there’s just some things there that, you know, unfortunately, here’s a hard truth, we kind of need to be everywhere all at once.

[00:35:49] Angie Callen: Now, that’s where AI can help streamline that a little bit if we’re careful. but to me, it’s like, you know, the last year and a half of LinkedIn, LinkedIn has been my platform of [00:36:00] authority for almost 10 years, and in the last year and a half, I can’t feel like I can’t eke out an impression. And, that’s, that’s one because of the jump of 50% more content, but also because they’ve li- they’re changing their algorithms.

[00:36:14] Angie Callen: And so what we have to be cautious of is not to over-rely on any single source, and having kind of a diverse lead generation system, that has maybe, like, 20% from five places, or 10% from 10, right? because if somebody changes something you don’t have control of, or the, you know, economy changes and it shuts down one angle, you still wanna have some, some diversity elsewhere.

[00:36:39] Angie Callen: That can feel overwhelming, but it’s not quite as bad as i- as, as you think if you don’t react and you just keep doing kind of what used to work in any iterative form of the process while testing out some kind of new stuff. And for me, I have definitely seen the human, the human stuff really come back and connect.

[00:36:58] Angie Callen: So referrals have always [00:37:00] been a really high aspect of my business, but it’s, it seems even stronger now, because, people are shopping around, but referrals don’t shop around. and so it’s, it’s a, you know, high close rate, quality clients, and people that you wanna work with.

[00:37:15] Angie Callen: and the, the newsletter thing, you know, I, I write a weekly newsletter called Combating the Sunday Scaries: Seven Tips to Improve Your Week, and that thing still gets 40 to 50% open rates. And it has, no matter whether I have 500 or 5,000 people on a list, because it has trusted content with, like, loyal readers who know they want to read what I’m giving them.

[00:37:35] Angie Callen: And so that’s where it seems strange, because there’s a whole lot of emails I don’t open, but, there are a lot of people out there s- opting into that as their means of content consumption because it doesn’t have as much noise around it. So y- it’s, it’s, in a way, it’s almost like we’re coming full circle and g- doing things the way we used to do them

[00:37:55] Jeff Sieh: Yeah. One real quick follow-up, ’cause I, I agree with you. Like, one of my favorite things is sending out [00:38:00] newsletters and getting response back, is never automate your responses back. Like, don’t use AI to, to write those. Take the time and converse with the people who are reading your emails. I just think it’s such a great way to, talk back and forth.

[00:38:13] Jeff Sieh: I mean, it’s, it’s a little… I, I love, like, doing live because I can pull up comments and like, “Oh, this person…” And it’s harder for email ’cause there’s, like, s- you’ll write a great email and then you’ll hear nothing. And then you’ll, you’ll do your, like, your story where you flipped over your mountain bike, and people are like, “Oh my gosh,” and everybody responds back, and it’s like, it’s so bizarre.

[00:38:30] Jeff Sieh: But, I, I agree, but don’t automate that, for goodness’ sake, whatever you

[00:38:34] Angie Callen: No. And that, you know, Jeff, that is, it- that is fundamentally what I mean when I say get out from behind the computer and out in front of your humans. It doesn’t mean, now I do mean literally sometimes, get out from behind your digital marketing, go to an event and be with people in the flesh. But ultimately it’s also don’t hide behind your automations and make sure you’re out and communicating directly with your people, and responding individually to e- like, to emails is one great way to do it

[00:38:59] Jeff Sieh: [00:39:00] Yeah. One, so one thing, and this is one of my favorite things, you have written. And by the way, go get her book, Scary Good. It’s really great. And I loved, ’cause I’ve never seen this before, and I may steal it if I ever write a book, but I loved how you, for every chapter, and you had breakout spots of a companion podcast that kind of goes over that topic.

[00:39:17] Jeff Sieh: I thought that was genius. I hadn’t seen that done before. Kudos to you, ’cause that was really, really cool. So great

[00:39:23] Angie Callen: Thanks

[00:39:23] Jeff Sieh: Yeah. the thing that I wanna talk about is, like, this is probably the f- the best thing I think you’ve written, is like you, and I want you to tell the whole story here. You accidentally sent out like a template email that had never been filled out and was totally blank.

[00:39:37] Jeff Sieh: and it was the, totally the wrong send, but it got more replies than your normal newsletter. So what did that… What was the t- what, what did that teach you about that no strategy that you, like AI would tell you would have? Like, what did that teach you having that happen?

[00:39:53] Angie Callen: spend a whole lot less time thinking you need to perfect things. No, to me, it reinforced what we were talking about earlier with if it’s clearly human, [00:40:00] people will respond. So the story is, since there’s a lot of creators and probably people who do marketing around here, you know, we use ActiveCampaign for all of our marketing communications and our funnels.

[00:40:10] Angie Callen: And I had an event funnel set up, for a big event I run in January where, they had, like, three or four emails up until it, up until the event, and then there were some, like, follow-up emails afterwards. And there was an email in the sequence that just never got updated but was still connected to the sequence.

[00:40:29] Angie Callen: And so it was one of those just placeholders, like, “Hey, write this email,” and nobody ever actually wrote it. And so it sent out the ugliest template you’ve ever seen. The background color was, like, this skin color beige, which should never be in an email to begin with, and it had all these, like, cookie cutter stock images and writing that any normal human should realize was nothing I would even ever think about sending out.

[00:40:51] Angie Callen: And one of the buttons was schedule a session with me. I got, like, 12 responses that were like, “Hey, the, the scheduling button’s broken.” And I’m like, “Of [00:41:00] all the crap in that email, that’s the thing that you found?” and so whether that means that was 12 people who wanted to schedule a session or they just wanted to let me know the button was broken, I thought it was hilarious that, like, in this complete ugly email that went out that had no value, not only was it opened, but it actually warranted a response from people.

[00:41:22] Angie Callen: And so it’s just, we try so hard to perfect things, but ultimately it’s like, who had pooped instead of popped in

[00:41:28] Jeff Sieh: Yeah, Sean.

[00:41:29] Angie Callen: earlier? Yeah, I’m gonna remember that,

[00:41:31] Jeff Sieh: Because Sean, you, he could have said poop. That’s what’s so funny is like most of the time he would’ve, but anyway, that was, that was good. Yeah. it’s so funny you said that because one time, so I usually schedule the Friday morning emails to talk about the show at like 7:15, and I screwed it up and it went out 7:15 in the PM, right?

[00:41:47] Jeff Sieh: Like, really easy to do on your scheduling. Everybody emailed back going, “Hey, I got this at night. What’s going on? Are you okay? What’s the sh-” It was so funny, but it was the exact same thing as like, you know, until something breaks, you, you don’t know if people are out [00:42:00] there or not, but when they, when it

[00:42:01] Angie Callen: tells us maybe we should break things more often

[00:42:03] Jeff Sieh: yeah. When I did magic, so I’ll go back to my little magic stuff, one of the things, I would always screw up a trick at the beginning It was a comedy bit, but it would make the audience, it would endear yourself to them. Like, “Oh, this guy.

[00:42:13] Jeff Sieh: Oh, poor guy.” And then it would be funny, and then, you know, it worked on. So there’s, there’s whole psychology behind that, but anyway, I digress

[00:42:19] Kira Pogge: I think that’s the human connection though too, right? It, that, you know, they see you kind of mess up and then they, they cheer for you the rest of the time, even though it was intentional, right? ’cause they want you to do well, and you, like you said, you endear yourself to them. Um, Imperfection is relatable,

[00:42:34] Jeff Sieh: Mm-hmm.

[00:42:35] Angie Callen: ’cause no one’s perfect

[00:42:36] Kira Pogge: Absolutely.

[00:42:36] Kira Pogge: And it, and it also I feel like gives you that accessibility, you know, ’cause we all make mistakes, and I think sometimes people hold, like a creator or s- or an author, somebody that they really have valued their content to like a really high standard, right, they’re on a pedestal. and then they have imposter syndrome about what they’re doing ’cause they’re like, “I’ll never get there.”

[00:42:56] Kira Pogge: but we’re all just human, like you said, like your T-shirt says. so [00:43:00] you said, you know, when it comes to, you get so many responses in that email. When it comes to sales, I love that people were like, “Hey, I need this button to to book a call with you.” When it comes to sales, you said people are kind of committing less, and it’s n- less about the cost and more about the commitment.

[00:43:16] Kira Pogge: So instead of saying, “Oh, you have six months of access to somebody for coaching,” or whatever, instead of that being a selling point, it’s like, “Oh, it’s six months.” Like, is, they’re kind of uncertain about it. They have to make the commitment to do it. Am I gonna spend money on it and then not follow through?

[00:43:32] Kira Pogge: Like, when you’re trying to sell a product or a service that has that type of commitment, how do you meet people where they’re at, and why do you think that commitment issue is coming up now?

[00:43:42] Angie Callen: I love some of the words you’ve used, because meet people where they’re at has ha- is how I’ve actually been, you know, coaching some of my small business owners and, like, coach clients in how to be, what I call offer agility, right? We have to be, be a little bit more nimble in how, how we sell and how we, even [00:44:00] package our, our services and our offers now.

[00:44:02] Angie Callen: because you hit the nail on the head with, like, you know, I … People used to want these longer engagements where they felt like it would be everything they need to complete some sort of outcome or get to a certain milestone. And to me, the, you know, 2025, in my opinion, w- had the tagline, “Everything is uncertain, therefore everything is uncertain.”

[00:44:21] Angie Callen: And that really creates complete lack of decision-making in, and it happened in businesses, it happened individually. We saw it kind of across the board that everyone just sat on their hands. And that sentiment started to shift a little bit in the beginning of ’26 to the tagline, “Everything is uncertain, and that’s a certainty.” And what I believe that has done is it makes … It’s now making people want to move because they realize they can’t wait any longer to do the thing, implement the new initiative, hire the member, whatever it is. But, at the same time, they, they are hesitant to go all in on it. And so what we have found is that, especially in knowledge [00:45:00] services where it can be hard to get people to invest in themselves, giving them an entry point to build the confidence that, one, they will get value out of it and they will put the work in to get value out of it, is better.

[00:45:10] Angie Callen: And then giving them ways to kind of continue a journey with you is more effective than saying, like, “Yep, I’m gonna get you to the top of the mountain.” and, and it’s funny that you ask that question the way you did, Kira, ’cause for eight years in business my bread and butter was selling getting you to the top of the mountain.

[00:45:27] Angie Callen: And so I’ve psychologically really had to change how I sell and present my offerings to be much more almost modular or multi-phase, which means now getting better at upselling and cross-selling and introducing an- you know, an, an, a continuation versus this idea of, like, sell them once and give them everything they needed more.

[00:45:48] Angie Callen: and that to me is how we’re meeting people where they’re at. Because I’m also seeing that people are more willing to vocalize an objection to something b- because they wanna work with you, they just aren’t willing to [00:46:00] do it in the big way, and they’re more willing to say that so that you can work together to find a solution that is gonna get them enough value but fits within whatever level of, like, risk tolerance they’re willing to take on.

[00:46:11] Angie Callen: So, you know, being agile in our sales process is being nimble and, and, and accommodating to, to an extent, and meeting people where they’re at seems to be working a lot better than, here’s everything you need to be successful.

[00:46:25] Jeff Sieh: So do you think that’s why, you know, there’s still people putting out courses, but do you think that’s why cohorts where you’re kind of working along somebody, are becoming a lot more popular? Like, instead of like, “Hey, here’s a course. Go through it at your own pace,” it’s more like, “Hey, we’re getting all these group of people together.

[00:46:38] Jeff Sieh: We’re gonna go through this, and by the end of the cohort you’ll have this, this, and this.” Do you think that’s why it’s more popular?

[00:46:44] Angie Callen: I think that’s part of it. and I think that, that to me it that dovetails into the, the need for m- more human connection, and people want- don’t wanna be alone together anymore. They wanna be together, together. But the other side of that coin, in my opinion, Jeff, is we have complete digital fatigue.[00:47:00]

[00:47:00] Angie Callen: People don’t wanna be in meetings anymore. They don’t wanna sit in front of, like, asynchronous digital content, because they also, c- don’t know whether they’re gonna be accountable to doing it. And so I think that a, a live, you know, a live experience, even if it is digil- digital, is more palatable than just more screen time, and they have the, you know, connectedness and the community of other people for accountability.

[00:47:24] Angie Callen: So I think there’s a bunch of factors there

[00:47:25] Jeff Sieh: Got it. the last question of this section I wanted to talk about was, like, you have said the goal is not to out-market the robots, it’s to out-human them. So let’s make that really concrete. Like, if somebody watching this has, like, one hour on Monday morning, what’s the, the single most out-human thing they can do with it?

[00:47:45] Angie Callen: reach out individually to other humans

[00:47:48] Jeff Sieh: Oh, that was easy. Mic drop there. Okay. So practically, like just call them, do FaceTime with cinema text? Like what w- like when you say reach out to other humans, how can we do that? What’s, [00:48:00] what is your favorite way to do it?

[00:48:01] Angie Callen: Well, and I, I decided to just have the moment, because then there’s multiple ways that could look, and I think it depends on who those humans are. you know, none of us pick up the phone. Literally, I got a call from an unknown number 17 times in a row in the last 12 minutes, right? I’m not gonna pick up the phone.

[00:48:15] Angie Callen: and so to me, it’s thinking about the human or humans that you’re reaching out to and what’s the best way to meet them where they’re at from a communication standpoint. So very simply, that can often be the method with which you most often communicate. So if you’ve decided that every Monday in that hour you are going to text a friend you haven’t talked to in two or three months and go through a cycle, that’s a great way to do it.

[00:48:40] Angie Callen: Maybe it’s going on LinkedIn or Facebook or wherever your primary, like, group of contact contacts or, customers are, and sending individual messages to 10 of them. it could mean going into your email and sending an email to a prospective client that you talked to three months ago to say, [00:49:00] “Hey, you popped into my mind.

[00:49:01] Angie Callen: How are things going?” Right? So it’s, it’s, to me, it is taking the very individual route to communicate with another individual human in the method that they typically communicate with you in order to show you’ve taken that time to personalize outreach to them versus something mass

[00:49:19] Jeff Sieh: Got it. But, you have this one line I keep coming back to: “Strategy without empathy is a plan no one follows, and empathy without strategy is just good conversation.” So where do you see people watching this land, and what does the fix look like for each side?

[00:49:38] Angie Callen: So let’s decode that for a second, because strategy without empathy means go implement this thing, I don’t care what it does to you as a human, right? So classic example of that is, you know, an autocratic leadership environment where there’s, s- if everything is moving so fast, everybody’s gonna get burnout trying to implement a strategy, [00:50:00] right?

[00:50:00] Angie Callen: the flip side of that is if, if all you have is empathy with no strategy, you’re gonna sit around a room and talk about your feelings a whole lot and never get anything done, which is great in therapy and not very effective in business. and so there is a happy medium in which we think about how to implement a strategy, leveraging the strengths and caring for the humans that are going to carry it out

[00:50:24] Jeff Sieh: I, I just wonder as leaders, as we do this, like, what, what’s really concrete that we can take away? Because, you know, like we said before, this is changing so much. Like, how do we, how do we act- actually implement, like, doing it in, in real life?

[00:50:38] Angie Callen: Yeah, and, and, and let’s be clear. There has never been a more complex time to lead in business today, and I don’t care whether you’re leading yourself as a solopreneur or you’re leading, you know, a team of hundreds and thousands inside a Fortune 500 company. It is way more complex. And to me, where we bring together strategy and empathy as a [00:51:00] leader is to make sure we’re in tune with the strengths, motivation, and interests of the individuals, and even the fears of those individuals, so that as we roll out strategic initiatives, we’re not doing it at the expense of them

[00:51:14] Jeff Sieh: So let’s say you’ve been told by a manager or a partner or whatever, like you need to be more empathe- empathetic, right? Like you’re, you’re lacking that maybe in your leadership skills, or maybe you even know, like I struggle with this. Where can people go or how do they learn to be more empathetic?

[00:51:30] Angie Callen: you know, I think empathy, if you don’t have it naturally, is something that you h- it’s, it, it’s a like, go back to muscles, right? It’s, it’s essentially like, stepping into, a, you know, a weightlifting gym when all you’ve ever done is run. You are about to experience a com- very new act with muscles that are not used to that activity, and they won’t build to their, you know, full strength overnight.

[00:51:54] Angie Callen: And so to me, em- you know, you have to kind of set the intention to be more empathetic in order [00:52:00] to build that muscle. And things you can do are, if you lead a team, go sit down and have a half-hour one-on-one with every single one of them and ask them about individual goals, personal motivations, challenges that they’re having, and see them as another human who has aspirations and, and fears, right?

[00:52:18] Angie Callen: And, and then take it another step and be willing to do something about what you hear, because you may have somebody working on your team who is the right butt in the wrong seat, and you’re holding them to a performance standard that they’re never gonna meet because you’ve never taken the time to activate them properly.

[00:52:36] Angie Callen: Those are really empathetic acts that make a huge difference for an individual, and if you are willing to hear things you may not wanna hear and act upon them for the betterment of someone else, now you are looking at, you know, empathy. The same thing can happen at home. And to me, in the leadership world, and this is a little bit of a soapbox, we have to remember that leadership is not about you.

[00:52:58] Angie Callen: It is about the [00:53:00] people whose care has been stewarded to you. And in that is where empathy will help build more trust, more retention, better performance, and better productivity. So there’s a whole lot of business outcomes from bringing this to the table. However, it’s something that you will have to practice over time if it doesn’t come naturally.

[00:53:18] Jeff Sieh: That’s one of the things I highlighted in your book when you were talking about leadership, and it was like leadership is not just bossing people around. That’s not leadership, right? Leadership is exactly what

[00:53:26] Angie Callen: That’s

[00:53:27] Jeff Sieh: Yeah, you talked about like leadership is getting people to and encourage them to get to this goal together.

[00:53:32] Jeff Sieh: It’s not like, “Hey, do this,” which I think is, has been confused in our society. So I love that part of your book, so

[00:53:40] Kira Pogge: Yeah, I, I think it’s so easy, right? Everybody says it’s not personal, it’s business, but like what you just said, it’s the opposite. Nothing’s really just business. It’s all personal ’cause we’re all humans, and what you just said, you said, you know, yeah, sure, it leads to good business outcomes, but it, it starts with humans first, and if you’re not taking care of them, none of that other stuff is gonna happen.

[00:53:59] Kira Pogge: [00:54:00] So when you talk about leadership in a space that’s kind of filled with AI and leaders can kind of leverage that for strategy or kind of lean on it maybe a little too heavily, and maybe it does, like, half the work, you know, you, you said that leadership is really borrowed and that trust can be lost and gained very quickly.

[00:54:18] Kira Pogge: So if they’re using AI for a lot of their work, like, what does, being a leader in today’s world mean, and how can they make sure that they’re not losing that human el- element?

[00:54:30] Angie Callen: You know, with AI specifically, in my opinion, it’s, as AI likes to say, take a beat, right? Take a beat before just hurrying up and rolling out the next shiny thing. And, and what I mean by that is intentional implementation of AI within an ecosystem where humans are leveraging it and remembering that the humans are driving that ecosystem, right?

[00:54:54] Angie Callen: We still operate the vehicles, people. I don’t care what Waymo’s doing right now. and so remembering that [00:55:00] is important to what I would say the intentional use of AI is, and looking at where within a team do we bring non-human coworkers, and how do I talk to my humans to make sure that integration and that onboarding is gonna go well?

[00:55:16] Angie Callen: So it’s almost, as weird as this is gonna sound, thinking about AI being a coworker who has to be onboarded into a team that already has a culture, already has a connectedness. And so, you know, that, that just, granularly with how AI should come in and how we should be thinking about it as leader- as leaders is important.

[00:55:35] Angie Callen: Because then you could also have the flip side happening, which is everybody on the team is using whatever AI they want, and nobody’s ever put guardrails around that. That’s similarly a space where we need to have intention. And so to me, where we come back to strategy and empathy, is sitting down w- like, with your team.

[00:55:52] Angie Callen: Get input, people. This is like, like, newsflash in leadership. Input is a good thing to get and to share, [00:56:00] and for some reason there are still… there’s still some autocratic leadership out there that’s like, “Stay in your lane.” And that’s the worst thing you can do to bring empathy to an environment, build trust, have people wanna stay and work, and feel like there’s enough transparency, appropriate transparency, to work in the environment.

[00:56:15] Angie Callen: And if you’re bringing agentic coworkers in, you best have transparency and a conversation with the humans to make sure these people aren’t just gonna operate in fear of losing their job every day.

[00:56:25] Jeff Sieh: That is such a great point. And I love agenic AI. I think it’s super cool setting up the teams and all that

[00:56:31] Angie Callen: So nerdy

[00:56:32] Angie Callen: and

[00:56:32] Jeff Sieh: it is, I am very nerdy. But the thing is, is it’s so cool. now, now y- I said that, so Yes. So, I love agentic AI. I think it’s great. We’re, I’m building teams right now. But I think what you said is so key is that, is you make sure that you don’t scare people. Like, you let them know if something’s, if you’re trying a new tool or you’re doing something, let them know, [00:57:00] “Hey, I’m testing this so you can use it to save more time or do whatever.”

[00:57:03] Jeff Sieh: So don’t just like, “Hey, I’m gonna replace you with this bot.” Don’t… Oh my goodness. Come on, folks.

[00:57:08] Angie Callen: And you know, I wanna add one thing to this. by the way, former engineer who loves people, nerd alert, love it. the same sentiment should exist in human hiring as well, right? We should be thinking about intentionally bringing people into a culture and, and, and having a culture, right?

[00:57:26] Angie Callen: ‘Cause if you don’t have one, you have one, and it’s probably not a good one. But, but it’s this, it’s a similar, it’s a similar sentiment, different actions, to creating an environment where people want to work, feel they can be heard, and that the trust exists. The s- the same need is there when you bring a new human into that as when you bring a non-human into that as well, and that to me is this idea of, you know, empathetic leadership, but being very intentional about how that looks in practice

[00:57:53] Jeff Sieh: Yeah. So many good things. We could talk all day, but I know we can’t. So I wanted to give the, the perfect amount of [00:58:00] time for you to be able to tell everybody, Angie, this has been such a great conversation, where they can find you, where they can get your services if they need them, your podcast, all the things that is Angie Callen.

[00:58:10] Jeff Sieh: Please tell us where we can find you

[00:58:12] Angie Callen: the easiest place is themoderncoach.co, which is where you can learn about all the things we’re doing to engineer human potential. my podcast, No More Mondays, is all about, the fact that humans still matter, mediocrity is expensive, and ownership will change that. And we, have an episode every Monday morning to help you kick off your week in style.

[00:58:33] Angie Callen: And, if you wanna follow along in my antics, I post about them, probably more than you would like on LinkedIn

[00:58:39] Jeff Sieh: Very cool. Yeah, her book’s amazing, and see, you’ve already got people buying it. Paul says, “Grabbing your book, Angie. Great session

[00:58:45] Angie Callen: Yay

[00:58:46] Jeff Sieh: It is very, very cool. Where can f- people find out the amazing Kira? Where, where are you at, Kira? Where can people find you?

[00:58:51] Kira Pogge: can go to kirapokee.com, and they can follow me over at Instagram @kirapokeecreations, where I talk about being a theater nerd turned marketer who’s now [00:59:00] shifting to work more with theaters, ’cause I too am a nerd. Nerd alert.

[00:59:03] Jeff Sieh: right. Well, and, and Kira has been doing some really cool stuff over at Instagram where she’s taking songs and talking about them. So if you are any sort of theater geek or like musicals, make sure you guys go check out Kira, ’cause she’s got some really cool stuff, and great content. So, and as always, we love you guys.

[00:59:18] Jeff Sieh: Thank you for, Ecamm for sponsoring the show. You can find out more about them at Ecamm.com/jeff. If you like this show, well, guess what? I take the notes for you. You can go to jeffsieh.com/cheatsheet and it’s free. You don’t have to sign up, but if you’d like them in your inbox, it’ll come every week.

[00:59:32] Jeff Sieh: But you can also just download them there if you don’t want another email. Either way, go get the stuff that Angie has. It’s amazing. And you guys in the chat room are amazing. Tech Troublemaker, Fun in Key West, Sean from But Mostly Disney, Magai, Dustin Stout, of course. You guys are amazing because you are

[01:00:02] Jeff Sieh: [01:00:00] Thank you guys so much for watching. We’ll see you guys next time. Have a great one. Have a great weekend. Bye everybody

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