Dear ChatGPT: What Are My Blind Spots?
Introduction:
This week, Jennifer Kerhin, Jaci Russo, and Sarah Segal talk about how they’ve been using ChatGPT. Jennifer has deputized the AI chatbot as a key advisor, feeding it all kinds of performance data and soliciting its analysis before making hiring, financial, and strategic decisions. Recently, she asked it to identify her biggest blind spots as a CEO. Five seconds later, it spat out five answers with detailed explanations and suggestions. And what did Jennifer think of the feedback? “It was right on,” she tells us. “I mean, it was totally, absolutely true.” We even brought ChatGPT into our conversation in real time, asking it whether Jaci had hired the right business development person, whether Sarah had been fully prepared two years ago to buy back her PR firm, and what’s the best podcast for small business owners. Plus: while we were talking, Jaci asked ChatGPT to evaluate the performance of her co-founder and spouse, MIchael. Let’s just say, it does have some concerns.
— Loren Feldman
Guests:
Jennifer Kerhin is CEO of SB Expos and Events.
Sarah Segal is CEO of Segal Communications.
Jaci Russo is CEO of BrandRusso.
Producer:
Jess Thoubboron is founder of Blank Word.
Full Episode Transcript:
Loren Feldman:
Welcome Jennifer, Jaci, and Sarah. It’s great to have you here. Jennifer, you recently had a really interesting conversation with ChatGPT, and you’ve shared that conversation with us. You started it by asking, and I quote: “Now that you have learned a lot about me and my company, please think of my top five blind spots as a CEO.” Before we talk about the responses you got, could you just tell us a little bit about your relationship with ChatGPT? How did you— [Laughter]
Jennifer Kerhin:
I like how you call it a relationship.
Loren Feldman:
How did you get so close?
Jennifer Kerhin:
Yeah, with ChatGPT, I feel a little bit like I’m cheating on my husband a little bit. But I’m part of a business group, Vistage, my CEO group, and my chair, for the last 18 months, has been on us to embrace AI. And so he’s made us sort of have a goal that we do it once a day. Very basic, very basic. So I started off 18 months ago and instantly bought the $20 a month one.
And over the past time period, I think I probably submit, I don’t know… four or five times a day about problems. And then I’ll go back. So I’ll have an issue on Monday, and you can go back to that discussion thread and add more details to it. So not only am I opening multiple discussion threads to ask for thoughts, advice, comments, whatever. Then I can go back to the one—like on Friday, I’m trying to go back on Monday and add some more details, and it spits out even more information. So I’m a heavy, heavy user.
Loren Feldman:
It sounds like you’re not just using it as kind of a search engine, which some people do. You’re using it as a sounding board.
Jennifer Kerhin:
Oh, yes. Sounding board, analysis. I’ve uploaded spreadsheets and had it give me analysis. I’ve had it make sample business plans. I’ve done some imagery. I wrote a LinkedIn post and created an image from Dali on it that I used that looked amazing—so quite a bit, not beyond the basic level.
Loren Feldman:
So you turned to it and asked it if it could identify for you what your blind spots are. And I’ll just list the five quickly, at least the headline on each of the five. They were, number one, “over reliance on personal stamina.” Two, “loyalty to underperforming staff.” Three, “innovation bottleneck,” meaning you’re the innovation bottleneck. Four, “avoidance of formalized systems.” And five, “delayed exit-strategy planning.” What was your reaction? Did you feel seen by that?
Jennifer Kerhin:
It was right on. I mean, it was totally, absolutely true. I asked a lot of questions about systems over a year and a half ago, but we have fixed that. So the avoidance of formalized systems was due to it seeing me track the first six months of a lot of questions. And then I never went back to it and said, “Oh, we fixed this. Oh, we did this now.” So I think that one was true, but it’s gotten fixed.
But the other ones, oh my gosh. And I didn’t realize how tones and how you talk to it—ChatGPT wants to make you feel good. It wants to spit out stuff like, “Oh, you’re the best CEO in the world.” So lots of times when you’re asking for advice, it comes back to you like, “Oh, you’re so great.” By forcing it to come back with my negatives, I was like, “Wow, how did they get the ‘over reliance on personal stamina?’” That was absolutely true.
Loren Feldman:
You know what I thought about that? You talked about that a good bit on the podcast.
Jennifer Kerhin:
Did I?
Loren Feldman:
And it made me wonder if ChatGPT listens to the 21 Hats Podcast. [Laughter]
Jennifer Kerhin:
I don’t know!
Sarah Segal:
Question for you: So you got this response immediately after that entry? Because I did the same thing based on what you shared, and it came back asking me for additional information.
Jennifer Kerhin:
So I asked it, “Please tell me my five blind spots.” And within five seconds, it brought those instantly.
Sarah Segal:
It didn’t ask you for additional information?
Jennifer Kerhin:
No, not at all. What you see is exactly what it asked, and then it instantly came back.
Sarah Segal:
Because mine, it asked me for additional details on my biggest challenges, team structure, where I feel like I’m crushing it. It asked me for additional input.
Jennifer Kerhin:
Nope, nope. This was it. So, with my five blind spots, it then wrote about three to four sentences under it. And then it said what to watch out for, and three bullet points. So it formatted it in a very easy to understand, easy to read—and then, at the end of it, it said, “Do you want me to help you come up with ideas to fix this?” basically. But my first glance: Oh my gosh, it’s perfect. This is exactly true. This is something that I need to—these are my blind spots I need to fix.
Loren Feldman:
Jaci, you, too, were inspired by what Jennifer sent us, to ask the same question.
Jaci Russo:
Immediately. [Laughter]
Loren Feldman:
Did you get answers? And did you agree with those answers?
Jaci Russo:
I did, and I don’t, but I do. So it did not immediately have an answer for me. So I used the same prompt she did because I wanted to be lined up. I said, “Do you have enough information?” And it said, “No.” And so it gave me some questions.
Sarah Segal:
Yeah, that’s what I got.
Jaci Russo:
Yeah, and so it gave me some great questions that really started an excellent conversation. It wanted to know daily and weekly responsibilities, what fills my time, executive team structure, who handles what in the company, and am I wearing multiple hats, current revenue goals and blockers, feedback from employees or customers that I’ve recently received (good and bad), and then my growth goals. And so I said, “I’ll answer those. I want to see your first pass, and then I’ll answer those.”
So it gave me what I think was probably a pretty sound answer: delegating versus owning too much, over-investing in new initiatives without a sunset plan. That is not wrong, because, you know, Loren, I’m always starting new things. Underestimating sales infrastructure, not fully leveraging brand equity I already have, and measuring success through activity and not outcomes. And I was like, “Well, I feel like fighting, so that must resonate.”
But then I gave it a bunch of information. So I gave it the answers to all of its questions about what fills my time, my executive team structure, my revenue goals. You know, in 2020, we grew 6 percent, 3 percent, 43 percent, 13 percent, 1 percent. Our goals for this year—which is a big jump because of our new salesperson. And so, then it gave me a refined answer that was very accurate. It was really good.
Jennifer Kerhin:
What was the big difference?
Jaci Russo:
Well, it took my actual answers and gave me real insight. And so it talked about scaling, execution, and making sure I’m not scaling my own bandwidth. You know, the fact that we were over-dependent on relationship-based sales, but that now we have the salesperson. And it even says, “Robyn’s hire is a big step. Good job.” I’m like, “I love when you talk to me like you’re my best friend.” And it even spells Robyn’s name correctly.
It’s like, energy dilution across brands, and it’s not wrong. You know, I am technically running three companies, and I don’t do it as well as I think other people that try to do it, because all of them are still growing. And so it’s hard to scale three things at the same time. It gave an antidote to every challenge it presented. It gave a solution.
Loren Feldman:
So Jennifer, you said that you were surprised by the reference to an over-reliance on personal stamina. And you weren’t sure how it came up with that, at least initially. Did you figure it out?
Jennifer Kerhin:
No, I didn’t go back to look. I have so many threads in it. I didn’t go back and look. I’m not surprised, but that was absolutely 100 percent true. I don’t know how it got that information, and I really don’t want to take the time to go figure it out, because it’s true, right? And regardless, it doesn’t matter. How am I going to fix it? So these are true blind spots. I think the only one that I think I fixed is number four: avoidance of formalized systems. But the rest of it, and the delayed exit strategy planning, boy, is that right on.
It says, “Your decisionmaking about selling or scaling further seems clouded by exhaustion. Emotional and physical fatigue can distort how you evaluate options for the future, from M&A to building new lines of business. It can cause hesitation or wait-and-see thinking at key decision points.” And boy, is that true. I met an entrepreneur once who said—and I think I even said this on the podcast a long time ago—that if you start a company, you should figure out how you’re going to exit. And when I started this company, I had no idea I could exit. I’m now at the point where my company is strong. I should think, “Do I want to stay in this for 10 years and build it up? Do I want to get investors? Do I want to sell? What do I want to do?” And I have been putting it off, totally.
Loren Feldman:
I was thinking about what it must be like to be reviewed this way. And the only thing I could think to compare it to is like a 360 review, where you ask people who you work with, who know you really well, for their feedback. I’ve never had that pleasure. But have any of you done that? And is this similar to that?
Jennifer Kerhin:
No, it’s not similar. I’ve done it. Your employees are not as smart as ChatGPT. [Laughter] Your employees tell you things in a 360 that affect them. They’re looking through the prism of them. ChatGPT is looking through the prism of what you input too, but it’s more, I think, based on a standard of other CEOs. My staff has given me good thoughts, but it’s everything I do and how it affects them. They don’t think about, “Hey, this company needs to grow. Hey, how do we add systems to increase profitability?” They think, “How does she communicate better about x or y?” I still will always do those types of 360s. I’m not against them. I think it gives a great ability for staff to give perspectives up, but I don’t think they’re equal.
Loren Feldman:
Did you share this with anybody you work with?
Jennifer Kerhin:
Oh, my whole staff. I sent it out to them immediately. So we’re in the process of hiring a new director. And so I’ve been using ChatGPT to help me go through resumes, help me look at our assessments. I uploaded—we use Gallup StrengthsFinder to check out different skills. We made them go through assessments. It analyzed that.
And so then I put this in there, and I said, “Based on the four finalists you’ve ranked—you’ve filled the top four—according to my blind spots, who would be the better fit for the director to balance out my blind spots?” And then I sent it to my other leaders, and I put their StrengthFinders and their job descriptions. And I said, “Which ones fit better with me, based on my blind spots?” So yeah, I have zero problems showcasing my faults. I don’t care, because good luck. I’m the owner of the company, right?
Loren Feldman:
In the suggestions that it made for dealing with these blind spots, I think one of the suggestions was that you hire someone to be kind of a number-two, chief-of-staff type person. Is that the position that you were just describing?
Jennifer Kerhin:
Yes, yes. And so I have that person now, and they have instituted systems, and they are in workflow and stuff. So it’s not completely fixed.
Loren Feldman:
What did you think about the “loyalty to underperforming staff?”
Jennifer Kerhin:
I actually thought that should be number one. I think this is an issue all founders have with the people who helped you create the company. It’s when you get to a certain level, they’ve been with you, and that loyalty stands for a lot. I absolutely have way too much loyalty to them, and it’s much more prevalent now that I’ve gotten high-performing staff. And I have to say to them, “Well, yeah, but they were with me, and if I called them on Sunday afternoon, they would say, ‘What do you need?’” The strategy ChatGPT said for me is to create a talent upgrade plan. It says, “identify key roles where an A player would change the game.” And that’s what I’m going to start doing—where an A-plus player might change everything, which I also think would help with my time off.
Loren Feldman:
Well, it also told you that you should step away for a month a year. Do you like that idea?
Jennifer Kerhin:
Love it. Love it. I took a two week vacation last year, and I have not been on vacation since, and I don’t think I’ve had two days off on a weekend since then. And I think that’s ridiculous. I think every owner needs to carve out more time. It doesn’t help to get to this level, and I need to take more time off. Absolutely.
Jaci Russo:
I do some consulting work for the Edward Lowe Foundation in Michigan, and one of the things that they do is called an EIR, an entrepreneur in residence. And you can do this on your own, which is why I’m mentioning it. You don’t have to go through the foundation.
The EIR is three days on their property for a conference retreat with no programming. Upon check-in, you’re fed lunch, and you’re given a guidebook that gives you some things to think about, about goals and processes and people and the deep thinking work we need to do for our companies. And then you have a place to stay, and for the next three days, you emerge to eat meals that they prepare for you. There are some fireside chats at night with others, if you want to engage. But otherwise, it’s walking through the forest, if you want to do that. It’s playing pickle barrel golf, if you want to do that. It’s kayaking in a boat, if you want to do that. But it’s thinking time away from work.
And Michael and I did it together, since we run the company together, and we did it last year. We had some discussions—some quiet, some louder, some very different opinions about what the next five years look like for us—and emerged with some real growth goals. And all of a sudden, this year, we’re achieving those goals, and I credit it to that time we took.
Jennifer Kerhin:
Yeah, I think setting time away is—it’s no longer a goal. It has to be a have-to-happen kind of thing. And I think that’s great that you did that. I think that it feels like one step back, but really, it’s helping you rest and recover and have your brain think, so that you can play it forward. I think that’s a great idea.
Jaci Russo:
And you could do that in an Airbnb, you know?
Jennifer Kerhin:
Yeah.
Loren Feldman:
While we’re talking about Jennifer, Sarah and Jaci, did anything else about this strike you? Did anything stand out?
Sarah Segal:
So, my concern is taking this too literally. Because it is churning out information based on whatever its inputs are and whatever the standard is—and the standard best practices for running a business. And I don’t know that I trust it, or would rely on it for alternative solutions. You know, maybe it’s giving you a suggestion on team structure based on, obviously, what other companies have worked on. But I feel like there’s innovation and new thinking and the ways that we did things in the 1950s are much different than what we do now. I would just be a little bit more hesitant to take this as gospel.
Jennifer Kerhin:
Sarah, do you read business books?
Sarah Segal:
Yes.
Jennifer Kerhin:
Do you take that as gospel?
Sarah Jordan
No.
Jennifer Kerhin:
Same thing, then. Same thing. I mean, ChatGPT, to me, is just another resource to help me be a better CEO. It’s not gospel, but I was amazed how accurate it is. But still.
Sarah Segal:
It gets you thinking. 100 percent, it gets you thinking. But throughout my career—I mean, you know this, Jaci knows this—that most business owners are figuring shit out as they go. And so to take anything as, “This is the best way,” I would take it as, “Okay, these are good things to think about.” Maybe go on a long walk and think about them. But I just think that there needs to be some filtering, for lack of a better word.
Loren Feldman:
I think that’s a good point. I think there’s a difference between this and reading a book in that this is so much more personal. And it’s based on actual conversations with you. And I think that gives it an air of authority that is beyond what you would get from a book. I even thought about it when we were talking about the issue of being too loyal to employees. You mentioned that one of the suggestions they made was to create a talent upgrade. They had another one that was to implement a three-strike feedback system: “Track performance over three structured conversations. If behavior doesn’t change by the third conversation, move to a transition plan.” That, to me, felt like a one-size-fits-all solution that, to Sarah’s point, maybe is appropriate for some people, but not for everybody.
Sarah Segal:
You know, we’ve all heard about whether or not you’re hiring for a match or somebody who fits in your system or somebody who’s going to add value to your business, right? And when Jaci recently was looking to hire somebody to help with new biz, everything she thought she wanted was not what she ended up hiring. And so I think I’d just be cautious about some of the assumptions that it’s making based on that. It’s only going to give you what you put in. I think that it’s a good thing to kind of start thinking on it. Like you said, a book is just somewhere to start. But I don’t know that the ChatGPT output is where to end.
Jennifer Kerhin:
It’s not, I agree. It’s not where to end. But it gives you much better advice than a book, I think. It hears what you’re writing. It sees the type of questions you’re asking, the type of advice, and so it’s like a customized book back to you, customized advice. I still have a business coach, I still have lots of books, I listen to podcasts, but it’s one more source, and it’s a bit more customized because of the input I’m putting in there.
I had not thought to use ChatGPT like this, and I am fascinated, and I’m going to continue to do it. Like, give me feedback on how we’re going through this hiring process. Have I been asking the right questions? Who knows what ChatGPT is going to say? But I’ve been saying: What do you think’s the best fit? What do you think based on these criteria? How should I rank this? How should I weight this? At the end of this, I’m going to say: Do you think I went across this process well? It’s kind of looking into a mirror and being like, “Am I giving myself the right feedback?” It’s not perfect. Of course, it’s not. I have no idea what this is. It’s a crazy loop of internet somewhere. I don’t know, but it’s another tool in our toolbox for us to use.
Loren Feldman:
Jennifer, how does it know enough about your hiring process to say if the process was the right one or not?
Jennifer Kerhin:
I have no idea. [Laughter] But for the last three weeks, I’ve been putting a lot of information in to help me go through this. So I put in about 50 resumes and the job description. And I said, “Go through all these resumes based on this job description. Give me the top 10.” And then we had already ranked our top 10. Did it fit? Was there something I missed? Then, out of the top 10, I put in our spreadsheet of how we ranked people based on a set criteria. “Tell me your thoughts on it.” Then I put in the StrengthsFinder.
So I’ve been feeding it a lot of our process and workflow, and our results or our assessments, and it’s helping me think through it. I asked it, “How would you weight the interview versus a StrengthsFinder? How would you do all of that?” Well, at the end of this, I might say, “How did I do as a CEO walking through this process?” And I would not have thought about that until this question came up.
Sarah Segal:
Jaci, you had talked a little bit about your recent hiring of your biz dev person. Do you think if you had gone through and leveraged ChatGPT in the same manner as Jennifer, that it would have spit out a recommendation to hire the kind of person you ended up hiring?
Jaci Russo:
I don’t know. I’m gonna ask it right now. Let’s find out: real world test. [Laughter]
Sarah Segal:
The reason why—so, my background, I was a reporter, right? And I wanted to move into PR, and I got rejected job after job after job because I was not apples to apples on the experience—until somebody was like, “Oh, well, she can tell a story, she can find a hook, and she can write quickly because of deadlines, etc.,” and saw a connection that I don’t know that a computerized system would find.
Jennifer Kerhin:
I actually think it would. I think that ChatGPT would do a better job. If you tell it to look at a resume and say, “Who’s the best fit?” They don’t look—they!—it doesn’t look at just experience, right? It will say, “Based on this person working here, they worked there eight years, they probably have good skills on x, and you need those soft skills.”
It does more than you think about reading between the lines, thinking of soft skills, especially if you tell it, “I’m a small PR agency with a niche here, based in San Francisco,” and you say, “The ideal person will be good at storytelling, be able to hire client management, and like working for a small company, not a big, bureaucratic agency.” I bet you it will give you more information than you think, than just looking at a resume for experience.
Jaci Russo:
Well, you want to know what it did?
Jennifer Kerhin:
Yes, please. Let’s do it, real time.
Jaci Russo:
First of all, I asked it for key characteristics, and I would tell you that it described Robyn to a T.
Jennifer Kerhin:
Ooooh!
Jaci Russo:
Not things I would have thought for, so “connector-minded,” “strategic communicator,” “curious and consultative,” “self-directed,” and “results-oriented.” And I’m like: Yes, yes, yes. Those weren’t things on my checklist. So then I said, “Well, actually I was thinking I need”—and I just rattled off my checklist. And it just told me the reasons why I was wrong, and why this is a better persona. [Laughter]
Jennifer Kerhin:
Jaci, did you have somebody who didn’t work out in the position?
Jaci Russo:
Oh, gosh, yes.
Jennifer Kerhin:
So I had someone last year who didn’t work out. And I said, “Here was the job description, here’s the resume. They worked for me for two years. It didn’t work out. Please tell me some reasons why you think they didn’t work out.” And boy, was it right! It reads between the lines way more than you think it does, Sarah.
Loren Feldman:
Jaci, what did it tell you you were wrong about?
Jaci Russo:
Well, my checklist. It said, “Your instinct”—and it reiterated, basically, what I had said. And then it said why this would make sense, but then it said, “In short, you’re actually looking for”—and then it walked through what I really need. And it said, “Based on the description you gave us, is that the only best fit? Not necessarily. Let’s consider these.” I mean, it’s nicely telling me I was wrong, going back to telling me the right answer, which it told me in the first place, which perfectly describes the person I accidentally hired who ended up being perfect.
Sarah Segal:
Do you ever have concerns that it’s telling you the things that you want to hear as opposed to things—I mean, because it’s supposedly giving you nice feedback. But like, the other day, I said, “What are the top consumer lifestyle agencies in the San Francisco Bay Area?” And of course, we came up number one. It was like—
Jaci Russo:
Oh, let me cut you off. I asked it “the best branding strategist that I should be paying attention to in marketing,” and it did not include me. And I asked it, “Why?” And it said, “Oh, you know what? You’re right. We probably should have.” And then it reiterated the list. But don’t assume it automatically did that just because you asked it to, because it would have done it for me, because it knows I have an ego.
Jennifer Kerhin:
It makes mistakes too, right? We’ve all heard of the word “hallucinations.” I asked it for—we have a management book club, and we’re nearing the end. We read a book once a year. We’re nearing the end of ours. So I said, “Give me top 10 books that you think would be good for young managers or inexperienced managers.” And around eight, nine, and 10, I looked them up on Amazon, and there was no such thing.
And so I went back, and I said, “So, I can’t find book eight, book nine, and book 10.” “Oh, you are correct. These books don’t exist.” Like, wait, what? And it had titles, it had descriptions, it had authors. And I’m like, “Did you just make these up?” And, like, “We apologize.” It didn’t say we—it said “Apologies. This was a mistake.” And so, Sarah, to your point, this is not the gospel, right? This is not Matthew, Mark, Luke, and John. It is ideas to think of. Can it make mistakes? Absolutely. But can it surprise you? It sounds like it just surprised you, Jaci.
Sarah Segal:
Can I jump in here? So I just typed in, “What are the best podcasts for small business owners to listen to?” With a big, little, fiery flame icon, “best overall for small business inspiration and strategy,” the top one is the 21 Hats Podcast. Second under that is How I Built This with Guy Raz, and then Smart Passive Income by Pat Flynn. But like, I don’t know. Part of me is like, “It’s gonna tell me what I want to hear.”
Loren Feldman:
It may know that you’re on the podcast, Sarah, to your point.
Sarah Segal:
Yeah!
Jennifer Kerhin:
Okay, Sarah, I have a great question for it. Say, “I was part of a large PR company, and I decided to go off on my own two years ago. What are the top five things that I should have been prepared for when I left?” Ask that, right? Isn’t that your story?
Sarah Segal:
Umm, well, no. I was bought and then bought myself back two years ago. Okay, but yeah, I could put in that whole kind of backstory.
Jennifer Kerhin:
And see if it gives you what you want to hear, or see if it actually gives you insight. That’s where I’m going with this. If it just comes back and says, “I’m so awesome and I deserve to be on my own”—but see if it gives you actual insight that you’re like, “Wow! Okay, okay.”
Loren Feldman:
While Sarah does that, Jaci, I wanted to ask you, you said that you were impressed with the second round of suggestions that you got after you answered the questions that ChatGPT had for you. Do you think you’ll take action based on any of that?
Jaci Russo:
Oh, absolutely. I mean, I think that it gave me some good feedback. There are some things I really need to consider. I disagreed with it on some assessments. It told me why it was right. It was right. [Laughter]
Loren Feldman:
Give us an example. What are you gonna do as a result?
Jaci Russo:
Okay, well, so hold on. It gave me one of the things that I really appreciated was this 90-day scalability audit framework and directions on how to use it, decision accelerator questions. It was kind of like it made me think about my business differently than the way I normally think about it. And then I was like, “Well, hold on, though. You’re giving me suggestions on sales and account service. I’m not directly involved in either of those things, and I haven’t been involved in account service in years.” My team is so rock solid. And so then it said, “Your attention is being pulled by the Downtown Workspace.” I said, “Well, update: the downtown workspace is completely booked on a waitlist for the next three months. So I’ve got nothing to do there except cash the check.”
Then it said, “You spent a lot of time on Train Yard Advisors.” I was like, “Well, I did a year ago, but I’ve deprioritized it because it’s humming along nicely.” So I gave it straight feedback. So then it came back with the growth lever I need to pull, a score from one to five on how I’m spending my time on each company: BrandRusso, Brand State U., Train Yard Advisors, and the Downtown Workspace. It incorporated my answers, gave me a ranking of 20 out of 30, 26 out of 30, 12 out of 30, and 21 out of 30 on how I spend my time, insights from the audit, and recommended next moves, and I’m gonna follow each one of them and see what happens.
Jennifer Kerhin:
See, isn’t that extraordinary, Jaci?
Jaci Russo:
I’m so excited. I have a 90-day action plan roadmap.
Jennifer Kerhin:
If it made you think about it in a different way, it’s been an amazing help for you as a CEO. All right, Sarah, what did it tell you?
Sarah Segal:
What was your specific question that you asked? I just want to make sure I wrote it in correctly.
Jennifer Kerhin:
You went back on your own two years ago. Is that right?
Sarah Segal:
Yeah, beginning of 2023.
Jennifer Kerhin:
So maybe five things that you probably should have thought about before you did. Like, hindsight’s 2020, but was there anything that it says, “Man, you really should have considered this as you went off on your own.“ You’re like, “Yeah, I should have.“ Or, “No, that’s not true. I did consider that.”
Sarah Segal:
Okay, so I asked it, “Were there any challenges or opportunities that I should have considered when restarting my PR agency?”
Jennifer Kerhin:
Okay.
Sarah Segal:
And it said, “opportunities,” that I reclaimed my creative freedom, I reconnected with core clients, building a team with shared value. Blah, blah, blah. This is all boring. Reestablishing brand recognition. I don’t know. It’s kind of generic. Now, it’s asking me questions about, “Why did I take it back?” And, “Why did I want to reclaim my agency?” So it’s asking me for more detail. But I wouldn’t say that this is—
Jennifer Kerhin:
It’s not actionable support, is what I’m hearing, right?
Sarah Segal:
No, it’s not. But it’s all about the prompts. On TikTok, you always see that you’ve got to put the right prompt in. So I think that there’s room for growth, in terms of my ability to put in the correct prompts.
Jennifer Kerhin:
I also think if Jaci and I put in the same exact prompt, we would get totally different answers.
Sarah Segal:
You guys should put in the same question I did about the top podcast.
Jaci Russo:
I did and I got different answers. But, you know what the funny thing is? 21 Hats was still first.
Loren Feldman:
Well, that’s what matters.
Jaci Russo:
But none of the rest of them were the same. I got completely different podcasts after that one, and it even made recommendations of specific 21 Hats episodes. But then it told me The Game by Alex Hormozi, My First Million by Sam Parr, Startups for the Rest of Us by Rob Walling, Build with Rob. It went through different ones, but, yeah, it was different.
Jennifer Kerhin:
So mine, the top one is not 21 Hats.
Jaci Russo:
You’re out.
Jennifer Kerhin:
This isn’t the biggest brain out there. This is just another support. But I think you can use ChatGPT in ways that you did not imagine. It can be your own personal business coach, and you can start asking it questions like that. Besides, every day, we’re learning more and more different ways to use it.
Jaci Russo:
Well, and just to throw this in there, a client of mine, who is a very well-regarded therapist, says she uses it as her therapist. And I was like, “Um, hello?!” She said, “No, it’s not going to replace the human that I see on a weekly or monthly basis, or whatever it is. But when I need an answer right now, I need clarity on a situation, I’m not looking at it logically or professionally, I’m just in it. It is really great at giving me things to think about, questions to consider, a different look. It’s helpful.”
Jennifer Kerhin:
I actually think it’s going to replace a lot of counseling. There’s a significant lack of good mental health counselors out there, and I think there’ll be some sort of customized one that some organization does, and maybe it’s occasionally monitored by it, but I absolutely think this might take over.
Sarah Segal:
So speaking of that, how are the two of you, or the three of you, planning and preparing to AI-proof your businesses?
Jaci Russo:
I think that, just like with being able to look up resources on YouTube, Googling how to create a marketing plan, reading business books, I think that ChatGPT is another resource in that list of how to get the information. But the ChatGPT resource is personalized, customized, and way better. But implementation still takes talent, and so I think that our work as a strategist who implements the plans that we research and create, there’s still a place for us.
Jennifer Kerhin:
Good answer.
Jaci Russo:
Thank you.
Jennifer Kerhin:
I don’t know. Haven’t thought that far.
Loren Feldman:
Jennifer, when you gave this out to your employees, did you get any pushback of any kind? Was anybody freaked out? I mean, even something like seeing in black and white that you were told that you’re too loyal to your employees, did anything give someone pause that they came to you and expressed?
Jennifer Kerhin:
No, if they had any concerns, they didn’t express them to me. We use tech a lot, all different types of platforms. And I’ve been talking about AI. We’ve done innovation afternoons where we’ve had different types of AI. So I don’t think any of them are fearful right now of it. That might change in a year. Are they surprised that I put in these types of questions? No.
Loren Feldman:
Do you think any of your employees use it as a sounding board the way you do?
Jennifer Kerhin:
Yes.
Loren Feldman:
Is that because you’ve encouraged them to do it, do you think?
Jennifer Kerhin:
I think it’s a combination. Some of my rock stars have, I know, put in things into their ChatGPT about, “I would like eventually to be x,” whatever that is: “Help me figure out a plan for my career development to get there.” I know several of them have done that.
Loren Feldman:
Sarah, have you done anything to try to AI-proof your business?
Sarah Segal:
Right now, we’re working on embracing AI. Because I am a small agency, there is a lot more focus. I love technology. I always have. And I’m always trying to find new systems and ways to do things better, smarter, faster. And it makes it so one person on my team is delivering, what, maybe two or three people—I mean, they can deliver beyond what a singular person used to be able to deliver. And so, right now, it’s like, okay, a project that used to take eight hours should really only take two or three hours, now that we’re implementing it.
So it’s really trying to help my agency grow without necessarily adding additional head count, because we’re putting in systems that are going to help us deliver beyond what we normally did. I don’t think that we’re protecting ourselves from AI, but we’re more like, “Okay, how can we use this to continue to grow the agency?” At some point, there might be challenges to: Can AI do what we do? But there’s a lot of stuff that we do in person, where we’re physically at events, we’re physically doing things that AI will never be able to replace, obviously.
Jaci Russo:
I did ask AI how to future-proof against AI, and it gave me some really good things. It said, “It’s not about AI replacing your agency’s creative brilliance.” I like that it thinks we’re smart. “It’s about embedding AI into your processes, offerings, and mindsets. You become more indispensable to your clients, not less.” And then it’s like, “Here’s a strategic breakdown of how to do it.”
Sarah Segal:
ChatGPT, AI can’t have relationships for you. And I think that’s a commonality across all three of us, that we have built businesses that are reliant on good relationships, and ChatGPT is never going to be able to replace that, no matter what.
Jennifer Kerhin:
Except, Sarah, what if those relationships turn into AI? What if there are no more newspaper reporters or media, and there’s just AI?
Sarah Segal:
I don’t think that that’s actually possible.
Jennifer Kerhin:
Okay, look, I have not prepared for it at all. I’m using it as a tool, but I am not prepared for if AI took over this business. I don’t really even know how to think about it. The only job I thought of, maybe, is like a surgeon. But honestly, they have robots now doing surgery. So my brain is not large enough to think about how to future-proof my company against AI. It’s just not.
Sarah Segal:
I take back when I said it’s not possible, because, theoretically, if there are integrations with AI, it could create news content based on first-hand accounts. So when people see a plane crash, they’re sharing that stuff on social and on X and all that kind of stuff. So it could use those details and create a story out of that publicly shared information. So it’s crowdsourcing the news. People’s first-hand accounts are going to be very subject to their perspectives. You can’t validate it, necessarily. So there’s a way to crowd-source news, I guess, but I just don’t know how you make sure that it’s true without having somebody there on the ground.
Jennifer Kerhin:
I mean, there’s a lot of stuff that’s not true now that’s in the news. But I think you have a great thought, they could crowdsource. I can’t think that big. All I can think is how I can use it today and next week. What I’m really waiting for is: When are we going to see ads on ChatGPT?
Sarah Segal:
Oh my God, I hope not.
Jennifer Kerhin:
Oh, we’re definitely seeing ads. But when? When is this going to turn into a monetization vehicle? Because that’s what I want to get involved in. I want to start selling ads on ChatGPT.
Sarah Segal:
But if you’re subscribing to it—
Jennifer Kerhin:
But that doesn’t pay enough. That’s $20 just so you have a little skin in the game. That probably pays nothing. I want to know, when all of this money dries up, how are they going to monetize this? It’s got to be through personalized—the same way social media does. Oh, no, I’m fascinated by that next level.
Loren Feldman:
It’ll be just like Google, and it’ll destroy the product. [Laughter]
Jennifer Kerhin:
Probably, probably, right.
Sarah Segal:
Oh yeah, absolutely. I mean, my Instagram feed now is just filled with people selling me business products.
Jaci Russo:
Yeah, there’s 10 million paying customers to the tune of $2.7 billion per year. It’ll be $4 billion by the end of ‘25. So I don’t think they need ad revenue.
Sarah Segal:
Yeah, because we’re all paying the $20-a-month version. There’s a $200-a-month version now, with the video generation and all that kind of good stuff. Are you sharing it with your teams at all? Because there’s a team plan.
Jaci Russo:
Yes, we’re on the team plan. Everybody in my company has an account that they use as part of our team.
Jennifer Kehrin
Wow, I’m not on that.
Sarah Segal:
And can you share? Can you create custom GPTs that you share with your team members, so everybody’s adding stuff to that? Can you see what each other—
Jaci Russo:
Maybe. That may be a possibility. We’re not doing—or I’m not doing that. I don’t see what they do. They don’t see what I do. But we have a shared account, so when Michael puts in messaging or some sort of tool, my answers know that information and respond accordingly. It’s like we’re all on the same dashboard. It’s like we’re all using Outlook, but I can’t see everybody’s emails.
Sarah Segal:
But it’s pulling information from all those.
Jaci Russo:
Yes, it’s a shared knowledge base.
Loren Feldman:
Have you tried asking it: How did Michael handle this particular situation? If you asked it the question Jennifer asked about herself, but you asked: How do you think Michael is doing?
Jennifer Kerhin:
Oooh, good one.
Jaci Russo:
Let’s find out.
Jennifer Kerhin:
Good one. What are Michael’s top five blind spots?
Sarah Segal:
I just did something interesting. I asked it whether or not I should be friends with Jaci Russo.
Jaci Russo:
Aww, I hope it said yes.
Sarah Segal:
No, but “shared professional background,” “commitment to education and mentorship,” like all these great things. And then, “If you’re interested in connecting with Jaci, consider reaching out through her professional channels.” It gave me your email, your LinkedIn, and your Instagram handle.
Jaci Russo:
Wow.
Sarah Segal:
Oh, I’m so using this for new biz.
Jaci Russo:
Yes. We use it for new biz
Sarah Segal:
For, like, searching people’s email addresses?
Jaci Russo:
I have used it for searching information about them and connecting with them. It doesn’t always give the email address. As always, you have to worry about the hallucinations. But it also gives other content in terms of things to talk to them about that they would be interested in. It’s a connector.
Loren Feldman:
All right, last question before we go, how’s Michael doing?
Jaci Russo:
Michael is doing okay. But according to ChatGPT, “He is under-utilizing AI as a creative collaborator. He’s only using it as a shortcut tool. He distrusts AI’s ability to capture tone and emotion. He still believes correctly that voice is sacred and that AI can sound robotic or off brand, but if he uses better commands, he’ll get better answers. He’s not embedding AI into the creative workflow across the team yet. He’s treating AI as a threat to originality instead of a catalyst to iteration.”
So then I said, “Help me help him.” And it gave me an AI toolkit with 30 days of things that Michael needs to do once a day, one thing a day, to help him better utilize the tools.
Loren Feldman:
Are you going to share that with Michael?
Jaci Russo:
I already sent it to him. [Laughter]
Loren Feldman:
All right. My thanks to Jennifer Kerhin, Jackie Russo, and Sarah Segal.
