The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Leadership/The Manage 2 Win Podcast
The Manage 2 Win Podcast artwork

#282 - Will AI Replace Executive Assistants in 2026? | Monique Helstrom

The Manage 2 Win Podcast · 2026-02-24 · 41 min

0:00--:--

Key moments - from our scoring

Substance score

41 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality7 / 20
Guest Caliber11 / 20
Specificity & Evidence8 / 20
Conversational Craft6 / 20

Monique Helstrom, a veteran executive assistant who worked with Simon Sinek, returns to discuss the misconception that AI will replace executive assistants and her new AI Powered Assistant course designed for admin professionals. Rather than replacing assistants, AI should amplify their existing skills in organization, pattern recognition, and logistics. The course covers practical AI applications across event planning (handling complex dietary restrictions and menu coordination), meeting management (generating department-specific summaries and emails from minutes), project management, travel arrangements, and email communication. Helstrom emphasizes the importance of proper prompting - detail-rich, specific instructions that don't need to be perfect - and maintaining human-in-the-loop verification for all AI outputs. She contrasts this with executives who mistakenly think AI alone can replace a skilled assistant, noting Shopify's approach of hiring entry-level talent and teaching them AI tools. The conversation covers how executives often lack training on delegating to and managing assistants effectively, and how AI helps with specific challenges like dealing with "blur words" (imprecise language like "ASAP" or "by Friday") and crafting tonally appropriate communications for different organizational levels.

Key takeaways

  • →AI should enhance executive assistant productivity in areas like event planning and meeting summarization, not replace the human relationship, analytical thinking, and forward momentum only an assistant provides.
  • →Effective AI prompting requires detailed, specific context with concrete examples - not perfect grammar - and should always include human verification before actionable outputs like sending emails.
  • →Assistants trained on AI become technical experts who understand organizational needs and can advise teams on tool adoption, multiplying their value beyond administrative tasks.
  • →Blur words like 'ASAP,' 'immediately,' and 'by Friday' cause miscommunication; clear deadlines with specific times reduce follow-up friction and clarify expectations.
  • →The AI you get reflects your prompt and your communication style - the same question asked differently by different people yields different results because the language model predicts based on user input, not objective reality.

Guests

Monique Helstrom

Topics in this episode

Simon SinekAI Powered Assistant courseMonique HelstromExecutive assistant coachingChatGPT promptingEvent planning with AIMeeting minutes summarizationCalendar and travel managementShopify entry-level hiringBlur words in communication

Questions this episode answers

Will AI replace executive assistants?

No - AI doesn't provide care, concern, forward thinking, or relationship building that a skilled assistant delivers. Companies like Shopify are hiring entry-level talent and teaching them AI rather than replacing admin roles entirely.

How should assistants use AI for event planning with multiple dietary restrictions?

Input all constraints (e.g., 'six vegetarians, three meat-only, two gluten-free') into AI and ask it to generate a menu that satisfies everyone, creating a first draft to send to venues rather than manually piecing together 35 individual preferences.

How do you generate meeting minutes for different teams from one meeting?

Provide AI with all your notes or transcription and ask it to create separate emails for sales, marketing, and leadership with role-specific action items and context - dramatically faster than manually sorting notes.

What is the biggest mistake people make with AI prompts?

Being too vague or assuming the prompt must be perfect; instead, provide as much detailed context as possible, even rambling naturally via voice input, because AI works by predicting based on the language and specificity you give it.

Why do different people get different answers from the same AI?

AI language models learn your communication style and preferences over time within your account, so your ChatGPT will increasingly respond in your voice and reflect your past behavior patterns.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

There are a handful of genuinely useful practical ideas - segmenting return-to-office emails by audience tier, using AI to rearrange event schedules on short notice, and the 'blur words' concept - but they're diluted by lengthy host tangents, repeated filler, and generic advice ('human in the loop,' 'prompts are everything') that any AI-aware professional has already absorbed.

I call those blur words. It's a ah, speech pattern which means it's words that mean different things to different people.
you put I got six vegetarians and three people who only eat meat and two people who do this, blah blah, blah, blah, blah. You put it all in there, find me a menu that works

Originality

7 / 20

The 'blur words' framing and 'assistants are not lamps' metaphor show some original thinking, but the central argument - AI is a tool that augments rather than replaces, prompts determine output quality, keep a human in the loop - is entirely standard 2024 discourse with no contrarian or first-principles angle.

Assistants are not lamps like you don't bring it into your office and plug it in and it works.
If you're waiting for the first answer to be the perfect answer. AI is not for you.

Guest Caliber

11 / 20

Monique Helstrom is a credible practitioner - a decade as EA to Simon Sinek, now running administrative recruiting and coaching - which gives her real operational authority on the EA relationship; however, she is a niche coach/course creator rather than a senior operator who has applied these methods at organizational scale.

I worked my way up from receptionist to office manager to an admin assistant to an executive assistant
working with Simon Sinek for the last decade, I realized that I was not the norm

Specificity & Evidence

8 / 20

A few concrete anchors exist - $295 course price, 13 modules, 68 prompts, the recommendation of three two-hour meetings in the first 30 days, and a rough '10% of companies' onboarding estimate - but client outcomes are anecdotal and unnamed, and most claims lack data, timelines, or measurable results.

There's 13 modules. I have 68 prompts, I want to say, so 68 usable prompts
I recommend three two hour meetings for the first month that they're there

Conversational Craft

6 / 20

The host derails the conversation repeatedly with unrelated personal anecdotes (the heat pump vibration trench story consumes several minutes), literally says 'blah, blah, blah' multiple times mid-sentence, never challenges a single claim, and closes with an overt paid-endorsement tone; follow-up questions exist but are mostly leading rather than probing.

And that's the exact thing. It's like, hire us as a hiring coach because you keep putting people in this places to make decisions on who's going to join your team. They've never been trained how to figure that out. You know, and so blah, blah, blah.
I don't know whether I've ever done this before, but I recommend everybody who's an executive go out and buy this course for your executive assistant because it's a win.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B62%
  • Speaker A38%

Most-used words

assistant54executive29different23back22blah14boom13team12office12first12help12email12course11sure11human11meeting11prompts11

Episode notes

Will AI assistants replace Executive Assistants in 2026? No, unless you ignore the transition. AI is changing executive support forever. The question isn't whether it's coming, it's whether you're ready. AI should be used as a tool, not a takeover. Monique Helstrom, leadership coach and former Executive Assistant to Simon Sinek, shares how AI tools for Executive Assistants can elevate the role instead of replacing it. After building a successful career as an assistant, Monique now teaches executives and teams how to maximize their efficiency and effectiveness working with their executive assistants. One BIG change in 2026: How to integrate AI strategically into your leader-executive assistant workflow. Monique breaks down her AI + Executive Assistant Course , including 68 practical AI prompts and modules covering business management, travel coordination, email strategy, communication, executive support systems, and more. Key insights: · #1. - Why AI won't replace Executive Assistants, but ignorance might. · #2. - How executives should properly onboard and train EAs. · #3. - How AI improves prioritization, productivity, and communication. · #4.

Full transcript

41 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Foreign. Welcome back to the Manage to Weight podcast. Today we have Monique Helstrom, and she has a course, the AI Powered assistant. Now, you know, you think about it, do I not have an assistant? And now I just go with AI Or I do I have an assistant, skip AI or do I assume my assistant knows how to use AI? That'd be nuts. She has a very low cost course. And so I said, you got to. Come on, we got to talk about how to maximize what we can get from our assistant in a positive, healthy way, working with them. And so I can be better as an executive. Right? And that's what we talk about. And there's a lot of great stuff here, a lot of stuff for you to consider. And I think you're going to be interested in a course. I'm certainly going to do it with the next assistant I hire. My current one is really good with AI but dive in, you're going to gain something here. You're going to learn some things that are really important for you and your team as you grow. And, and you have other leaders that are going to have assistance. And when they have an assistant, you want that to be a very powerful professional relationship. So let's dive in, see what you learn. Thanks, Monique. Great to have you back on the show.

Speaker B: Well, thank you so much for having me back.

Speaker A: Well, you got this thing with AI for your assistant, but, you know, it, uh, always occurs to me when I think of you, it's like, why aren't you, like the top EA for the President of the United States or something? Because you're like just the queen of how to run, you know, how to support someone in a, in a significant role or run a team to do that? Did you really just love the coaching thing and, and the training thing and so you'll never do that again? Or is it something where, if that optimum opportunity came up, you might consider

Speaker B: it going back to a real. To a real job. To a real job, quote, unquote. I would. I. Oh, I will never say never to anything. Uh, you never know what could come up in the future. Right now, I'm extremely content doing what I'm doing. I love my job. I love. I wake up every day smiling about what I do.

Speaker A: So, yeah, now you have your new

Speaker B: greenhole and I have a new green ball. I mean, why didn't you. Don't you want to come to work when all your walls are green? It's like you're in a forest.

Speaker A: Well, that's great. That's wonderful. So I Wanted to. I, uh, saw this thing where you have this new AI course for assistance. And I get some people that are thinking like, well, maybe I don't need my assistant. Maybe I could just use AI. I think that's not a good plan. Matter of fact, I saw something today. I think it was Shopify. Went the opposite where you're reading. Some companies are not hiring entry level people. Oh, AI can do that. And Shopify was like, no way. We're going to hire entry level people and teach them how to use AI and they've hired a thousand.

Speaker B: Fabulous.

Speaker A: Yeah, yeah, yeah. So, so talk to me, Talk to the audience. Really? We have people who have assistance and we have a lot of entrepreneurs who haven't gotten an assistant yet because they don't trust the assistant will do a good enough job. Sure. So for those members of the audience who don't know you, will you please tell them what you do and how it's life changing for the executive and others.

Speaker B: Wonderful. Well, thank you for that intro. I have, I've spent my career as an assistant. Uh, I worked my way up from receptionist to office manager to an admin assistant to an executive assistant and uh, just kept my career going. I loved my career. I loved everything about it. I was very fortunate to have fabulous executives that I worked for who communicated and were open with me and trusted me. And then when I left my last organization, working with Simon Sinek for the last decade, I realized that I was not the norm. Uh, that there were many partnerships out there that were struggling that were not coming together for many multitude of reasons. No shame, no blame. One of them being executives are never taught how to use us. You know, they, there, there is no manual on what support looks like, what administrative support looks like. And I feel for the executives. You know, how do you know how to delegate to this person? How do you know how to, uh, give them a review? How do you know how to tell them what preferences you should tell them and which ones you shouldn't tell them? It's not an easy process. So I don't fault a lot of executives for not knowing. But what I will encourage them to do is start learning about it because it will save your life.

Speaker A: It's funny to hear you say that, and I've heard you say it before but had forgotten it. Exactly. But I'm going all in on our hiring system this year. And that's the exact thing. It's like, hire us as a hiring coach because you keep putting people in this places to make decisions on who's going to join your team. They've never been trained how to figure that out.

Speaker B: Absolutely.

Speaker A: You know, and so blah, blah, blah.

Speaker B: Absolutely. I mean, again, the executives, you know, an assistant will come in and the executive either doesn't know what to do with them, so it doesn't give them a lot to stimulate them or to have them, you know, do anything that's memorable enough that it makes a difference in the principal's life. Or, you know, they come in and don't communicate at all and it just turns into a bad situation no matter what. The other thing I always see is that when, sometimes when they're hiring their first, you know, their job description is like, must be organized, must know how to use a computer, calendaring travel arrangements or. I mean, yes, but, uh, if that's all you're going for is the technical skills, then you can complain when you get someone who doesn't match your personality. So anyway, that's a whole other podcast.

Speaker A: Yeah, it is, it is. But it is a good reminder for me because I have a superstar that works for me now, Gabby. But someday she will move into other responsibilities, which is coming up soon, possibly this year. It almost strikes, uh, me as I should. Do you hire. Do you work with the, the executive or do you work at the ea or do you work with Both?

Speaker B: I work with both.

Speaker A: Okay. Yeah. Yeah. So, and how long does that typically run? How many months a coaching program?

Speaker B: It depends on, you know, it depends on what's going on. So, um, I'm also an administrative recruiter. I think I mentioned that before. And my coaching comes with all of my recruiting packages. That is a. You have to do it, no fail. You have to have at least three coaching sessions with me because I want to be able to set you up for success. So I would usually do one with the executive, one with the assistant, and then one with together and help them just get over that first month of like, who are you? How do I figure you out? You know, I'll get them talking on some communication topics and ways that they can start having their meetings and outlines for their one on ones and things like that. So it can be three sessions or I've worked with people for about a year and I check in once a month, you know, not unlike therapy. And once a month we all get on and they talk about what's going on, we go through the crunchy parts and everyone moves on a little bit happier.

Speaker A: I really like that. Particularly when you think of the value of someone in a leadership role, whatever it might be, doesn't have to be huge, but I mean, I know project managers who are lousy at managing their project coordinator. And then it runs. You know, the more simple stuff. You know, tech services managers get 5, 10, 15, text struggles with that and needs an admin to offload some things like, or even a team lead. And then blah, blah, blah, blah. So I can see how it. It's a, uh, if you really look at the numbers, there's a big upside there. Anyway, let's talk about the AI piece. So AI is coming in. Uh, we're all. Maybe not. I shouldn't say we're all, but a high percentage of us are using AI to some extent. Whether we're doing it well or not is another situation. But talking about how do I take. I don't have enough time. I m. Never have enough time. Okay. I always have too many ideas, too many things I want. Yeah, yeah. So how is A.I. uh, going to help me get aligned with an assistant better so that that assistant has more value for me? Taking stuff off my plate and also protecting my time so I can work on the things that have the highest value.

Speaker B: So the question is, how can AI help you as the executive?

Speaker A: As the executive, yeah.

Speaker B: Get to know their assistant. Is that well.

Speaker A: Or work with my assistant or improve my assistant skills.

Speaker B: Oh, okay. Well, I mean, uh, that is, that

Speaker A: is anywhere you want to go with it. How can I help me and my assistant? Assistant firing all cylinders.

Speaker B: Sure. So, you know, on. On one end of the spectrum, you know, having your assistant be a master of AI and be the technical expert is a really positive thing for your office. I mean, this is someone who's got logistical skills, organization skills, pattern recognition. This person has all of that, plus the ability to incorporate that into AI So this person can really individualize their help with your team and say, you know how, you know sales guys? This is how I think you guys should use AI because they know, they understand and they know what the CEO is looking for because they're on that side of that. So it's a way for assistants, uh, to streamline every thing that they do. Um, I want to be very clear that everything I talk about with AI I always will end with, there must be a human in the loop. Always have a human in the loop. I'm never going to tell you to go to AI and do something. Plop it into an email and hit send. AI is a great builder. It is a great first draft for a lot of things, and they can use it for that. On the other end of the Spectrum. You know, you had mentioned earlier about some executives not getting an assistant and using AI instead, which, you know, again, you're going to get what you pay for on that. You know, you're not going to get care and concern, you're not going to get forward thinking and momentum. You're not going to get any of those things. As far as the relationship building part, honestly, I use AI a lot for, how do I say this to this person, you know, giving feedback. So how can I tell my brand new assistant that the way she is doing XYZ isn't working for me anymore? Maybe they've had trouble figuring out how to say that in the past. So it's a way to really help with communication and or prioritization.

Speaker A: So with your service, where you're training, how AI can help your, your assistant, or the AI powered assistant I believe you call it, then how does that work? What are you focusing on? And I hope you've got some stories before and after that you can tell us so we can really visualize what you're talking about.

Speaker B: Sure. So this course is hands on for assistance only. It is all of the things that we do in our daily lives just simplified. So there is a module on event planning, there is a module on office management, there is a module on project management, there's one on travel, there's one on emails. So it is encompassing all of the different major buckets that an assistant would be involved with you in. It really encompasses all of that. So for example, you know, one of the things that we go through in event planning is picking menus, picking venues, picking all those sorts of things. And with various dietary restrictions these days and various needs and wants of people, it's hard to put those together. And you're usually individualizing a dinner for 35 people with many different wishes and dreams. One thing that I've showed people how to do is go in there, you put, I got six vegetarians and three people who only eat meat and two people who do this, blah blah, blah, blah, blah blah, blah. You put it all in there, find me a menu that works and let's go with that. And then you can send that over to the restaurant or the hotel or whatever to try and smooth those things over. So little things like that where it was a puzzle to figure out with humans and getting to the other side of that. So the logistical aspect of it, another thing that we do is, uh, meeting minutes. So that is something that I've heard a lot from my various admin crew as well as the executives. My assistant is in all the meetings. She has all the stuff, but it's all in her head. And trying to get that information disseminated out to all of the different departments is difficult. Maybe too many people or whatever it might be. So you can use A.I. uh, you can throw in all of your notes, whether you have a transcription, your own meeting minutes, all things, and say, here's everything. I need an email for the sales team. I need an email for the marketing team. I need an email for the executive leadership team breaking down everything that they have to do. So just a way to. It's doing everything that we were doing before, but 10 times faster and with a clearer first draft.

Speaker A: So two things come to mind when you're saying that. One is, I have one client who records everything and he has, I think, copilot, uh, or read AI that does the meeting, the meeting notes, meeting summary. Okay, so in that case, should the leader or the assistant be also keeping notes, or do you just kind of sit back and have the conversation? And if AI misses something, then they miss it because AI is not perfect as you've alluded to.

Speaker B: I'm always going to recommend a human in the loop. There's no way that I would just sit there and listen and have AI record it and not write my own things down. That is just who I am as a human. I want to. And even if it's. Just pay attention at, you know, two minutes into our conversation, I'll even do things like that so I can go back, listen to the recording and say, you know, he told me a lot between minutes 12:05 and 12:10. Go back and review those. Make sure you have everyone's names right. So I always say human in the loop.

Speaker A: Okay. And I really like that. I hadn't even thought of that. That if you have different groups in the meeting. Uh-huh. Asking the AI to do the first draft of the emails, going out with each person's responsibilities. Because I try to teach in my MAP process, I have this, this map process that I say should be the. The agenda for all meetings. You start with metrics, which is the past. So that's what we agreed to do. That's our standards. That's maybe what's the status of your goals, whatever it might be. But that's passed then. So you got self accountability at the beginning. Then you move to a. Which is action items. What's before us right now? What do we want to discuss between the. And that's present. So between the metrics and the Action items. Then you come up with the plan, the P and the map. So boom. So I try to teach all my clients that at the end of the meeting you don't just say okay, that was good. You say okay, what are the action items out of this meeting? Who's got what? When? And I always say, I don't know about you but I always say would the when has to have a time of day because you knew say I'll have it to you by Friday. That person's thinking 8am and you're thinking 5pm or midnight. So you got to have a time of day 100%.

Speaker B: I call those blur words. It's a ah, speech pattern which means it's words that mean different things to different people. So I m like it get it to you by Friday. I don't know what that means. My version of Friday might be 8am you know even the word immediately. Can you do this immediately? To some people that means put down what you're doing and do this immediately. To some people it might be when I'm done this. Yeah, yeah, be my immediately next. So let's, you know, in general I always say let's reduce blur words and make sure that you're using more exacts when it comes to work deadlines and such.

Speaker A: Yeah. So I really like that idea that it could save on the follow up

Speaker B: with uh, so another perfect example of that is I had, I was coaching uh, an assistant and the office was going back to. Everyone had to come back to office. And so the executive asked the assistant to put together an email. It was going to come from the executive but to put together an email to send to everyone to let them know that everyone needs to return to the office. And so there was, she was coming to me and saying how, how can I word this is for so many different people. I said why don't you make it for many different people? Why don't you send one to you know, all of the leadership. It's going to have a very different tone when you sending it to your leadership team. Make another email for that next level down, your managers, your directors, you know that the highest level is going to be this is how you be a cheerleader for what's going on for the director is it's, this is how you're going to, you're going to hear a lot from your team and I'm really sorry but here's the party line, here's the value of why you're doing this. You know, you send another one to the Entire admin team and you say admins. Here's what you're going to need to figure out when you come back to the office. So taking one concept and using it in different language again just as a starter, I think is really helpful for things, even emotionally. Act like going back to the office.

Speaker A: No, I think that's great. Now talk to me about prompts because I find that prompts are super important and then I want to touch base on something, um, on um, one of the flaws in AI. But there's the prompts piece. What advice would you give to people as far as prompts? Or maybe you have a story of someone who wasn't doing good prompts and you gave them some advice and it got better.

Speaker B: Sure. Well, I mean prompts are everything. What you put in is what you're going to get out. If you put in general information, you're going to get generalized information out. AI and, you know, chatgpts and co pilots and whatnot. It's not the Internet. It is a language model. So it uses language to interpret what you want and to what you need. Basically what it's doing is predicting your language. So it's not roaming through the Internet. You know, like when you Google something, it's focused on words. So if you're not putting in the right words, the language that you need, it has nothing to go off of. It's not in your brain, it's not in that meeting that you just had. So prompts are everything. Put in as much information as you can. The biggest tip I'll give you is it doesn't have to be perfect. I thought when I started using AI it was like, how can I say this perfectly so that AI understands what I'm about to say? And it took me a while to figure that out. Instead, now sometimes I hit the microphone button and I'm like, so let me tell you what happened earlier. Oh my God. I got this email and I just ran, I rando talk into the chatgpt and then I say, make me an email that says that please. And it creates it. It's a beautiful thing. So you have to be really detailed with your prompt. What am I putting in? What do you want out? What do you want it to sound like, smell like, taste like, touch like everything. Put so much detail in there and it doesn't have to be perfect. Ramble.

Speaker A: Yeah, yeah, no, I, I love that. I love that. So. And I had a situation recently with someone I know where they have a neighbor who put in a heat pump and the Heat pump in general doesn't bother people, but it's outside the house instead of in the attic. So there's noise. It's not only noise, but it's vibration. And this friend of mine can't sleep at night because the vibration that comes through. And so he went to ChatGPT, entered in boom, boom, boom. What do I do about this? Oh, you need a vibration trench. Boom, boom, boom. Long story short, it's like, okay, this is going to be like 30ft long, 18 inches wide, 3ft deep. You're going to do this, you're going to do that, all this stuff, huge project. Then the guy's wife went into chat GPT, same AI entered her version of the prompt, and it came back, oh, vibration trench isn't going to work at all. And you know, boom, boom, boom. You got to do it this different way. Okay, very interesting situation. So I think that AI is kind of like in some ways a perfect match for the relationships you're working with people. Relationships. Executive assistant. Boom, boom, boom. And as a warning that when you get into more technical things, depending on the prompt or the day of the week you enter it or the person who's entering it and how well the AI knows that person, you may get opposite answers if it has to do with something more technical. So just beware.

Speaker B: Yeah, again, the ChatGPT or, um, Copilot, they're not, uh, search engines. It's not a Google. So do not follow instructions on how to change your oil in your car from ChatGPT. I mean, actually, it might not do that because that was probably entered into it. But, yeah, you know, it's really not out there to search for a way to do thing and then show you a, uh, video and give you instructions like you would on YouTube or something like that. So, getting me ideas, what are the. What are the 10 different ways that we can work out this vibration and noise that's coming from my neighbors? It can definitely give you a list. But then I would go research, what does that mean, and who builds this trench and yada, yada, on the Internet, that kind of thing. And I'll also say we were just talking about prompts. It's interesting how each of these two people put in the prompts. I can tell you that ChatGPT was not behind the scene going, ha, uh, ha.

Speaker A: Uh-huh.

Speaker B: Ha. I'm going to give this person a new answer. I'm going to make this totally different. No, it's reading whatever the person put in and giving them the answer that it's predicting, uh, they want. So for a male putting in there he would be like, I need this to be fixed now I want an answer. And maybe that's why it came back in that way. And hers was more what can we do to squash this issue that we're having between me and my neighbor? So everything is about the prompt you put in.

Speaker A: Well, the interesting thing that's even more concerning is that the guy ended up going back and loading in the response his wife got from her chat chat and saying, here's what I got. You know, this seems to indicate the vibration trench is not going to go go well. Although he had gone back and forth several times and his chat then came back and said, oh yeah, you're right, the vibration trench is not, not the way to go. That's black. Yeah.

Speaker B: But it also, if you're working in chat GPT and you have an account, it's learning you. Oh yeah, you and remembering you as you go. So it's going to continuously give you the answer that you're probably needing or wanting. If you went into my chat GPT and said, read me an email that says, you know, we're all going back to the office, it will come out in my language, not yours, because I've used it so much and it's m. It's learning. So I understand. You know, a lot of people say, why do you get different answers? It's well, like you're a different human. You're a different human being and you're, it's learning you as a human. So unless you're exactly the same as the human next to you using it, it's going to be different.

Speaker A: So one thing I noticed in your list of what you teach in this AI program is how to streamline things, projects, processes, you know, working with people. Do you have some examples on that? Because none of us have enough time.

Speaker B: Sure. Um, again, event planning is something that is very, very successful to do in within a chatgpt or an AI bot. I need a, ah, script, you know, everything from we're going to this mountain lodge, it's going to be a board meeting for this many people and getting all the logistics. You can also ask it to give. I need a script for my executive for his opening dinner. What is he going to say to everyone and how is he going to welcome everyone in and then what's, what's the PowerPoint going to look like the next day? Give me a, uh, schedule those sorts of things and also problem solves in that way. I had one One assistant who uh, now naming names but it was like my boss changes everything at the last minute all the time. We're having an off site and the off site is in three days and he just told me that he needs an extra 90 minutes on the main day for a different session for a different speaker to come in. She's like I got this schedule so long I don't know what I'm going to do. Uh, she went into ChatGPT and she said how, here's the schedule, I need 90 minutes somewhere before launch. Tell me how to rearrange this day so that it all makes sense. Pops right out. Yeah, so it just helps with different logic and, and gave her some options. What you can do is you can move this thing there, you can maybe have the lunch be more of a box lunch so that people are eating at their tables etc. Etc. So that's definitely one example.

Speaker A: Okay, I like that example. I like it. Now you also give some teaching for the assistant I assume could uh, maybe be for the executive too about how they can leverage AI for personal growth. Um, although AI is not going to be perfect, it can give us some ideas just like you talked about with the agenda change giving ideas. So can you give me an example of that? Because that sounds kind of interesting. I don't know whether it, to be candid, I don't know whether I would trust AI to give me ideas on personal growth. It does make sense. It's got all this data out there

Speaker B: but I mean again it's depending on.

Speaker A: Depends on the prompt pencil routes.

Speaker B: Yeah, depends on what you put in. So for example something that I would do if I wanted a personal growth strategy I would put in maybe some of the cliftonstrengths or the personality tests or the skills assessments that I've taken before that I'm a D in disc that I, I'm um, this and Myers Briggs. Here's my cliftonstrengths. Here's two past reviews. Here's one of the favorite emails that I've ever had. You know you load it full of information to so it understands you and then you say to it I'm feeling a little stagnant. I don't know what to do Next. Give me 10 ideas of something that I can learn this year. Give me one idea that's a language. Give me one idea that's a sport. Give me one idea that's a uh, mental health and whatnot and have it make you a plan. And again you go back into it and you go you told me you recommended me. Tennis. I hate tennis. I don't want to do anything with a ball. It's not going to get insulted and yell at you. It's going to go great. Here's 10 different exercises you could do that don't involve a ball. Um, so you go in and alter. If you're. If you're waiting for the first answer to be the perfect answer. AI is not for you.

Speaker A: Yeah.

Speaker B: You have to keep massaging it to get it to where. As close to where you want it to be as possible. Back and forth.

Speaker A: No, it makes perfect sense. And that way, if I went and I said, well, let's see, I want to improve my critical thinking skills. And I like these particular writers. I like this podcast that was on critical thinking. I like this. I like that. This is what I feel are my current strengths. This is what I feel are my current weaknesses. I may be wrong, though. What would you recommend then? Because I've given that detail and like you mentioned that you're putting in a bunch of files. I might put in my talent assessment results. That where I've got my disc profile and I've got the driving forces we do, and I've got 25 competencies. Gives it a lot of data points.

Speaker B: 100%.

Speaker A: 100%. Yeah. Then I'm gonna get some good data.

Speaker B: You can also ask it to interview you. So you can put all that information in there and go, I'm stuck. I actually don't even know what I need right now. I don't know if what I'm missing is my goals. I don't know if I'm missing a plan. I don't know what I'm missing. So why don't you interview me, chatgpt and start asking me questions, and then when I answer you, you'll get a feel for what I need, and It'll list out 10 questions for you or 20 questions for you, and you answer back. And then it goes, well, wait a second. You said this in number one, but you said this in number four. And it'll tune you out. And then, you know, it'll figure it out for you.

Speaker A: This makes me think of something. So you hire an executive assistant. What type of training has an executive assistant typically had before they're hired? Let's say they've got five years experience.

Speaker B: Uh-huh.

Speaker A: Doing something. Admin work. Yeah. What type of training have they typically had before they go into the job? Because I'm wondering if one way for a leader to really connect with a new EA is to say, okay, as part of your onboarding, I have this training you're going to do can be the AI training. That's a piece of it. Maybe they've got you as a coach for a period of time. So, because I want us, uh, if we fire on all cylinders, if we're super strong together, we trust each other, this is a healthy professional relationship. I'm going to be so much better at what I do and you're going to love what you do. So I'm curious, I would think the vast majority of EAs just get thrown in the role and there's limited or no training.

Speaker B: Yeah, yeah. Everything that you just said is like the land of Oz for us. I mean, we don't get there is. I want to say, maybe 10% of the companies that I've talked to onboard have any form of onboard, any form of training. You are thrown into the deep end and you better swim.

Speaker A: It's so much like hiring, but it just strikes me it so much the other way, it's like hiring is that this is in many ways such a critical role.

Speaker B: Uh-huh.

Speaker A: Because you're asking the most out of this person in a management or leadership role or C level role. Absolutely. And why do you want to. And it's not the EA's fault, but if they're not trained properly and they're not hired properly, you do the recruiting piece to help line them up so they have the right person in the role, then it's almost like you're giving a leader kind of a boat anchor or somebody who's not going to be very helpful. And there's no fault of theirs.

Speaker B: Yeah, yeah. Uh, yeah. Onboarding in general, for every industry, I think everywhere onboarding and training is a huge hole in our workforce and how much more powerful the workforce of the US could be if we all actually focus in on our strengths and had onboarding and training in their jobs. I mean, there's none. There's just none. And again, for assistance, when I talk to the executives, when I'm doing my recruiting, I always ask, what's onboarding like? Well, that's one of the things that I'm going to need this assistant to help me with. That's nine times out of ten, the answer is, well, we don't have a great program now, but maybe that's what the assistant could do once they get here. So, yeah, we need more of it, Period, end of sentence. I mean, it's atrocious.

Speaker A: So if you were to. Let's see if you were consulting with or you were a senior executive or a board member of a company and you wanted to structure something so that every time someone was moved into an executive assistant role that they were properly onboarded. I'm not asking for every little detail, but what are some of the key highlights, some of the key pieces to that, uh, puzzle that are going to enable the EA to succeed in that role, to meet or exceed expectations.

Speaker B: Number one, always time, time, time. We need your time. Nothing will help your executive assistant know you better than spending as much time as you can with this human being. In the first 60 days, especially in the first 30, I recommend three two hour meetings for the first month that they're there. Just talk, get to know them, get them, get to know you, tell them about your priorities. You know, I always want to get home, even if it's a really late flight because I want to get home for my kids so I can be up in the morning. Those kind of things are really important to us. We will always make sure you get home by the nighttime so that you can be there for your kids in the morning. So time, time, time, time. If you're not spending time with your executive assistant in the first 30 to 60 days, it will not work or it will not work as good as it should.

Speaker A: Now as part of that time, just observing the executive in their role and sitting in on meetings 100%, uh, sitting in on meetings.

Speaker B: What are they tasked with? Having them go through, you know, sitting next to their executive and having them go through your, their email inbox. You know, here are the folders that I really like, I really like this kind of flag and this, this and this. Show them directly, like have them look into your email inbox with you, point things out. So it's, yeah, it's, it's um, preferences, it's how you like your calendar. It's all of those things. The other thing I will say is if you don't exactly know what to ask your assistant, I guarantee you your assistant will know what to ask you. So if you're just sitting, sitting down with your assistant and you say, just go ask me as many questions as you want, I guarantee you they will have 72 to keep you talking for the next four hours. And it's stuff that they need to know. So rely on them for that. The second thing is constant communication, you know, constant back and forth. This is where I'm at on this. When we're not getting, you know, one of the things I always say is assistants are not lamps like you don't bring it into your office and plug it in and it works. And that's not, that's not what you're buying here. You're buying a human who's going to stand next to you and want to know your, your abilities and your strengths and your priorities. So we plug into you. The executive, the assistant plugs into you. That's where we're getting our energy from. That's where we're getting our information from. That's where we're getting our priorities from. So if you're, if you've ever said, God, my assistant just doesn't know what the priority is, it's probably because you don't and you're the information. So I can guarantee you, you know, they're getting that information. So communicate, communicate, communicate. Even if it's little things. Hey, the way that that agenda went out yesterday was good, but can you make sure to add this on the next time? Great feedback in the moment. Which brings me to number three. Feedback, feedback, feedback, feedback. There. We do not care if you tell us that you want it to be in blue and not black, but don't not tell me and then get frustrated when I don't put it in blue. Yeah, tell me and, and make sure you're giving me constant feedback in those first 60 days to tweak, tweak, tweak, tweak, tweak and make it perfect.

Speaker A: So do you do work with the executive assistant to understand themselves better? Their, their issue, their Strengths, their weaknesses? 100%, yeah. Okay. Because that's kind of the important. And then would you also teach them how to. That would be. Another class would be great for an ea, I think would be Paul Erdman's, you know, microfacial expressions and the body language and the rest of it. Do you teach them how to read that? Because they're going to be representing this executive, and if they're sitting in on a meeting with a bunch of people, then can they read the room and also read their executive, which would help them understand all the dynamics going on?

Speaker B: Sure. I kind of think that's one of those skills that sort of you have it or you don't with the ability to read the room. Some people don't, and that's fine. I'm not saying that that's bad or good. There was no bad or good to it. But that, uh, comes from a strength and empathy. I know a lot about Clifton strengths, and one of the strengths in there is empathy, and that's being able to read and feel other People's emotions. Not everyone has that skill, you know, for good reason. So, um, generally speaking, you kind of have to know how to do that. But absolutely. I talk about not only what you're seeing from them, but when their voice goes up and when their voice goes down and what does that mean? And when they're loud, does that mean that they're hungry, you know, and trying to really pay attention to the sound? If there's a specific question that they always ask you over and over and over and over and over again, pay attention. What is he always trying to get from me? He's always trying to get the why. That's why he's always asking me why about every question, everything that I tell him. So pay attention. What are they asking you? What do they look like? What are they sounding like? Nothing helps you more than a voice, I'll tell you that much.

Speaker A: This is great. This is great. Well, I hope that the audience does something on this. Overall, what you teach on how to work with an executive assistant, I think that's huge value. But specifically I invited you on because I've never seen a course like this, how an EA can use AI. So talk to us about the course as we close out here because I am sincerely recommending, you know, for the amount of the course, $295. This is nothing to invest in someone who's your right hand person.

Speaker B: Yeah.

Speaker A: And you'll get that back easily in the first month with higher productivity for you and this individual. Yeah. It's a no brainer. And you're also going to say to the person, hey, I value you, I care about you, I want to invest in you with this course and let's see what we can make happen out of this.

Speaker B: There's nothing better than investing in your staff, investing in your team, 100%. You know, if buying this quote unquote for your assistant, absolutely, it tells them you care about their your growth and development not only for your office, but in general. But yeah, I designed this specifically for assistance. I was an assistant. It's the world that I live in. And we specifically have a very different job function than many other people in the office. The administrative world is quite different. It's quite unique. And I saw so many AI courses out there, but none of them were specifically for me and my job. So that's why I broke it down. There's 13 modules. I have 68 prompts, I want to say, so 68 usable prompts that you can take from the course and use in your daily life. There is a, um, workbook, ah, that you can download that has some reminders and templates in it, so you can download that as well. But again, the reason that I put this out there is to help the assistants understand that AI is not going to replace them. If you have the power over it. If you don't hold on and don't take any knowledge and say it's. I'm not going to look at it, that it will overpower you and it will take your job. But if you know how to use the tool and you can stay current and fresh with what you know, you'll stay relevant in this industry for a long time.

Speaker A: Fabulous. So where do they go to learn more?

Speaker B: Moniquellstrom.com is my website. And then under my resources bar, you'll see, uh, the AI powered assistant. You can go on there and purchase it.

Speaker A: Fabulous. Well, I don't know whether I've ever done this before, but I recommend everybody who's an executive go out and buy this course for your executive assistant because it's a win. It has to work. Okay. It might. My current person doesn't need it, but when she moves on, I'll make a commitment online here that I'll buy it for my next one to make certain that they're firing on all cylinders and they can save me time. I need to save.

Speaker B: Saving them time saves you time. Saving you time saves them time. It just really works for everyone, huh?

Speaker A: Fabulous. Well, thanks for joining us, Mimique. It's always a pleasure to be with you.

Speaker B: Thank you for having me.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Winning Trust: What Championship Teams Teach Business LeadersBehind The Numbers With Dave Bookbinder · on Simon Sinek78 / 100
  • Creating Brave Spaced: Culture & Leadership VisionScaling Culture · on Simon Sinek67 / 100
  • 260: Why Leaders Must Be Great StorytellersCustomer Service Revolution · on Simon Sinek44 / 100
  • The Growth Tool Hiding in Plain SightFaith-Led Founders · on Simon Sinek43 / 100
  • How to Become Known for Something (Instead of Posting Random Content) | Ep. 353The Brands On Brands Podcast · on Simon Sinek39 / 100
  • 27 | Are You Building an Authentic Brand or Just Performing Online?Crafter’s Online Business Playbook · on Simon Sinek37 / 100

More from The Manage 2 Win Podcast

All episodes →
  • #281 - John Krotec on Truth, Courage & Critical Thinking
  • #280 - The Powerful Introvert: Greg Weinger Transforms Your Quiet Nature Into a Strength
  • #279 - Untangling Complex Challenges: Reuven Shelef's Framework for Clear, Confident Leadership
  • #278 - 57 Sales Secrets That Separate Top Performers with Glenn Poulos
  • #277 - Flip Your "Life Switch:" How Joel Steele Turned Setbacks Into Success
Explore the best B2B Leadership podcasts →
All The Manage 2 Win Podcast episodes →