Career Coaching Secrets

Redefining Career Success in the AI Era with Cheryl Simpson

• Davis Nguyen

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In this episode of Career Coaching Secrets, our guest is Cheryl Simpson, a seasoned career coach with over 30 years of experience helping mid-career and senior professionals accelerate their job searches. Cheryl is an award-winning resume writer (ACRW), certified LinkedIn strategist (COPNS), and creator of the "Get Clear, Get Found, Get Hired" (G3) coaching program. Her expertise has been featured in top publications such as U.S. News & World Report, Readers Digest, and CIO.com. Cheryl specializes in transforming job searches from the U.S. average of 12–18 months to just 2–8 months by crafting achievement-driven resumes and optimizing LinkedIn profiles. She has also been honored for her 40 years of service at the Endependence Center, where she supported individuals with disabilities in obtaining employment and advocated for their inclusion in emergency planning .

You can find her on:
https://www.linkedin.com/in/cheryllynchsimpson/
https://theresumerescue.com/
https://cherylsimpson.brandyourself.com/

Official Email:
csimpson@executiveresumerescue.com


You can also watch this podcast on YouTube at:
https://www.youtube.com/@CareerCoachingSecrets

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Cheryl Simpson:

I see the value of AI when it comes to job search processes, career branding, career management. And so I want to develop and have already started to develop some products, some sort of one off products that people can purchase to help them to learn how to do some of these things, because I think it will sort of set them free in the sense of being able to do these things for themselves for an ongoing basis.

Davis Nguyen:

Welcome to Career Coaching Secrets, the podcast where we talk with successful career coaches on how they built success and the hard lessons they learned along the way. My name is Davis Nguyen, and I'm the founder of Purple Circle, where we help career coaches scale their business to seven and eight figures without burning out. Before Purple Circle, I started scaled several seven and eight figure career coaching business myself, and consulted with two career coaching businesses that are now doing over $100 million each. Whether you're an established coach, or just building your practice for the first time, you'll discover the secrets to elevating your coaching business.

Rexhen Doda:

Hey, everyone, welcome to another episode of Career Coaching Secrets Podcast. I'm your host, Regine, and today's guest is Cheryl Simpson. Cheryl is an award-winning executive resume writer, a career coach, and a LinkedIn network strategist. With over 30 years, and that's 33 years plus of experience across 30 plus industries and six continents, Cheryl has helped countless mid- to senior-level executives accelerate their job searches and reinvent their careers. She's the founder of Executive Resume Rescue and a quadruple certified coach whose clients regularly land rolls in just two to four months. And it's my pleasure to have you on the podcast today, Cheryl. Welcome to the show.

Cheryl Simpson:

Thank you so much, Reginald. I appreciate it greatly.

Rexhen Doda:

It's a real honor. So tell me a little bit more about what inspired you to become a coach and start your own coaching business.

Cheryl Simpson:

Well, actually, it was an accident. I mean, it's just true, I think, for a lot of people in their careers. Sometimes we don't necessarily, I mean, there certainly are people who set out to do X and who then become an X in In their career. That was not me. I was actually working as a rehabilitation counselor, helping people who've been injured on the job return to work. And in that role, I had to liaise with a resume writer so that he could write resumes for these folks who were unable to return to the same type of job. And this gentleman that I had to liaise with was on the grouchy side. And he got mad at me one day when I asked for help on a resume. And he literally threw a resume writing book at me. Well, I didn't want to have to deal with that anymore, so I read the book. and I started to learn and I got better and better at it and then kept going on in subsequent roles into what was beginning to look like at that time career counseling. And this was in the time period when coaching was just starting. So some of the early pioneers in the industry were just beginning to define what coaching is, how it was different from counseling. And I decided to make the transition from counseling to coaching because I thought what they were up to was really vibrant and important and very action oriented, very And so I started in getting some of my early coaching training and because I'd already had so much experience in career related themes, it just made sense to start as a career coach because I have a real passion around helping people to find or create meaningful work for themselves in whatever modality that works for them. Work is so critically important, now more so than ever, as we're in the midst of another transformation of the workplace as AI really comes integrated everywhere. And it's going to overhaul so many different things in the landscape. And when people are able to find or create meaningful work, then it's easier for them to navigate challenges like that.

Rexhen Doda:

And as someone who has been part of different market transitions, so you have been doing coaching when Zoom wasn't the thing or when it was the person. So your journey kind of like has shifted and has been adapted to technology over time and not just technology, but even like the economy has changed a lot. How would you describe the journey?

Cheryl Simpson:

Oh, yeah, it's been at times a chaotic one. I mean, because I've worked through, you know, recession and, of course, the pandemic and lots of other smaller but still critical. There are a lot of ups and downs in the U.S. economy, let alone the world economy, and those shifts career coaches have to help our clients navigate, and we ourselves have to navigate. So one of the keys that I've tried to pay attention to in my own business is this is not This is old news. This is not anything earth shattering, but I think it's important that I really focused in the very early stages of my business on having multiple streams of income, right? Different kinds of income, not just working with different segments of clients or one-on-one versus group coaching, but also just other things, online classes, contractual assignments, outplacement, which is very project oriented. So doing a variety of different kinds of things that kept streams of money coming in that helped me weather the storm. And I went through those periods of paucity of clients like the pandemic that probably wiped out a lot of career coaching businesses for that very reason. They weren't ready for that.

Rexhen Doda:

Like we just mentioned that you basically are working with mid to senior level executives. Is there a specific like industry or demographic when it comes to that?

Cheryl Simpson:

Not really. I really wouldn't care. I tend to be somebody who's really needs a lot of variety in my work. Focusing on one industry, to me, would be really boring. So I've always preferred to work with a wide variety of clients. Certainly there are a lot of sectors where I get a lot of referrals, and so I do have some sort of subspecialties within those different sectors. But broadly speaking, it's more clients who may be senior management level and up, all the way to the C-suite ranks. And so those are clients who, generally speaking, are in their late 40s, 50s, and on up in age across a wide variety of socioeconomic and education backgrounds, ethnicities, countries, you name it. So that variety is very, creates a lot of vibrancy for me personally. And I'm a passionate believer that a resume writer doesn't have to be an expert in a particular industry because if you know how to write resumes, you can write resumes in almost any industry because there's so many rich tools available. And because our client is the expert in the moment, if we know how to question and draw key details from them. And then we supplement that with information we may draw from the web, from some specific information sources. It's not a problem. So I never felt the need to specialize in that way, but certainly a lot of folks do and more power to

Rexhen Doda:

them. When it comes to currently, you just mentioned that some clients you're finding through referrals, what would you say is the main way? And if it's referrals, is there any secondary way that you're utilizing to generate leads for your own coaching business or is it all referrals at this point?

Cheryl Simpson:

Referrals, but certainly it's probably the majority is referrals. But a key secondary resource for me is LinkedIn. When I was, I don't like marketing and I'm not good at and don't really care for social media marketing. Again, that's a great solution for a lot of folks. It just wasn't my personality. I tend to be more introverted. So when I stopped and thought about what kind of a marketing strategy would work for me, I tried to go toward my strengths. And for me, that's writing. Not only because I'm a resume writer, but because I enjoy writing, period. So I started writing articles on LinkedIn, long form posts when that function first became available on LinkedIn a long time ago and developed a thought leadership following. And that has been a very significant source of clients for me.

Rexhen Doda:

And are you continuously writing content on LinkedIn?

Cheryl Simpson:

Frequently as I used to, but I still do some. Yeah, I've taken a break from some of it for a bit, but I'm about to get back into it because I'm kind of shifting my business. this a little bit and entering some new sort of sectors in the market. And so I'm developing content specifically for those pillars once they're available.

Rexhen Doda:

The reason why I mentioned that is yesterday I had a coach I was interviewing and he was talking about the importance of posting on LinkedIn from his perspective, a coach, but also as an SEO expert, he said that a lot of these LinkedIn articles are right now also being indexed on Google, meaning they also are showing as articles on Google. So they're getting attention outside of LinkedIn for anyone who's searching for topics like those topics that, for example, you'd be covering in your LinkedIn. When it comes to the future, moving away a little bit from marketing, do you have goals right now that you're working towards in the next one to three years? You did mention that you're shifting a little bit the focus. Would you mind to share a little bit about that?

Cheryl Simpson:

Sure, sure. I see the value of AI when it comes to job search processes, career brand career management. And so I want to develop and have already started to develop some products, some sort of one-off products that people can purchase to help them to learn how to do some of these things. Because I think it will sort of set them free in the sense of being able to do these things for themselves for an ongoing basis. There are already showing up businesses who specialize in AI-driven career stuff, but a lot of those are subscription models. And just finances being what they are, I can see people maybe taking advantage of those in the short term, but not necessarily utilizing them over the long term. And I'd rather encourage the use of some of this AI prompting over the long haul, because I think it really, it's an important skill for people to learn, number one. Number two, even people who aren't technically minded need to learn this skill. It's so critical for the future. But I personally find it fascinating to work with AI systems and come up with prompts that help people to prove their LinkedIn profiles or resumes. But even more importantly, you know, interviews prep, salary negotiations, career management, what direction should I go, which industry should I go. I mean, there's so many rich possibilities that AI can help with where the person is totally in charge of where their career is going, but they're getting the help of an AI system that's even more powerful than a Google search. I mean, that's pretty awesome when you think about

Rexhen Doda:

it. Yeah, and I'm also kind of like passionate about AI, especially because I feel like the whole era has changed a little but it's not about information anymore. Information seems to be rather cheap right now or easier to get. Like you can get information on anything. Right now, I think we are in a business of asking the right questions. Answers are cheap, like AI will give them, but knowing what questions to ask has more value. And asking the right questions, I feel like do make a difference when it comes to being able to use AI and just like you mentioned, prompting.

Cheryl Simpson:

Absolutely. I mean, it's a science unto itself. I mean, I read an article just the other day about how, as we've had these various technological advances since, say, the Industrial Revolution, every time these new advances come into play, some jobs disappear from the economy, but lots of other jobs suddenly come about that didn't exist prior to that and weren't even on anybody's radar prior to that because they weren't needed. And so now we have prompt engineers, which is an occupation that did not exist a few years ago, but now it's a thing. And there could be many many, many examples of that as we move forward into this AI revolution of some jobs disappearing, other jobs appearing for the first time. And I think the potential here is for people to really unleash their talents in new ways. That's what speaks to me as a career coach, is people being freed up from some of the drudgery. We all have jobs where we have too much paperwork or other things that are just less interesting, and we can free up our energies and use more of our creativity and just imagine the possibilities for all of humanity when we do that and when we help our clients to do that. I just clearly, I think that's a cool thing.

Rexhen Doda:

Yeah, it's a really cool thing. And yeah, we live in a golden age right now to be able to have that all. Even before, okay, you could go in Google and find a lot of information, but right now it's gotten so much easier with AI that you don't even have to read multiple articles and do the research around, but you actually get the exact answer you were looking for. from the start.

Cheryl Simpson:

AI is like a metabrain, right? So yeah, you can conduct a Google search or fill in the blank search, but you still have to do a lot of the reading and a lot of the work and AI is going to step in there and almost not completely eliminate the need for that, but dramatically reduce it and help to begin to synthesize things before you even have to begin, you know, internalizing your own synthesis. So your ability to stand back from something and learn from it is many times better than it was even, you know, three, four years ago. So the prospects for insight and for fresh directions and for new career possibilities and new ways of thinking about problems. And the job search process, for example, is a process that is boring and burdensome and takes up time. And it's just people have to put part of their lives on hold to do it. And what AI can do is AI can condense all that frustration, take care of a lot of the work, not completely, but certainly, again, dramatically reduce the burdensome part, free up people to have more of life while they're job searching, particularly for those who are job searching while they're working. But even for people who are unemployed, you know, it gives them so many more opportunities to think about and to consider and to explore and apply for.

Rexhen Doda:

And the other thing is that it keeps on evolving, right? So like it's not stopping here, obviously. In

Cheryl Simpson:

the

Rexhen Doda:

last two to three years, it has evolved a lot. And now we're also seeing these AI agents, which you could give it tasks. And he's going to go ahead and do the whole thing for you. Like even I've seen an example, I haven't used it yet myself, but seeing examples of people using AI to find the cheapest plane tickets and book it for them, giving them the credit card number and everything. And he's going to do it for them. He's going to go search, find the routes and make sure that, yeah, it's all good. That is wonderful. Like so much admin work gets pushed to AI and quality work is still left with SSU Yeah,

Cheryl Simpson:

and we're needed for that. So that's why AI is not going to take over all occupations because there's so many of them and there's pieces of parts of most of them where our human qualities and capabilities are of key importance. But I think the goal for us as coaches is to help our clients focus on those parts, to develop those parts. Yes, they're going to need to learn some AI stuff, but it's all doable. And the beautiful thing, I think, and fun thing about AI is AI will teach you how to use AI. You know, that's pretty freaking

Rexhen Doda:

awesome. Yeah, it's very awesome. So I wanted to ask you when it comes to investments, when it comes to your investments in your coaching business or investments in yourself that would help the coaching business. Since you have been in the industry for a while, what would you say have been some of the best investments you have made to grow or that have made like an impact in you growing your coaching business?

Cheryl Simpson:

I think one of them was getting some additional certifications. I came into the industry, already had a lot of experience, but I didn't have any of the standard certifications, which at that time was the route by which people entered into the business. And so in getting those and multiplying those, in my case, four times a over was really valuable because certification gives you instant recognition in the eyes of the client. It doesn't guarantee that they're going to work for you, but it helps them qualify you, if you will. And so I think that's enormously helpful. And then the other thing was in the resume writing industry, there's a global contest that you can participate in. And it's often referred to as the Oscars for resume writers because it's very high profile. And so I started to participate in that. And I didn't participate in it every year, but I participated in a number of years and won a lot of awards. And that also, I think, was an investment of time and a little bit of investment in money. There is a cost. It's pretty minimal. But those two things, I think, really made a huge difference. Additionally, I think there were some things that I've purchased over the years that helped with things like forms. It's not necessarily the best use of my time to sit around and spend hours developing forms when somebody else has already developed those forms and I can download those and use those. And adapt them from there. So those kinds of easy admin solutions, I think also make a lot of sense.

Rexhen Doda:

Have you also invested before in like either coaching programs or business coaches or masterminds or like communities that you found helpful

Cheryl Simpson:

for your coaching business? is without question enormously valuable. And going through coaching myself for a coach, I think it's critical to have that experience of knowing what it's like to be coached. And so you have a greater understanding of what happens on the other side of the couch, so to speak.

Rexhen Doda:

And actually for a lot of coaches that I've interviewed, it has been a thing that got them inspired to start their coaching business is they received great coaching and then they decided to start their coaching business and like get certified and everything else. I'm also going to share with you, like when you see the research that goes into investments, you're going to find it interesting to see what investments, at least from the, which is that I've interviewed, which were about 71, you would see which investments had the highest return and which investments were of the lowest returns. And it's going to be a little bit funny because when it comes to our research from the people that we have interviewed on the market, we have interviewed, it actually ended up that the certificate themselves did not bring a lot of ROI for the amount of money that they took to get certified. Or there were coaches that did not do the certifications that still were able to do well as a coaching business. That is a different topic. I just wanted to share that because we found that on our research.

Cheryl Simpson:

Well, but I think that makes a key point about careers is that most careers, the vast majority of them, there are multiple pathways in. And that's just what you just described. There are, you know, My experience does not match that of some of the other coaches that you talked to. And that's the beauty of it. There are relatively few occupations where there's one way in and either you follow that path or you don't gain entry to that occupation. So that's a very powerful thing about particularly the U.S. economy. But I think most is that we have more options than we know what to do with, which is another reason why we need coaches.

Rexhen Doda:

Absolutely. Throughout your experience, is there something that when you were getting started, you wish you had known? Like the lesson learned or even expect the lesson learned that would actually, had you known that made the way to growing your business faster? I

Cheryl Simpson:

think one big one would be automation. I didn't pay enough attention to automation. I was in the business before automation really became a thing. And I didn't really pay a lot of attention to it once it started to become a thing. And I wish I had, because I think it could have really hastened my growth of my practice. Not to mention save me like automation, like AI, save me time, save me energy. energy, remove some of the tasks that I like the least and struggle with the most. And those things could have just been done. And of course, the payoff in terms of what the client sees is a smoother, more professionally run coaching practice, which certainly reinforces their perception of you as a qualified and serious professional, which

Rexhen Doda:

It's kind of helpful. Yeah, it absolutely improves the overall quality of the services that you can provide because of like everything coming in a timely manner because it's the machine like sending all of the emails and everything and making sure that it never misses them compared to us humans, which can sometimes like a lot of things can happen in our lives. And sometimes like, let's say we had a newsletter, we send it every Tuesday, like a certain Tuesday we couldn't send it, but the machine will always send it. So yeah, absolutely. And what would you say are the biggest challenges you've either faced or are still facing today in further growing your coaching business or getting your coaching business from where you are at today to where you actually wanted it to be, if there's any change you want to make to your coaching

Cheryl Simpson:

business? Well, for me personally, it's finding ways to work with AI, not just learning AI systems and learning how to prompt, but what role does AI have in my business and how do I leverage that? How do I make AI work for me? How do I streamline that process? Because you talked about information is everywhere earlier, and it's true. And AI kind of exacerbates that because it can give you access to a phenomenally increased amount of information, even more so than you can get already through the internet. But you have to have a way to deal with that. And to me, I think AI can be a huge asset for me in understanding how to do that and developing processes and procedures for how to do that you know everything from okay i want to build out my blog calendar for the rest of the year i can go to ai and i can ask for you know some possibilities some different topics i can get help in actually drafting those i can get help with editing those i can get help with marketing those but in order to do any of that i first have to learn some things and i have to have some systems in place for how to do that and i think that's what i'm that's where i'm at right at the moment and that's where i'm probably going to be for a while because because so many new things are happening with AI every week, every week, that if you're staying in touch with it, you can really see the evolution happening pretty fast. And it can be overwhelming at times.

Rexhen Doda:

Yeah, I was just going to say that it can be quite overwhelming and maybe it's hard to keep up with. So is there any final advice you'd like to give to other coaches who are looking to scale their impact?

Cheryl Simpson:

I think first and foremost, don't give up. When you have a passion for coaching and you have a difference you're trying to make in people's lives, you can assume that it's broadly needed now you might need to evidence that you might need to research that but so you just it's important not to give up to to really keep working at get whatever help you need to package your offerings to clarify the difference you're trying to make you know to do the marketing or whatever pieces are that you're because that's the problem right a lot of coaches are really good at the coaching piece the people piece but less good at the admin piece or the marketing piece or the finance piece. But the good news is that you can get help with all those pieces. So you're not alone with that. If you have the inherent person-to-person skill, that's the hard thing to learn. If you have that, then the rest of this stuff you can get help with. So get the help you need with that stuff so that it doesn't get in the way of this stuff because this is the stuff that changes people's lives.

Rexhen Doda:

Absolutely. It's been a real pleasure, Cheryl. For anyone who wants to find you or connect with you, They can find you on your LinkedIn at Cheryl Simpson. They can also find you on your website, executiveresumerescue.com. Is there any other way people could reach out to you?

Cheryl Simpson:

Well, they're welcome to email me at clynchsimpson at proton.me.

Rexhen Doda:

Thank you so much, Cheryl. It's been lovely.

Cheryl Simpson:

Thank you so much for the opportunity, Reg, and have a great day.

Davis Nguyen:

That's it for this episode of Career Coaching Secrets. If you enjoyed this conversation, you can subscribe to YouTube, Spotify, Apple Podcasts, or wherever you're listening to this episode to catch future episodes. This conversation was brought to you by Purple Circle, where we help career coaches scale their business to seven and eight figures without burning out. To learn more about Purple Circle, our community, and how we can help you grow your business, visit joinpurplecircle.com.