The Business of Life with Dr King

Career Transitions After 40: Navigating Age Bias and Finding Your Value, Gina Riley (USA)

Dr Ariella (Ariel) Rosita King Season 2025 Episode 43

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Ever wonder why highly qualified professionals sometimes struggle to land their dream roles? The answer lies not in their capabilities but in how they articulate their unique value.

Career transition coach Gina Riley joins Dr. Ariel King to reveal the essential elements that make candidates stand out in today's competitive job market. Drawing from her extensive experience working with executives aged 40-69, Riley shares insights from her forthcoming book "Qualified Isn't Enough: Develop Your Story, Land the Interview and Win the Job."

The conversation tackles the challenging reality of age discrimination, which legally begins at 40 in the US job market. Riley offers practical strategies for professionals to navigate this bias through strategic upskilling and powerful storytelling. "Don't wait to get plucked out of obscurity," she advises, emphasizing that career advancement requires proactive self-advocacy.

Riley unpacks the gender differences in executive presence, referencing Sylvia Ann Hewlett's research on how women need to demonstrate confidence and decisiveness while being mindful of communication patterns. She also addresses cultural factors that can make self-promotion challenging for professionals from collective-oriented backgrounds.

For mid-career professionals looking to future-proof their careers, Riley recommends cultivating curiosity, creating a personal board of directors with diverse expertise, and seeking meaningful mentorship. Her advice on thought leadership provides a roadmap for increasing visibility and establishing expertise in your field.

Whether you're actively seeking a career transition or preparing for unexpected opportunities, this episode delivers actionable insights on crafting your unique value proposition and positioning yourself as the candidate of choice in any selection process.

Tune in to discover how to move beyond being merely qualified to becoming truly compelling in your next career move.

Music, lyrics, guitar and singing by Dr Ariel Rosita King

Teach me to live one day at a time
with courage love and a sense of pride.
Giving me the ability to love and accept myself
so I can go and give it to someone else.
Teach me to live one day at a time.....


The Business of Life
Dr Ariella (Ariel) Rosita King
Original Song, "Teach Me to Live one Day At A Time"
written, guitar and vocals by Dr. Ariel Rosita King

Dr King Solutions (USA Office)
1629 K St, NW #300,
Washington, DC 20006, USA,
+1-202-827-9762
DrKingSolutons@gmail.com
DrKingSolutions.com


Dr Ariel King:

Hi and welcome to the Business of Life. My name is Dr Arielle King and today we have a special, special person, ms Gina Riley. Hello, lady Riley, how are you?

Gina Riley:

I am wonderful, I am caffeinated and I am ready to go, ready to have an awesome conversation.

Dr Ariel King:

Wonderful. Could you please tell us a bit about yourself?

Gina Riley:

Absolutely. I live in Oregon, on the West Coast of America, and what I do for a living is I am a career transition coach. I work with primarily leaders and executives who are really struggling with making a career transition and or being very planful to strategically make that next career move. And some of the people I work with have a job already. Some are trying to position, to move outward from their organization, some have been laid off, and I get to hear and see and witness a lot of different kinds of stories, which is absolutely fascinating for me and it really calls forth my why, which is really helping people articulate that story in a way that comes across in a powerful way that makes them the candidate of choice when they are actually interviewing for a job when they are actually interviewing for a job.

Dr Ariel King:

That's fantastic. I really love that. May I ask, in general, what has been the trend? What is the trend of the type of people that you see and some of the issues that they might have, and how do you go about helping them?

Gina Riley:

Trends. The thread that runs through the storyline of what I am doing with people most of the time is I have found that most people, especially when they get to the mature stages of their career and I'm working with people generally ages 40 to 69, is they have wisdom and experience. Is they have wisdom and experience. However, they don't know how to explain it succinctly. I have one story, in fact, one thing that we didn't talk about when we first started chatting is I've just finished the manuscript of a book that I turned in at midnight two days ago, and the book title is called Qualified Isn't Enough. Develop your story, land the interview and win the job.

Gina Riley:

It's not coming out until September, but the whole crux, the whole first five chapters, is putting together the building blocks of a person's unique value proposition, and a unique value proposition is the components of what are my strengths? What do I do naturally in the world? So if you're familiar with StrengthsFinder, I'm leveraging that. What are my values? What calls me forth to do the work that I do? What is my why? And then, what are the things that I am most known for in my career? What are the themes and the patterns so that when I'm asked that question. Dr King, tell me a little bit about yourself that I have the content to quickly and succinctly tell that story so that I can move into like the real juice of an interview, which are all the questions that people have for me. So the reason why I start with that is because I also I've got HR expertise.

Gina Riley:

I've done executive search, I'm affiliated with an executive search company and then I have my own career coaching company and what I have learned when I have launched executive searches is I had a CEO candidate one time and I told him very expressly I have one hour, I have eight skill-based questions to ask you. I need your help managing the time. First, I want you to tell me about yourself Just a highlights reel in five minutes, and that man spoke for 20, 20 minutes. So I wasn't able to advance him in that process and put him in front of the board of directors, because my job as an executive search consultant was to be discerning about leadership behaviors and one leadership behavior is reading the room. That's part of executive presence. He didn't read the room. I spoon fed him what I needed and I couldn't get through the eight questions.

Dr Ariel King:

That makes all the difference, doesn't it? That's amazing, you know. It's so wonderful to know that you wrote a book. Would you like to just tell us a little bit more about the book? I know it's coming out in September, so that's wonderful. And why did you decide that we all needed this book, and I'd like to understand the process of you writing it.

Gina Riley:

Oh, that's so sweet of you to ask. So when I started developing my career coaching program, I call it Career Velocity. It's a nine-step model that moves people, for the first five phases is creating the unique value proposition and really understanding what those key results are that I can deliver on as well. And then we have to have a resume. Unfortunately, I think that the way that we present ourselves in the future will change, but right now a resume is still required, our LinkedIn profile, vastly important. And then there's interview preparation and job search strategy. And then, for especially leaders, a thought leadership strategy.

Gina Riley:

And as I started researching in the marketplace what it takes to make a successful career transition, I listened to 102 podcasts in one year. I read 20 books in that year. I synthesized all that information and I started realizing there's really nothing on the market that tells me what the blueprint is, or that framework to move from point A to Z, if you will. And so that is the thrust of what called me forth to create this book. It's a how to create that unique value proposition, or what I am known for best. Why me value proposition? Or what I am known for best like what? Why me? What if I am sitting next to four other qualified candidates that made it to the interview process. Why are they going to choose me and that's what I do with my private clients is pulling out. Why them?

Dr Ariel King:

I really love that. I'm really looking forward to the book, so I'll be one of the first to buy a copy and have a signed copy. Thank you so much for that. That's fabulous. You know, I really love the way you tell stories to really understand what you do and how you do it. Do you have any stories of, for example, someone over 60, since we have a lot of people who have already done so much in their careers and who have gained an upper level of where they are and for whatever reason they've shifted, or the company shifted, or you know there's all kinds of reasons for shifts and how you've been able to guide them in a modern world, because many, many people, of course, stay in the same company for a long time. And then any success stories of people finding a new possibility for growth and development within their career.

Gina Riley:

You know you're asking an interesting question and there's there's really so many nuances to what people are trying to navigate today. It's so different than even five years ago and what I would, what I would say to people and I know you have a global audience, so I'm going to contextualize in the US. In the US we have, we have a bar where if you're 40 and above, legally you're, you're considered old, like that's the, that's the. You know, if if I was going to say someone discriminated against me 40 and above, which seems odd because you and I are both more mature than that but I'm even seeing millennials now complaining on LinkedIn that they've not been chosen for a job because they're too old, and these are people that are hovering in that 40 years old. So I think things are going to shift. Actually, 40 years old. So I think things are going to shift actually. And when we look at the generations, there's a larger population of millennials than there is in Gen X. So I think we're going to have to see a shift as we all age together.

Gina Riley:

But yes, I have seen people making some shifts and it gets more challenging because people need to continue to educate themselves and upskill.

Gina Riley:

So you're on.

Gina Riley:

You're constantly, you know, educating yourself, you have a lot of degrees, you're super curious.

Gina Riley:

I think that a lot of people have gotten comfortable with where they are in their careers and then technology now has surpassed you know where we sit in our organizations and all of a sudden we realize maybe the skill, the toolkit that we have to move into the next thing is starting to be less relevant, and so there needs to be a combination of what is my current unique value proposition, what am I most known for, what am I great at?

Gina Riley:

But what are the skills and the skill gaps that could hold me back from the next ideal opportunity so that I can start to upskill while I can, while I may have a job already, and I'm working with a lot of senior leaders. So, in particular, what's coming to my mind are CEOs that I've worked with in the nonprofit sector, and they're having a particularly challenging time in you know, as they get past 60, they're trying to get past the age discrimination bias, they are coming up against different lenses that those boards of directors are reviewing candidate pools, and so it's shocking because they haven't, they're not prepared to break through the biases that they face as they go through these various processes. So that was kind of a long-winded explanation.

Dr Ariel King:

But I would say short story is upscale, you got to upscale and upscale does. Upscale just means continuously learn, continuously figure out how to add to what you do and just continuously read, learn, develop yourself. Is that what that means, to upscale?

Gina Riley:

The way that I would answer that is yes and yes and yes. If you're someone who wants to continue working as you know 55, 60, 65, as the people I'm working with do you need to ask yourself this question what top skills are most relevant to the future decision maker? So it's not so much what am I interested in? I'm going to just go read whatever or take whatever certification, because some one person told me to. If that certification isn't the turnkey, I would question why you're going to invest your time and resources and money into that. So you need to ask yourself what, and this information is not hard to get. Hold a few informational conversations. Research. And this information is not hard to get. Hold a few informational conversations. Research.

Gina Riley:

Look at what the trends are in the news that are telling you what is the most important. Linkedin just did they just put out an article in the past, like seven days, about the top 25 upcoming or consistently hired for jobs of 2025, read articles like that and go, okay, where do I fit into that ecosystem? Where does my toolkit fit? And oh my goodness, these top two or three look really interesting to me. But go find out what your skill gaps are if you want to be targeting those kinds of roles?

Dr Ariel King:

That makes a big difference. So I mean, what I really love too is you're talking about the fact that 40 or so is considered older, but what's really interesting is that many of us think that youth is from 18 to 35. So I guess the 35 to 40 is the mid before midlife. I have no idea.

Gina Riley:

Yeah, I think you and I both would argue that, you know, the actual number doesn't match how we feel about life. And we're, we're, we're in a pool of a lot of people that are, you know, 50 to 70 that still want to be working.

Dr Ariel King:

That that makes sense. May I ask what's really interesting is you said there is a trend of CEOs and people that have run and helped to navigate organizations, which is not easy, but that means that they've been in it for a while, and I understand that. I have a foundation that I've been navigating for 23 years, so this makes sense to me. Are many of the ones that you are working with trying to go into business or what are they trying to do? So the skills are changing right, so the tides are shifting. What are they trying to shift for? And can I ask how are you uniquely able to help older, older and when I say older I'm talking about 60, because I believe that 67 in many countries, or 68 in retirement I don't know, depends on the country. So you're talking about people that perhaps have anywhere between five to 10 more years to work before, most likely, they'll retire. So I'm just curious how are you able to help these people shift? And is there a difference between shifting between men and women?

Gina Riley:

Oh gosh that's multi-layered, excuse me.

Gina Riley:

So I've got a couple of stories that help answer this question. And have the people been exactly 60? Not necessarily, but a lot of the people that I am working with are like 55 to 65. So kind of that swath, if you will. So the older, gen X, younger, boomer, if you will, right in there. So one interview.

Gina Riley:

So I have a series that I call how your next executive role finds you, and it's a series of seven interviews that I did with leaders who have used the power of networking to land that next opportunity and to answer your question. One of my favorite stories of the seven is I interviewed Keith Tomajan, who was the CEO of the United Way here in Oregon I think, maybe the Pacific Northwest and he and I had a conversation about he wanted to position, to go into corporate. He had goals, he wanted to maximize his upside, he wanted to increase his salary, for example, because he had a couple of kids going to college, and so he's like I want to make a change. I've had 20 years in the nonprofit sector heart, forward, leader, amazing human being. So what did he do?

Gina Riley:

First? He leveraged his network. He started talking to other executives in corporate and he would ask these questions what are the perceived skill gaps that I have moving from nonprofit to a corporate role? You know what's going to stop me, what are the barriers to success? And so I think, to answer your question, the older workers need to find out what, even if they don't have a skill gap, they need to go ask the smart questions to find out if there's a perceived skill gap.

Gina Riley:

Then you go and you evaluate and create your story so that you can position with the right language that lands with the future decision maker. So is Keith using, was he using, you know, words and phrases that land with boards of directors and executive teams and nonprofit? No, he was using business language that resonated with people who are working in corporate. And so if we free ourselves up from worrying about what we're going to say blah, blah, blah, blah, blah force ourselves onto people and we get curious and we go find out what problems those organizations are trying to solve, then we have a better shot at creating the right story.

Dr Ariel King:

That's so helpful. I didn't answer all the questions.

Gina Riley:

You gave me a couple of layers.

Dr Ariel King:

Yes, I am quite curious. So my question was. The other question was is there a difference between men and women specifically in this category of those who are CEOs, presidents of non-governmental organizations that actually want to move into corporate or even move into other industries besides corporate?

Gina Riley:

I'm going to answer generally. Between men and women. Yes, there's definitely a difference, and I know that there's science that backs this up. I can't espouse all of it. However, I am a student of executive presence, so there's a book by Sylvia Ann Hewlett she wrote it over a decade ago on executive presence. There's 17 dimensions of executive presence, but there's three main categories appearance, communication and gravitas.

Gina Riley:

And so our appearance is the first barrier to success. We have to, like get through whatever bias people have as they make a three second judgment about us Once we move past that and people are like okay, I see you. Now we're talking about how we communicate and how we behave, and so the science tells us that women need to show up with more confidence and decisiveness. We need to pay attention with our communication to our pitch and our tone. We need to not speak as rapidly. So there's things that women can educate themselves about so that they understand what some of those biases will be, even as they step into each virtual or actual room and men tend to have, you know, the scales tip in their favor. A lot of this science really helps. I think women understand what they could do differently, and I work with a lot of women on this.

Gina Riley:

However, I've worked with a lot of humble men as well and I just wrote an article. I published an article in January with Forbes and the article is about how different cultures around the world, specifically Asian cultures I had a woman who started an alumni group for the business school in Illinois and she's got a group of over 100 people and she calls me up and she says you know, the people in my community are from Asian countries all around the world. We're all working on our MBA and we all struggle with promoting ourselves. So, whether that's internally just trying to get, you know, even promoted within a company versus even looking for a job, we come from cultures where humility and the collective is more important than promoting ourselves individually, as we do in America oftentimes. And so the article it brings together six ideas about how we can talk about ourselves without overpromotion, and so I would also bring into this conversation for women.

Gina Riley:

There are humble men out there. I work with a lot of humble men, but for women, in created I cross-functionally collaborated and created something, and then my team we delivered on what? So I'm just loosely saying that out loud, but balancing the I and the we, it's okay to say you led something, and if you don't, the decision makers don't know that you did it. They're not going to guess. You have to tell them.

Dr Ariel King:

That's such a good point. That really is a good point, the idea that you have to say what you've done rather than assuming that they know what you've done. And I think you're right about culture also. Sometimes it's just cultural ideas of how do you put yourself forth or not, and it's not just the confidence, but you learn within your culture how to navigate various social situations and also job situations. So that's very interesting, very interesting. Can I ask are there any more insights that you think are really important for especially those who are in mid-career, for example, those who don't know that they necessarily want to change, although we know that most people will change at least five to six times their career within a lifetime minimum, who are not looking to change. But how do we prepare ourselves for change without necessarily knowing that that's going to happen, including, I think, upskilling or, you know, learning and so on and so forth?

Gina Riley:

Yes. So, aside from that part of the conversation of upskilling one, I think, always remaining curious, being curious about people, being curious about problems, being curious about the future and asking questions and keeping those ears open, that's one you know, being aware, I'm going to bring in something different into the conversation, which is how, how do you do this? Create a mentorship circle around you, or a personal board of directors? We call it in short, p-b-o-d personal board of directors. What's the difference between mentoring or maybe that personal board of directors? So I believe that, even at late stages of our career, that we all can use mentors and advisement, so people that you admire, that are ahead of you in some capacity, and creating a contract, if you will. It's not necessarily written, but I think it's a good idea to have a relationship where you, the mentee, owns that relationship and what you want out of it, and I interviewed a woman named Lisa Fane, who is the CEO of the Center for Mentoring Excellence, and she and her mother wrote at least five books about how to develop those mentoring relationships. So I highly recommend going and checking that out and looking at especially those later books that they wrote together.

Gina Riley:

The other thing, though, is, I think of a personal board of directors as cherry picking and asking people with different kinds of expertise to be an advisor in your career. So I'm an HR person. That's my background. I've done recruitment. I've been an HR business partner, meaning I've sat next to a VP of a group inside of Intel and been the advisor for his leadership team, and I've also done training and development. I'm not a finance person, I'm not an operations leader. So if I was trying to keep my eyes and ears open and looking at the landscape of the future, perhaps on my personal board of directors I would cherry pick someone who understands operations, leadership or lean six sigma. I might choose someone who's in a finance advisement capacity, for example, and I would go to them and say I want to get smarter about these areas so that I'm a stronger HR business partner, whatever that is. So that's my recommendation is look at getting mentors.

Dr Ariel King:

That makes all the difference in the world, doesn't it? The mentors. May I ask for someone like you you've done so much with so many different types of people who were your mentors, and what do you most remember about them, and how has it affected your life today?

Gina Riley:

Yes, I do talk and write about this. Actually, I did a Disrupt HR presentation about two years ago in Portland and it was about I believe that it's important for us to do some of our work time in offices. I don't think that we need to return to work and be in the office 40, 50, 60 hours a week. However, I believe that our Gen Z needs actual in-person mentor and advisement. I believe that my children, who are in their early 20s, need to be sitting in a room with people who have experience so that they can see the mistakes people make. They can hear and see how people move their body and talk with each other and communicate. And so, to answer your question, I flashed up in my Disrupt HR speech with this sort of idea.

Gina Riley:

My mentors, particularly from Intel, and I got to a place in my career where I really wanted to be an HR business partner. I was in recruitment and I wanted to be one of the people advising those leadership teams and all of my internal mentors and advisors said you have to have a master's degree. At this point in time, we cannot put you in that role. That's what we require, and that was so hard to hear because I felt like I could do it. I'm mid 20s, I know everything. Finally, though, to bust through, I did buckle down. I went and got my master's in whole systems design, and I came back and they made good on it, and so what I would say in my key learning is one I had to listen to people.

Gina Riley:

Then I had to make the hard choices about how I spent my time and money so that I could advance my career and get the kind of job that I wanted. So I would say to people don't expect things to be handed to you. One of the quotes that I'm known for is don't wait to get plucked out of obscurity. People are not coming for you. They're not gonna pluck you out and go wow, you're so amazing, you just knocked it out of the park. This year, I'm going to promote you. Yes, people get promotions it's a part of the whole corporate process, if you will, but you can't wait to be that one or two or three out of 300 people. You've got to advocate for yourself, and you have to listen to people and make good choices about how you're going to advance your future.

Dr Ariel King:

That makes all the difference in the world. And can I say is there, without naming, is there one or two mentors that really have affected your life in a way that, even if it was 20 years ago, that today you can look back and go, wow, that really made a difference, that even if it was 20 years ago that today you can look back and go, wow, that really made a difference.

Gina Riley:

Oh my goodness, there's so many.

Gina Riley:

But beyond the Intel folks because there's just so many smart, amazing, dedicated people that I worked with in the nineties I would go back to my master's degree program and the advisor I had for my the small part of my cohort.

Gina Riley:

So I was a part of 40 people, but there was like or so, and then there were about 10 of us that were in a cohort with one advisor for the 18 months to two years and what I learned from her was really how to listen and how to ask the right questions without leading the witness. So when you're in the presence of someone who is that magical, who is able to ask these incredibly deep, insightful questions that make you think and make you realize that you have growth still yet to do, that is life-changing. To have a mentor like that. I can still remember being in her presence. It was kind of like sitting at the feet of a guru. I got to be with a bunch of those kinds of people who know how to ask the right questions so that I could choose to get the movement I needed in my life.

Dr Ariel King:

That's amazing. That's really wonderful. I want to thank you. Our time is almost up and the three minutes has gone so quickly. I'm wondering is there something? Is there, um, another subject that you'd like to talk about, or something that you'd like to leave our audience with that we haven't covered yet, because there's so much that's so interesting oh, gosh, we covered a lot.

Gina Riley:

we talked about the unique value proposition, which I believe everyone has one. We talked a lot. We talked about the unique value proposition, which I believe everyone has one. We talked a little bit about executive presence, which I think is super critical to people as they advance through their career. Gosh, I could talk about so many subjects. I would say one additional thing that we didn't really touch on in my career velocity model, which is step nine, and that's thought leadership Tying back to don't wait to get plucked out of obscurity. One way to not be hidden in your life and I was listening to your podcast with Nick Nelson, who I greatly admire, I've been following him for years is stepping out with your brand and being known for something and not being afraid to be out there talking or writing about it. Participate, particularly on LinkedIn where, professionally, that's where it's acceptable. But if there's other places, like trade magazines or conferences, or you don't have to be a TEDx speaker to be known for something, but you do need to participate so that people know you for some kind of expertise.

Dr Ariel King:

That's really great advice. So I want to thank you for being with us today. I've learned so much. I've really enjoyed it. It's gone by so quickly. We have to meet again and I want to say thank you to our audience for joining us and remember if I am not for myself, who will be for me? If I am only for myself, what am I? If not now, then when Hillel said that and I said if not me, then who? Thank you and we look forward to having another podcast of Business of Life.