Jackie Ferguson: [00:00:00] Thanks for listening to Diversity Beyond the Checkbox, the podcast where we explore bold ideas and real stories that challenge how we think about leadership, work, and belonging. I'm your host, Jackie Ferguson. Today I'm joined by Debra Boggs, a powerhouse and the world of executive career strategy. She's a Forbes award-winning entrepreneur who went from leading university career services to building a nationally recognized firm that helps VPs, C-suite leaders and board candidates land top opportunities.
Deborah's insights have been featured in the Wall Street Journal, Newsweek, the Washington Post and more, and she's here to tell us why your resume, your networking strategy, and your mindset might be holding you back. Whether your mid-career and aiming higher are already in the C-suite and looking for your next challenge.
This conversation will give you the tools and confidence to navigate your next move. Debra, welcome [00:01:00] to the show.
Debra Boggs: Thank you so much, Jackie. Thanks for having me. I'm really excited about this conversation. Me
Jackie Ferguson: too. Well, Debra, let's go back to the beginning if we can. What led you from career services in higher ed to founding your own executive career management firm?
Debra Boggs: Yeah. You know, it seems like a leap, right? It, there's not a natural, uh, progression from that. And what happened was, you know, I got what I thought was my dream job, which was leading career services. I really thought that was what I wanted to do with my life. 'cause I had always been interested in the, you know, the workforce, the relationship between employers, employees, all of that stuff, right?
When I started that role, I found out quickly that what I really loved was helping candidates put their best foot forward. We were with a lot of returning alumni and things like that too, so not just students. So I really loved helping people put themselves out there, go for stretch roles, land jobs they didn't think they could get, earn money they didn't think they could earn, and, and I really, that really gave me a lot of, of energy and excitement.
And what I found out I didn't [00:02:00] love was being a university administrator and all of the work that came with that, that had nothing to do with really doing my passion piece. So. I, when I left that role, started this really on the side as more of a passion project. I was really just really excited about working with candidates, helping people build their standout resumes, things like that.
And it snowballed and took over my life. Uh, that was about nine years ago, but really a couple years into it, I realized that the executive search is totally different. It's a completely different animal, and people have to show up. In a different way. The roles you're used to finding aren't where you expect them to be, and no one teaches you how to do that.
And so we really niche down into working only with senior leaders, navigating high level, complex job searches, and that's really where we started to grow.
Jackie Ferguson: Absolutely. Now, Deborah, let's talk about the mindset shift that you had to make right from when you transitioned from being an employee to an entrepreneur.
Tell me how that evolved, right? Because many of us have [00:03:00] these passion projects or, or things that we do that we're great at, that we love, but how do we make that shift from our. In our mindset and also, you know, in our career from employee to entrepreneur. Can you tell us about that?
Debra Boggs: Yeah. Um, I love this question 'cause I think it's, it's so interesting, right?
At the time that I was building this, I had, so when I left career services, I was VP of business development for an online training company. So, and I was breadwinner of my family. My husband's a stay at home daddy, has been for 10 years. And I tell you that to say this was my side hustle and I had a, a well paying full-time job.
But this began to grow and it's where I got my energy and I really loved doing it. And it got to the point where I knew I was holding myself back. What could it be if I could make it full-time? And at the same time, it's really hard to let go of that full-time income. Right. Especially my kids were Yeah, that's right.
Uh, four and one at the time. Uh, wow. So, you know, I, I get what all of those things that can hold us back into our careers and, and not make that [00:04:00] leap. I'm fortunate to have an incredibly supportive husband who said, you know, I believe in you. If you leave your job, I, I have no doubt that we will be making, you know, we'll be fine.
You're gonna be fine. Now, I spent about a year really building up the business, but then when I launched it, honestly, where it is today is not what I had in mind. I thought I, I was gonna be happy making. Basically making up my full-time income as a solopreneur and I would be happy. That's, that was my goal.
And now we're a team of 15 nationwide, right? Um, working with the most amazing team, uh, working with sea level from all over the world. And so where we started and where we are totally different. And the reason I tell you that is how I got there was. I have always worked with a coach, right. Um, a different coach at different times of my career because I think you be different people who know you in different stages of your life, that's great.
But I needed a, uh, an executive leadership coach that could help me get out of my own way. I am, uh, I'm a mid-westerner. I'm from a blue [00:05:00] collar, blue collar family. Um, you know, leaving your job to go do something random is not okay, and I needed to get. Out of my own mindset, right? I needed to get out of my own limiting beliefs on what I could do and what opportunities were out there for me.
So I worked with an executive coach for a couple of years to really learn how to delegate, learn how to let go, learn how to be okay in this new space as an entrepreneur. Um, it's really uncomfortable to talk about, and it still is uncomfortable for me to talk about myself and here's how amazing I am and look at how great I am at these things.
But this is what I tell my clients to do, right?
Jackie Ferguson: That's right.
Debra Boggs: And um, and so, you know, working with a coach and then working with a communications coach, and now I work with a. Business coaching firm, right? You need people at different stages of your business and your life to get your, get out of your own way, to understand what you are and aren't good at, to really level up.
And especially if you're an entrepreneur, no one's telling you what you suck at. No one's telling you where your blind spots are, and then when you start to hire people, they're not gonna tell you what you suck at, right? Mm-hmm. That's right. Now I'm lucky, I've got a good team, full of good friends, so they, they will say, I say [00:06:00] this with love, but I'm gonna need you.
It
Jackie Ferguson: is. That's helpful. You, you know, you have to have that Deborah, because you have to have those couple of people around you who are gonna tell you the truth. Yes. Because you're right, as you know, as the the top. Person in that organization, that title is intimidating and a lot of people don't wanna tell you what it is that you need to hear mm-hmm.
To go to that next level. So that's one of the things as an entrepreneur that, uh, I've learned and, and that I've been able to watch and that entrepreneurs around me is make sure you have those. Team of, of a few people that will always tell you the truth. It's so important and tell you the things you need to hear.
Absolutely. Yeah.
Debra Boggs: It's absolutely vital. 'cause otherwise you're gonna be digging your own holes and not realize it. Right. And and I find absolutely know the coaching, the coach I had early on, to be honest with you, it was expensive. It was more than I'd ever spent on myself. It was very uncomfortable. I felt like I was spending an absorbent amount of money.
And it's [00:07:00] uncomfortable in general like. Yeah, to go through the coaching and self-development process. And so I told my coach at the time, her name's Marian Reman, uh, she's in Europe now. Um, she, uh, I said, I feel like I'm paying you an absorbent amount of money to torture me every week. Like, this is un, I don't like this.
And at the same time, it was transformational for me as a person and in my business, and I don't know where I would be now without doing it.
Jackie Ferguson: Absolutely. You, you definitely need those coaches around you to help you grow and, and help you stay out of those potholes, right. That so many of us fall into. Yeah.
Uh, just because we're navigating things for the first time. Debra, you've talked about, I. Not bragging on yourself. Right. And, and part of being an entrepreneur is you're the, you're the, the salesperson. Right. Tell me, and, and then you are building a brand on your brand. Mm-hmm. Right? So, but many women, and especially if I think of women of color Right, are [00:08:00] taught not to talk about themselves in that way.
Mm-hmm. Right. How do you coach your clients to reframe self-promotion?
Debra Boggs: Yeah. You know, it's so interesting and it is something that so many people struggle with, and specifically women and people of color. Mm-hmm. You know, we're not taught to say, look at how amazing I am. Let me tell you all these things I'm great at.
Let me get in front of the class and, and be all the things right. That's really uncomfortable. Mm-hmm. And we're really, you know, early in our lives, punished for that kind of behavior.
Jackie Ferguson: Sure.
Debra Boggs: Um, I, I know I've spent a lot of time and money trying to work that out of my own personality if I can. But when I work with my clients and advocating for them, it's really about knowing that you are, you are not doing yourself any favors by holding back when your competition, who are.
Either as qualified or less qualified than you are, are putting themselves forward, right? We're, we're immediately taking two steps back in line for these roles or these opportunities that we want. If we're thinking, I'll just, you know, my work should speak for itself, I'll keep my head down and do my work, I'll, you [00:09:00] know, I don't wanna take too much credit.
'cause I wasn't the only one who did X, Y, Z at work. I led a team, so that wasn't really me. I can't take credit for that. And meanwhile. Our competition, some of our legacy candidates for these roles are have no problem saying, I led the team that delivered X, Y, Z. That's right. I delivered X, Y, ZI, you know, taking as much or even more credit than they should, right?
Mm-hmm. When you're up against these, these opportunities, and especially at the highest levels earlier in our career, it's not a big deal 'cause everyone has the same amount of experience and the stakes are lower. But when you get up to a level where you're competing against a role that's going to lead a business unit or lead a large team, or it's, it's high stakes because there's big money on the line.
Not only how much they're gonna pay you, but the the value you're gonna deliver to the company. They want someone who they, who is confident in being able to come in and solve those challenges, who's confident in being able to move the needle immediately? And so now is not the time to pull back and be, be reserved and be in hedge.
Right. Because we really need to be pushing [00:10:00] ourselves forward to show that confidence.
Jackie Ferguson: Absolutely. And you know. Confidence is one of the things that, that leaders look for in organizations because you have to have that to succeed and to lead teams. Absolutely. And so even though that's a skill that so many of us have to develop a little bit later and it feels a little bit uncomfortable, that is part of our, our growth to success.
So I, I appreciate that info. Let's talk about systemic barriers that exist for underrepresented leaders in networking and, and job advancement. How can we begin to address those, Deborah?
Debra Boggs: Yeah, absolutely. You know, it's interesting when you're, there's those differences, you know, we'll, we'll talk just class in general, right?
Mm-hmm. Sure. There's those differences in the network and the opportunities and people around you being able to open doors for you earlier in your career or really at any level, right? And. [00:11:00] Because so many opportunities are filled through our network who we know, things like that, and that's even more true later on in your career where most roles aren't posted, where most roles are filled through a network.
Then if you don't have access to those circles of influence, then you're not ever gonna be front on the line. You may be in the interview process, but that's after they've already picked who they're gonna hire. Now they're interviewing everybody, right? Um, that's not helpful. And you put just as much time or more time and energy and effort into the interview process and you lost before you ever walked in the door.
And, and that's so incredibly disheartening for so many people. And, and what we have to think about is how do you get in the rooms of the people that are making the decisions, right? How do you mm-hmm. And sometimes that's, it's not necessarily waiting for an invitation. It's making the space to show up at those rooms to show up in those places.
It's really uncomfortable for me. I mean, I know I am. For anyone listening, I'm sure it's probably obvious I'm a white woman, but I am a blue collar background white woman. My mom was a truck driver, my dad was an [00:12:00] electrician. I did not. Working with the CEOs all over the world is a weird space for me to be in.
I will say this, like, you know, and, and people that know me ask like, how did you start doing this? And like, I kind of bullied my way in right Of, of really being out there in terms of being in the rooms. Where is my audience? Where do, who do I need to know? And how do I get in front of those people? Right?
Is it going to conferences that it attending live events and, and connecting with people? Is it attending, you know, if money is a barrier, which often is for a lot of people, especially in job seeking, is it attending virtual events and then having a natural reason to reach out to people? Hey, I saw you and I were both at the x, Y, Z webinar.
I'd love to meet, um, and chat about your work, right? Having natural connection points and putting yourself out there, because if we wait to be tapped on the shoulder, it's just never gonna happen.
Jackie Ferguson: Absolutely. Debra, you know, this is such an important topic area, and I'm so glad you covered it the way you did, because so many of us believe that, well, my competence [00:13:00] speaks for itself.
Mm-hmm. My experience speaks for itself, and it doesn't. Right, right. Because sometimes you have to, your name has to be dropped in a room. You've gotta be in a room. Where you are top of mind for, for a role that's upcoming. Mm-hmm. And it's not just about the experience because there's 10, a hundred other people with similar experience.
So what differentiates you? And it's the, the power of that network and I, I. I'm so appreciative that you said that because that's a thing to put a bookmark in with this podcast from my perspective, because you have to really build that network. You've gotta get in those rooms, you've gotta introduce yourself, um, because it makes all the difference as you're building your career.
It really does.
Debra Boggs: That network is everything, and you have more value to add than you know, to your network, right? Because as you build your network, you can make introductions for other people. You can be that person, I think sometimes. Especially women, [00:14:00] especially people of color struggle with, with asking for something of their network because they feel like it's so transactional.
But really you have so much value to add. You can add perspective, you can add friendship for people, you know, be a bright spot in someone's day. Simple act of kindness. I think there's a lot we can do to keep networking from feeling so transactional. So, um, you know, I think everyone thinks about going to those horrible networking events where everyone's training elevator pitches and, and, and business cards.
No one wants to be in that. Right, right. I, I understand that deeply. And that's not what we mean, but it's about building relationships with humans, which is where women Yeah. Do. Um, really thrive and they do great work. We're not going by asking and activating that network. Um, and that's what we need to get better at too.
Jackie Ferguson: Hmm, absolutely. So Deborah, let's talk a little about executive job search, because in the, in the US right now, um, the economy is moving, right? It's fluctuating. Yes. And, and it's, it's doing some, some things that are a little [00:15:00] unexpected. And a lot of times, um, these senior executives are being moved out of these corporations, right?
Mm-hmm. And so, okay, so now. Executives are looking for jobs, right? And it's multiple, right? And so talk to us about what most senior executives get wrong when they start a job search. What? What should they be leveraging first? How do they begin that?
Debra Boggs: Yeah. Love this question. So the absolute thing that is the most critical piece of the process, and the thing that I see most people get wrong, is that in the executive job search, you have to be hyper-focused on your deal.
Next role. In this market at this moment, people are not hiring generalists. And what I see is that executives have done a lot of different things in their career. They can do a lot of different things next, but you can't put all that in an, in a unique value proposition. You can't put all that in a resume.
And so instead, they don't wanna, they don't wanna narrow their, their opportunities [00:16:00] too much. They try to be too broad and they say, oh, well, I'm a marketing leader. I can really help any company grow. Well, great, any company isn't interested. I have 25 years of experience in a variety of industries. Okay, great.
So does everybody else. So what are you doing to stand out and you can't really. Tell a hyper-specific value proposition without having a hyper-specific role in mind or company or an industry. And so with all of our clients, as we work with candidates going through that process, we start with what does an ideal next role look like?
Because you have to know that to build a compelling brand, resume, LinkedIn profile, interview, process, negotiation to maximize your final offer, it all hinges on being really clear. And I find a lot of people struggle with that piece.
Jackie Ferguson: Absolutely. Now let's dig into unique value proposition a little bit.
How do you help your clients uncover their own unique value proposition?
Debra Boggs: Yeah, absolutely. So the unique value proposition is [00:17:00] interesting, and I do workshops around it too sometimes, and we do this individually with clients as well. But it's really around, okay, so what does, what does that ideal next role look like?
Right? And, and it includes what does that company, and, and we're talking not just industry, but. Size, um, ownership structure. Is it public, private, PE backed, you know, um, the, their go to market, their location, all of these things to get as specific about the kind of company that you are uniquely equipped to serve.
Because then you can go deeper into what are the challenges going on for that company, that industry, that hiring manager right now, what are the challenges in the market? What are the challenges that that role you would be coming into are, are being asked to face at this moment? And then your unique value proposition is really around how are you uniquely equipped to solve those challenges for X, Y, Z?
And it's a little bit of a process 'cause you're starting broad and you're really narrowing down. And I want everyone to think about their unique value proposition, not as a statement, not [00:18:00] as an elevator pitch, but as the essence of the value that they bring. That they weave into every conversation, every bullet on their resume, the headline on their LinkedIn profile, and every section after that.
It's not just a, it's not just a branding statement. It's really guiding every aspect of your search.
Jackie Ferguson: Absolutely. That makes so much sense. Now let's talk for just a moment about LinkedIn. Tell us some of the mistakes that you see even high level professionals make on their profiles.
Debra Boggs: Yeah, so a couple of things.
You know, I'm gonna get on the soapbox about our headshot for a minute. And, you know, I was talking to a woman that leads the board program for the New York Stock Exchange yesterday. Um, and she said this was an issue at the highest levels of even public company board candidates, is that we are not paying enough attention, uh, to our headshots in LinkedIn on our documents if, um, that's common on board resumes, not on American, uh, career resumes, but.
It's around having a [00:19:00] current professional headshot that looks like you would want to look when you walked into an interview. What are people going to expect to see if you're gonna walk into an interview? And I think a lot of people don't wanna spend money or time on that, or we think it's an afterthought or, or reusing a picture from 15 years ago, or we cropped our friend out of a wedding.
Flo, though, right? Or you know what I mean? And at this level, we want, this is our first opportunity to make a first impression. And as we know, we, it's really hard to change your first impression. So that headshot on LinkedIn is really pushing us, um, forward a little bit. I'm, I'm young for what I do. I'm, I don't feel young anymore, but for what I do and the company I run and the clients we serve, I'm actually really young.
And, um, I was at a conference recently and a friend said that, met at this conference, said, oh wow, you look just like your picture, but from your picture, I thought you were 10 years older. And I said, that was. Actually intentional. I appreciate that. It is me, it's my actual photo. But it, you know, but it, it's putting something different out there into the world of, of how I wanna be [00:20:00] perceived because that's the first impression.
And so I think we wanna think about that. And I know I'm going deep into the, the headshot piece of it, but it's the piece that I see a lot of people get wrong. And we want it to be, I'm gonna get really nerdy with everyone for a second, but we want it to be collarbone and above of a closeup of our head and our face looking straight on.
Okay? And the reason is. You want people to make a human connection with you and they can't neurologically without being able to see or fix. Huh? So zoom in, make it very clear it's you. Um, I say this to men and women. You wanna smile, you wanna be approachable, right? You wanna be someone someone wants to know.
And, and that's, that's really critical to having a a, an effective LinkedIn
Jackie Ferguson: profile. Makes, that makes total sense, Debra. You know, and in my background, understanding and studying bias. Right. And, and the way that our brains make these snap judgements about people. Mm-hmm. With no information. Right. Right, right.
Exactly. [00:21:00] That, that is something you can decide. Right. I'm going to do the best I can to make sure that. I'm eliminating as much of that as I can, or that, or you have to decide. I'm going to spend the first 10, 15 minutes of a conversation. Establishing credibility, right. That at least in part, not fully right.
There's, there's lots of biases out there, um, that, that we all have. But at least having that baseline of, of credibility, of approachableness, right, of, as you said, someone that you want to know and you're not having to combat that, right? Right. And so I think that's, that's so important and the detail.
Awesome, because I, I didn't know that either. And I'm thinking about my own LinkedIn and I'm like, not quite, not quite the right picture. I might need to [00:22:00] change mine, right. If
Debra Boggs: we don't think about it. But it's one of those things, what we want from LinkedIn is for it to invite a conversation with a human.
And we can't do that without making that. And like you said, that credibility piece is so important too. So we think about headshot, we wanna do a background photo, image of something, even anything better than that. Mint green LinkedIn. General one is better, right? I tell people like, don't overthink it.
Pick a different color. I don't even care. And then, you know, the other piece that I see people miss a lot is that headline, that headline on your LinkedIn profile is crucial for several reasons. I. Number one, it's the most heavily weighted section for keyword searching on your profile. So we want it to be keyword rich on the things that we wanna be found for.
And again, that goes back to having an ideal focus. So we can say, mm-hmm. I'm a I, I'm an A, B, C, that does X, Y, z for companies like this. Right? We want it to be something very specific, but we also wanted to tell what we're looking for or what we're open to. Sometimes I see things that. All they say is like company name and title, which is the default, which I understand [00:23:00] and that's fine if you're currently in a role, but if you are looking for something or you wanna be open to new opportunities or you wanna be tapped on the shoulder for something different, that's not going to serve your purpose.
Then the other thing is I see people who are open to new opportunities and it literally says, open to new opportunities and there's nothing else there. Open to what? Underwater basket weaver. Veterinarian. Like, I have no idea what that means. Right. And so really using though that character space you have there with intention really helps you set, 'cause the other thing is that it, it follows you everywhere you go on LinkedIn.
Right? So anytime you comment on something That's right. Your headshot, your name, and your headline follow everything. And so that headline is really prime real estate because it's the little tagline to everything you do anywhere on LinkedIn.
Jackie Ferguson: Mm-hmm. Mm-hmm. Absolutely. Great advice. Thank you so much.
Absolutely, Deborah. Let's jump back into networking a little bit because this is such an important, um. Part of the spectrum of like moving ahead in your career. [00:24:00] Yeah. What are a few ways that executives can network effectively without it feeling transactional or self-serving? We talked about that a little bit.
I'd like to dig into that a little bit more for those who networking is new for. Right? Absolutely.
Debra Boggs: Well, I like to say start with who. Who is in your network that you might not already think about, right? So, so the, your network is so deep. Um, my, my colleague, um, Michelle Merritt, who's our chief strategy officer, often says, you know, she has three levels to her network.
And I want you to think about it this way. It's the, it's the 2:00 AM network that the people in your life, you can call in the middle of the night and they'll show up with a shovel and not any questions asked. Right? That those are your closest people and most people only have a handful of that 2:00 AM network, right?
And you can think off the top of your head who those people are. There's your 6:00 AM network and those are the people that will answer your call before or after business hours, but you wouldn't call in the middle of the night and expect no questions asked. Okay? [00:25:00] And then there's your 8:00 AM people, and those are the people that during the course of a normal workday, would probably pick up the phone or answer your email or something like that.
And so thinking about your network broadens it a little bit beyond just like the. Contacts at work we can think of, but you know, in the workspace we're thinking not just, you know, it's our past and present coworkers, anyone who leaves the company and goes somewhere else. Great. That's a new network, whole new network you have now of their entire.
New company. Yeah. If you keep those relationships warm, your vendors, your clients, all of these things in your current role that aren't just people you meet at networking events, right? This is about everyone you come in contact with that we don't think about actually having their own networks and their own spheres of influence and, and opportunities for us.
And then it's all the other people in our lives. Um, it's so funny. We have, we get a ton of referrals from a running group in London. It's a group of. Parents who all of their kids go to the specific private school and they run in the mornings after they drop their kids off and talk about careers and [00:26:00] stuff.
It's the funniest thing. I don't know who, where, where we, where it started for us, but for some reason this running club in London is a great support network for each other. Um, in their own careers and things like that. So where are you, you know, your nonprofit boards, your, your extracurricular activities.
We have a client that recently got a job offer from, um, she does an exercise class with, uh, the CFO of a company that was looking for a new chief marketing officer. Right? So like all of these places can be opportunities for you that we need to think. Outside the box of our traditional networking and start getting used to telling our story and asking for things and having conversations.
'cause once we get used to that, then reaching out to strangers is a little bit easier.
Jackie Ferguson: Absolutely. That makes total sense. De let's talk about the power of a personal brand. Yeah. So we talked about, you know, what your LinkedIn should look like. We talked about networking. [00:27:00] Let's talk about personal brand.
What are your thoughts on how we build that for ourselves? Right? Because that's one of the things that I'm finding in some of the work that I'm exploring, uh, that's new for me. The difference for executives and Right, so the economy's weird. People are getting laid off. There's a hundred executives that have similar qualifications.
What different differentiates you from those other 99 and personal brand is one and one of the ways that, uh, that can be done. Yeah. So. Tell us what you think about building your personal brand. We talked about LinkedIn a little bit, but what does that mean? How do we do that? Is that helpful? Right, right.
In in, as you're climbing your, your career ladder. Yeah. You know, it is
Debra Boggs: so incredibly helpful and it's something that can be done in a way that doesn't feel. Disingenuous, uh, inauthentic.
Jackie Ferguson: Mm-hmm. I was
Debra Boggs: talking to a gentleman. Um, he is a [00:28:00] new client of ours and he's a chief accounting officer for public companies.
He's, he has a big role. He's starting a job search for the first time, and he's just not that guy to be wannabe out in front. Right. He's very. Humble, he's very heads down. I do my work. But now he's, he's up against some of the best in the world of what he does and how do you stand out. Yeah. And so we're talking about ways to make it more comfortable for him to be a little bit more out in front in ways that he is not his natural.
Right. And some of the ways, the reason it's important to go back to your question is that you're not gonna get plucked out of obscurity. You have to not only have a brand, but also. Have what we tell our clients is like executive visibility, right? Where can people find you? We were talking to an executive recruiter the other day on a LinkedIn Live that said, you know, I look on LinkedIn, but I also, you know, are you showing up in Google searches?
Where am I finding you Other places to know, oh, he's someone who's at the top of his game, or, you know, she's really an industry thought leader in this space. I need to call her. And so it's around. Building out [00:29:00] that unique promise of value. As a person, what do you wanna be known for? What do you wanna be known that you do?
And then from there, all the opportunities you have to tell that story. Is it LinkedIn? Is it a LinkedIn newsletter? Is it podcasts like this where you can talk about your area of expertise? Is it speaking at conferences or speaking at, you know, local events? Where can you. Do those things and then where can you also promote those things?
I joke with our team because our team does a ton of speaking, um, and on Wednesday next week, three of us have three different presentations for different groups around the world. It's crazy. I dunno why Wednesday everyone wanted something, but I joke that we don't do these things for fun if we don't post it.
It didn't happen. We don't get, no one knows. Right. Um, and that's part of the personal brand. It feels uncomfortable. I'm, and again, I know it doesn't seem like, I guess I'm talking to the podcast about myself. This is not my natural state. Yeah, but it's really around getting out there and putting it out there consistently all the time.
So people are used to seeing us and, and it gets more comfortable every time you do it, but really that's right. Doing the [00:30:00] things and then also promoting the things that you did are incredibly important.
Jackie Ferguson: Absolutely. And for those listening, Debra just said it gets more comfortable every time you do it.
That's exactly true. Absolutely. And so important. It's very, it feels very awkward. I remember, you know, I built my career behind the, the spotlight. Right. And then in the recent years in the. Company that I built last, the diversity movement, I had to come out in front and it was very scary. Um, and uncomfortable and weird and like, what do I do for a living?
I don't know. I write and I ask questions, right? Oh, that question, answering
Debra Boggs: that question. Right. I'll, I'll never forget as I was building my business, I'm very uncomfortable, even now when people at a party and things like that ask me what I do, and I'm like. I, I help job seekers. Like, I'm not gonna be like, well, I'm a Forbes honored entrepreneur who blah, blah, blah, blah, blah.
Right? Like, it's, that's not me. [00:31:00] And so, um, but I was at a, like a Chamber of Commerce event here in my local area and uh mm-hmm. And this was as, I was like building a team, really kind of getting out of the day-to-day work and really into building the company. And somebody asked me what I did, and I'll never forget 'cause I said, I'm a resume writer.
And he literally looked above me, above my head and walked away. Huh. And I thought, oh, I need to change how I present myself in these business settings. Mm-hmm. Now, I don't wanna be that guy sc cringe, but in general I need to show up differently. Right. Absolutely.
Jackie Ferguson: Wow. Deborah, let's talk now about salary negotiation.
'cause this is something that you're passionate about. Yes. Tell us one tip that you'd give to someone preparing. For that conversation because this is another area that we feel uncomfortable and awkward talking about. Right? So tell us how we prepare for that [00:32:00] conversation.
Debra Boggs: Yeah. So this is such an important conversation that matters so much, and especially to women and, and I'll back up by saying a couple of things.
Make sure you're answering the question that was asked because. When we work with candidates, the one of the first questions we always ask people, you know, we talk about people, you know, what, what do you wanna do? What does your ideal next role look like? What does your ideal compensation look like? And the reason I ask that is to make sure, are they, what are they looking for and does it fit the market?
Right? What they tell me, and this is men and women, 98% of people don't answer, what do you wanna make? They tell me what they make right now or what they made in their last role, and that is not the question I asked. For most of your listeners, in most states, that's not the question they're going to be asked either, because it's actually illegal in a lot of states now to ask, what do you currently make?
And the reason is because as many of us know, women have a pay disparity. And if you tell people what you currently make, then they're gonna offer you just a little bit more that you currently make. And the [00:33:00] pay disparity continues. That's right. So don't,
Jackie Ferguson: absolutely
Debra Boggs: don't answer questions you aren't asked.
'cause you're not helping yourself. And instead, when you're in those initial conversations with recruiters or hiring managers or the, you know, the HR team just kind of doing the fit check and they say, what do you wanna make in your next role?
Jackie Ferguson: Mm-hmm.
Debra Boggs: What I want everyone to remember, and especially the women and people of color in this group, is you have no idea what they're offering.
You have no idea what their pay looks like. And oftentimes your frame of reference is a lot lower than what the market actually pays. And so we don't want to cap our opportunities by saying, oh, I wanna make 70,000 if the job actually pays one 20 because they're gonna come at 75 and think they're doing you a giant favor and you're gonna be super excited.
But you left a ton of money on the table. Mm-hmm. And instead, I want you to say, you know, something around the lines of, I'm sure this job has a range. I'd love to know what that range is, and then we can talk about whether it's a fit. [00:34:00] That way and most often, and you'll be surprised how often people will give you that range.
And then what I want you to say is, you know, as long as it's not a crazy low range, you can say, you know, thanks so much for sharing that with me. Based on my experience, I believe I'd like to be at the top of the range, but I'm sure we can work out those details at the end. So my best friend has been in a job for a really long time and, and pays what we call the loyalty tax, right?
Every time she gets a promotion, she's not getting the same amount of money she would get if she went outside. Mm-hmm. And, and so she's making way below market value. And so she tried this for the first time, uh, recently, and the range was four times her current salary. Oh my goodness. And, and it's not something that's gonna happen for everyone, but our frame of reference is often very
Jackie Ferguson: skewed.
You know, but the thing is, Deborah, if we think about whatever it is that we make, right, and the difference 5,000, [00:35:00] 10,000, 15,000 would make to our light, right? We don't wanna leave that on the table when it can be an easy yes for that potential employer. Mm-hmm. And what happens is for so many of us women especially, we don't wanna say the thing that's gonna cost us the job.
Right. That almost, that almost never happens, right? Right. It's a, it's a conversation about, well, I'd like to make this much, well, this is where our cap is, whatever, and you, you find the number that works. Right. Most employers will never say, well, nevermind. Right, right. Unless you're so far apart that you can't figure it out.
Um, but. That's such good advice and something that we need to practice, we need to get more comfortable with because if we think about what that gap right between what we make or what we think [00:36:00] we wanna ask for and what they can pay, can mean to ourselves, to our families. It, it can be a big difference. A
Debra Boggs: big difference.
It really can be. Um, and, and I. I wanna also speak to the people that are looking at a raise or an increase income that feels uncomfortable. Mm-hmm. And I will say, I've only had this conversation with women and I've only had this conversation with women of color. Men don't ever tell me, well, I don't wanna make too much.
That feels uncomfortable, but, but there's a, a sense of shame that women feel, and a lot of times women of color, and I'm speaking for you, but just from experience talking to clients, is that. At a certain point, you're making so much more than your family did than you ever thought possible that your friends do all of these things and you feel like you don't deserve it or you shouldn't be asking for it.
Mm-hmm. Or you're being greedy and, and that's not helpful for you. It's also, it's no one's business what you do with that money. [00:37:00] And we talked to a client, I said, you could put your niece nephew through college. Doesn't matter what you're doing. Take the money that's being offered. You're worth that money.
And there's, you know, we have to let go of that sense of shame around making more than say our parents ever thought we could. Right. Or whatever that might be. And sometimes that's really hard to
Jackie Ferguson: do. Yeah, absolutely. Now, Deborah, on the same vein, let's talk about, we're in a company, we like this company, but you're right, we're paying the loyalty tax.
We're right. Right. How do we. Have that conversation with our manager within the company.
Debra Boggs: Yeah. So the, the way we suggest to do this is a, is a couple of things. It's around having honest conversations with your manager around your career goals and the value that you bring, right? It doesn't ever, you don't wanna come at it with a, I'm being underpaid in the market, um, because that's very often ignored, but it's more around.
Here's what I wanna do with this [00:38:00] company. Here's why I'm excited to stay at this company. You wanna be an investment for them, right? So you wanna come at it not as an ultimatum. Mm-hmm. But as a, you know, I've been here 5, 6, 7 years. I love the work that I do here. I'm passionate about this. I wanna create even more value for the company.
I wanna be even more integral to what we're doing here. And to do that, I'd like my pay to. Keep up with the level of value I deliver or whatever it may be. But it's around knowing the value that you bring and being able to communicate that and being able to pull receipts right of, of here's, here's why I'm worth what I'm asking for, uh, is a really big part of it.
And then also coming at it collaboratively and, and enthusiastically, especially as, as a female of, you know, helpfulness. I'm here to help and I need paperwork. Uh, but it's, it's really knowing how to frame that conversation around value. Delivery and not necessarily pay equity, because that falls on deaf ears.
Jackie Ferguson: Absolutely. And I think the collaboration part is so important because you're not [00:39:00] saying, you know, pay me what I'm worth. You're saying, here's what I'd like to make. Mm-hmm. Here's the value that I bring. Tell me how to get from here to here. Right, right. And then you have a partner. That conversation, a partner in that growth and it, it can make a big difference.
I love that. It
Debra Boggs: really can. Yeah. People are very rarely gonna tap you on the shoulder for opportunities unless they know you want those things.
Jackie Ferguson: That's right. Absolutely. That's exactly right. Deborah, you've created a job search diagnostic tool and more than 150 videos on YouTube. Tell us what inspired you to offer these free resources at that scale.
Debra Boggs: Yeah. It's so interesting because our team, um, answers the same questions all the time, right? So many people have the same struggles in the executive job search and the senior leader job search, and right now in any job search right this second. Um, but we don't talk enough about what those challenges are.
And so, so many people are coming at these things with the same challenges and, [00:40:00] and really we have the opportunity to deliver answers to these questions at scale, really to make it more accessible for people that. That may not have been able to, you know, to be, to be honest with you, we're not a cheap firm, right?
Mm-hmm. And when we talk to people and they have real needs for job search advice and there's so much out there that isn't good, I'd rather point people to quality, expert led advice to know that they're getting what they need, even if they can't pay us for that. And so that's why we love our YouTube channel.
We launched it, um, seven or eight months ago. Uh mm-hmm. But we have really. Put a ton of really high quality content out there for people that really need that support. And then that executive job search diagnostic is really a free tool to help people understand where their process may be breaking down.
Because we talk to a lot of people about their job search, where things, you know, may be kind of going off the rails where things are stalling and they have ideas about, oh, well it's my resume, or it's my interview style, and all of these things. Right? But really there's about seven areas. That are [00:41:00] critical to a senior leader job search and this tool is, takes about five minutes and will help you see where it may be breaking down for you and where you have areas to really level up.
Jackie Ferguson: That's so helpful because a lot of times, you know, we might think we know where the breakdown is, but we might be just guessing. Right. So that can be so helpful. And you know, I love the tools and the, the videos that you're offering because. You are right. Like there's so much no matter what the topic on the internet, right?
Right. There's so much information and half of it's saying, do this, and half of it's saying, no, don't do that. Mm-hmm. Do this. Right. And so you need to find credible. Sources of information on any topic, but especially this one, right? Where you can say, okay, let me go through these steps. Mm-hmm. Am I doing this?
What can I improve on? So I, I I love that. I [00:42:00] think that's so important. Deborah, what topics are resonating most right now on your YouTube channel? Uh, what are people struggling with?
Debra Boggs: Yeah, a few things. You know, interview questions always resonate on LinkedIn or on, uh, YouTube. People wanna know, um, how to answer common interview questions, how to get over certain hurdles.
Certainly, uh, compensation, negotiation, even if people are in the very early stages of their job search, they wanna know, how can I make more money? So all of those topics are interesting and then we lay around what. What we're seeing right now is how to make a career pivot. So we have a whole playlist right now on how to make a pivot because you, you have so many people either coming from federal government making a pivot, their industries are drying up right this second.
Other industries are booming and how do you, how do you transition from something you've always done into something totally different? And so that's something that we've find to be really popular on YouTube as well.
Jackie Ferguson: Awesome. Deborah, this has been such an insightful conversation. Thank you [00:43:00] so much. Tell us, what do you want to leave our listeners with today?
Debra Boggs: Oh, wow. Um, I've had such a great time in this conversation and so beyond have to be hyper-focused in your search. It would be that at this level and in this job search. Your old playbook is not gonna work. And so really thinking about the way you go to market is gonna be different. And so, you know, don't spin your wheels in those online applications where if you get an interview, they already have someone picked out for the job.
You really need to focus on your network and focus on getting in in different ways so that we're not constantly getting rejected throughout the process.
Jackie Ferguson: Absolutely. Deborah, thank you so much for such a powerful and practical conversation from redefining self-promotion to negotiating without apology, you're.
Insights are helping leaders take control of their careers and their values. So thank you so much. Thank you for having me. This was lovely.[00:44:00]
Thank you for listening to Diversity Beyond the Checkbox. This episode is produced by Walk West. If you enjoyed this conversation. Share it with someone who inspires you and leave us a review to help others discover the show. Follow us on Instagram or LinkedIn to join our growing community of change makers.
Until next time, keep pushing boundaries and building a world where everyone belongs. I'm Jackie Ferguson. Take care of yourself and each other.
In this episode of Diversity: Beyond the Checkbox, Jackie Ferguson talks with Debra Boggs—career strategist, Forbes honoree, and founder of D&S Executive Career Management.
Debra shares how she went from working in higher ed to leading a fast-growing company that helps C-suite leaders land their next big role. She opens up about mindset shifts, personal branding, and why networking isn’t optional—especially for underrepresented professionals.
In this episode, you’ll learn:
- Common mistakes executives make when job hunting
- Smart strategies for salary negotiation
- Why your LinkedIn profile might be working against you
You’ll also hear how Debra used coaching, self-awareness, and a little discomfort to grow from solopreneur to CEO of a 15-person team.
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Hosted by Jackie Ferguson, award-winning business leader, best-selling author, and co-founder of The Diversity Movement.