Better Business for Small Business Leaders

Erika Hill on Positioning Self and Closing the Generational Gap

• Chrissy Myers • Season 1 • Episode 28

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Confidence doesn’t show up on command; it grows after courage. That’s the heartbeat of our conversation with Erica Hill, the creator of Positioning Self—a coaching framework that turns soft skills into daily, practiced habits for interns, first-year hires, and emerging leaders. We dig into a two-sided model that pairs early-career professionals with mentors or supervisors who actively make space to practice, so growth isn’t left to chance or squeezed into yet another classroom.

Erica breaks down why “questionable” curiosity is a superpower when it’s grounded in self-checks, research, and safe, specific prompts that invite dialogue rather than trigger defense. We unpack how to transform questions into collaboration, move from fear to action, and build a “confidence bank” you can draw on when the stakes rise. You’ll hear how borrowing others’ belief can bridge the gap as you develop your own, and why courage—tiny, repeatable acts of it—is the real front door to confidence.

We also explore “sociable” networking that starts with the people who already know your work, then expands through warm introductions, volunteering, and one-on-ones that actually fit your wiring. Instead of generic advice, Erica’s micro-lessons arrive by text and include audio, written guidance, and live challenges designed to fit real schedules and diverse learning styles. For leaders, the takeaway is clear: if you can’t make the time to mentor, at least create the space—safe sandboxes, explicit invitations to practice, and support that turns potential into performance.

If building soft skills, smarter questions, and durable confidence matters to you or your team, this one’s a bookmark. Subscribe, share with a manager or mentee, and leave a review telling us the one soft skill you’re committed to practicing this week.

🎙️ Connect with Chrissy Myers and discover how resilience, expertise, and community can transform your world:

🔗 Follow Chrissy on LinkedIn for behind-the-scenes insights, leadership tips, and updates on her journey as the CEO of two thriving businesses.

📘 Grab your copy of 'Reluctantly Resilient' to learn how Chrissy turned challenges into opportunities and how you can do the same in your life and business.

🤝 Explore Clarity HR and discover how Chrissy’s team simplifies HR for small businesses, giving you peace of mind to focus on what matters most.

💼 Visit AUI to see how Chrissy's employee benefits expertise can help you build a healthier, happier workforce.

SPEAKER_01:

Let's start with who is confident in you and the reasons they're confident in you because you can borrow confidence also. There may be things that other people see in you that you either don't readily see about yourself or that you do see about yourself, but you discount.

SPEAKER_00:

Soft skills have the ability to transform your workplace. And today we are talking to an expert who can help transform your workplace by adding more soft skills into your work environment. So Erica Hill, thank you for being here today. Thank you for having me. So can you tell me a little bit about positioning self?

SPEAKER_01:

Sure. So just in the name, position positioning self, it's all about the individual that is doing the work. You know, when we think about career coaching, which positioning self is a career coaching series that is for early career professionals, we think about, oh, a career coach. I'm receiving career coaching. So that means that I can come to the table with all of my challenges and my woes and how this is not working and why is this not moving forward in my career journey. And positioning self is all about, okay, well, where are you in your career journey? Not where everyone else is, but where are you? And how can you better position yourself in order to get to the place that you want to be and accomplish the goals that you have? And so uh the positioning self program is all about where is the best place, where is the best position, where is the best purpose for yourself and what you want to accomplish in your career.

SPEAKER_00:

So positioning self has a unique structure. Can you kind of talk about what that structure looks like and then what you've learned about, you know, communication gap between generations and how positioning self is filling that gap?

SPEAKER_01:

Sure. So the framework of the program is uh it has two sides to it. So one is the early career professional, whether they are um a work-based learner, such as an intern or a co-op student, or if they are new to the workforce in their first permanent, full-time or even part-time position, or if they're an emerging leader who is new to um being in the forefront and um having a team hear what they have to say, follow what they have to say. Um, it is for that side. And then the second side of it is the support. And that comes from either their supervisor or a mentor or even someone on faculty that can help them see, okay, you know, in in where you're at with your career journey, this is either the next step to take, or this is the um approach that you need to apply to this situation. And so the coaching program provides support for both sides. It provides education for both sides so that uh it's not just the early career professional doing it alone or in a vacuum or in a silo, which is how most of us typically work. But becoming a professional, the only way to become a professional is to be a professional. And so that's a daily journey in regards to learning what that means for you. And so knowing that, okay, I'm not going to be by myself as I apply these strategies, that someone knows that I'm applying some problem solving strategies or communication strategies, and they're not taken aback or surprised. That's where that other side to where the supervisor or mentor or whoever that support person is can say, okay, I know what you're learning right now. You can practice on us, you could practice in this space, and you have my full support to do that.

SPEAKER_00:

What I love about your programming is it's it's creating collaborative dialogue, the opportunity to really work in tandem and alongside whether it's it's your intern, your new employee, your new team member, and kind of help them get engaged. You've got some interesting thematic names in your modules. Yeah, questionable, sociable, workable. So can you walk us through the philosophy behind a module like questionable? And really, I mean, my question is how do you teach an intern the fine art of asking insightful questions without seeming like they're challenging authority? Because that tends to be, I would say, an opportunity for growth oftentimes within new working relationships.

SPEAKER_01:

Yes, definitely. So the the terms that the modules are named after, um, some of them are actual terms, some of them are made up, but they definitely speak to, okay, this is what's going to be discussed um this week in this module. So if you take questionable, the program is all about self-awareness and self-reflection and strategies to position yourself. And so when you think about questionable, you do readily think about, okay, how can I ask someone else questions about whatever they're working on, whatever they're uh um speaking about or delivering to me. Um but you can start with, okay, what questions can I ask myself? Um as I work on a task, um, let me question the work. Let me question my own work to see if it's uh rid of mistakes, rid of uh incorrect information, rid of anything that is not um that should be in that, in that work. So let me question my own work first. Let me question if this is a valid question to ask someone. Could I have Googled it first? Could I have done my own research and demonstrated that I've gone this far in my research or in my investigation and now I need assistance? And so that question is a bit more relevant and shows the work ethic in real time to say, I've done this is as far as I can go. Now I want to bring someone else in, and that will help the other person say, okay, that makes sense. Yeah, I'm ready to come in. If it's something that's being delivered in a team meeting, um, a new initiative or a new directive, having a conversation, you can get curious about what that new initiative is. You could get curious about a process that's been in existence for 10 years but needs some improvement. Okay, I'm curious about this. How does this work?

SPEAKER_00:

Yeah.

SPEAKER_01:

That's a good question. That's a safe, secure question that someone can be comfortable in answering. And then as you have that dialogue, then it gets into answering maybe some of the questions that you have about what is not working the best way or what can be improved, or here are some suggestions. Have you thought about doing it this way? And so it's less about attack, it's less about um coming at um the issue or addressing something. And it's more about how can I become curious based on the position that I'm in so that people are comfortable in having this dialogue with me as you do break down or or pick apart what's on the table, but it's in a constructive way to where everyone benefits from having that conversation.

SPEAKER_00:

There are so many positive ripple effects to the work that you're doing in this type of training and development. Because while it is, it's a simple concept of, you know, how do you ask the right questions? There is a significant amount of value for the organization, especially as those individuals, as they become more educated, become more aware and skillful around how to ask questions, how to have dialogue, how that company can grow. So I appreciate the work that you are doing in this space. Thank you. Yeah. So what is one of those single biggest soft skill deficits that you see at this point? I know that they're, I mean, when we're talking about interns early on in career, I don't like to think about it being a deficit as much as it is like just lack of awareness. But as you're seeing the trend, what is the trend around, you know, this is something that we're seeing needs to be addressed, you know, is what and um what are you addressing in the program directly? That's that's that maybe significant deficit.

SPEAKER_01:

That significant deficit, that soft skill that is lacking, um, that you could bet money on is confidence. Oh, tell me more about that. And so, you know, when I think about confidence, a lot of times it doesn't come until the back end. It doesn't come until after you've gone through a situation or after you've worked out a challenge. On the front end is the courage that it takes to um address a situation or to move beyond the fear that you have to um play your part in a situation. And so until you have, you know, take that courage and get into the thick of it, you won't be able to fully have the confidence after to say, I actually survived, I actually uh thrived, I actually accomplished something that I didn't think that I could do. I moved past my fear, it's not as scary as I thought it would be, or it is, it was just as scary as I thought it would be, and I did it anyway. But it's definitely a valuable place that you want to get to, that you want to strive to get to to build a bank of confidence because you take that into the next situation because there's always going to be a next situation. So, in order to do that though, that situation that you're navigating, you want to have the right tools and strategies to navigate it. You want to have the support to navigate it so that you can get to the other side to build up that confidence bank that you could take into new job opportunities, new uh freelance opportunities if you work for yourself. You want to have that bank to say, okay, this is a situation I've been in before. I already know how to approach it, or this is a situation I've never been in, but I know that I've had the confidence to overcome something just as scary or just as severe. And so let me, you know, lean on that. And a lot of times I even had a student ask me, you know, I'm not really confident in a certain situation that she had with her team. And I said, well, let's start with who is confident in you and the reasons they're confident in you, because you can borrow confidence also. There may be things that other people see in you that you either don't readily see about yourself or that you do see about yourself, but you discount it.

SPEAKER_00:

Yeah.

SPEAKER_01:

And so looking into, okay, let me take stock of what I already know about myself that I can be confident in and stay aware of that to add to my confidence bank. And what are other people saying that I may shoe off or dismiss that I really need to take a critical eye to and say, let me add that as well, because I need all the confidence I could get. We we all do.

SPEAKER_00:

Yeah. Dan Sullivan, so creator strategic coach, talks about how the most important thing that we can protect in entrepreneurs is their confidence. So as you're talking about it, I'm hearing you, you know, we're talking about it with interns, with lower level or entry-level employees, but those ripple effects are so important. I feel like while you're teaching some of these soft skills and it's a collaborative approach, there's so many ripples that that echo back to the business leader that can kind of be a reminder of the things that they need to do also moving forward. And I'm also hearing you going, I wish I would have had this.

SPEAKER_01:

And I was absolutely early on in my career. Well, even in you saying that you wish you would have had it, it readily made me think, you know, we don't get any older in regards to having to face a challenge or having to get through a situation that doesn't get old. We haven't arrived to say that, okay, now we can conquer the world and we can solve all the problems, and there's nothing that we can't handle. And everyone should come to me for every you know, way to approach a situation. That that is not true. That won't happen. We don't arrive fully. And so we're always in a new state and a new problem. As we advance in our careers, as we become more successful in our businesses, we still need to add to that confidence bank. Yeah, that doesn't get old.

SPEAKER_00:

No, I'm waiting for that like achievement unlocked where you don't have to do anything. Like it's just always there.

SPEAKER_01:

It doesn't seem like it's the we're all just just cutely naive in that era to where we want to have that hope that okay, one day I can sit down and rest on this, and that day never comes.

SPEAKER_00:

No, constant, continuing improvement. Yes. So let's talk a little bit more about the delivery system that you're using. So you're talking about in your programming micro lessons, how they can be impactful. So can you kind of talk about what that interaction looks like within the program?

SPEAKER_01:

Sure. So for the early career professional, we try to meet them where they're at in the workplace. And so who knows what hours they're working, what their schedule is, if they're balancing school and other responsibilities. Uh, who knew, who, who knows, you know, if they have exams coming up and they may be a little checked out uh as they're on the job that week. So we instead of pulling them out into a classroom, another classroom setting, and telling them what they need to know and hoping that it sticks, the program meets them where they're at by sending them a text message. And that text message has a link to a page where they learn about the lesson. And it's in a couple of different forms. So they can read about the strategies for that lesson or they can listen to an audio clip. You're hitting the learning styles. Absolutely. Every p everyone has their own unique combination of learning styles, and so they can select the ones that suit them the best to where they can process the information, um, where they can understand what it's, you know, what it's about and they can process it. And also with the lesson, the lesson are actually challenges. And so it's not just learning um something that you may already know and just being reminded of. It's asking you to put yourself in a position to where you can practice this uh soft skill. So if it is about a questionable module, then let's put yourself in a situation to where you are learning about a process, you're seeing everything that's wrong with it. How can you voice your input in a constructive way? Well, let's ask someone can you walk me through what this process is and what it's about, what it's for, what are the steps to it? And then as you had that dialogue, you can point out areas. Oh, okay, well, I've done this part before. Instead of it taking me five steps, steps, it only took me two. And would you like to know how? And so that is a form of taking on that challenge of being questionable. So there's three challenges to choose from. You could choose one, you could choose all three, and you can understand, okay, which one works best for my work environment, for the my own work style, my personality. Um, there, whether I'm remote or in person, there's really no excuse to not take on one of the challenges for the week.

SPEAKER_00:

I love it. So you've had diverse work experience. You've you've been in alumni relations, you've built, um, you've been in community engagement. You have built your career around connections and building relationships, and you have a deep understanding of really how to foster networks. So I, one of my favorite modules for you is sociable. I'm looking at the program. So it's about building that professional network, building that group of people. It differs from the typical like go-to networking events. So, um, what is the difference between the things that you're doing with sociable versus what people would say those traditional things that interns often get from a networking perspective? What's your unique take on it? I'd love the listeners to understand that. Sure.

SPEAKER_01:

So, you know, I love to network myself. Same. Um, it doesn't mean I love to be in every networking environment. Absolutely not. So, you know, as far as seeing familiar faces is always helpful uh when you come into an environment to where it's a small group versus a larger group, you know, you have to assess, you know, how am I gonna find my comfort level or how am I going to regulate myself in this environment? And so again, that all starts with self-awareness and self-reflection and what strategies can I apply to how I'm wired and how I'm made up. So with the sociable module, you start with your own network. And your network should include your siblings, it should include your mom and dad, it should include your teachers, it should include your fellow students or your fellow colleagues and people that you see every day. Those who you see every day know you, they know how you work, they know your personality, they should know a little bit about what your interests are and what you're working on. And so that's a ready-made starter, um, no matter how small it is, for you to get comfortable and practicing saying, I'm pursuing this scholarship, I'm pursuing this job opportunity, I'm pursuing this client project. Can you give me some pointers or can you connect me to some people that you may know that can help out in this area? And so start, and we all need to start with what we have and whom we have in our access. And so that's one way to network. Another way to network is to get comfortable with saying what your passions are, what you're excited about. And that could be directly tied to where you want to go. It could be indirect as far as what your hobbies are. If it's playing pickleball, you may be invited to go play pickleball and meet someone there that can help with one of your uh tasks or one of your projects that you're that you're passionate about. If it is, you know, you're at work and you want to have a meeting with an executive and you can ask your boss, hey, you know, I want to learn more about this area while I'm here at this internship. Can you help me? Can you introduce me so that I can schedule a meeting with this other person? Because I would love to connect with them before I leave. And so again, this is just starting with what's beside you, who's beside you, so that you can continue to grow and develop that bank of people that can be a good resource and a variety of resources for you in your network.

SPEAKER_00:

Yes. Learning to advocate for yourself, I think is so important. I've I've in some of the connections that I've had with young people, individuals that are young in their career, there's always been that conversation. Well, I'm an introvert, so I really don't know how to build relationships or I don't want to go to a networking event, or I don't like there's that there's that shrinking, and you can see those individuals that that have so much potential, but without having some of that coaching that you're providing, just knowing that it's a simple formula, you know, it's it's understanding that it may be uncomfortable for a moment, but what you can do to move yourself forward. So I really appreciate the work that you're doing to help people kind of break out of their shell, continue to see where those skills can take them. And I think that as an entrepreneur, as a business leader, when you're we're you're working with people that are a little bit um newer to their career path, being able to give them those steps and show them the right spaces to be able to walk into and how to have those conversations is so vitally important.

SPEAKER_01:

So And it is about the right spaces because we should take a moment to list out what we don't like or what we're not comfortable with or what isn't of interest to us. We should stay there for a moment.

unknown:

Yeah.

SPEAKER_01:

And then we should move on to okay, well, what is the opposite of that? You know, what you don't want, what do you want? Yes. And that may help a springboard into the list of what we do want. And so if you are someone who is a bit shyer and reserved and doesn't do well in a large, you know, space of strangers, then maybe it's better for you to volunteer and be a member of a team that works on a cause that you're passionate about. And that way you can slowly get to know people. You're already there for a purpose, a common purpose that you can lean on to talk about and for people to readily want to meet you because you're all there for a whole reason to say, okay, we've come together, we don't know each other, but I feel comfortable in talking to you because I know you're here for the same reason that I'm here. So that may be a different strategy for you as a form of networking. Volunteering is a form of networking. So definitely the right place. You're right, is is what we all need to know about ourselves.

SPEAKER_00:

Yeah. So as our uh individuals are listening today and they want to connect with you, they want to learn more about the program, how can they do that?

SPEAKER_01:

So they can go to careerlog.co and that's that's the website, careerlog.co. And I have three positioning self-programs. Again, this is for early career professionals, whether they are in a work-based learning environment as interns or co-ops, or if they are new to the workforce in their uh career year one is a program that I have for those who are in their first full-time position. They know they're in a first full-time position, their supervisor, they may or may not know they're in their first full-time position. Definitely an interview is a place where we're all sort of playing a part. Yeah. And it's usually an acting part to get the job and for the employer to assess if this person is the right person to be in this role. But once you're in that position, that interview's over. Yeah. The acting role is over. Yes. And now you're needing to be your true self. And some people come in and they have all the technical skills, but they may not have those interpersonal skills. Yes. Or they may not know how to advocate for themselves, or they may not know how to present as well as you want them to. And you may say, Oh, I don't know if I hired the right person. Well, you may have hired the right person, and now they just need some more professional development. And are you willing to invest in them? Are you willing to redirect them to a program that can help them make a good start to their first year on the job? And so that's where the career year one program comes in. And then I have a program called Up and Coming, and that's for the emerging leaders, for those on your team who you see has a good influence on the people around them. They have, they serve as a resource, as a contributor that people count on, and you want them to grow and advance. And so this is where they can build up their professional development as an emerging leader.

SPEAKER_00:

Wonderful. So, last question, question we end every podcast with. How can business leaders get 1% better in their business today?

SPEAKER_01:

If they don't make the time, at least make the space for their team to develop and grow. And that is one area that I get a lot of feedback on from employers is that I just don't have the time to mentor. I just don't have the time to check in and make sure that these new hires are good. Okay, that that's real. That is real life, that you may not have the time. And it's a challenge that you have to choose to take on if you're gonna make the time.

SPEAKER_00:

Yeah.

SPEAKER_01:

But even as you work on that challenge, because that doesn't happen overnight, at least make the space. At least make the space for them to have uh a sandbox to play in and to practice and to adopt best practices that work for them and work for your organization. Because you you will all be the better for it. So make the time or make the space for them to develop as professionals.

SPEAKER_00:

Erica, thank you for your time today talking about making space, making time, and continuing to help develop the team members that that we need to want and grow as business leaders. Thanks for having me, Chrissy. I had a great time.