Hey BOSS Ladies

How to BOSS Up and Lead With Purpose with Cheryl Powell

• Candice Dorsey

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Hey BOSS Lady,

Welcome back to another episode of Hey BOSS Ladies podcast. 

Today, we’re joined by Cheryl Powell, CEO of Learn to Engage, a powerhouse in the learning and development space with nearly 30 years of experience helping organizations transform how they train and support their people.

Cheryl opens up about:

  • Her transition from full-time contractor to full-blown business owner
  • Why being a mom to a special needs daughter gave her the push she needed to create her own path
  • The challenges (and wins) of finding the right audience and pricing her services with confidence
  • How poor leadership causes team disengagement and high turnover, and what to do about it
  • Her mission is to help leaders truly see and support their teams

This episode is filled with practical wisdom for anyone leading a team or building a business. If you’re navigating growth, team development, or looking to create more meaningful impact in your leadership style, this one’s for you.

Connect With Cheryl:

Website: https://learn2engage.info/

Email: info@learn2engage.info

Instagram: https://www.instagram.com/gc_learning/

Podcast: The Learning League Podcast

Promotion:

Now offering a new L&D Training Manager for Hire service with packages as low as 5 hours per week | $2000/mo. It's for organizations that cannot afford to hire for this $150,000 salaried role, but still have specific training tasks they need help with, such as retention strategy design, onboarding audits and redesign, or remote workforce process setup.

💼 Ready to grow your network, amplify your voice, and actually plan collaborations that move the needle?

Join us at the next Hey BOSS Ladies: Connection + Collaboration Hour
✨ Register here → heybossladies.com/event

Let’s build relationships that build your business.
Now’s the time. Let’s BOSS UP. 🔥

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Hey boss lady. Welcome to the Hey Boss Lady podcast. We're real conversation, powerful connection and intentional growth collide. I'm your host, Candace boss, founder, community builder, and your biggest hype lady around here. We don't do surface level. We talk strategy, systems, success, and the real stuff that happens in between. Whether you're tuning in on your morning walk during that client work, sprint. For a late night hustle session. I'm glad you're here. Let's get into today's episode and boss up together.

Candice Dorsey:

Hey, boss slaves. Welcome back to another episode of the Hit Ball Slave podcast. I have the boss lady herself, Cheryl Powell, CEO, of Learn to Engage. tell everyone who you are and what you do.

Cheryl:

Uh, I am CEO of Learn to Engage. I actually started out as GC Learning Services, but once I became a S Corp by rebranded, so now we're learn to Engage. That was 29 years ago that I started. And uh, we're a learning solution provider is what I like to call it. So everyone has a different solution based on what their industry is, what their organization does. and so it could be virtual training, it could be, training manuals. It could be e-learning. But I will say that our niche is definitely interactive, e-learning.

Candice Dorsey:

Oh, I love that. I love that. When I was working a full-time job, I loved the interactive learning part of things because I couldn't stand like reading all the texts that they had for us to do.'cause I worked for a financial institution and. We had to stay abreast on all the regulations and everything. So just reading that and then taking the test, I'm like, Uhuh. So they started implementing like interactive learning and everything. I was like, yes, I love it.

Cheryl:

text on the screen. I hope

Candice Dorsey:

Yes. Oh, so much better. Yes, it is. It is. So tell us, how did you get to Boss status and what was that journey like for you?

Cheryl:

Boss status. I actually never thought of myself as a boss, but but I guess it started as a contractor. I was a corporate trainer for many different organizations. But the last one I remember was Bristol Myers Squibb, which is a pharmaceutical company in New Jersey, which is where I'm from. And if I really think about it, was my daughter that really pushed me to that status because I had a special needs daughter and I had to leave for work a lot, at one point it was something going on she was sick or something. they told me, well just get a neighbor to go get her. I need you to stay late, but a neighbor. I said, no, it doesn't work that way, you know? and so that was really for me the push that I needed to go off on my own.

Candice Dorsey:

It's always something in your life that give you that drive to

Cheryl:

Yes.

Candice Dorsey:

something bold and generally it's family.

Cheryl:

Yep.

Candice Dorsey:

Yes.

Cheryl:

it was the best decision I ever made. It, it just allows the freedom to live your life on your terms I've, I would never. Do it any other way, honestly.

Candice Dorsey:

I love that. So what's one pivot that surprised you the most and saw and taught you something game changing about yourself?

Cheryl:

I guess for me it was really. Maybe about five years ago, just identifying my audience. I really was able to reach a whole nother level just by narrowing down not only my audience, but my niche a little bit more that's really the work that you have to put in for probably many years to really get it right. It's not something that you can just overnight. It's just not, it's it, you have to take the time and do the research. So I think once I realized that leaders were the main people that needed. type of guidance for their teams. I think that my learning solutions, my social media posts, my podcasts, they all just came together.

Candice Dorsey:

That's good. That's good. Yeah. That's the hardest part. I'm in it now and I've been in this since, I've been in this a long time, like the online everything and trying to. Down, who you talking to? Your messaging and everything. They talk about that, but I'm like, can you please show us how to do it? But you have to be in it and doing it,

Cheryl:

I still talk to, it's so funny, I still talk to companies that have been in business for like 20 years and they're like, yeah, we just service everybody. I'm not just like, how do you maintain that? It's, that's, it's, that's hard. You can't say you help everybody, and so that's what I had to learn. That's, these are not your people over here. Because I spent a lot of my early years like focusing on small businesses and they were like we only got$500, and I'm like I can't give you all this with the bells and whistles and, for$500. It was a lot of, haggling and stuff, and that's where, you know that's not your audience.

Candice Dorsey:

Yeah. Yeah.'cause if it's a struggle bus, like I mean, you know, if you keep getting like a lot of pushback and they're not within the budget and everything, or they like, oh, can you decrease your prices? Or something like that, you're like, this isn't for me yeah. Yeah. A note to the audience out there, everyone who's listening, definitely work on niching down and finding your people. That is so important. And definitely work on your messaging as well. It'll take time. Maybe take a couple of years, but you'll get there.

Cheryl:

that's right. It takes research. I

Candice Dorsey:

Yes.

Cheryl:

do a lot of research. Of course, it was not, I wasn't using chat GPT when I first started. It wasn't out. So the research was real research,

Candice Dorsey:

Yeah, tell me about it.

Cheryl:

a button.

Candice Dorsey:

Yeah, that's another conversation. Chad, DTP.'cause it saved me. It did

Cheryl:

right?

Candice Dorsey:

Oh my goodness. Yes. So let's dive into your mission. Your mission to inspire leaders to truly see their teams, to listen actively and follow through. Can you talk more about that?

Cheryl:

Yeah. So, I don't know if a lot of people are aware of this, but. 86% I believe it is, of a screening on LinkedIn of employees said that they were miserable at their job. most of that is from really not being seen, feeling invisible and not feeling heard. And so. in conjunction with my main goal to reduce turnover and improve productivity, right? This mission is what drives it, right? So we really need to focus on, how we're making our workers feel, honestly because that's why they're miserable. So if you are just assigning tasks. And you're never following up and you're never meeting with them to ask how you can help, how you can support them, or what their goals are. Are they looking to upskill advance, just learn a new thing. Not everybody wants to advance, right? If we're not taking the time to do that you're, going to. your turnover rates or your productivity.

Candice Dorsey:

Yeah.

Cheryl:

Yeah.

Candice Dorsey:

Oh, this is dead on because I've, I just left corporate in 2023. Yes. I just left, I left corporate in 2023. And it was the same thing. It was the same thing. It was more, it wasn't more about my goals, it was like the goals that they set for the department and how each one of the team members, they each had a goal. If they wasn't hitting it, it's let's what they call pip them the performance improvement plan. I'm like, no, we're not doing that to my team. I was like, not here. I was like, no. And they wonder why my department. Had less turn less turnover. I'm like, because it's about people. I'm like, if you don't have people, you don't have a company. Come on now. They're the ones that's running it. So I, yeah, I get it 100%. So I think a lot of leaders definitely need a come to Jesus moment,

Cheryl:

and one of the things that I teach in one of our leadership programs is about partnering with your teams, right? So be somebody's to help them achieve the goal. Don't tell them what to do all the time. Let them. Give you suggestions, right? Just listen and encourage and provide the necessary support.

Candice Dorsey:

Yeah, I agree. Hello?

Cheryl:

Than a micromanager.

Candice Dorsey:

Oh, I've been there. Oh, I could write books about that. I have so many matches that was like that. I had to just be like. Hold up, chill come on.

Cheryl:

Yeah.

Candice Dorsey:

Yeah. And I promise that I'll never be a leader like that, ever. It's, it is a learning it is a learning lesson. You being in it and you actually being the person to lead. They didn't understand my lead, like my. Management supervisor style, and they was like, why aren't you doing this? it's like, no, that's not what it's about. Come on now and don't give us a pizza party when you know we hit the numbers. You wanna give us a pizza party? What is that all about?

Cheryl:

I don't know.

Candice Dorsey:

Oh my goodness.

Cheryl:

something that they think everybody wants.

Candice Dorsey:

Yeah, that's crazy. Oh,

Cheryl:

want recognition more than they want pizza,

Candice Dorsey:

you right about that. Yeah. Yeah. So as you know here at Hate Boss Lay, we're all about connection and collaboration. What type of collaborations are you looking for right now?

Cheryl:

Oh, I

Candice Dorsey:

I.

Cheryl:

collaborations with those in hr. People, leaders are great if they have decision making power. if they have to revert back to HR to get approval for their budget, then you know the logical solution for us would just be to focus on hr. So those of you who are in staffing, you have HR for hire firms, fractional firms. Anything like that, we'd love to step in and just accompany your expertise with quality training.

Candice Dorsey:

I love that. I love it. So how can people connect with you?

Cheryl:

I am all over LinkedIn, Twitter. Uh, YouTube. There's, a million ways to get in touch and um, our email is info@learntoengage.info. Our website is learn to engage dot com. it's learn the number two, engage. Don't put to but we would just love to hear from you. We offer free sessions, free assessments. Free consults. So you know, we're here to help.

Candice Dorsey:

Awesome. Yes, we'll definitely link those up in the show notes. Well, Cheryl, this has been really, fun. I love conversation with you. Really sparked something in me when we talk about, you know, leadership and I'm like, yeah.

Cheryl:

yes, it's been the hot topic, for the past year now, so I've been doing a lot of. Carousels and videos and stuff like that on leadership lately.

Candice Dorsey:

That's good. Well, I truly do thank you and appreciate you for that.'cause this is definitely something that needs to be, people need to be aware of as well.

Cheryl:

We want everybody to be happy.

Candice Dorsey:

Yes.

Cheryl:

it should be a win-win situation when we go in and do a learning solution, like a win for the stakeholder, right? They get their numbers and a win for the employee. Because we do thorough assessments and we listen and we, we don't do anything. Storytelling and e-learning is great, but if you don't have the metrics and the input. From the people. There's not gonna be any performance impact at all.

Candice Dorsey:

Yeah. Yeah. No, that's true. That is so true. Thank you so much for being on today.

Cheryl:

Thank you so much for having me. This has been great. Love it boss lady.

And that's a wrap for today's episode of Hey Boss Ladies, if you love what you heard, don't forget to follow the show, leave a review or share with a business bestie. And if you're ready for deeper conversation and powerful connection, join us inside the hey boss ladies collaboration experience happening every month. The link is in the show notes below. Until next time, stay bold, stay brilliant, and keep showing up like the boss you are.