Scaling With People
Tired of spinning your startup wheels but never gaining traction? Buckle up, founders and CEOs, because this podcast is your rocket fuel to profitability! Every week, we ignite explosive conversations with bold-faced founders, brainy experts, and even a few out-of-this-world vendors. Get ready to crack the code on growth, master employee engagement, and blast through your scaling goals. We’re talking real-world strategies, actionable tips, and perspectives that’ll make your business do a cosmic dance. So, strap in and prepare for lift-off!
Scaling With People
Inclusive Leadership: Turning Noise Into Team Power with Kelli Lester
Micromanagement can’t fix burnout, noise, or fragmented teams—and perks won’t, either. We sat down with inclusive leadership expert Kelli Lester to show how clear vision, better questions, and real follow‑through unlock performance across stressed, remote, multi‑gen workplaces. From aligning on what “empowerment” actually means to closing the loop on engagement data, we unpack specific plays you can run this week to build trust and ship results.
We start by reframing the manager’s job: know your people as individuals, not personas. Kelli shares practical ways to discover what motivates each person—recognition, time, money, learning—and how those drivers shift with life stage. We dig into remote realities where new hires change team chemistry and “breaking bread” moments are rare, then map out rituals that create connection on purpose: pre‑reads for introverts, rotating facilitation, designed in‑person time, and consistent one‑on‑ones that end with clear commitments. We also tackle proximity bias and why visibility must be engineered, not left to chance.
The heart of the episode is a simple engine: ask, define, decide, and deliver. Ask better questions than generic surveys. Define shared terms like respect and empowerment so expectations are aligned. Decide on actions that leverage strengths as much as they fix gaps. Deliver by closing the loop—communicate what you heard, what you’ll do, and what won’t change. Along the way, Kelly explains why self‑awareness is the top leadership skill, how to amplify quieter voices without putting them on the spot, and how pairing diverse thinkers produces stronger decisions and faster execution.
If you’re building fast and want your culture to compound, this conversation is your blueprint—practical, human, and immediately usable. Subscribe for more bold, unfiltered strategies, share this with someone scaling a team, and tell us: what does empowerment look like for you right now?
Welcome to Skilling with People, your weekly playbook for turning chaos into compounding growth. Each week we go under the hood with Bible test experts in all areas of business, from marketing to sales, operating finances to sports, as product and leadership, to unpack the plays, numbers, and systems that turn chaos into compounding growth. Learn straight from founders and experts who've done it and continue to do it successfully. There's zero plus, just moves that you can still immediately. This podcast is brought to you by Guide to HR. Human expertise, AI-powered impact. Welcome everyone to today's Skilling with People podcast. I'm Gwynnivre Cruy, your host and founder and CEO to Guide to HR. So, what's the secret to getting the absolute best out of your people? Hint, it's not micromanagement, ugh, I don't even want to say that word, or flash perks. This week on Skilling with People, we're joined by Kelly Lester, co-founder of Onyx Rising and a master at transforming teams through inclusive leadership and crystal clear vision. So we're going to unpack today how to tap into what truly drives performance, creative environments where people want to show up and contribute and grow. We're talking employee engagement that goes beyond surveys, leadership that brings out potential and strategic visioning that aligns everyone on the path to scale. If you're ready to lead in a way that actually unleashes your team's full power, not just managing it, this is your blueprint. So let's dive in. Kelly, it's so great to have you on the call today. Tell the audience a little bit about yourself.
SPEAKER_01:Thank you so much for having me, Guinevere. My name is Kelly Lester, as you mentioned. And just a little bit about me. I have been in the space of change for 25 plus years. But I did start my career in media for a decade, thought I wanted to be Oprah. Didn't work out. You all know me already. But long story short, that that particular grounding around communication was really useful when it came to really communicating broadly in organizations. So for the last 25 years, I have been in human resources, done specific work as a strategic consultant and director of diversity and inclusion inside organizations. And then for the last 15 years, I've been consulting, went off on my own, and here we are.
SPEAKER_00:I love it. Okay, so let's dive into this. How in this particular environment that we have today, technology, the social media, the environment outside of our own countries, the safety of people, the health of people, I mean, so much that we could probably spend an hour just listening to all the things that are happening in today's society. But in a business setting with all of that going on people's minds, they're bringing it into the office. How does a manager and a leader get the most out of their people when they are so stressed out about what's going on and they're taxed already? They're already like max capacity. I could probably keep going, but I'm gonna get you, give it to you, give you the floor and help me answer this question.
SPEAKER_01:Yeah, absolutely. That's a huge question, right? Um, so no doubt we are all faced. I think it's too much noise, right? It's just too much noise. And um, we also have an environment just externally from our organization where we're being pulled in many different directions. And it's thought that we should just leave all of that at the door, right? But people cannot. And so um I think we went from a phase of calling work-life balance to work-life integration. And I would say post-COVID, uh, we really have to understand what that looks like. It has changed cultures dramatically, how we dress, how we lead, how we develop, how we look at promotions. Um, and then you add the complexity of the younger generation into the workforce and with multiple, four, sometimes more generations working together with very different expectations. This is super difficult. So if you're struggling with it, you're not alone. A short answer to it is inclusive leadership, quite frankly. Um, so I believe it's actually a twofold answer. So one would be what can you do as a leader when leading your teams or your people or your organization? And then what might the organization do? Um, so I'm gonna start with the leader, right? Because many of us don't feel like we probably can lead our organizations um without the help of our teams or our CEOs or our leadership teams. So, what can you do individually? The first step I think is really understanding who your people are and what their motivations are and what their career aspirations are. Um, and I wouldn't say that this should be done by someone else. So I think a lot of times leaders actually point to HR, point to DPI practitioners, point to, you know, this is your job. No, leading people is part of your job. When you move from an individual contributor to a leader, a lot of organizations are not equipping leaders for that. And we are ascending almost to the C-suite, and we still don't have that skill. Um, so really, what does it look like to really know your team? I liken this a lot to a family. Um, so for example, I have two children, um, a girl and a boy. They couldn't be more different. Um, one is a super extrovert, the other is a super introvert. And I always tell this story how I wanted them both to go to college, but what it took for them to really be motivated to do so was a very different path, even though the objective was the same, the goal was the same. And so what it looked like for my son, it was very easy. It was just push him along, send him down a different path. With my daughter, it took a lot more conversation around, well, what do you want to do? Let's let me go with you. What does it look like? What are you most interested in? How might I tie those things that you're interested in into potential careers? How might I connect you with people? So it was a much uh different path. And so when we think about our teams and our organizations, we have to see people uniquely for who they are, and we cannot push upon uh them what worked for us in the 90s, right?
SPEAKER_00:That's an age us.
SPEAKER_01:It also is not a great business strategy, right? Because if you're developing people based on what worked for you, they will fail today. If you develop people only for today, you won't necessarily achieve your objectives in your business. So you really have to look at your future self or your future organization, your future talent in that uh individual. And I think another big thing is that when we add people to our teams, we have a new team. And I don't think leaders really get that. Like when we have a new team member added, there is a need for additional team building. In this environment, I have uh worked with clients where the direct report has never seen their boss in person, and and that is not in common anymore. And it's a lot easier to build a team once you've been in person and now you're remote versus what I've been dealing with with a lot of my clients post-COVID is yeah, they've never met.
SPEAKER_00:And so there's that breaking of the bread moment with someone is such a key relationship builder.
SPEAKER_01:It is, and so we have to be strategic about what does it look like to build team and take advantage of those of the moments that matter. Um right, we bring everybody in for an annual meeting. Are we building in dinner? Are we um and then uniquely, and think about it like this we all have cable, most of us, right? Um, and even the channels that we select, right? Is very much in a space that it's uniquely what Guinevere likes, what Kelly likes, even Netflix has your own profiles for everybody. Very similarly, we have to really understand what are the motivations for team member A, B, C, D, right? And how might I give them feedback? How do um, you know, I would I motivate them with money? Do I motivate them with events, time off? And it's very different when you start looking at the generations as one aspect um alone, right? Many of uh younger Gen Z millennials in particular, uh, haven't worked with a ton of Gen Z. It depends on the culture, some some tech cultures I have. Um, but when with millennials in particular, they want time off and they're not like Gen X uh or boomers where we will just wait our turn. They're not, they will leave your organization if people aren't really looking at your people strategy where it looks at the uniqueness and the need. Uh, career uh development. There was a time, I think, early on, where um, you know, people with you get hired and people say, okay, and this is what you're gonna do next, and this is what you're gonna do. You know, we don't have that anymore. There's a lot of ownership on the individual to own their own career, but the organizations aren't providing the career pathing understanding. And so the default is that you end up with cultures where they're the way we build relationships is informal. So if you're not close to leadership, the proximity bias, right? You're not promoted, you're not getting exposure. And so when you think about global teams or remote teams, you really have to make the time. And I think we did a great job in the United States in particular, at least what I've seen during COVID, but post-COVID, I'm hearing some of our CEOs say, everybody come back to the office. And so we're so hard to hear that. Right. We went back to business as usual, and that business as usual could really mean um a potential dip or failure in your business strategies and your goals.
SPEAKER_00:Well, and too, like I've worked with one CEO who is like, he wants to do that, but he also recognizes that he doesn't have the power of an Amazon or a Wells Fargo, right? Like he's not a big organization that has that power that knows that, like, well, their brand can go out and hire five more people tomorrow if five people walked out the door and or not walked out the door, it never came through the door, right? So you also got to understand what your buying power is, what your brand is, and what you need out of your people and what's gonna be the right culture fit for you.
SPEAKER_01:Yeah, absolutely.
SPEAKER_00:Yeah. So uh I love this inclusive leadership mindset. And I I think about it too. Like I I've kind of shared, you know, post-COVID, it's really been all about, well, I should say pre-COVID's all been all about the employee has to get figure out their manager and has to work towards basically like what the manager needs. And then COVID happened, that really shifts to as a manager, I now need to figure out what is each individual need. And it goes to that inclusivity leadership. And you're right, like people are motivated by different things. Now, you have a sales org, most likely the majority of those people are all gonna be motivated by money, right? But outside of that, in any other kind of org or or department function, it's probably gonna be a mixture. And it's gonna be depending on where the person is in their life, what's happening. Maybe, maybe they are motivated by money because they want to get engaged and they want to buy a house and they know they want to have a baby soon, right? Like, so that might be their motivation in that moment, but that might not be their key motivation over their entire career. So it's not even just understanding who they are as a human being, but where they are in their lifespan too.
SPEAKER_01:Yeah, and it's a great point. And I think, you know, a simple takeaway or strategy, and this is going to sound really interesting because people are like, what is ask. Um, I'm working on a project right now. So I do work with for-profit and nonprofits. The particular uh study and project I'm working on is a health equity study. Um, and the they coined the phrase, I believe, the community is the expert, right? Uh and I love that concept because if leaders begin to understand that the expertise and the answers to our business problems, to how to motivate people, it really lies within our people. But we typically ask. So we either aren't asking or we're asking the wrong questions. So many bigger organizations, even mid-sized, we do engagement surveys. Um, and I don't, and and some of my clients do pulse surveys as well. So, which I really trying to measure belonging, for example, I'm seeing that being done quite a bit now. Um, so they'll ask pulse questions every quarter, right? Um, so I ask a lot of my uh clients, and particularly uh the HR leaders, to really take a look at what your trends have been in those surveys and really understand where your weak points are and then understand where your uh your you know your greatest strengths are. Um I think a lot of times uh HR leaders have been uh taught to look at what's wrong and fix it, um, but we don't look at what's right and leverage it. Um so on organizational level, I recommend that leaders and organizations really look at where, you know, do a heat map. What do you do well, where were you weak, and then create strategies for both.
SPEAKER_00:Well, so analysis a little bit, right? Your strengths and weaknesses.
SPEAKER_01:But what we see is like action teams on what did wrong, right? Yeah, so I but versus like let's match a great leader with uh an leader that has some opportunity because why we'll listen to our peers better than we'll listen sometimes in you know in any other direction. Um, and then actually it moves moves things forward. But the whole point is ask. And so ask at an organizational level, at a survey, you know, being being very particular about what are those muscles that we want to build in our culture, and then answer questions that way, and then ask within your teams versus make the assumption, like you said, I'm at a different stage in life, and then you just prove continuously ask. So something as simple as how you structure your, you know, perform. I mean, I'm sorry, your one-on-one meetings, your performance reviews, uh, those kinds of conversations, um, where you have them. Do you do one quarterly, like you said, the break bread moment? Um, at least try to meet in person uh at a minimum, uh, one-on-one with each staff, and do that consistently across every group. For example, if I you um if I only see Guinevere speaking to Kelly in person, but not John, right? Then you create a very different um, it can lead to potential biases or perception of bias, right? So the big point here is ask. The answers to most of our questions really lies in that I have seen organizations spend millions, if not thousands and millions of dollars on, oh, everybody needs this, let's give them that. And if we ask, it could be something that doesn't cost you anything but some time.
SPEAKER_00:Yeah, that is so true. Uh, two things I was thinking on as you were talking about that, some of the things I will call out is don't ask in a check the box off kind of way. Be in the moment, be authentic and sincere when you're asking what's going on. I can't tell you how many times I will get on a call with someone and they'll ask me how's it going? What's going on, like, you know, how are you? And I can tell based off of the video, based off the tone of the voice, based off what follows after I answer it, they aren't they don't care. They are literally just saying it to check the box off. So I would actually prefer you not ask me that if you don't care my answer. And I've tested it with a couple of managers and and direct, you know, people that I peers and my man, my managers in past, and I've I've specifically using different words to answer their same question to see if they will respond differently. And if they don't, it is a clear sign they don't give a crap. Yeah, and that is like that is worse than not asking, in my opinion.
SPEAKER_01:I think uh and so I liken that to how do we demonstrate it, right? Yeah, and so well, I you know, we can get into this, but in those kinds of conversations, career conversations, one-on-ones, yes, don't ask if you don't in if you don't care, but how do you demonstrate that you care, right? So at the end of those conversations, you can literally end them and say, okay, here's what I can do. Here's what I I can't, you know. So be honest, it's how you close the loop on that to me. Um right. So organizationally, if you're doing surveys, if there's no action from the survey, right? What was the point? And you do that over time, it actually can hurt your team or your culture, hurt engagement because it's like, yeah, you asked, but for the last four years, you've done nothing. What if you don't even I've seen uh organizations that don't even report back any level of the results, right?
SPEAKER_00:That's the worst case scenario.
SPEAKER_01:Exactly.
SPEAKER_00:Yeah, don't do it then. Just don't do it. Yeah, yeah.
SPEAKER_01:So I think we demonstrated on a broader on, you know, since I use the survey example, you want to think up front. Are we going to match two leaders together, one in the red, one in the green, right? Are we going to communicate the results of the survey and monitor belonging all year? Um, you know, so be very mindful of that and intentional doing that in team meetings, et cetera. At an individual level, you can really ask and then follow up at the end around here's what I can do with without, you know, what will work, or I can't do that. What would it look like if we did this? Would that demonstrate XYZ? Would that work? And I think people don't do that to your point. They're checking the box um at my one-on-one. And I think this gets very difficult if you're like a sales leader with 50 or 100 people. This is fine, right? Yeah, so we really have to be careful with the more people we have, the more of these conversations. You know, our eyes are rolling in the top of our heads every time HR says, Oh, we got to do this again, right? So um, you want to be mindful of how you're going to structure those conversations, making sure that they're meaningful, not scheduling them, you know, and then that this is minor, right? I mean, you and I know this, but I think it's preparation, right? Our preparation uh before any conversation, and particularly with those that report to us. I often put the onus on my direct report. I do the same. Right? Like, you know, what are the things that are important to you? You know, how do you like these conversations to go? When I have a new team member, I ask them to fill in the blank. A good day for me looks like what? You know, fill fill the blank, right? And those types of things help you uh to proactively get ahead of any issues. What often happens is that people wait till there is a mistake uh or a clash, and then we address it.
SPEAKER_00:Yeah. A couple other questions that you're getting to know new team members, or maybe even just like if you're a manager and you're like, oh, I've had my members under me forever. Why don't you just throw out a curveball and be like, hey, I want to just like sit down like I've never talked to you before and I want to learn something new about you? Throw in some questions like, how do you appreciate being acknowledged, right? Some people do not like public recognition, some people do. Some people would prefer you just say, you know, send me a thank you and a$25 gift card to Amazon, right? Like, like, how do you appreciate acknowledgement? How do you want to hear feedback so that you're open to it? One of the things I've really learned recently is asking, are you open to hearing some feedback or feed forward? Right. And kind of getting that person in the mindset. And then when I get stuck, because I'm not a word girl, I'm a math girl. Uh, so words can be can fail me sometimes. When I get stuck on what I should ask next to next to try to dive in deeper, I go to my go-to question. Well, what is good look like for you?
SPEAKER_01:There you go. That's beautiful.
SPEAKER_00:Yeah.
SPEAKER_01:And that, and but by the way, what we're talking about works in relationships at home and work. True. Yeah. Before we can put this in our toolkit and make it part of how we operate. Um, my old mentor used to say there's words and there's meaning, right? So I can ask someone, what does respect mean? And every person will give me a different answer, right?
SPEAKER_00:This is true, yes, yeah.
SPEAKER_01:And so I love what you just shared around that. Very simple.
SPEAKER_00:Yeah. The semantics of a meaning of a word. I mean, I had a guest um several podcasts ago who she wanted to start with, let me explain the definition of this word I'm I'm putting out here, so that we are all starting this conversation on the same playing field. And I was like, whoa, that was a game changer right there. Because it's you're right. We all hear a word, and the interpretation of that word is based off of how we were raised, the experiences we've had along the way, the people that have influenced that, right? And so even in the same household, children will have a different definition. Even if they've been raised by the same parents in the same house, in the same location, in the same schools, they're still gonna have different experiences. And it's gonna impact and influence how they understand and see the world.
SPEAKER_01:Yeah. And all of these things go a long way. I often will say that when I am vulnerable as a leader, uh, my teams will take a bullet for me. They will do literally almost anything. And I didn't learn that until, you know, I was a young leader at the time. And I I really appreciated that lesson because I literally thought I had to be, you know, I mean, I think, you know, given my age, I we really had it was a command and control style of leadership that was acceptable, but it's been turned on the dime, right? So I don't think that leaders in that Gen X space have learned naturally. So we have to be intentional about understanding ourselves, which is one of my first keys to inclusive leadership is self-awareness.
SPEAKER_00:Yeah.
SPEAKER_01:To the point you just made, we have to understand how we see the world before we start interacting with others. Because if we're not aware, well, where did I get that from? Why do I think that people that come in to work at 8:30 in the morning in person are more productive? And is it impacting how I even hear them? Right. And so I think we have level bias around that too, right? Our go-to people, right? And so, um, so what I've had to do with my own personal journey of self-awareness is be mindful of that and then intentionally force myself to go to other people. Um to keep that in mind when I'm assessing talent. Uh, so I still I have a colleague that I used to work with, her name is Fran. We still are really actually good friends. And um, she thought so different for me, an amazing talent. She really could have probably retired, but she chose to be on my team. And so there was an age difference as well. Um, and one of the things I remember I would always intentionally go to Fran because I know that she would A, tell me the truth. She was at a stage and age in her life where there was literally almost no filter. So she she had no problem with the truth, right? Because sometimes reports won't tell you, right? But because she thought so different from me and she had different skill sets than other people on the team, different experiences and backgrounds. Um, I always got a better product when she looked at it. And so I had to be intentional to go to people that didn't think like me, didn't act like me, that had a different leadership style. And that really proved to be uh make our team successful because I was literally leveraging the strengths of everyone on our team, whether it was lived experience, age experience, industry experience, and that really proved to be very successful. So I think self-awareness is the number one inclusive leadership trait. And I always start with that. The next thing, and you were talking about it, so I wanted to bring it up is our ability to amplify others. Uh, to the point you may, we may not want to put Sarah on Front Street, right? In the meeting. And hey, are you ready to talk? Like Sarah may be an introvert, first of all. So are we sending notes in advance to Sarah, you know, to the team saying, here's what I want to talk about. Another way is if you're amplifying others, let's have Sarah lead the meeting or someone. Yeah, I really would love for you to lead the meeting. It takes the pressure off of us if we're a middle manager, right? We're stuck with the executives need this, my people need that. Let's empower the team. You don't have to do everything. You don't have so true. Yeah, let's see what your team is made of in the first place, right?
SPEAKER_00:Well, maybe it makes you be a better manager and a leader because you're now giving your directors the capability to experience, grow, and be able to become you in the future, right? Uh, so I love all this. And I feel like we could probably talk about this for hours on end, but unfortunately we're coming to an end. So, Kelly, as we wrap up, is there any last thought or tip you want to share with the audience today?
SPEAKER_01:Um, I think the biggest tip I would share is um think about what empowerment means for your team and learn those different definitions or words and and create an action behind the question to the point you were making. Let's not ask if we have no intention to truly demonstrate inclusive leadership.
SPEAKER_00:Yeah, I love that. Thank you so much, Kelly. It was great having you on the call today. And for those listening, I hope you got some great tidbits. And we'll see you on the Nick Podcast. Have a great one, everyone. Bye. That's a wrap for today's episode of Scaling with People. If you got value from this conversation, do me a favor, share it with someone building something big. And hey, I'd love to hear your take. Drop a comment, share me a message, or start a conversation. And don't forget to subscribe so you never miss the bold unfiltered strategies we drop every week. I'm Gwynery, founder and CEO of Guide2HR, where we help high-growth companies build smart with people for strategies and AI-powered systems that don't just keep up, they feed. If you're building fast and want your HR to move faster, head to guide2hr.com and let's talk. And remember, scale isn't just about speed, it's about people. Until next time, have a great one.
