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
From Founder to CEO: The Messy Journey of Scaling Leadership with Aviva Leebow
Ever wonder what happens when your startup outgrows its scrappy beginnings? The transition from founder to CEO isn't just about a new title – it's a fundamental shift in how you lead, who you hire, and sometimes, the painful decisions about who stays on the journey.
Gwendolyn R. Curry sits down with Aviva Leebow, a Vistage Chair who coaches ambitious CEOs, to explore the leadership evolution necessary for sustainable growth. Their conversation dives into the uncomfortable truth that the people who helped build your company from nothing might not be the right ones to take it to the next level. They share strategies for having these difficult conversations while preserving relationships and respecting the contributions of early team members.
The discussion highlights a critical mistake most growing companies make: promoting skilled individual contributors without providing management training. "We do not train and coach people to become good managers," Curry notes, pointing out that leadership development remains the most overlooked investment in scaling organizations. Lebo emphasizes the importance of peer groups and external resources to help leaders grow beyond their current capabilities.
Perhaps most compelling is their exploration of founder self-awareness. Knowing when you've reached your leadership capacity – and being willing to surround yourself with experienced executives or even step aside – can be the difference between stagnation and continued growth. As Lebo shares through powerful examples, sometimes the greatest act of leadership is recognizing when someone else can better realize your vision.
Ready to evolve your leadership approach as your company scales? Listen now to gain insights that will help you navigate the messy, inspiring journey of growing with your business rather than just alongside it.
Welcome everyone to today's Scaling with People podcast. I'm Gwendolyn R Curry, your host and founder and CEO to Guide to HR. So as companies scale, so do the people leading them. But how do you guys, as founders, evolve from visionary to empowering CEO, and how do your managers become true leaders? What does it take to grow with your company and not just alongside it? Join us today as we dive into this messy, inspiring and transformational journey of leadership growth. We'll be sharing real stories, hard-earned lessons and the evolution of those steering the ship. Whether you're a founder, a rising leader or someone hungry to grow, you're in the right place. Let's grow together and get started. I'm super excited to have Aviva Lebo here with me today. Aviva, tell us a little bit about yourself.
Speaker 2:Yeah, so I'm a Vistage Chair in Atlanta, georgia. I lead two groups of incredibly driven and ambitious CEOs who want to accelerate towards their goals faster. I also facilitate a group of key executives who are driving transformative change within their organizations and a group of trusted advisors consultants great advisor to these larger companies who also want to grow and learn and be the best versions of themselves. Before that, I was a CEO myself and a member of one of these groups, which is why I love them so much and got so inspired to lead them and facilitate them and do the coaching that I do to help other CEOs find their best versions of themselves and really go after their big dreams.
Speaker 1:Yeah, and as a member of Vistage, I know the power that those groups can. Those core groups can bring to you not only as a professional but as a human being, and what's going on in your personal life and how to manage both sides, especially as founders, ceos and top executive leaders. We got a lot on our plate and having a place that you can come to to just speak to other people that are dealing with similar situations safe place. If you haven't heard of Vistage, I'm plugging it for sure right now. I normally don't do that, but I do have to say it is a great, great group of people and you will learn and grow like you've never, ever grown before.
Speaker 1:So check it out. But I mean, let's talk about this. We're talking about growing too, right? So as companies grow, you know whether you're starting out by yourself or you've got a couple people you're about ready to. You know your pre-seed or your seed, or you've got series A or series B. Wherever you are in the world, you have different levels and layers of management leadership. So take us through kind of like the life cycle from your perspective of how a founder should be thinking about leadership in their org.
Speaker 2:Yeah, so I mean, many companies start out with a couple of people who have an idea right. That's where your startup comes from. It might be you with a couple of people in your team, or maybe you've got a co-founder right, and so initially it's just intense collaboration. But as you start to scale and grow, when you have people come into your organization who have to do things, then you need to start to be able to develop those people, manage those people, coach them, help them be the best version of themselves, and so you start putting leaders in place.
Speaker 2:And you know, I think the evolution is interesting because as you go through different fundraisers or even if you're not following a startup path like that and get larger and larger and start to develop layers in your organization especially when you've been a founder you're moving up past, typically, your prior capabilities right. At some point you max out on what you've done before. So maybe you've never led a team of managers who now lead a team of people, and now that's new for you. And if you started it with somebody else, maybe they haven't either. So you're starting to professionalize any processes and systems, and so I think it's interesting because you have to develop yourself as a leader at the same time as you're developing other people as a leader, and that can be tricky and challenging.
Speaker 1:Yeah, absolutely yeah. So for those listening that might be like oh gosh, that's exactly where I'm at. What would be maybe like a step or two or a thought process that they could start, you know, considering or taking action on to help them really start to be growing in these areas.
Speaker 2:Yeah, I mean. So one of the things it's it's lonely at the top you don't know what you don't know.
Speaker 2:And, um, you know, especially when you're a small organization, you don't have a lot of people to help you figure it out. You may have some massive experience from your own past background, which is great, but you're still doing something new and different than you did prior. Of a peer group like a Vistage group is a great way to learn from other people's experiences, not reinvent the wheel right. You can understand what others are facing or who have similar challenges, who've tried similar things, and take what you like from the conversation and leave the rest and build something that fits you and your organization where you are. So that's one thing that fits you and your organization where you are.
Speaker 1:So that's one thing I love that I want to reiterate like not rebuilding the wheel, Like you are in your business. You've created this business because you are trying to create something different and new, but there are aspects of your business where you shouldn't be doing that and recreating the wheel on. You know, like you don't need to recreate the wheel on how you actually put your finances together, on how you manage people, like how, like there are so many things within running a business that you can just plug and play and go and use that power of your brain to create something new for why you are creating this business.
Speaker 2:Yeah, I mean, like you know, developing systems and processes for training and following up or even communication and setting expectations. You know, to make sure that you're clear, how do you do vision and what kind of structure should you put in your place? How often do you do certain types of meetings or even common mistakes people make, which kind of goes to the other realm of like things you're going to have to deal with as you evolve as a leader Right and develop yourself. But you know, people have the wrong person on the team. Maybe they were the right person to get you where you are today, but now they're not a fit either for your new culture or they're not a fit for where you're going. They don't have the right skill set.
Speaker 2:And having to make those tough calls Like do I? You know I'm loyal to them, they helped me get here. What do I do next? Do I bring them up with me to the next layer and just promote them anyway? Do I bring somebody in above them? How awkward and hard is that? Like, there's a lot of hard decisions that, as you're scaling, you have to make and some of them are if you really want to make your vision happen. There's some really not fun. Decisions that have to get made along the way because you can't take everybody along with you into leadership, into the next roles, to take you to the next level, because you're going to have the wrong people doing it. You have to upskill along the way.
Speaker 1:Yeah, absolutely, and I always use the analogy of your business is just like human beings we get born, born diaper stage, walking stage, young education, finally graduating high school, and not everybody goes to college. And it's the same situation here. A lot of times I see I'll come into orgs where it's like gosh, okay, wonderful that these people were able to get you to where you are today, but they're not necessarily all going to be the people that are going to get you to where you need tomorrow. And a lot of times you know time is money right and as a founder, you don't have a lot of time.
Speaker 1:You have to prove that you can grow two times rate. You have to be able to do it within the funding that you have before you go and ask for more funding. There's a lot of different, you know, factors that are happening inside of growing a startup and not having the right people or having someone who might have the potential to grow into this role.
Speaker 1:But you don't have time for them to learn, test, figure it out, trial and error. To get there, you need someone that's been there and done that and can grow your business, and that can be really hard that transition is. I think one of the toughest things I see for founders is when do you bring on those powerhouses that have been there and done it more expensive but hey, they're going to shrink the timeline, Right, and yet you have these people blood, sweat, tears working beside you weekends. You know all their kids, you know birthdays and best friends and everything Right. And it's hard to make that decision of do you layer them, Do you say goodbye to them? How do you make that work? And that's really tough, yeah.
Speaker 2:It is, and you know, when you think about it, like a lot of the people who are great in early stage companies. They are scrappy, they're full of grit, they're willing to do anything, they're good executors. They'll jump in here, they'll jump in there, and that is an amazing skill set. At some point you need a more functional, structured person who understands the processes of a given area, not that scrappy, I'll go into everything person, but one who more can put the structures in place. That person isn't your micromanager. They're not going to dive in and do all the work Right. And so the person who's scrappy often can't really translate great to a non-micromanager, because they you know it's hard for them to give up some of the doing, and so at some point, as you move up layers, that person may or may not be the person who's able to do that, and you can't scale if you're still doing.
Speaker 2:At some point you have to be more strategic and, I hate to say it, I mean some people actually are much more passionate about the doing so as much as they're like. Well, I was a part of founding this. I should literally, you know like I need the title, and I mean this was, you know, my baby too. At the same time, they may not be happy leading people. They might much prefer being an individual contributor, still being scrappy, making sure all the pieces fit going, that have the right skill sets. And that's a hard thing to do, especially with the loyalty and relationships that get formed when you found a company and you're early on and you guys were in it together from the beginning.
Speaker 1:Yeah, and I think that, like part of that too, is just having conversations with people, because I've seen, I've seen it where you know, if you come into the conversation and really understand what their career aspirations are and what they want out of life and they can really help them understand, hey, this is what I need. I need someone who can come in here and build this overnight. I want to support you and I want you to be able to have that experience, but we don't have the luxury as a company to be able to give you that time and bandwidth to do this, because if we don't succeed in the next six months, we're not going to be able to be successful in our fundraising. We can just close the shop now and I want to make sure that you have a job, I have the company's alive, we're healthy and you know, if you give them those insights and not everyone's adult enough to hear- them but you would hope that the people we're talking about in this situation are adult enough to hear this.
Speaker 1:I have seen that most of the time the people recognize it and actually get pretty excited about being layered because now they're seeing the potential for opportunity to be mentored by someone who's been there and done it, getting that coach and professional growth. Where a CEO, you're not going to be able to professionally grow every function of the company, of the org, even if, like as a startup, a founder and a lot of founders are engineer, product driven individuals how are they going to be able to grow a marketing person or a finance person, right? So having that layering doesn't have to be a negative thing Understanding what that person is looking for and what they want out of life and then sharing where the business is at and what is needed for the success of the business and that you value and appreciate them. And here's how you're excited that they're going to be able to grow and learn Like. Okay, I'm ready to double down on that.
Speaker 1:I think that'd be great. Grow and learn like. Okay, I'm ready to double down on that. I think that'd be great. Right, like, and so I've seen it be very successful.
Speaker 2:Yeah, it's amazing, you can even make that mistake.
Speaker 2:I've seen many companies who have pushed someone past where they're supposed to be. They put them into a leadership role or whatever and they you know they're so afraid to have the tough conversation at that point because now they've done it, that's the title and they're not supposed to like are they just going to leave my organization if I have this tough conversation and you'll talk with them and they're not performing and they're not happy because they're not really living up to their capabilities, and you know what they're like. No, I really actually just want to be that individual contributor and you can realign them and get them placed back into the right seat in the company and you'd be amazed how many times that actually goes well. Yeah, because people don't want to do something that they're not passionate about and not happy doing every day. There's a few people whose egos are strong enough that not having that struggle whether they want to really do that work or not. But outside of that, most people genuinely want to do the work that makes them happy and to feel like they're contributing.
Speaker 1:Yeah, and they feel like they're going to be successful at it.
Speaker 1:Exactly yeah, and they feel like they're going to be successful at it, exactly, yeah, yeah, and I find a lot of startups where they go wrong as they promote people in at any level within management and they don't have the right foundation or structure in place to support that person's growth. And what does a manager mean? What does a leader mean? And how are we going to help you learn to be a good one, a great one and that could be external resources too. But a lot of times I can't believe.
Speaker 1:You know, we're still in this day and age where, as an HR professional, I think the biggest issue that organizations have today which was the same thing back in the 80s, I'll say is management. We do not train and coach people to become good managers, great leaders, and, you know, actually keep them accountable for that. It's just one of those things like, oh, this person's a good individual contributor, they'll probably be a good manager and they're two different skill sets, but yet we don't give them. There's no like college I mean, I guess you MBA or whatever but there's no like, hey, I'm going to go out and become the best leader by going and getting my master's degree in leadership. Like, you know, there's coaching and other things, but like it's not like an engineering degree where I'm going to go out and be the best engineering and that means I'm going to be the great leader? No, no, not at all. But companies just like make this assumption and then wonder why everyone's failing. I'm just like, oh, so painful to watch.
Speaker 2:I see it all the time and I also coach. In addition to being a visit chair and leading peer groups, I do a lot of one-on-one coaching and that's actually where a lot of my coaching comes from. Is somebody that's gotten promoted past, that really has the desire. They want it. They've just never been given skills. They don't know how to have the tough conversations. No one ever taught them how to or to give feedback appropriately, and so they need, you know, just coaching and some skills and training and guidance. If companies only put those systems and processes earlier and that is probably one of my tips for scaling companies is invest in your leadership development, whether it's internal development programs you put in place to develop your next layer of leaders, or use external resources like Vistage.
Speaker 2:So Vistage peer groups they do have ones for high potential associates, they have them for mid-level managers, all different layers.
Speaker 2:But find those people you're planning on moving up in the organization and, before you're ready to move them, make sure they've gotten that training, they have the places to go to ask the questions that you don't even know the answers yourself. And when I said earlier because this is important, I don't want to be thought of the wrong way Like every time you move up, you need to replace your leadership team. That's not the case at all. But as you're moving up you need to bring in some people who have experiences you don't yet have in your company and supplement so that you're not necessarily overlaying all of your leadership as you grow, but you're starting to add pieces in so you get some expertise and some different perspectives and skill sets that will help challenge you, to make you stronger. And as you move up and there's more and more layers of that then at some point you know it gets a little bit stickier. But you've got to make sure you're supplementing with the things you don't have.
Speaker 1:And I think the key too is don't assume that because someone has 10 years of management experience, that that makes them a good manager leader, and no matter what level you're hiring, you should still be level setting and making sure everyone has that same basic foundation that, because it impacts your culture, it impacts your employee engagement and morale, and it's it's a vital thing not to make that assumption with people that come through the door like oh, I have 20 years of experience leading people Well okay, what do they say?
Speaker 1:about you. They might be like, really like you might have the highest turnover rate in all of your career versus other leaders that have 20 years of experience, right. So there are key things not to make the assumption, just because they have the years of experience, that that means they're good at it.
Speaker 2:Well, so you've got the years of experience and you also have the title right, because companies put all kinds of random titles on everything. So it's a matter of really testing to make sure they have the right skills that you have and you need that they've had the right training Because, again, like if you were a leader, you could have been a leader or manager in an organization for a while but no one ever trained you. Then you may not really be bringing that professional management skill set in. So I find that you know, asking really good behavioral interviewing questions where you can understand how they handle different experiences in the past allows you to get a feel for how they'd handle situations and do they have that real experience to help you take things to the next level?
Speaker 1:Yeah, exactly, so we've been talking about leaders, but how about for us founders who are out there and we're growing businesses right? At some point in time, the business might outgrow you. I think one of the key things is understanding what is it you want, what do you enjoy and where do you see yourself being the most successful? But then how do you continue to grow with the business? So what are some of the things that you see in your conversations and in your coaching that are maybe that you share with us today, of how to validate you're still where you should be as the founder CEO and how do you keep that being the case until you're ready to sell or, you know, change your role or whatever it might be, so that you're not being asked by the board to leave?
Speaker 1:That's the worst and I've actually had that experience. So you know it's tough. It's tough to like tell the CEO hey, you're not, you're not the right thing for your business anymore. You got to go. And it's like, oh, like I would love for every listener that's a CEO out here Like never to get to that point. What are some things that you could share with us to help them to never get have to have that conversation?
Speaker 2:No, first is just the willingness to be vulnerable and be self-aware, like if you can be self-aware when you're starting to be capped at knowledge. That's critical. Some founders just they can't let go, it's their baby, and they don't realize that they're holding their company back. And if you don't have a board of directors, that's fine. Your company will just stay stagnant at some point and maybe start to recede a little bit. And it's your baby. You have every right to let it, you know, go great or go terrible, right.
Speaker 2:But the ones that are self-aware, they do one of a couple of things. One they really pay attention to those they're hiring around. It goes back to the discussion we were having earlier, right? So the greatest thing that they can do is say I don't know enough anymore, I'm not the right person to do this or to scale or to do these things. I've got to start to make sure I have those heads around me. And so their job, key job, is to set the vision for where they want the company to still go and make sure they have the right people on the team to get there, knowing that they're not going to be the one to build the systems or the structure. They're not the one who even really knows how to lead. They need to have probably a really strong COO or president or, if it's a company that uses EOS integrator, right, that knows how to do those pieces and to execute and their talent is finding those people and surrounding themselves with it. The other is knowing when it's time to call it because, right, like sometimes that loyalty to those team members is so huge that you know what you're not ready to go replace that leadership team and to do those pieces of what's next. And that's okay too.
Speaker 2:I've seen some really great leaders. I have one member you know. She built her company to a certain level, got it to a great place, sold it off and then went and built a whole nother business. And that's amazing because she got this company with this amazing idea on what it could do for the world up and running, got someone to buy it who could scale it majorly, make a big impact on her original idea, and then use that money and went and started another really great idea. So, just because you can't take it from inception to scale, that's not everybody's skillset. Sometimes it's like I have this amazing idea, let me get it into the world, breathe life into it and let someone else take that vision from here to there, and then let me go do that again, cause that's where I live and breathe. Um, so it's not always about getting one idea to the end and version of the vision. Sometimes it's about knowing where you're at the end and you can't get your vision met anymore and someone else can take it better and go do the next one.
Speaker 1:Yeah yeah, I think it's so true. It's self-awareness, it's knowing your skillset it's and growing it right. Just because I know my skillset, you also should know where your gaps are and growing that. If that's what you want, hopefully it is right. We all want to learn and grow. Continue to grow, um, and and really seeing those as opportunities to reevaluate what you want in life.
Speaker 1:And yeah, I think growing is hard, it's very challenging. You're always kind of in this like up, you know you're going up that mountain and it's like got a mudslide that you're trying to work through right. But if that's what you want to do and you can see the outcome, great. But there's also times where it's like maybe that's not where I want to be as a human being and recognizing I love that story where she's just like I just want to get this idea out, grow it enough so someone can make it really successful, and then go and do it again, like that is so great to just understand what you enjoy out of life. We're on this planet for a very short period of time, so you might as well do something you really enjoy and not be forcing yourself into a pay hole that you think is the right thing, because that's what you need to do is the next step in your career. Well, it doesn't have to be.
Speaker 2:At some point you lose your passion, you get burnt out, and then you're not really doing good for anyone not for the employees, not the team, not for your idea not for yourself, your family, your friends, yeah.
Speaker 2:So it's important to really be checking in with yourself. Am I still accomplishing what I really wanted to be doing with this in the first place? Like, yeah, it can impact. Am I having the life I want? Am I enjoying what I'm doing? Because if you're not, there's no shame in making changes to make that happen. It's better for everyone in the end. If you're miserable, your people are miserable. You know so, and there's also no shame. You know we've talked a lot about scaling growing companies. There's also no shame in having a lifestyle business.
Speaker 2:I you know I love to work with driven leaders. So I'm constantly talking about the scaling growing companies, because those are the people I really. I want to help them achieve those big visions and dreams. However, you know, some people you know have a great idea. They build it and they build it to a place where they just that's where they want to keep it and live. They support that. They don't want to go past where their scale and growth is and they have a lot of fun doing it and they have a great business there and they leave it there and that that's okay too. So you know, it's really about being self-aware of what you want, what you want to see happen um and where you can take it, and making sure you're still happy and enjoying life in the process.
Speaker 1:Yeah Well, yeah, enjoying life in the process. I think that is a great place to end today's episode Go out and make sure you're enjoying life. While you're building your business, you're growing yourself, you're growing your leaders. I hope you really had some great takeaways in this conversation with Aviva and myself, and thank you so much, aviva, for joining us today, and we wish everyone listening a wonderful day, wherever they are in the world, and looking forward to you joining on the next episode, absolutely. Thank you so much for having me. I really appreciate it Absolutely. Thanks, bye.
