A Fractional COO Mindset for Scaling CEOs: Angela Lapovsky’s Playbook for Scaling Success

Summary

00:00 - Introduction to Scaling CEOs

02:01 - Angela's Background and Expertise

06:11 - The Chaos of Startups

09:17 - Staying Motivated in Business

11:36 - The Role of a Fractional COO

14:42 - Transitioning to Fractional Leadership

18:07 - The Importance of Complementary Skills

20:30 - Understanding the CEO's Journey

23:43 - Identifying Strategic Clarity

26:35 - Frameworks for Success

29:51 - Overcoming Resistance to Change

32:23 - Earning Trust and Driving Change

36:07 - Recognizing Breakout Moments

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Full Transcript

Jeff Holman (00:01.215)

Hello again, this is Jeff Holman with the Breakout CEO Podcast. I am so excited to be here with you today and talk again about scaling CEOs, some of the issues that they have, some of the struggles and successes that they deal with and glad to have some expertise here with me to help this show go well. I've got Angela Lapovsky, did I say that right? I hope I got it right. I've been struggling with that as I've been practicing it beforehand, but Angela is here with us. She's an expert, she's a fractional COO,

Angela Lapovsky (00:21.644)

You did. You did.

Jeff Holman (00:30.229)

of experience working with companies like you guys who are listening to this podcast. And we'll get into her background in a little bit as we get going. But for now, Angela, just want to welcome you to the show.

Angela Lapovsky (00:42.264)

Thanks, Jeff. Appreciate the invite.

Jeff Holman (00:44.221)

Yeah, it's so good to have you. You reached out to me at one point. I don't remember how we connected, but I'm like, yes, finally. think, and I don't know this is like an admission of guilt or a statement of victory. I think that you're going to be our first woman guest on the show. And I have reached out to a lot of women. like, we need women on this show. Cause I can't have a show full of just people like me. That's that doesn't go over very well. So fortunately we've got a queue that's building with a lot more people in it, but

I don't know, again, I don't know if that's like a good thing to say or a bad thing to say. That's just me being open about being very glad that you're on the show for both your expertise and the perspectives that you're gonna bring.

Angela Lapovsky (01:25.41)

Well, I appreciate that. I'm very honored to be your first woman guest. So hopefully I'll set a good standard for us here.

Jeff Holman (01:31.729)

I'm sure you were, you will for sure. So give us just a little, so you know that this show is dedicated to work towards CEOs who are with scaling companies and these CEOs deal with a lot of the same problems. You've seen it, I've seen it in my legal practice. They deal with the same things, just not everybody dealing with the same things at the same time, right? Somebody's dealing with fundraising and then they deal with employment issues and then they deal with partnerships. Other people start with the partnership problems and then they go on to other.

Angela Lapovsky (01:33.262)

Thank

Jeff Holman (02:01.139)

other things, give us a little flavor about your background and what skill set and expertise you bring into the picture when you show up and you're talking with people like these scaling CEOs.

Angela Lapovsky (02:14.028)

Yeah, sure. So I'm usually the call when somebody is looking at their strategy and their operations. So what does that really mean? It usually means that this is a scaling company. You've found success, you've had success, and now something is not working well. And you just said it, Jeff, sometimes it's a process, sometimes it's people, sometimes it's the strategy, sometimes it's just generally the overwhelm.

really hard as you and I both know to run a business. And sometimes it's just where do I start first and how do I think about that? So usually people are reaching out to me when they know what they want to do. They have a picture of what success looks like, even if it's a fuzzy picture. And they're just not clear on how to actually drive that forward, how to really codify and clarify that strategy and really just feel confident that they can continue to drive that success that they've had already.

in the future in a consistent way.

Jeff Holman (03:15.945)

Yeah, yeah. And you used a phrase earlier when we were chatting, you said something about seeing over the next mountain, I think. And I use a phrase often about seeing around the next corner. I love that phrase. I want to get into that in a minute, but what is it about your background that allows you to bring this added perspective or this, know, see what the CEOs aren't seeing because that's a lot of times why they're hiring you, right? Cause they're like, I am like in the thick of it.

I've seen success, they're probably hiring you mostly because they're being successful and they're trying to be more successful, but they've got a couple things, you know, maybe blockers or just maybe need some new inspiration. What is it in your background or tell us about your background that where you got your insights from that you can bring into the picture with them.

Angela Lapovsky (04:00.738)

Yeah, I think it's an interesting question because it's a question that I also ask a lot of CEOs in different ways to understand what their true superpower is, right? You start a business because you have a skill set in something, but nobody is an expert in everything. So when I think back and think about my world and what I love doing, what I've always loved doing, it's that balance of cause and effect. I think back to even to my undergrad, I wound up with an undergrad.

in economics and sociology, cause and effect in business, cause and effect in people. What are the little levers I can pull over here? I know where I wanna get to. How am gonna get there when I'm pushing my way through that as I can think about it? And so when I think about even my career, that's been the common thread. So the undergrad cause and effect, actual kind of classical training. I worked at big companies and always driving bigger change initiatives or...

things that just seemed hard and it was that same concept of there's a problem we're trying to solve. There's definitely a way to get there. How can we really do kind of that cause and effect and move on from there? So I did that at big companies. I moved on to a startup and that is the whole world, right? That you and I are talking about, right? Where there's, there's so much to be kind of pieced together and really drive that cause and effect. And what's the way that you can put that puzzle together to really kind of drive it successfully going forward. So my background is,

is in marketing, finance, strategy, bringing that all together to be able to kind of sit really at the right hand of the CEO and be that trusted partner for them. I think that's what oftentimes you need to be able to kind of push through, break through as you're talking about it. When you're the CEO or the senior leader of a team or an organization, it's lonely. It can be very lonely at the top, right? You're supposed to have all the answers, but

your superpower can't be having all the answers all the time. so oftentimes the question is, who can help you think through the right questions? Who can help you really challenge yourself to focus on the right things? Who can help you really challenge yourself to make sure the strategy is right to drive the success you're trying to drive? So yeah, that's kind of my background, my world.

Jeff Holman (06:11.764)

I love that. I want to ask you in just a second about making that jump. I know we're talking about scaling CEOs, but I'm always curious how people made that jump to say, hey, you know what? This is my superpower. I'm going to go from this corporate job or this other stuff and made that jump into actually starting a fractional CEO business like you've done. But first, what is it that draws you to the chaos of startups? And I say it that way because I worked with

know, big companies helping with their patent portfolios for a long time. And I'm like, you know what? I just love the startups. And I think what I love is the chaos. Why? I don't know. My wife thinks I've got some sadistic aspect to me, like the Joker on Batman or whatever, like just chaos for chaos sake. I don't think that's it, but there's something, you know, exciting about chaos, especially maybe as an attorney saying, I can help maybe bring a little bit of order to the chaos. I expect that

I don't know if you would describe it the same way, but what draws you to wanna work with clients who really realistically are in chaos a lot of the

Angela Lapovsky (07:18.572)

Yeah, they are in chaos on a lot of the time, but there it's exciting chaos the way I think about it, right? So I loved what you just said. I love bringing order of chaos, right? The more complicated it feels for you, the more it feels like it's just so many problems. And then there's a problem on a problem on a problem on a problem. The more I can take that apart, put it back together again, put a nice little bow around it, hand it back to you and your team and you can feel confident in, I got it. I can see it. I can see the path forward. That's just that that like

That's a high for me, right? I love to see that aspect of it. When you think about the startup world, I have, I think the privilege to work with some of the smartest business owners, innovators, people who are really trying to bring the world what the world needs, whether it's an individual product or a business product and what a privilege that is. So if I can help be able to do that and bring order to their chaos or help them be successful in what they do there.

I guess that is what kind of drives me in that startup world.

Jeff Holman (08:20.136)

Yeah, there's certainly something magical working with people who are saying, I've got this in here and one day it's gonna be out here and I'm gonna share it with everybody else and I'm gonna bring people in. Like I'm gonna build community. Like it's magical to see that innovation and that spark lead to actual life. So I totally understand where you're going from. We might be two peas in a pod here. So what is it that motivates you?

Angela Lapovsky (08:43.276)

Right.

Jeff Holman (08:48.424)

personally from day to day. I know you like doing what you're doing, but there's ups and downs with every business owner, every business. What do you do to stay motivated as you go in to work with these CEOs? Because you know you're going to go in and there's a demand, there's focus. It requires a lot of you to bring to the table so that you're ready to work with these people who are looking for that skillset. Is there anything you do on a daily basis?

Angela Lapovsky (09:17.976)

Yeah.

Jeff Holman (09:18.394)

your routines that helps you stay motivated.

Angela Lapovsky (09:21.602)

Yeah, I mean, I think the different businesses for me is something that does help me stay motivated in that I like the different business problems. That's part of why I wanted to do the fractional and kind of consulting world and consulting business. I have this motto just generally in life, personally in business, that life makes you stronger. I fully believe that every experience you have, every person you meet, every moment that you overcome, whatever that is, just makes you stronger and it teaches you for what the next...

the next thing is that's going to come. And so I feel like that is what motivates me even in my business world, right? So when I'm working with these CEOs, they're going through a moment of complexity, moment where they really, they're gonna get stronger if they come out the other side successfully, if they can see over the mountain. And so if I can help them do that, right, that motivates me on the back end. I think...

Being an operationally minded person helps in a world of being a fractional. So similar to a CEO, if you have multiple teams that are demanding your time, you're expected to understand where the market's going. You're expected to flex the way that you speak to an investor and then to the most junior person on your team. And then back to somebody who's challenging you from a sales perspective. You have to wear multiple hats. It's similar to the fractional world, right?

And so having intention with your calendar, the way that you focus your time, there's always an infinite to-do list. My way of managing that really is being very intentional about my time, where I'm spending my time, how I'm prioritizing different things. Sometimes I get it right, sometimes I don't, right? It's no rosy picture on the other side, but that helps me stay motivated because in the end, it's what does success look like? How am going to drive that success? How do I get to the end of the week and feel like I've...

driven that success going forward for my business and then for my clients that that's a big motivation.

Jeff Holman (11:18.462)

Yeah, as you talk about roles, it makes me wonder, and this is maybe oversimplifying a bit, you can, I'm gonna ask it and you can clarify for me. Being a fractional COO, do you often feel the integrator role if we're talking like, know, traction, EOS type stuff, or is it different from that?

Angela Lapovsky (11:36.654)

It's all of it. So I've had three people this week just this week I've had three people say you're gonna be my therapist right now. And so sometimes it's that right I mean the world of managing your own business means that you're bringing your whole self to work all day every day and that includes Your priorities the co-workers you have your own personal demands on your time Whatever those are and you're you're trying to kind of make it through a successful day and all those pieces so

Jeff Holman (11:45.528)

You

Angela Lapovsky (12:05.72)

Coming back to it, think sometimes it is the role of an integrator for sure, right? Sometimes what a company really needs is the ability for somebody to see the big picture, to be able to champion the big picture and to be the glue so the CEO can go do whatever their superpower is and have that kind of role in there. Other times it's being the constructive challenger, right? So.

You know, you might think you have the best idea as the CEO, but it's the idea that's spinning around in your head, maybe with a little bit of chat, GPT conversations in the mix, but having the ability to actually have a sounding board and somebody come back and say, well, have you thought about it this way? Have you talked to this person? What if we do it a different way? What if, what if this is the ripple effect? If you throw the stone and six months from now, this other thing happens, are you going to be okay with that? So oftentimes it's that role. I think.

The third one is usually the role of some sort of an advisor, right? So oftentimes they need, as the CEO, you are the person who is holding everybody else accountable to driving that strategy all the time, but you don't have any support on somebody strategically holding you accountable. And that's not in a way of, you're not gonna do your job because you're always gonna do your job. You're 100 % invested in the success of this company, but.

Are you doing the right things that day? Is your mind focused on what is most important to be able to drive this success? If you're just firefighting all day today, and then three months from now we snap our fingers and you said, I did a lot of firefighting for three months, is that gonna drive the business forward? And are you thinking about some of those aspects of things?

Jeff Holman (13:44.595)

Yeah, no, that third one really strikes a chord with me. I just finished a conversation with another guest. That episode will probably come out right before this one. So people will have heard it already, but it's with Earl Foote. he, among other things, he stressed the importance of coaching and what a positive impact that had on his career. So I know you didn't, I don't think I heard you use the word coach, but I think what you just described was a lot of coach-like aspects, really practical application coaching, you know.

boots on the ground type of approach to being that second in command or that right hand person that's helping be a resource that the CEO might not otherwise have. good. Well, I have one more question. do want, I really want to get into some breakout moments with you and maybe some of that you've had and seen and helped facilitate with your clients. But I want to hear just one more little piece about you, because I'm super interested. What made, you what was that moment when you decided

Angela Lapovsky (14:25.228)

Yeah. Yep.

Jeff Holman (14:42.876)

I'm gonna switch. You mentioned corporate, you did your MBA at a nice, very nice school, other stuff. What was it in your path when you said, do you know what, I think this is for me. I think I'm gonna go this direction. Was it gradual? Was it abrupt? Was it prompted? Was it accidental?

Angela Lapovsky (14:54.146)

Yeah.

Angela Lapovsky (15:01.402)

That's question. It's a great question. you know, it's one that I spend a lot of time talking to people who are just starting out on their career about because you feel like when you're in school, right, you need to know what you want to be when you grow up. But the reality is how many people actually have an undergrad and they're doing the same thing as their undergrad. think you just mentioned to me before that you studied engineering, right? And now you do.

Jeff Holman (15:09.961)

Mm-hmm.

Jeff Holman (15:25.693)

Right.

Angela Lapovsky (15:26.816)

And so the practicality of that is probably you're really good at certain things, you're really interested in certain things, and that drives a path that you take and then so on and so forth. And I think that that's been the way that I've seen my career go. It's the advice I give people oftentimes when they're thinking about their own career. I often say, right, think about the things that you really love doing that you're good at. Think about the things that you're really good at that you don't like to do, right? And then think about the things that you're just really interested in.

and then start to think about what are the things you're really good at that you love doing and the things you're interested in and think about what that job might look like when you take that next step. That's how you find your next opportunity. At least that's my thought of how you find your next opportunity. It's not necessarily about I want this particular title. That's how I've kind of made my shifts in my career. So, what...

Jeff Holman (16:18.942)

So it sounds like they were maybe intentional moves, going here to here to here and.

Angela Lapovsky (16:22.242)

They were intentional. Yeah, they were intentional. They were intentional for things I wanted to learn. So when, when I was in that corporate world, I realized that I was doing marketing and I didn't really know how a P &L worked. And so I needed to know that in order to drive big business decisions. So I looked for what are the kinds of roles I can move to internally where I can learn that part of it. And that kind of, you know, translated to the next one. And then when I moved over to the startup world, it was because I had all this big company experience.

And I wanted to take the big company skills and help a business build from scratch, maybe help them learn how to pitch the business for a sale or something to that effect. And so I kind of made that move. then most recently, when I decided to start my own business, it was because I wanted to help more businesses. I love the ability to just be in different industries and helping different people. There's a lot of commonality in the problems that people face that we're about to kind of get into. But you just don't see it when you're in your world.

And so my ability to bounce around and learn new things, learn about what the world is doing, doing the trends in what's happening and apply that to somebody's business problem and see the outcome on the other side was just super exciting for me. So I wanted to give that a shot.

Jeff Holman (17:37.3)

Yeah, I mean, it makes me think as you're talking about that, I'm a learner myself, so that really resonates with me. That's why I did engineering and MBA and law and people like, who are you? What are you doing all this for? But I like to learn. And it makes me think a lot of the people in our audience, people who are scaling these businesses, I think they're probably learners too, they're experimenters to some degree, but a lot of them are at that point in their career, you get into execution mode.

And you have to execute whether what that means you're, you know, fundraising day in and day out, or you're building your team or you're pushing your product or you're like whatever your superpower is, you're executing on that to the, to the nth degree. And what a, what an opportunity is to bring in, you know, maybe somebody who is a true learner with somebody who is a true executor and mesh those together in a complimentary way that does that. Have I described that in a way that maybe resonates a little bit?

Angela Lapovsky (18:37.26)

Yeah, I I think it does go back to that point of everybody has a different superpower, a different thing that drives them. And your ability to understand yours as a CEO and put together the team of people that's going to fill in the rest of it, you don't have to be the best at everything, right? But you do need to be the best glue or the best person to tell everybody where we're going so that everybody can apply their skills.

to be able to drive that when you think about it going forward. And so, yeah, I mean, there are some people who really love the rinse and repeat, right? So let me follow a process. Let me be the best at making sure that I am doing these things on a repeat basis. I don't wanna think outside the box. That's not what I'm passionate about. That's not personally my world. But if you pair that person with somebody who loves to think about the strategy, that's what you need because you need somebody to do the same thing every day and drive that.

Jeff Holman (19:24.105)

Mm-hmm.

Angela Lapovsky (19:35.342)

consistency, as well as somebody to be looking over the mountain and pair kind of the strategy side together with that. So yeah, I think it does absolutely resonate.

Jeff Holman (19:45.97)

Yeah, cool. Total quick side note, over the mountain, are you a hiker? Are you an outdoors person? Does that come from experience?

Angela Lapovsky (19:51.39)

Yeah, I am. I am. Yeah. I'm also an analogies person, but yes, I do. I do love to hike. My kids like love to hike. So yeah, we do like a lot.

Jeff Holman (20:00.71)

Awesome, very cool. Well, let's get into a breakout moment or two from somebody that you've worked with in your role as a fractional COO. Maybe set the stage for us around the type of company or the type of individual you're working with, some of the things they maybe achieved along their road before they ran into a roadblock or a bump or they hit the side of the mountain, cliff side of the mountain perhaps.

set the stage for us as to what that looks like in that scenario, that situation before you stepped in.

Angela Lapovsky (20:37.294)

Yeah, so I think about a particular CEO that I worked with that has always been the achiever, right? So set big goals, personally, professionally set big goals, put his head down and achieve those big goals. And when you think about that and then think about the team aspect of it, it goes back to what we were saying before about when you're small as a startup.

you can do all the jobs. And especially if you're somebody who's motivated and a smart person who loves to do new things, right? You're really good at figuring it out collectively. The analogy of, like sometimes you might be changing the toilet paper and other times you might be pitching, right? There's always that when you're thinking about it. In this particular scenario, the company was doing really well.

Jeff Holman (21:22.589)

Yep.

Angela Lapovsky (21:29.748)

had brought in a lot of other senior people through some acquisitions and various different things. They're on the trajectory for the next step in thinking about really that next step. But one year later, the revenue wasn't reflecting all the work that was being had, right? Everybody was working hard. And what's really interesting is we talked earlier about the people. The people here at this company, the people are the selling

They were phenomenal, they're skilled, and they were dedicated to the mission of the company. But the traction, you weren't kind of seeing any of that traction. And so really...

Jeff Holman (22:06.621)

Was this a service-based business then? I mean, were the people the actual providing service or was it product or?

Angela Lapovsky (22:11.022)

Service and technology, service and technology product. And so there, what really was the issue was there was not clarity in the strategy. So there was clarity in the success measure, right? The fact of we want to reach these revenue markers based on the business that we're selling, on and so forth. But truly what the strategy was going to be and how we're going to get to that point, that part wasn't clear.

Jeff Holman (22:14.801)

Okay, okay, thank you.

Angela Lapovsky (22:40.034)

being able to come in and really observe that, right, as that co-pilot, that second in command, right, being able to see that from the outside in and say, yeah, you're doing all these things and it's all really important and it's all really great work. But if you're spending all day doing the tasks without thinking about the end in mind, you're gonna get to the end and have done a lot of work, but not actually the one that's going to drive success when you think about it. And so for that, the question really is,

So how do you get everybody on the same page? How do you make sure everybody's motivated into that strategy? And some of this, yeah.

Jeff Holman (23:15.315)

Well, did the team know, I mean, you're working with smart people. they recognize and say, we're just, did they label the problem in a way that, there's a problem? Or did they say, we're not really on the same page, we don't have the same vision for strategy? Like how well were they defining the issue when they brought you in? Did they know how to articulate it? Or were they just saying, we're just, something's off, something's, we're stuck a little bit, we don't know why or where.

Angela Lapovsky (23:19.713)

Yeah.

Angela Lapovsky (23:43.384)

problem is our revenue should be growing and it's not. Sometimes it's going in the opposite direction. So it being a strategy problem, that wasn't super apparent. Because if you think about it, oftentimes for a startup, for any business, it's the long term tail on some of these things. So all the actions that cause and effect, the actions that we're taking today, you're going to see the impact of it a year from now, sometimes 18 months from now, depending on what your pipeline looks like and how

you're thinking about things. And so with everybody focused on what they thought was the right thing to do in that moment, they couldn't really see what that effect was going to be later on, which goes to one of the biggest tools in that breakout moment was really defining what does success look like? What do those markers look like between now and that success point? And how are we going to measure them in an easy way and not a highly complicated big dashboard with

charts and we need a data scientist, no. What are the very basic ways that we can measure if we're on a path so everybody can then put their head down, put their great skills to work and be able to drive toward that particular path. That was truly what drove kind of the breakout moment for this particular CEO and this particular company. Instead of him having to take the entire strategy on his shoulders and be thinking about it by himself all the time, the ability to...

Jeff Holman (24:43.827)

you

Jeff Holman (25:06.875)

in all of his free time, right?

Angela Lapovsky (25:08.512)

In all this free time, exactly while he was doing four other jobs, right, and thinking about it, it was more about how do we make sure that we're clear about what that strategy is. It's on a piece of paper. Everybody understands it. We all feel it, right, and can see what our goal is in that particular strategy. And then we can be looking at it on a regular cadence to say, how are we doing? Are we driving to where we should be or do we need to take a turn and think a little bit differently about the actions we're taking?

Jeff Holman (25:37.342)

So do you bring, for that conversation, I mean, you come in, you're like, hey, what's going on? No revenue. through discussions, you get the sense that there's a lack of maybe unified vision or strategy in the company? So you say, let's talk this through. Do you bring a framework in or do you bring, what kind of tools or resources do you bring to the table that help the team to work through that type of process?

Angela Lapovsky (26:06.242)

Yeah, I mean, I think, I think the formality of a framework definitely helps. Some startups run a hundred percent in the other direction every time you mention a framework. So I think, I think the commitment to a process that is consistent is really the most important part. mean, the two most common frameworks that I use is OKRs or EOS. Even if you don't label it that way, right? The practicality of the EOS model is it's in depth, but

Jeff Holman (26:13.543)

You

Angela Lapovsky (26:35.842)

What we're talking about, having KPIs, having quarterly goals, having a long-term vision that you're driving, having the right people in the right seats, that is EOS, right? That's the evil of just EOS. So helping people work through that particular type of framework, oftentimes I do bring to the table. I think you have to meet people where they are. That doesn't matter if it's a startup or a leader in a bigger company. You have to understand the tools they have, the willingness that they are on.

willing to change in what they do, the people that are surrounding them, what motivates them. That discovery process is the most important part of the work that I do. The ability to come in, oftentimes the ability to come in and have somebody else look from the outside so you can see over that mountain is the most important piece. Because sometimes it's financial, sometimes it's process, sometimes it's people, sometimes it's strategy, right? Like sometimes it's a combination of all those things.

But if you can have somebody help you look in the mirror and see all those pieces and say, hey, you know what? Your people are solid. You're good on that part of it. You don't need to worry about that, right? Your financials, while they're not growing fast enough, like that is okay in the way that you're managing it. But where we really need to clarify is we have 12 months to achieve this big goal that you have. And what everybody's doing all day every day isn't pulling the boat toward that big goal. So let's think about how we reach in this case, right?

how we shift the deck around a little bit to be able

Jeff Holman (28:07.505)

Yeah, and I love that you're going back to the over the mountain thing. It makes me think, you know, as an outside consultant, we often have the ability to either assist with or see or lead people over that same mountain many, many times, right? Whereas the company that you're consulting with or that you're advising, this is their first and maybe only time going over that mountain. They've got a lot of other mountains they're going to go over, but that mountain, might not have ever been there before.

Whereas oftentimes people who've been there and seen it and helped lead others through it, it's kind of back of the hand. this, you know, this Canyon's going to lead over to this ravine and then we're going to go up and over. There's going to be a big rock on the right hand side. Listen, don't worry about it. It's, know, we're, know where we're going. Just trust me that you won't be able to see the trail, but it's there. It's there. I'm thinking back to some of the times I've taken my own kids hiking and mountain biking and stuff like that. Listen, Hey, you're going to be fine. This is the hard part.

Angela Lapovsky (29:00.801)

Yeah.

Jeff Holman (29:04.517)

It gets easier after this. that's a, that's a huge perspective, benefit that you're able to bring. Now I want to know, did you get any pushback in this situation? Do you have any team members who just kind of say, why are we doing this? Or I don't know that this is the right direction.

Angela Lapovsky (29:22.542)

my gosh, do we need to spend the time on this? Right? That's usually right. We have so much work to do and really do we need to spend the time on this? Do we need to actually like spend a half a day and talk about the strategy or a full day? Do we need to be spending the time in our team meetings going over a dashboard? Like, is this really that important? Do we need to spend the time putting together the numbers? Right? So going back to the point of you have to meet them where they are, right? You have to make sure you're not

Jeff Holman (29:29.885)

Cause they're busy.

Yeah.

Angela Lapovsky (29:51.022)

engineering any one of the processes that you're putting in place, but helping them understand what that consistency gives, why you need that level of consistency, what the problem is that is just a symptom of something broader, right? Like to the point of what you saying before, I've done this before, right? You're telling me you want to drive success in this way. I'm telling you, you can do it. Oftentimes what CEO needs to hear is like, you can do this.

Jeff Holman (29:57.533)

Mm-hmm.

Angela Lapovsky (30:18.444)

You can do this. It's just, have to, here's the plan, right? Here's the plan that we need to sit down, put on a piece of paper, and then we need to consistently drive it. We need that operating rhythm that it becomes just like you wake up, you brush your teeth, you sit down at your computer and you do, right? Like that process ultimately is what will help you make sure that you're driving in that direction and you didn't waste the time on the strategy.

Jeff Holman (30:43.495)

Yeah. I'm going to, I'm going to share a quick story that maybe reveals a failing point of mine once. And you can tell me then how you overcame these obstacles with this team. I went into a meeting. We were talking about IP strategy at this company that had a ton of IP. mean, this is a hundreds of millions of dollars in revenue company. And, and a friend of mine brought me in and said, Hey, come talk to the team. Our engineering, our tech team really needs to know about IP strategy. We need better systems in place. And you know, you've done a lot of stuff. And I.

So I came in room full of, I don't know, it's 12 or 15 people, mostly tech and engineers. And I probably should approach it in a different way. But I said, hey, here's the system. Here's how we do stuff. We create these rankings, look at these factors. And one of these guys just bluntly said, this just sounds like a made up system. Like, is this any different than any other made up system? Why are we, like, I don't know why we should put any faith in this. And I kind of stumbled on that question because

He is in fact, right. It's, it's made up in a sense that it didn't exist. You know, it's not at a widely adopted system, but it's a system that works in the sense that I've used in other places. And, and I kind of stumbled because I'm a sarcastic guy sometimes. And I, my first thought was, yeah, it's, it's a made up system, kind of like the concept of time. Have you heard of time? Time is a made up system, but it works, but it works really well. Anyway, I did not handle that well. That didn't turn into a bigger project for me. And you know, it's, it's okay.

But I'm sure you handled this situation differently than I did and were able to walk through that. What did that look like to walk the team through or maybe walk the CEO through? Maybe that's who you were really directing this to.

Angela Lapovsky (32:23.502)

Oftentimes you have to earn the right to make a change is the way that I would say it. Sometimes it's one conversation, they're going to put all their trust in you and you're going to go forward. Oftentimes, especially as an outside consultant, that's not true. You have to actually earn that right. The question really is, what do we need to do incrementally to be able to get to that point? We're talking about something in hindsight and saying, okay, this is done and it happens.

But the reality of it is it took almost a year to kind of get that process rocking and rolling. It's the way that I think about oftentimes the story of an entrepreneur or a startup, right? If you watch the movie version of it, in 90 minutes, there was a big problem. They had a great solution and then they triumphed over it and everything is good, right? But the reality of business, when you're the CEO, it feels like it should work that way and it doesn't.

Jeff Holman (33:15.08)

Right.

Angela Lapovsky (33:20.046)

The reality of business is life is complicated. Business is complicated. It's hard all day every day. And so how do you make sure you put the right tools in place to be able to drive that? So just going back to that point is you can't, I don't at least, none of this is personal to me. Ultimately, I'm here to help you drive your success of you, your people, your business in whatever fashion I can be. I don't know how to sugar coat. I tell people that right away. I don't.

Maybe that's the New Jersey New Yorker in me. I just, don't. And so it's constructive in the feedback I give you, but it's going to be very honest. And I find oftentimes that that works really well. That is what the CEO is looking for is really that honest feedback to be able to say like, okay, I don't think we need to do this, but I'll trust you for a month, for two months, right? Just for a little bit of time. And then if it doesn't work, we'll make a change. It's no big deal.

Jeff Holman (34:09.522)

Yeah.

Jeff Holman (34:12.839)

Yeah, so if I were to have this CEO on the podcast and say, hey, Angela shared with me this story about the team going through these things, I would want to ask him, what was the end result? How did this create any type of transformation or an inflection point or new perspectives or what benefits came from this? How do you think the CEO, he or she might describe

the rest of the story from here.

Angela Lapovsky (34:47.278)

Well, recently I kind of asked him this particular question and he said, you understand me and where I'm trying to go and you help me get there. And that would be the end of the story, right? Which is to say, maybe the way we designed it day one isn't the way we were operating it by six months later. It's definitely not the way I still work with this client. It's not the way that we are operating the company now.

In fact, I just talked to him earlier in the week and we're going to make a change to the way that we run the weekly meetings yet again. But that's the nature of business. You have to put in the framework to be able to make the change. And the conversation we just most recently had was not, think this meeting should go away. It was, I see the value in it, right? I think we can get a little bit more value based on where the business is now. How about we think about doing it this way? What are your thoughts on that part of the-

Jeff Holman (35:34.163)

Mm-hmm.

Angela Lapovsky (35:42.19)

conversation. So I say that to say, if your CEOs are listening here, you have to understand that the business runs just like a heartbeat does. It's always going all day every day. And whatever you're doing today is not necessarily going to be what drives success in the future, but there are some core threads that will drive the consistency of your business. You need to find what those things are and make sure that you're driving those consistently every day.

The how you do it is going to change. It's the what you're trying to do that should be consistent when you think about things. If your what is not consistent, you make the process more difficult. You demotivate your staff. You spend money where you don't need to spend money, right? That's where it starts to be a lose-lose proposition.

Jeff Holman (36:28.806)

Yeah. No, this is, this has been fantastic. I want to ask two more questions. First one, and I'll ask them both and then you can, I'll give you a heads up on the second question, but first one, I want to know how people can get ahold of you because if they, if they're looking for something, some outside perspective, some organization, some, you know, strategy in their business, I want to know, I want our audience to be able to know how to reach out to you. And then I also want to know what do you think as maybe the parting wisdom here?

What do you think our audience of scaling CEOs should be looking for when they're saying, hey, I need a breakout moment. Like I'm at the brink, like we're up against the edge or whatever it is. I kind of need a breakout moment. What would be the things they should be looking for to say, this is an obstacle that I can overcome with the right resources.

Angela Lapovsky (37:20.686)

So let me take that one first, because that one is a harder one. Yeah, the second question first. I think you know you need a breakout moment when you're not getting traction in what you're trying to drive. When or if you feel like you're going round and round in circles and coming right back to the start again. If you're clear about where you want to get to, but you're not sure how to get there. Or if you feel like...

Jeff Holman (37:22.552)

okay.

Angela Lapovsky (37:49.236)

every action you're doing, the opposite reaction is happening, right? So it's like, I'm doing all these things, I think they're the right things. And then like the opposite part is happening. Yeah, Exactly. Attrition. Exactly. Like all those are just symptoms of something else that's just structurally or some strategy or something that's just not there. Right. And so it's a moment to just pause, right? Pause, reflect and ask yourself the question of what can I do differently? And that really will be the lead to that break down.

Jeff Holman (37:57.019)

revenue is going down or team members are leaving or whatever.

Jeff Holman (38:18.674)

Okay, I appreciate that. Yeah, so how can people hold you?

Angela Lapovsky (38:18.958)

Yeah, the easier question. Yeah, how to get in touch with it. Yeah, so going back to that last name, the benefit of the married last name is there's no one else on LinkedIn, Angela Lepovsky. can find me on LinkedIn, Angela Lepovsky, or email Angela at arlelevate.com.

Jeff Holman (38:39.536)

Awesome. Thank you so much. I'm so glad people had the chance to hear you share some of these stories and insights here. And please get ahold of Angela if you need some help. She's got great resources for you and hopefully can create more breakout moments so that you guys can then come on the show and be a part of the Breakout CEO podcast later. But it's been a pleasure having you on the show, Angela. I hope to stay in touch with you. I hope to hear more of your breakout stories, maybe offline. And thank you to our audience.

This has been a great episode. Please share it with people. it if you want to on your podcast platforms you listen to. But for now, I'm Jeff Holman at the Breakout CEO Podcast. Thanks for joining us.

Angela Lapovsky (39:21.112)

Thanks, Jeff.

Jeff Holman (39:22.236)

Thanks.

Jeff Holman (39:26.163)

All right, stop the recording.