Sara Lobkovich | OKR Expert

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Can EOS and OKRs Work Together? Bridging Vision and Execution With Expert Jessica Lee

Sara Lobkovich
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What happens when two powerhouse collide?

In this episode, Sara dives into a fascinating conversation with Jessica Lee, exploring the dynamic intersection of EOS® (Entrepreneurial Operating System®) and OKRs (Objectives and Key Results) in business management.

As both an EOS integrator and an OKR coach, Jessica shares her unique expertise, offering actionable insights into how these two frameworks can work in harmony to help organizations not just survive but truly thrive.

Episode Highlights:

  • The complementary relationship between EOS and OKRs in business management

  • Understanding the crucial visionary-integrator dynamic in leadership

  • How EOS provides structure for businesses ready to scale

  • The importance of proper goal setting and measurement systems

  • Role definition and its impact on organizational success

  • The value of coaching in implementation of both frameworks

Key Concepts Explored:

  • EOS Framework Components

    • Vision Traction Organizer (VTO)

    • Rocks and Measurables

    • People Analyzer

    • Accountability Chart

    • L10 Meetings

  • Leadership Dynamics

    • Visionary (CEO) role and characteristics

    • Integrator role and responsibilities

    • Creating effective partnership between both roles

  • Goal Setting and Measurement

    • Integration of EOS rocks with OKR methodology

    • Importance of measurable outcomes

    • Balance between vision and execution

  • Organizational Structure

    • Role definition before performance evaluation

    • Right people in right seats concept

    • Simplified organizational structure approach

Notable Quotes:

"Having a shared vocabulary and shared words and meanings within an organization could probably alleviate 75 percent of conflict that happens in businesses." - Sara Lobkovich

"Find out what matters to your people. That’s how you’re going to get the most out of the people you have." - Jessica Lee

"What I learned from OKR coaching was that staying quiet and letting someone else reach the answer can be the hardest—and most impactful—work." - Jessica Lee

"Research shows that we will dramatically overestimate what we think we could do in a short amount of time, but we will grossly underestimate what we could do in a larger amount of time." - Jessica Lee

Chapters:

00:58 Live from the Race Trailer

02:16 Guest Introduction: Jessica Lee

03:06 Understanding EOS and OKRs

04:40 Implementing EOS in Small Businesses

13:55 The Role of the Integrator

20:31 Accountability and Goal Setting

26:57 Conclusion and Farewell

Guest Information:

Jessica Lee owns Optimized Execs, a business consulting firm helping CEOs of small and medium-sized businesses who feel overwhelmed and unsure about growth strategies. Her experience includes serving as a COO and implementing EOS in various organizations.

Jessica's Resources Mentioned:

Sara's Links & Resources:

Find full show notes and the episode transcript via https://findrc.co/thinkydoers !

Full Episode Transcript:

Sara: Welcome to the Thinkydoers podcast. Thinkydoers are those of us drawn to deep work, where thinking is working. But we don't stop there. We're compelled to move the work from insight to idea, through the messy middle, to find courage and confidence to put our thoughts into action. I'm your host, Sara Lobkovich. I'm a strategy coach, a huge goal-setting and attainment nerd, and board-certified health and wellness coach, working at the overlap of work-life well-being. I'm also a Thinkydoer. I'm here to help others find more satisfaction, less frustration, less friction, and more flow in our work. My mission is to help changemakers like you transform our workplaces and world. So let's get started.

Sara: Welcome back, friends! I am [00:01:00] coming at you live from inside the race trailer at CVMA down in Chuckwalla today. So, again, a lo-fi intro for an episode that definitely deserves better because Jessica Lee, our guest, is such a pro. But wanted to get this out to you. And if that means a lo-fi intro, then we'll do a lo-fi intro. Before the holidays, we dove into the alphabet soup of goal setting. And today, I'm really excited to share a conversation I recorded with Jessica Lee, owner of Optimized Execs, who brings a unique perspective on being both an EOS integrator, and we'll talk about what EOS is in the episode, and an OKR coach. If you are leading or supporting a small or medium-sized business, or even larger, really, there's a lot to learn here. You're especially going to want to tune in today and give this a listen because we explore how the frameworks of EOS and OKRs work [00:02:00] together can work together to help your organization thrive. We will dive into everything from the visionary-integrator relationship to practical ways these tools complement each other for better goal setting and execution. So let's get into the episode.

Jessica, I want to welcome you to Thinkydoers today. So, let's have you introduce yourself to my listeners. Who are you and what do you do?

Jessica: Sure. Thank you so much, Sara. My name is Jessica Lee, and I am the owner of Optimized Execs. We are a business consulting firm that helps CEOs of small and medium-sized businesses who are feeling overwhelmed and unsure how to grow by offering some support and some strategic solutions.

Sara: You and I connected thanks to the amazing Liz, who both of us know. She played matchmaker—another amazing OKR professional in both of our network. She introduced us based on your [00:03:00] background in EOS. And so we're going to talk about other things today, but I'm kind of on an acronym kick right now. So let's start with what EOS is and how you use it.

Jessica: Absolutely. So EOS is actually one of my favorite tools that I have in my toolbox for helping entrepreneurs and small businesses to stabilize and turn their vision into execution so that they can grow and scale. Those who have maybe never heard of EOS, I'll just start at the top. EOS stands for Entrepreneurial Operating System. It was founded by Gino Wickman in 2008. He wrote a great book. I actually have it here if anyone hasn't read it, it's Traction. The book was written off of Gino's firsthand experience as an entrepreneur, weeding his way through figuring out how to have a system to be able to do all of the things that a business needs to grow during that important phase of launching and then growing. It's [00:04:00] a very practical hands-on framework, perfect fit for startups, entrepreneurs, businesses under say 400 folks. I got excited about EOS when I was the COO of a small business that was in that exact predicament. So we were small, but mighty and had some really big growth goals, but lean in terms of leadership structure and constantly feeling unsure. Do we have the right people? Are we doing the right things and are we truly ready to grow? And so that's when I first started hearing folks in my network, that I was explaining the challenges that we were facing to say, " Have you heard of Traction? Have you read Traction? Have you done EOS? You've got to do it.

Sara: When we started talking, it was about the intersection of how might EOS and OKRs be aligned or different or work together. And since then, you've become an OKR coach. I would say you're probably a pretty good expert on that. So for folks who are wondering, how does [00:05:00] EOS and OKRs or Objectives and Key Results, how do those things complement each other? How are they different? Tell me a little bit about those two acronyms together.

Jessica: Yeah, absolutely. As you spoke to earlier in the conversation, I was sharing with Liz, who we have in common, something that I was running into time and time again, as I was working with the small business CEOs through the EOS framework, was difficulty or pain points related to measuring outcomes. So EOS has what they call Rocks. Quarterly Rocks. They recommend about five things that are the most important things to focus on right now this quarter and then measurables being how do we get together each week and confirm that we're doing the things that we should be doing to get these rocks accomplished. And often I was being called in as a consultant saying, "Hey, we've implemented EOS. We like EOS, but we are having a hard time and we don't know if our people are the [00:06:00] problem, or if we are just writing really bad goals." And a lot of the work I was doing, or a lot of the time I was spending with CEOs, was really around taking that vision and turning it into powerful rocks or objectives, making sure we're focusing on the right things and then measuring both iteratively and at some sort of outcome milestone, how we've done. And so as I was explaining what a need there was in the EOS world for just better coaching and advice and help for CEOs to really get those rocks and measurables right, an aha moment went on for Liz and she was like, "I know who you have to talk to. Have you heard of OKRs?" And to keep with the acronyms, Sara, I said, "Nope. But I know KPIs are, so KPIs, but I don't know OKRs." So we had a chuckle and she's like, "No, go check out Sara's stuff." I checked out your stuff and was like, yes. And then as you know, took your course and just so much value in terms of how they can intersect, because of the focus on aligning vision and being very clear at the [00:07:00] top about what our vision is, and then making sure that aligns downstream to our folks.

That's awesome. I know your work isn't limited to EOS and OKRs. Are there other methodologies that you put together with those two in your practice?

Yeah, that's a really good question. what I typically do when I engage with a new potential client is I go through a series of discovery questions to figure out what the right fit solution is. That involves really taking a look at what's working, what's not, big picture goals, And that's what I like about EOS. They do challenge business owners to look at the 10 year and then the three year and then the one year.

 Research shows that we will dramatically overestimate what we think we could do in a short amount of time, but we will grossly underestimate what we could do in a larger amount of time. So taking time to make sure that you're thinking big picture down the road. And not just always looking at what can I do this 30 days and feeling like I missed it. But really taking a look [00:08:00] at the end goals as well, or the longer-term goals is powerful. That's something that I really like about EOS and that first kind of visionary piece of work. When I work with CEOs and business owners about defining their vision and then what their pain points are and what opportunities we have to grow on, that's a time that I then reflect on what tool or framework will best serve them. So sometimes that's EOS, but sometimes it's not, right? And for a variety of different reasons, and sometimes it's pieces of EOS. So EOS has some great practical tools for, you know, there's one called the people analyzer. That's taking the time in a space separate from your goals and objectives to think about and talk to your people and say, "Do I have the right people in the right seats?" And do they get it, want it, and have the capacity to do it? And I love that about EOS because again, one of the pitfalls that I find when people come to me as a consultant is they say, " We're not meeting our sales revenue goals, so I'm pretty sure I just have to fire everyone." And lumping [00:09:00] performance in human motivation in with business objectives, of that caliber is just wrong for all the reasons you and I have talked about before. I love that piece of EOS and OKRs, where it takes the time to coach to say, it is really important to talk about what the business needs to do and make that big and lofty and measure it. But that does not mean that we tie all of our individual contributors to, and we need to find intrinsically motivating ways to really motivate our people and measure growth for them.

Sara: you mentioned the People Analyzer. What are some of the other building blocks of EOS that you find particularly helpful with clients?

Jessica: Yeah, so I'll talk about the main components. And the first one is the Vision Traction Organizer, and that's really about sitting down and making sure that the company, the CEO, the owner is very clear on their vision, their core values, and their mission. And then not only that it's clear at the leadership level, but that there is a system within the business for communicating that [00:10:00] downstream. That also involves identifying your key clients, your target goals, so really figuring out how we can take our big vision and then boil that down into traction. So a lot of vision exercises and then a 10-year, three-year and one-year plan. So that's a very powerful roadblock of EOS. The second one, I would say, is the rocks and measurables. There's a lot of emphasis in the book Traction that talks about uh, the pitfalls for small businesses or overworked business leaders who feel like they have to solve for everything right now, or oil the squeakiest wheel right now, because today it's the squeakiest wheel. When in reality, we should get clear on what the most important few things are for a longer period of time, like a quarter, and then try very hard to stay focused on that. And the fires will come up and people have to respond to fires and business, we all get that, but the majority of your day, the majority of your work, should some way be feeding those big rocks that we agreed on. And if not, then the leadership team should [00:11:00] come together and have that conversation and acknowledge that. And then similar to OKRs Objectives, Key Results, there's the rocks and then measurable. So after you've identified your quarterly rocks, you go through an exercise of: What does that look like on a day-to-day? If we are doing the things that we need to do to move this rock forward this quarter, how can we measure that we're making progress?

Sara: how are EOS measurables and Key Results different or similar?

Jessica: So that's a good question, and the best way that I can answer that is that in my training on OKRs, and everything I understand about OKRs, there's just a lot more substance into the important ingredients to coming up with those and making sure that we are measuring things both iteratively, like indicators, and then outcome-based results. And that's really why I think learning and leaning into this practice of OKRs was something that I wanted to do to complement my abilities as an EOS integrator. I think that EOS is great [00:12:00] about giving the basic tools and frameworks for a business to implement and grow. But I don't know that there's enough deep-dive guidance given in the framework to say, "And here's how you could do a really bad job at setting objectives and key results, there are rocks and measurables, and here's some key points for doing it well."

Sara:

So it sounds like Key Results might provide a little bit more rigor —you learn my approach to Key Results, so there's a lot of rigor around my approach to Key Results. But for EOS practitioners or consultants who want to apply more rigor to the measures, is that where Key Results are potentially helpful?

Jessica: Yeah, that's exactly it, Sara. I don't think that there is a lot of guidance and even. I've helped several companies implement their EOS framework, and then I serve as their integrator, but I've also consulted where, like I mentioned earlier, folks have come and said, "Hey, we're doing it, but we're struggling. Can you help?" And that is a pitfall. And I just don't think [00:13:00] that there is a lot of, Really good guidance on how. And so it's left up to, if folks were not that great at setting goals and objectives prior to implementing EOS, it's not going to solve that or take them to the next level. And I think it's so important for a variety of reasons. But yeah, I think it's absolutely a good idea for anyone using EOS to learn about the focus that the OKR framework places on doing a good job of defining the what and the why, and then being smart and intentional about how we measure progress.

Sara: So earlier on, you mentioned business leaders who get into that overwhelmed state, or they're really focused on having to solve for everything,

Jessica: Yeah.

Sara: How do you create space for leaders who are in that space to kind of zoom out and see that they need to get above the fires that they're fighting on the present day?

Jessica: Yeah, that's great. And I can speak specifically, to the EOS framework. And I know we talked about a couple [00:14:00] of the foundational pieces or the tools, as they call them in EOS, but another one is the L10 meeting. So there are weekly meetings that are pretty structured in format that the EOS framework gives you, and it really engages that leader or leadership team back into: What is our vision? What are our top priorities? And what are we measuring? really good facilitator or integrator in an EOS system will make sure that we're keeping folks on track about talking about those most important five things or the rocks. And if we're starting the meeting off on a tangent and we're in a responsive mode, then that's a time that a good, strong integrator will come in and say, "Hey, I'm going to call time out for a second. This sounds really important. I want to get to it." But they do at the end of the meeting, and it's intentional that it's at the end. They call it IDS, Identify, Discuss and then Solve. And so they do an IDS phase. And so if it wasn't a planned, proactive rock that we're discussing, it's a new issue or the fact that it's a hot [00:15:00] topic and you want to put it on the front of the agenda, where we're here to talk about the five most important things that's an issue. And maybe we need to adjust things. That's the power that an integrator in the EOS system will bring is to be able to say, "Hey, I'm hearing this, and I'm not ignoring it, but let's talk about this during the IDS phase because we're gonna have to talk about how we give this the right amount of attention without distracting ourselves from the five things that we agreed were the most important for this quarter."

Sara: So it's cool. I was familiar because I run into so many methodologies. I can't become an expert in every one, but I was familiar with the concept of rocks and measurables, and I didn't realize that EOS had roles and responsibilities. So tell me a little bit more about the integrator and the role of the integrator.

Jessica: Yeah, absolutely. So really, at the core of the foundation, and in my opinion, other colleagues share this with me. I know a great pairing between the visionary, Whitman refers to him as the visionary, him or her, and that's typically [00:16:00] the CEO but not always, but the visionary and then the integrator. Very often the COO, which is how I became an integrator, but doesn't always have to be. It's one of the few systems that is acknowledging the kind of push and pull that happens in an organization because a very good, strong visionary CEO is so important. And we want them to be visionary. We don't always want to spend our time being the COO and the operations person being like, "Oh my gosh, there we are like chasing purple squirrels again. They need to chase purple squirrels, at least a few of them." And so having that duo sets you up for that success. We create space. A good integrator is going to create space and say, " I don't want you to not be the visionary. I'm not going to tell you're distracting people by being the visionary." A great visionary is at the core of a lot of successful companies. We are going to spend time regularly to say, Do we agree that these are the most important things for everybody else in the company to focus on for the next quarter?" You [00:17:00] keep dreaming big and you think about what we're going to do. But I want your buy-in. And then I can help make sure that the rest of the organization is marching towards what we've agreed upon as the most important things for this quarter

Sara: I was just writing a response to a media inquiry the other day about the role of the chief of staff. EOS might be a really helpful toolkit for our chiefs of staff who are in that right-hand role but who might not be enabled around how to do it. I'm a stickler for shared words and meanings, and just having something like EOS, that's an established framework could really help leaders and chiefs of staff improve their clarity of expectations for each other and negotiate what's challenging about those integrator-like or chief-of-staff relationships with leaders.

Jessica: You're 100% right. And like you said, chief of staff, COO, integrator, really that second in command or that partner that's a little bit more operational focused, [00:18:00] operational minded to a visionary CEO, really is an important dynamic. To have a strength at that leadership level and not have a CEO who's feeling frustrated. You know, CEOs call me all the time and they say, can you coach? I'm the problem. Like I'm driving my people crazy. I'm not focused. Like I tell them one thing, and then I think of four more things. Can you help me?" And that's, yes, I can. And you don't have to change. Like you can keep doing that, but you can't do it all on your own. And you need people to understand that there is a space and an importance to what you do, and every idea doesn't need to make it down to everybody else who's trying to focus on the last important thing that you told them to work on.

So I agree with you a hundred percent on that. And in fact, besides the book Traction, there's another book called Rocket Fuel. It's a little smaller, shorter read, and I recommend that all the time. Some companies are ready to roll out an operating system, and some just aren't yet. It takes some work and some commitment, but either way, I think there's some fundamental pieces, like the visionary and integrator duo relationship and respecting the strengths [00:19:00] of each personality type, that I think we can pull from that framework. and it helps empower business leaders.

Sara: That's fantastic. Those relationships I think are so under served in terms of education and business books. And so it's great to add a couple more resources to my " So You're a Chief Of Staff Now" guide. What is a particularly fertile ground? What organizations would you say should really take a look at EOS? Are there characteristics of an organization or a situation that EOS might be part of the prescription for.

Jessica: Yeah, I would say it is businesses from anywhere from two to, I would say, 250-300 employees, that are really starting to feel like they need help in order to grow and scale. So they're feeling a little bit overwhelmed by their current operations. The CEO or leadership team is just feeling like there are not enough hours of the day. [00:20:00] They cannot do it all. I hear that so much. I, as an entrepreneur, I thought I could do it all, and now I can't, and I know that I need help. Really any business between two and 250 folks. that just know that they are ready to grow and take things to the next level, but they need that structure. That is somebody that I always say, "Read Traction, or at least skim through it and call me because I think this could be a great solution."

Sara: Awesome, Jessica. What haven't I asked you that I should? What else do you want to get out there today?

Jessica: I know we touched on a few of the core components and tools of EOS, but one we haven't talked about yet that I think is really powerful

 is, um, the Accountability Chart. So the Accountability Chart really just takes the concept of the traditional org chart, but it challenges business owners to simplify it down into only a couple of key buckets, like sales and marketing, operations or delivery, and then finance. And then it has you create seats. [00:21:00] And so you define the seats that you need filled, and then there's a process for aligning to make sure you have the right people in the right seats. And then as you grow, um, kind of filling those seats. And it's a framework that's done just a little differently because a lot of times we try to measure people based on this kind of nebulous job and how they're doing it a lot of different things. But we don't have the seat well-defined. And so before EOS has you go in and analyze how somebody is doing it a role, they really challenge you to say, "What does that seat look like? Do you have your role well-defined?" And then we can talk about having the right people in the right seats. And I think that's huge for business owners. I think there's quite honestly, often doubt when outcomes don't start coming in the way that we want. When numbers aren't where we need them to be as a business leader, we start saying, "Do I not have the right people? Is it the people?" And I love that EOS has a system for, "Why don't we take a look at the structure and the seats that you need filled to do a really good job before we start analyzing [00:22:00] people."

Sara: I do a lot of work on the how do we map goal-setting to individual evaluation and performance pay and all that. And it's a complicated question. But one of the things that I struggle with has been the relative arbitrariness of evaluation based on job descriptions. So I love that idea of identifying what are the core mandatories for this seat type. Or even,you said sales and marketing, finance, operations, like even saying, those seat roles could be described in terms of alignment to those seat types or those disciplines. So you might have someone in operations that needs to work on internal reputation or someone in engineering who needs to work on developing skills to sell.

Jessica: Right.

Sara: So, I don't know, am I understanding that right? That it's like there are certain kind of skills that are identified that then can be aligned independent of what function someone [00:23:00] sits in.

Jessica: That's absolutely correct, Sara, and that's what I love about it, there is focus in the framework on. Taking a look at seats and roles independently of people. And then other tools like your People Analyzer tool, has a component where you actually have people separate their paper into four and, "What do you love doing? What are you great at? What do you hate doing? What are you not good at?" And then just filling it out and self-reflecting, instead of saying, "This was the job, and here's how you're measuring." What are you going to do differently, which we know is toxic and doesn't help? You give your people the opportunity to fill that out, and then you wanna make sure that at least 80% of the work that they're doing is falling in that top tier. And if it's not, and you either talk about, "Is this the right role? Is there a different role? Do we split roles up?" There's a lot of strategic ways. But it takes the time to say, "Find out what matters to your people." And that's how you're going to get the most out of the people that you have. And I think that's important, especially at the small business stage, where sometimes we forget to take that kind of [00:24:00] time.

Sara: I'm also just hearing the importance of shared words and meanings. I think having a shared vocabulary and shared words and meanings within an organization could probably alleviate 75% of conflict that happens in businesses and challenge that happens in businesses. So I'm really a fan of identifying and defining words and meanings with a little more rigor than most organizations do. But I'm hearing that when you talk about EOS too, that there's Set of words that can be given meaning that then help with shared understanding within an organization, which is really what drew me to OKRs, but EOS gives additional tools and frames beyond OKRs that people can align on words and meaning for together.

Jessica: Yeah, absolutely.

Sara: If people want to learn more about you and your work, where can they find you?

Yeah, you can find me on LinkedIn. Otherwise, you can go to my website at [00:25:00] www.optimizedexecs.com. I think we might have to work on a little side project for chief of staff integrators around EOS and OKRs. That would be really fun.

Jessica: I love it, too. EOS does a really good job at laying out a lot of groundwork, fundamental tools. But I find business leaders remain, in the "help me" phase when it comes to their goals, their measurables, their rocks. The OKR framework is amazing as a tool for people to lean into.

Sara: Yeah, I even have a little section in my book if doesn't everyone already know how to write goals. It's just something that, unless you're in strategy or behavioral sciences or motivation science, we just don't think a lot about the discipline of goal creation. So I think it's really cool that you spotted that opportunity in your EOS work to dive deeper into the discipline of goal setting.

Jessica: And Sara, I'll tell you one thing from learning from you when it comes to [00:26:00] Objectives and Key Results that I really took away as powerful was the actual coaching aspect. And I know you watched that transformation for me, but I learned so much about the speed with which I was going through that portion of the EOS with CEOs. They're like, "Oh, goals. Yeah. I wrote some down once in a while," and we were just slapping things on paper. You know, like I'm a problem solver by nature. It's hard for me to stay quiet and let somebody else reach the answer sometimes. And what I learned from learning how to be a good OKR coach really was to allow for that silence and to challenge, "But why? Tell me more about that." And really the coaching element, and I think that was the biggest aha moment for me and has helped me become better in doing that piece of EOS with clients.

Sara: Awesome. Jessica, thank you so much for joining me today. This was fantastic.

Jessica: Thank you so much for having me, Sara. It's been a pleasure and I'm sure we'll stay in touch.

Sara: Thank you.

Episode Specific Outro

Sara: All right, that wraps up my conversation with [00:27:00] Jessica Lee about EOS. I want to thank Jessica for sharing her expertise and insights with us today. If you found value in this discussion about practical frameworks for business growth, you're going to want to subscribe to my email newsletter at ck.redcurrantco.com. You'll get early access to new tools and resources to increase your efficiency and effectiveness, plus practical tips and frameworks to help you transform your strategic vision into undeniable results.

So until next time, bye y'all!

Sara: All right, friends, That's it for today.

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