Imperfection Is Commitment’s Secret Weapon With Flywheel COO Karen Borchert

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This is a podcast episode titled, Imperfection Is Commitment’s Secret Weapon With Flywheel COO Karen Borchert. The summary for this episode is: It’s that time of year when everyone is taking stock of what they accomplished (and didn't accomplish) this year, and we are all in the midst of setting our goals for next year. Luckily, self-proclaimed goals nerd Karen Borchert, the COO of Flywheel, is here to help. In this conversation with Karen, we go deep on the goal-setting framework she uses at Flywheel, the special quadrant she has built to help you plot all of your goals, and if you stick around until the end, you’ll get to hear about how Karen was inspired by Hamilton creator Lin-Manuel Miranda (seriously). Want to hear more from Karen? Here's her talk on Imperfection and Commitment:

Sean Lee: Hi everyone, welcome to Operations, the show where we look under the hood of companies in hyper growth. My name is Sean Lee. It's that time of year where everyone is taking stock of what they've accomplished and not accomplished this year. And we're all in the midst of setting our goals for next year. We've got a blank slate, we're ambitious, maybe sometimes even a little naive. So to help all of us as we mold our goals for next year, I called in self- proclaimed goals nerd, Karen Butcher it for some help. Karen is the COO of Flywheel, a managed WordPress hosting platform based out of Omaha, Nebraska. And in my conversation with Karen, we go deep on the goal setting framework that she uses at Flywheel, a special quadrant that she's built out to help you plot all of your goals. And if you stick around until the very end, you'll get to hear about Karen's connection to Hamilton creator, Lin- Manuel Miranda. I'm not kidding, it's awesome, stick around. But first, let's set the scene. You should know that in the three years since Karen joined the company in November of 2016, the employee count there has nearly tripled and now stands at over 150 people. And with that progression, Karen has found that it's been basically like working at a completely different company every single year.

Karen Borchert: I came to Flywheel in late 2016, so like you said, just about three years ago, and when I got here, we're really new to a lot of things. So we had really just putting together our first leadership team, really the first concept for management in the company. At that time, we were about 60 people at the time. And until then, it had been like you said, a real all hands on deck, very, very, very scrappy company. Everybody did everything, and it was just kind of dug in and got the work done, which was awesome. One of the big things that drew me to the company is that it was a company of doers, a company of people that just wanted to make amazing things happen every day, and they came in and they did that. So but 60 was sort of right at the point where there were true teams forming, an actual full marketing team a sales team, product team, and we'd taken funding our first A round not very long before that. And as part of that, there was a lot of hiring around leadership for different functions and different areas of the company. And through that we sort of had this ad hoc leadership team or management team that was starting to form, but nobody really knew what that was like, so we spent a lot of time really just continuing to tackle the work as it came. And a lot of my role when I first started was tackling work that didn't have an owner yet, but was a need as we were growing. And then we didn't have a budget, that was my first project was our first budget, and there are a lot of things that we just hadn't ever done before. So we just tackled those things. That was a lot of my job early on, it was that firefighting or that jump on whatever problem is going to be the biggest thing this week. And then as we have grown, and as we've come along, a lot of that work that evolved to what I call the parachute in phase where I think this happens in a lot of high growth companies. That will be an area that company that needs not just a little bit of help or a single project, but a look at and a question of how do we scale this? How do we take this larger? So I did that for a long time in the support and customer experience side of the house and helped that team. And then we promoted an extraordinary leader into the VP of customer experience role, and that made it really simple and easy for me to step out of that. And that was great, because it was just at the same time where we were moving... One of our founders who really built the sales and marketing departments, he moved him over to a product role, and that left a space in the sales organization that really needed filling and the sales organization was at a time where it really needed scaling. So I kind of jumped into that. And so for that first year or two, it was a lot of big, audacious projects and work from a departmental level of how do we scale this function of the business where I spent a lot of time, six to 12 months in leadership or in those roles. And then in the last six months or so, and less probably 12 months, I guess it's been a lot more about helping to empower leaders with the right tools. We now have it a pretty extraordinary leadership team, and then also extraordinary management team underneath that and that has been really exciting to see Flywheel grow a group of managers and leaders that are truly leading the company in their teams. And so a lot of my role now is supporting them and helping to synthesize all of the things they're trying to do and work toward help them set goals, help them know how they're doing against those goals, help them tell the story of what they're doing in their departments, and get them their resources and the support that they need to do that. So it's been really fun to progress in that way, but it's been an evolution every... Each of the three years has been a really different year.

Sean Lee: In just three years, a lot has changed for Karen and her team. If you're listening to this while working at a company in the early stages of hyper growth, I think you can identify with the all hands on deck super scrappy approach that Karen is describing. And if you're working at a company that has been in hyper growth for a little bit, I think you can identify with the challenges of having to start operationalizing some of the early work you did because the hey, everyone does everything approach is starting to break. I think a common trap for people going through this transition is that employees start to get nostalgic for the way things used to be. And especially for those early employees in your company, it can be hard for them to let go of the way things used to be and embrace the way things are. And Karen is the one at Flywheel who has to tackle that challenge head on.

Karen Borchert: I think for us, it's been really about honoring exactly what got us here. And we've said a lot this year, the phrase what got us here won't get us there. That concept or idea is that it honors what got us here is significant. It's a big deal what we did when we were really early, and I even feel terrible saying, I tend to say they because you know what the original 12, 20, 30, 40 people that were here, they really did do every single function every single day. When I got here, our founders were still taking evening on call shifts for support and answering support tickets on Saturday nights, and you have to honor that. There's a huge contribution and a big deal in that, and it helped build our DNA as a group of people who are doers. who are unafraid of getting in the weeds, who are willing to do whatever it takes to get something done and be scrappy. So we've really tried to make sure to honor that and make sure that that doesn't go away, that's still a huge part of the story, and it's a huge part of our DNA. But we also know the other side of it, what got us here won't get us there is that it takes a new set of tools to scale at the size that we are today to lead teams in that way, to inspire teams with a vision that we used to count... We used to count on our founders to really describe the vision of the entire thing to everyone. And now our leaders rely on their teams to those leaders are casting that vision, and it's aligned with the overall vision for the company. But each department also and team also has to really cast a vision for the individual contributors that is exciting, and that gets them mobilized and motivated to get going in the morning. And that's just something we didn't need when we were 12 people, but we need it now. And so I think generally a lot of our leadership team is part of that original group. And it's amazing to have that history and that that deep history with our leadership team. It's also exciting to see some of the newer leaders who have come in in the last couple of years, and to see what they add to it also.

Sean Lee: This is so, so important. Karen has identified that her team has now reached the size where vision can't just come from the founders. Vision needs to be communicated and communicated effectively by each team leader. And while I've never been a founder myself, I have to imagine that this is terrifying for them. What if the wrong vision gets communicated? What if the communication is poor or the vision of one team contradicts with that of another? And that was why I was so excited to talk to Karen because she spends huge amounts of her time aligning her team's visions and their goals. And she helps enable leaders to articulate their goals in a cohesive way. Now, every company has a different framework for goal setting. You've got OKRs, you've got SMART goals, BHAGS. So first, I just wanted to understand the framework that Karen and the Flywheel team use to get everyone on the same page.

Karen Borchert: So well, we use the OKR framework we have since we started. As far as overall frameworks, that's what we use. And the reason we do is because of the concept of the OKRs employees around cascading goals. So the company objectives have key results. And those key results become the objectives of each department, and they develop their key results. And so the idea or the thesis we went in with as far as goal setting for our teams is that every single Flywheeler should understand their impact on the business every single day. And that's partly because that's part of the value proposition we bring to our employees. You come to work at Flywheel because you can know your impact on this business. You go work for any other really big company in Omaha, and you may know your impact on your team or even your department, but it's harder to see your impact on the business overall. And Flywheel we're very fast growth and we're a different kind of place to work in that way. And so we really want our teams to be able to see and understand how the work they're doing today impacts the business's goals and vision. So that's why we chose that framework. We really like it overall. It has been an evolution in and of itself, and so we've developed somethings that really help us understand more about that. And then I'm a sort of a nerd about goals and really enjoy thinking about why some goals work and why some don't. And so we start to apply some of that thinking to our goals on a regular basis and talk about why things work and why things don't and then how we then set better goals and set ourselves up for better success in the future. And we talked a lot about how audacious do you set your goals? And do you set these absolute reach goals? That was a really hard thing for people to wrap their heads around really early on when we started with OKRs and goal setting, if I will, and 2017 is when we started it. And the idea that you set your goals so high that you want to hit a six or a seven is kryptonite for overachievers. It's really painful concept to think about being at a 60 to 70% for a lot of us. For a while there would be goals that people would set, and they were like, " Well, my six, seven threshold is this metric, but I'm setting it at this. But if we hit the six, seven threshold, we're going to consider that 100% of the six, seven." And it was ridiculous because it's really hard, but that's a hard thing to do, and I think different teams have different ways of setting goals. So it has not been a super smooth process. We've learned a lot through it, and there have been times where we have gone an entire quarter and just not set goals for a quarter because the business was moving too fast, or things were going crazy and we didn't score them, we didn't set them, we didn't talk about them. And then we come back around in a quarter or so to bring it back, and it's been a learning curve for us for sure. But it's been overall good framework this year. We really dug into the idea that at the company level. We had four objectives, and underneath those four objectives, 13 total key results that were the 13 big things we're trying to do this year in the company. And we said, " Okay, for each of these goals that are at the company level, we're going to assign an owner, and that owner might not be the person that runs that department or that leads that effort overall, it might be, but sometimes it's going to be somebody who is really passionate and excited about it, and who works on it in some way, but isn't necessarily the owner of that department." So we have a individual contributor who's a recruiter, and she owns our diversity and inclusion goal for all Flywheels. So her job is to really enlist and get support, widespread support cross departmentally for that company level goal and to help each department work, diversity inclusion work into their own department level goals. And that's really cool to see because we've that, we have a department head in our customer success department, and she owns the term goal. And obviously, you can't control all of inaudible, and how many customers leave Flywheel, but she has taken ownership of really deeply understanding it, and because of her work, she has influenced work in product and in finance and on her own teams, of course, and customer success, but that cross departmental ownership was new this year, and it's been really neat to see that kind of work because it does create a much more cross departmental effort.

Sean Lee: And I would imagine it gives them license to take real ownership, right? And it gives them that ability to build confidence around this initiative that they're working, or I think in the recruiting example, maybe there's a topic that they're particularly passionate about, right? Like these are other ways that they can contribute in a way that is going to be more meaningful to them than just checking a box.

Karen Borchert: Yeah. And then one of our big areas of learning... That's exactly right. One of our big areas of learning the first year or so of goal setting was around the idea of dependencies and interdepartmental dependencies where we have people who would set extraordinary goals, but they were completely dependent on product launching a certain thing by a certain day or a sales selling a certain amount. And so then when those dependencies didn't happen, it was really frustrating and disappointing to the people who would set these goals that have those dependencies, but rather than saying, " Okay, nobody set any goals with any dependencies," which basically gives everybody permission to operate in a silo. We said, " No. Okay, so this model of having that customer departmental ownership over the top goals of the company not only does it pretty much gives permission to each company owner to really bring those dependencies together and to say, " Okay, if we're going to move the needle on this goal, I'm going to need marketing to do this and sales to do this, and product to this and finance to do this." And it kind of gives that owner permission to enlist that cross departmental work. That's been really neat to see. So it kind of gives a framework for those dependencies rather than trying to make goals a dependency free environment.

Sean Lee: One of my favorite things about talking to Karen is that she doesn't pretend like all of these goal setting exercises at Flywheel have all gone perfectly. She recognizes places that they had shortcomings, and even said, " Look, there have been some times where we missed an entire quarter of goals, because we were trying to figure this stuff out." So if the self- proclaimed goals nerd isn't perfect in this area, don't beat yourself up for not being perfect either. One of the areas I wanted Karen's help in was, what does the timeline look like for these goal setting exercises? I've been part of OKR processes at previous companies. And one of my challenges was always how long the process would take. We'd be a month into the quarter and still trying to hash out what that quarters goals are going to be, especially when you're working on all the interdepartmental dependencies that Karen was talking about. So I asked her advice on how to deal with these timeline problems and how she designs her process, and like anything else, she said, this has been an evolution for them at Flywheel as well. And they're doing something a little different this year.

Karen Borchert: For this year, what we're doing as far as this, right now, this week we've done a bunch of work as an executive team on the sort of company level objectives or pillars that are the big areas of focus for next year for us. We've done that work and then this week, we're getting a little bit more granular with our executive team and our leadership team around what are those company level objectives and key results? So probably the 10 to 12 things we really, really want to accomplish. So by mid- November, beginning November to mid- November, we'll have that. And then in December, we will do workshops with each department. And each department will go through the exact same process, which is a learning that we had is that we used to just tell the departments, that your OKRs, good luck with that. And we found that they came in at really different levels of granularity, they were really different in the way that they came about those. We said, "Would it help to have a single process?" And everybody said, " Oh, my gosh, yes, please." So we are running everybody through the same workshop that will really look at the company level goals and the company level work that we want to do and say how is our department going to drive this? How is our department going to move the needle on some of these goals, not all of them, but on some of these goals and which ones and then we will work in the set by the end of December or mid- December. Each department is actually going to lay out an entire year's worth of OKR by quarter. And that's new. We've always set them... For the first two weeks of every quarter, we have scored our OKRs from last quarter, written a narrative about our OKRs for our department and then set our new OKRs. And so the first two weeks of the quarter has always been that time, but it always feels like we are really far into the quarter before we have really good set OKRs. So we're going to try this this year. I'll report back in a year and tell you inaudible. What we're going to try is setting out basically a roadmap of OKRs that we believe push us towards those company goals in each department, and then every quarter rather than starting with a fresh sheet of paper on OKRs, we'll actually just start with the roadmap and the OKRs that we set out and say, " Is this still correct? What needs to be changed? What needs to be tweaked? And hope to really bring that kind of editing process down, so it's really succinct and quick. Because the whole idea of OKRs is that you spend time working on the work not on the goal framework. So we don't want people to have to feel like they're spending a ton of time every quarter trying to figure out what we're working on this quarter when their teams are sitting right there working on the things that they're already working on. So that doesn't work as well. So we're going to set them out for the year and roadmaps and then we'll continue that monthly and quarterly cadence. So on a monthly basis, everybody gives their OKRs two scores. One is actual progress. So where are we on this goal, on this key result? And then what's our confidence high, medium, low, for it being successful for the quarter, and that confidence score, that's not really a part of the original OKR framework, but it's really helped us. So when we do that, when we look at things on a monthly basis, we know, " Okay, OKRs are falling here and this is where they are, but these OKRs are really high confidence for being successful for the quarter, and then these ones are really low confidence and might need some additional support."

Sean Lee: My favorite part of Karen's advice here, spend time working on the work, not the goal framework. Spend time working on the work. Simple as that. But let's face it, we all have goals at work that we wish weren't on our list. You know the ones I mean, the ones you have to do because the business needs them to be done, but you put off doing them because they're just the worst. Luckily for us, though, in addition to this new confidence score that Karen has introduced to us, she has also developed her own unique way of grouping and categorizing her goals. And what initially started as a personal system for herself, she is now incorporated into her professional system. And like any good ops person would do, Karen has created a quadrant to help us understand.

Karen Borchert: I love a two by two quadrant like any operations person does. I started to think about goals a while back, and I was giving a talk about goals and about the idea of what happens when you fail a goal, what happens when this huge thing that you've put in front of you doesn't happen? And where does that go? What do you do with it? And how do you set goals for the future that you're proud of, and that are audacious enough to be exciting, but that you can win at and that you feel great when you do. And so in thinking about that, I put together this little quadrant, and on one axis on your y- axis, if you will, is sort of on a scale of one to 10. I think sort of what I call the effortless scale or the joy of the work scale. So at a 10, it is the kind of work that you love doing that just brings you tons of energy, it's super energizing, it feels almost effortless, not that it is effortless, just that it feels like it's right in your wheelhouse, like absolutely just that sort of excellent, effortless work that we all love when we find. And on the one end of that scale is the grind, the really effortful like, yes, you can do it, man, it's hard, it takes a lot of energy out of you to the really, really difficult stuff. So that's kind of that scale, that one to 10 scale, effortful to effortless. And then one on the other axis is flexibility with the result. And I used to call this tolerance for failure, but I have started calling it flexibility with the result because I think people feel better about it. On the one end of the scale is total inflexibility. So the goal is extremely binary, or it has a very, very, very clear definition of success, and it's that or nothing. We have lots of goals that are like that. And if you say like, " I want turn to be at X percent," then that's a pretty binary result, that's a pretty inflexible goal. And then on the 10 end of the scale is a lot of flexibility with the result. So you say, " You know what? I want to run a marathon, but I just want to run a marathon, I just want to do it, I don't have a really specific time. I'm okay if I walk a little, I'm okay with lots and lots of different things. There's lots of ways that I could feel really successful with that." So that really high level of flexibility. And I think when you put those two concepts together, that effort less than effortful, and flexibility, and inflexibility with result, you basically end up in four quadrants. So I apologize if this is boring, but here we go. So the high effort, the super effortless really energizing work that has really inflexible results, so that top left that are the things that you love doing, the right in your wheelhouse, but man, you got to hit the number. That's the big achievement quadrant. It's the place of where you can do your best work and do amazing things, but you got to do it to hit the number. That's where your revenue goals go if you're in sales, it's that kind of stuff where it's big achievement. And then right below that in the bottom left is the really high effort fall really, really tough work with really inflexible results. Those are really hard goals, but they drive extraordinary results. Those are just results, goals. Those are the kinds of things that you're like, " Man, this is going to be difficult. This is going to be super hard, but we're going to do it and we're going to hit the number." And it's very, very satisfying when you do it, but it's also extremely draining. So like if all of your goals are in that bottom left quadrant, you're kind of screwed as far as feeling really, really great. So you've got that big results quadrant on the bottom left. And then the ones on the right are where you put goals that are a little bit more about learning creativity. So that bottom right where you're very flexible with the result. But it's really hard work. It's that low end on the effortless scale, but really flexible with the result. That's the big learning quadrant. That's where you put things where you're like, " Man, I have no idea how to do this. I don't know how to build this, I don't know what to do, it's going to take a ton of effort, but I'm going to be cool with whatever I've got here. I'm going to learn something through this." That's where I put the marathon for sure. It is hard work and it's difficult, but you're going to learn something from it, and your result can be a little bit flexible, you can feel good at lots of different levels of success. And then in that top right is what I call the big creativity quadrant. So it's the stuff where you can be flexible with result. You don't even quite know what winning looks like in it, but you can picture something amazing, and you love doing the work, the work is super high energy. And that's like sort of the big creative quadrant where you can feel really open and flexible with the result, but you know how to do the work and it's in your wheelhouse, and you love to do it and that's where you see some really big creative things happen. So that's the quadrant. That's my dorky goals quadrant. I use it personally, but we're also starting to use it at Flywheel because what you want to see is understanding you take every goal you've ever set, and you plot them on that quadrant. And you look at the ones that you have achieved, and the ones that you failed at. It can teach you a lot about where you're winning, and where you're failing. Maybe the learning quadrant is just not the place for you right now, maybe you need to be in the creativity quadrant, or maybe you're really just driven by those results, and you need to be in that results quadrant. That can really help you develop goals that you can feel amazing about and win that and that fit really well with where you are right now, and that might change over time. And it can change for departments. If your department is setting goals, and all of your goals are in this big creativity quadrant, that might be good, that might be good, because you might create some extraordinary things. But if what we need for the business is some results, some clear results, we might need to pull some of those goals over to the other quadrant and think about how to reframe them or rethink about them in that way.

Sean Lee: So you're actually starting to map that quadrant based off of what phase your team or you individually might be in in terms of the company's growth, your individual growth.

Karen Borchert: Yeah, yeah. So as part of our workshops this year, for our departments, we are going to take all of the OKRs that they set for the year, and then we have their scores on all of them so far for the year, which ones on a quarterly basis, which ones were a win and which ones weren't. And then we're going to have each department kind of plot them against those two axes, and then see where their green goals are and where the red goals are, like where did we win and where did we not win? And what does that tell us about how we set those goals and what we want to think about setting for next year? And also kind of what does it tell us about our team and what's changed since the time we set those goals on our team? So just kind of opens up a conversation about what makes a great goal because everybody sets goals to win them, like nobody sets goals to end up feeling bad about themselves later. So we're just kind of trying to drive towards the goals that are out there are going to both move the needle for the company, but also feel really energizing and exciting for the teams.

Sean Lee: Nobody sets goals to feel bad about themselves later. Not a unique idea, but also not something that we're usually considering when crafting our goals in the first place. So I'm literally sitting here drawing out my own quadrants and filling them in as Karen is describing them to me. And if you're not operating a motor vehicle right now, I'd encourage you to do the same. What I wanted to know, though, was if Karen had found any patterns by plotting her own goals, and the goals of others inside of these quadrants, is there anything that we can take away from this exercise?

Karen Borchert: I've actually run this exercise with some different groups and all the way to the point where we had a huge data visualization that we built in real time at a talk I gave where everybody had red flags for a goal that they didn't win, that they didn't achieve and a green flag for one that they did, and then they plotted them on the actual visualization. It's really fun. And we looked at them overall to see where people set goals and where people won. And one of the things we saw was the goals that were in that top right quadrant that really high energy for the work, but also flexible with the result, that really big creativity quadrant. There were very few goals out there actually I think maybe because perhaps they would feel less measurable or they feel squishy or something. There weren't very many goals set up there, but the ones that were almost always a win. So people who set those goals and said, " No, I really want to do something in this. I want to develop a new artistic skill," is a good one. Tons of energy, but pretty flexible with the result, like does it matter if it's painting or pottery? I just want to develop a new artistic inaudible. People really wanted those goals, where we saw the most goal set was in that really effortful, that bottom left quadrant, really effortful, no flexibility with the result. And that was an almost 50/ 50 split of winning and losing those goals. And I think that feels aligned with what I imagined might happen in our exercise with our departments is that I think we set a lot of goals with really, really binary results sometimes, and that's good. Again, they can create big results that way. But if all of your goals are there, you might miss the opportunity for larger creativity or larger learning on your team.

Sean Lee: And I can see for operations in particular, 2020 is around the corner. It's end of year, we're starting to do in the middle of annual planning for next year. And so I could see a lot of those planning exercises in that bottom left quadrant. So territory planning comes to mind in terms of having that very little flexibility, but an enormous amount of work. Should I be thinking about either for myself or for my team actively trying to limit how many of those bottom left quadrant goals we are setting for ourselves?

Karen Borchert: It's a good question. I would say it's less about limiting any quadrant of what you're setting, but if you think about it from the perspective of horizon planning, most of what you're going to do in the bottom left quadrant is going to affect 2020. And it's not going to probably affect very much in 2021 or 2022. So for companies that are or teams that are looking at a larger, longer scale or a big picture, let's dream up a new product, let's really dig into and get super clear about what our customers care about and what our customers want. Those are big, open- ended flexible result sorts of things, but they can be really energizing and really fun. And they can be the kinds of things that you're going to act on and create super measurable, clear results for next year. And so my general overall theory is that you want your goals to span it a little bit, you don't want your goals to all be in one quadrant is what I would say. And if you really care, if the long- term is really, really important to you, and you want to see you're really in it for the long game, you want to continue to build products, and delight customers, and build what Flywheel we call it the beacon on the hill companies. So the team that everybody wants to work for all around the area. That's the stuff that happens in those big learning and big creativity quadrants. It's harder to be quite as binary with those sorts of things, because you want to be open to all of the possibilities for the long- term, but the results are really important for right now. Our board members and investors don't ask about a lot of questions in the big creativity quadrates. They've got a lot more questions about the results, about the bottom left quadrant. So I think it's good to have a mix. And I think it's good for team members and individuals to have a little bit of a mix themselves of what they're thinking about and where they're putting their work because nobody wants to be in the super high effortful, but also not terribly energizing work all the time. That's a good plan for burnout. So having a mix of those different goals that push them towards creativity, and towards learning, and towards achievement and towards the results can be really positive that way.

Sean Lee: Yeah, I like the way you frame that as almost like a talent or workplace differentiator. Every job in the entire world has the bottom left quadrant, but not every job in the entire world has those two right- hand quadrants. And so thinking about it that way as a way to attract people and retain them and develop them on your team, I think it's super interesting. And this is something that you... You said before you're self- proclaimed goals nerd, like this is not just at work for you, this encompasses your whole life.

Karen Borchert: That's right. There're two days of the year that are the best days. One of those days is the day that you buy all of your school supplies to go back to school which I can attest to, also a day for adults that is perfectly great to go ahead and go to the store and get all of your school supplies. I love new school supplies. I love new notebooks and new pens day. And I also love New Year's day because it's the day that I sort of solidify and set my goals for the year. It's a holiday in more than one way for me. I love to reflect back on goals set for the year before. I love the possibility and opportunities that come with setting something audacious out there and saying, " Okay, we're going to do something big this year and let's dream up what that can be instead of course, for getting there." So yeah, I definitely do that in my personal life as well.

Sean Lee: I can totally relate. My wife, one of the biggest days of her year is when she gets to buy her planner for the following year and that's an enormous moment. Do you have your personal 2020 goals in the works? Is that its own OKR process you're digging into it?

Karen Borchert: Yeah, we're working through it, it's a working progress. But it's definitely in the works. I have some contenders. Mostly I've spent a lot of this year looking at, or time recently looking at what I set out for this year and what worked and what didn't, what was unexpected, and what things came up that I wasn't expecting to spend time and energy on that I did, and how that kind of ends up reflecting in the other goals and things like that.

Sean Lee: And one of the things I think is most interesting about your view on this is I watched that talk that you were talking about, it's amazing talk, it's on YouTube, we'll put a link in for people to find it. But one of the things you say in your talk at the end is that imperfection is commitment's secret weapon. What does that mean?

Karen Borchert: Imperfection is commitment secret weapon. So what that means is that embracing imperfection, embracing the idea of not every goal hitting, or not every goal being exactly right is the way that we find our way to the next commitment. So imperfection always teaches us something. It always gives us information. And so those of us who say, " Okay, I'm going to create these commitments, I'm going to do this, I'm going to see imperfection in them," and then there's going to be moments of imperfection in some of these commitments, in some of these goals. It becomes sort of the thing that nobody else has where everyone else is focused on a perfect result. And potentially in that case, staying in that bottom left quadrant always, it is very binary, that is very much a grind, that can be kind of a painful place to be. Those who say, " You know what? I'm going to get flexible with the result on this one, or I'm going to find a way to do this work in a way that feels really effortless to me," that will sometimes create imperfection and that imperfection will create huge learning and huge creativity. And that takes us back to even greater opportunities for commitment.

Sean Lee: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. Did you stick around for the Lin- Manuel Miranda reference? All right, ready? Here we go. Best book you've read in the last six months?

Karen Borchert: I really love Malcolm Gladwell's new book, Talking to Strangers. Is the framing of the way we think about the idea of people who are different than us. Was really, really, really interesting look, I loved it.

Sean Lee: All right, I'll have to check that one out. Favorite part about working in ops.

Karen Borchert: Oh gosh, there's so many. Goals oh, okay sorry no. Actually my very favorite part about working in ops is getting to work with extraordinary leaders. I get the chance every day to dream, and scheme, and then synthesize, and build roadmaps with all of the leaders in our company and that's a really extraordinary day. Just if you look at any given day, it's a pretty extraordinary way to spend a day is to really get and understand the minds, and strategies, and ideas that these leaders are bringing to the table. So that's my favorite part, they're amazing.

Sean Lee: That's an amazing answer. I don't think we've heard anyone say that before and I completely agree, so that's a great one. All right, flip it over, least favorite part about working at ops?

Karen Borchert: Oh, waiting for results. I'm the least patient person you've ever met in many, many ways. And I think a lot of times in ops one of the things that you have to do is decide on and implement a strategy. And then you have to let it do its thing. You can't change strategy every five seconds because you don't see a result immediately, but I do like results and I do like to see progress. So I think the patience for letting the strategy settle in, and letting people get a chance to process it, and work that strategy and build with it a little bit is something I... I wouldn't say it's my least favorite, but it's the thing I have the hardest time.

Sean Lee: Someone who impacted you getting the job you have today?

Karen Borchert: This is a strange answer, but I will say it anyway. The person that impacted me the most in getting the job I have today is Lin- Manuel Miranda, and that is because when I was in the job I had before this, I was in a job that I wasn't challenging myself very much, and I wasn't doing things that I was really, really proud of and energized by and excited about. And I heard for the first time the full Original Broadway Cast Recording of Hamilton, and I stopped dead in my tracks on a 10- mile run to marvel at that work and that creative accomplishment of his. And I quit my job because I decided that I wasn't doing something that I would marvel at someday, that I was truly proud of. And so I quit my job, I flew to Chicago, I saw Hamilton. Then I decided that it was the right choice to make. And then I said about finding a job that I could do something that I would marvel at someday and be really proud of.

Sean Lee: That is an incredible story. I need your number so that if I'm ever having a down day, I'm just going to call you and have you retell me that story and just continue to feel like that's amazing.

Karen Borchert: It's a inaudible creative work. So I was really moved by it.

Sean Lee: Incredible. All right last one, one piece of advice for people who want to have your job someday.

Karen Borchert: I would say stay in the weeds. Which is funny one of the biggest pieces of advice my CEO has for me is to learn how to get out of the weeds a little bit, which is fine, that's true. But I think the importance of understanding deeply the problems that you're focused on, or that you're looking at with somebody else, or that you're helping solve for an organization in any way is really about actually understanding what's happening at the heart of it, understanding the heart of the matter. And so if that means making 20 phone calls to canceled customers to understand better why customers cancel, then that's what you do. And if it means really deeply understanding the products by building with it, that's what you do. And I think there's no work that is close to customers and close teams that is not worth doing in this role because all of it informs the larger strategy. And that, I think everybody gets excited about the idea of being in this sort of strategic, setting strategy for a department or for a company kind of role. But at the end of the day, the most important thing is understanding clearly exactly what is happening at the customer level, at the employee level, at the level where the true heart of the matter. That's my advice is to stick with the heart of the matter.

Sean Lee: Thanks so much to Karen Borchert from Flywheel for joining me as this week's guest, and thanks to all of you for listening. If you want to learn more about Karen, we put the link to that YouTube talk that I was talking about, Into the Show Notes. It's an amazing talk about commitment and perfection, highly recommended, you can learn a little bit more about Karen. Also, if you want to join the hundreds of people who have become certified in conversational marketing, go to drift. com/ insider and you can get certified as well. Amazing content on there. Hundreds and hundreds of people have been posting their certificates online, has been amazing to watch, check that out. And last but not least, if you're enjoying the show, please, please leave us a six star review on Apple podcasts, six star reviews only. That's going to do it for me. Thanks very much. We'll see you next time.


It’s that time of year when everyone is taking stock of what they accomplished (and didn't accomplish) this year, and we are all in the midst of setting our goals for next year. Luckily, self-proclaimed goals nerd Karen Borchert, the COO of Flywheel, is here to help. In this conversation with Karen, we go deep on the goal-setting framework she uses at Flywheel, the special quadrant she has built to help you plot all of your goals, and if you stick around until the end, you’ll get to hear about how Karen was inspired by Hamilton creator Lin-Manuel Miranda (seriously). Want to hear more from Karen? Here's her talk on Imperfection and Commitment: