Giant Robots Smashing Into Other Giant Robots

502: OKRs and Business Coaching with Evan Hammer

November 30th, 2023

Today's conversation revolves around the importance and challenges of goal setting within organizations. It highlights how identifying and articulating real problems can be transformative, turning abstract desires for growth into concrete plans for improvement. Host Victoria Guido and special guest Evan Hammer discuss the nuances of leadership and organizational self-awareness, emphasizing the need for honesty and a growth mindset when addressing weaknesses. They touch on Evan's role as an OKR Coach in fostering alignment, focus, and excitement around goals, particularly in small to mid-sized companies.

Evan shares his enthusiasm for goal setting and believes his passion can inspire others. He points out the positive outcomes when employees engage with goals that address problems they care about. Victoria and Evan agree that success is not solely measured by hitting OKRs but also by engagement and alignment within the team. They discuss the ideal organizations for Evan's work, which include small to medium-sized companies seeking to improve focus and alignment, as well as start-up teams needing more straightforward goal statements and go-to-market strategies. Evan also recounts his experience as a Techstars mentor, noting that a common issue across companies is the lack of clear goals, and he emphasizes the power of focus as a lever for growth.

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VICTORIA: This is the Giant Robots Smashing Into Other Giant Robots podcast, where we explore the design, development, and business of great products. I'm your host, Victoria Guido. And with me today is Evan Hammer, OKR and personal goals coach. Evan, thank you for joining us.

EVAN: Thank you for having me. I'm excited to be here.

VICTORIA: Wonderful. Me too. And I wanted to ask you first, before we dive into business, tell me a personal goal that you've achieved recently that you're most proud of.

EVAN: I guess a couple of months ago, I did a 100-mile loop of Mount Rainier. So, it was a 10-day backpacking trip. My younger brother, I went with him, and it's the kind of thing he does more regularly. Yeah, it was something I was kind of excited to do but really unsure of, and worked super hard between the gear and the training and just, like, the mindset. But it was also just awesome being out in the woods for ten days.

VICTORIA: I also love being out in the woods for long periods of time. I guess, like, how long did your brother plan this trip for? And how long were you involved before you decided to go?

EVAN: You know, it was something he was planning to do since the spring. He won a lottery to be able to do it. And I was going back and forth for a few months. And I think it was just maybe in the end of June where I was like, okay, I'm doing this. I need to put together a gear list, figure out a training plan. I live in Fort Greene in Brooklyn. And it was a lot of, like, waking up early and going up and down the steps in Fort Greene Park, which is, like, you know, 6, 10 flights of steps, something like that outdoors --

VICTORIA: [laughs]

EVAN: With a heavy backpack on for two to three hours, like on weekends.

VICTORIA: Oooh. Wow.

EVAN: Yeah, it was one of those things I was like, you know, you don't know when you do something like this how it's going to go until you're there doing it or how your body is going to respond. So, it was a little bit of, like, trying to train as much as possible but also being aware that I just have to deal with whatever will happen on the trip.

VICTORIA: I love that, at first, it sounds sort of, like, fun. Like, "Oh, do you want to go on this trip with me?" And you're like, "Yeah, okay." And then you look at the training plan, and it's like, "We'll wake up at 6:00 a.m. every day and walk up and down ten flights of stairs [laughs] with a heavy backpack on," you know, like, "Oh okay, [laughs] a lot of prep work to have this trip." [laughs]

EVAN: It's fun in that you're doing something amazing, and it's beautiful. And it was just one of the more beautiful places I've ever been. It was really interesting and meaningful to me to kind of be detached from everything that I normally do and just focus on being in the woods and hiking these mountains. But yeah, you don't know how it's going to go. So, it's like you're putting yourself in an extreme physical situation. I think that's anxiety-inducing, and it feels good and is healthy and protective to train for it.

VICTORIA: I agree. Yeah, I mean, I totally relate to that. I'm a rock climber and hiker myself. And sometimes I spend all this time, you know, on gym memberships, climbing in the gym, running up and down hills. And then, I get all the way out to rock, and I'm about to start my climb, and I'm like, why am I doing this? [laughs] This is a lot of work to get to this point. But then it is all fun, and it's super worth it. And I always feel restored whenever I come back from being a long time in nature. It's really great.

I think maybe to get towards, like, a metrics conversation that we talk about a lot in climbing is the type of fun something is. So, there's three types of fun levels. Have you heard this framework before, Evan?

EVAN: I have not.

VICTORIA: Okay, so there's three levels of fun. Level one fun is, like, you're having fun while you're doing it. We're, like, laughing and enjoying recording a podcast together. Like, oh my God, it's so much fun, super easy, not stressful. Maybe it was a little stressful for you, I don't know. [chuckles] It's a little stressful for me.

Level two fun is it's a little difficult while you're doing it, but you're still looking back on it and having fun, but you're never really in any kind of intense danger, right? Like, you're going on a backpacking trip. It's relatively within your health expectations, and the trail is walkable. You're not, like, going to fumble and fall down a cliff. It's level-two fun. So, you're mostly enjoying it. Like, it's kind of difficult, and there's some effort involved, but it's still fun.

Level three fun is when it's very dangerous, and you're really scared the whole time [laughs], and, like, you maybe, like, could have died. But looking back on it, it's fun. So, how would you rate your Mount Rainier trip?

EVAN: It's funny because we actually...we didn't come up with the levels, but we spoke about how when you're hiking, often, in your head, you're just trying to figure out how much longer you have to hike as if the whole point was not to be hiking. And then you finish hiking for the day, and you're like, "Oh, that was so great. I'm so looking forward to waking up tomorrow and hiking some more."

VICTORIA: Yeah [chuckles], exactly.

EVAN: That fits the level two fun pretty explicitly.

VICTORIA: That's great. Yeah, it's a very, you know, I've found it to be pretty useful. And, you know, as I get older, I tend to try to avoid level three fun more often [laughs]. Like, I don't really need to be frightened [laughs]. I have enough stress in my life. I don't need to also endanger myself too aggressively.

But, you know, everyone has their own risk level as well, right? Like, someone else might think the type of climbing and hiking that I'm doing is level three fun, but, for me, it's more...and, like, there's other things like skateboarding and riding a bike where, for me, is level three. I'm scared and [laughs] --

EVAN: Right. And I think you also frame level three as, like, sort of physical safety. But, you know, people have different risk tolerances and classifications across the board. So, like, for me, I try to stay away from things that I would consider physically dangerous. But I'm very comfortable, like, taking financial or social risk, where I know other people have an inverted kind of spectrum where, like, social risk is, like [laughs], you know, is a terror to them when physical risk doesn't seem that scary to them, you know, so...

VICTORIA: That's so interesting. And especially for me, I do a lot of networking. And I'm, of course, been really active in San Diego Startup Week this week. We're recording this in October. So, for some people, going to an event where there's going to be hundreds of people, you maybe have met some of them before, but you really don't have a buddy that you are coming to this event with. You're on your own. You're going to have to walk up to people, start conversations, figure out who is who, and, like, find your people. That's terrifying for a lot of people. And they're like, "Absolutely not." [laughs]

EVAN: Well, it's interesting how, like, level one and level three can be inverted. I went to a conference last fall by myself, and I actually had some voice issues. So, I couldn't talk for a little bit before this, so it was like...or even that well, during, you know, it was kind of an environment that I think a lot of people might be feeling like, oh, that's level three social experience. And I just remember how much fun I had there. Like, for me, it was totally a level one thing. But, you know, there's definitely moments on this hike where I was like, oh, this is level three. This feels physically scary, even though most of the time it wasn't.

VICTORIA: Yeah, no, I think it's helpful. So, maybe that helps us segue a little bit into telling me more about what you do and how you came to do what you do. What's your background?

EVAN: What do I do? I'll give you, like, a list of the things that I do. I will say I help people focus and maybe communicate better. You know, the list is, like, I am an OKR coach, right? That's objectives and key results, coaching business leaders on how to set goals and get everybody aligned towards the same goals. I do personal goals coaching, and that's, like, helping individual people set goals that are meaningful to them and live more intentionally. I'm a Techstars mentor, where I mentor companies. And I also do, like, a fractional head of product role.

And it's a little all over the place. I mean, it's something that, obviously, a lot of that is, like, business coaching but really focused around focus and how you can use goal setting to accelerate growth for a business or an organization or for yourself personally.

VICTORIA: How did it get started? What led you to be the coach that you are today?

EVAN: Yeah, you know, I get asked this question. And I feel like there's a story about how I kind of tested goal setting. I was a founder. I went to Techstars in, like, 2013. And I was running the company. So, I had to, like, mess around with goal setting and then ended up being at Codecademy and Vimeo. They were doing OKRs. And there were certain things I liked and certain things I didn't. And there was, like, this progression.

But I think the truth is that I just really like systems and organizing things, and I think I've always been like that. And OKRs are a way of taking something that's really messy, which is, like, a group of people running together in some direction and saying, "Oh, well, what if we come up with, like, some agreed plan here, and some rules, and some guidance? And we can split this out between what, like, the company and the organization is doing versus what individual people are doing or what the department's doing."

I think I just find that process comforting. It's just, like, gleeful for me to be working with people on how they're going to focus and organize themselves, and then also how they're going to communicate that focus to each other, which I think is, like, a key part of people staying on the same page.

VICTORIA: I love that. And I really want to dig into some examples of OKRs and maybe even get some free OKR coaching for myself on this episode. But, you know, but with your background, I wanted to start with looking at the founder experience versus being someone in a larger organization. How do you bring in that context of where you are in your journey into how you think about setting goals for an individual?

EVAN: I think it's a hard question for me because my viewpoint on how goal setting and strategy and achievement in organizations has changed over this whole time, right? So, I was a founder, then at these larger organizations. I think I've tried to synthesize some, like, through line rather than difference between them. So, let me start there.

I think when you look at a founder, or a founding team, or a larger organization, the key thing to figure out is where you're going and coming up with really clear goals. And then, depending on the size of the organization, there's different tactics you can use, right? So, if you're a founder, it might be just sitting down with your co-founders once a week, having a clear Northstar metric, and having a clear goal, and then everybody's running, and that works.

Zoom to a 100-person company, which is, like, I probably focus on, like, 20 to 100-person companies. And now you have a lot of confusion between departments because you have people who are working on very different parts of the business. So, I think OKRs, at that point, are really great because it is this, like...and we will talk more about OKRs. But it's this cascading goal-setting technique where you have company goals that everybody understands and agrees to, and then each department is carving out how they're going to support that, which is, like, less necessary for a small company.

But I still think the key thing is to know what you want, what your biggest problem is in getting there, and what your approach is going to be in overcoming that problem, which is, you know, is, like, I guess, strategy 101.

VICTORIA: I like that. And it's funny; it makes me think of a tarot card layout. That's a situation I'll come and approach. Anyways, I wanted to get, like, down to the basics. I think we said OKRs earlier, but what is an OKR, if you can define that?

EVAN: Yeah, so objectives and key results. An objective is any goal you have, so that can be launch a feature, revamp your sales process, or achieve some sort of milestone or some capability, right? So, often, that's, like, build a new department, or come up not just with a specific feature but a new offering, like launch a whole product line. Anything that's important to you can be a goal. It should be clear and inspiring. And that's the objective piece.

Key results answer the question: how will you know if you're successful in reaching that goal? That might be if you're building a new department, a certain number of hires. If you're launching a feature or want to have a new offering, that might be some KPI for the product team, like, you know, onboarding rates or retention rates.

VICTORIA: Yeah, and let's maybe even go into a real example: myself, I'm a managing director here at thoughtbot. People who aren't familiar with thoughtbot...I'm sure everyone listening has [laughs] familiarity with what we do as a product and business consultancy. And our team at Mission Control, the goal was to innovate on our approach to how we were deploying and managing software.

So, over 20 years, the trends and modernization of infrastructure was something we wanted to be a part of, and we wanted to enable and accelerate not just our own development teams but our clients' teams in deploying software securely and efficiently and meeting everything that we need to do. Like, it's an incredibly complex environment. And there's lots of choices to make. So, that's, like, the big vision of what we're trying to do at thoughtbot. It's a new service. It's touching not only our internal processes but also, like, the growth of our business overall.

So, what I've done as a managing director I talk with my team. I work with the CTO of thoughtbot, Joe Ferris. He's my acting director [chuckles] on identifying what is our overall approach? What's our strategy? So, one of the things we do at thoughtbot, one of our strategies, is to put content out there. So, we want to build stuff that works for us, and we want to share and talk about it.

And we believe that by putting good stuff out there, good stuff will come back to us [laughs]. So, really just increasing the amount of blog posts, increasing the amount of open-source contributions and [inaudible 13:03] people we talk to and hear about what their problems are. We think that that will be an indicator for us of whether or not we're being successful in growing this business. So, that's just, like, one small strategy, but I've got five other ones if you want to talk about them.

EVAN: Yeah, I mean, you highlighted a large goal that you have, and then some of the, like, sub-objectives in reaching that goal. And you could imagine key results being metrics along number of blog posts, audience size, number of readers, engagement. I mean, all those have different values, depending on what your goals are.

VICTORIA: Exactly right. Like, there's the overall leading indicators we have of, like, whether or not we're successful as a business [laughs], which is, like, revenue, and, like, margins of profit, which really aren't going to change. And as a company, we don't change our policies or things that often to where those costs are ultimately going to change. It's all about, like, are we bringing in new business? Are we retaining the clients we have? And are we able to sustain, you know, work that centers around this problem area?

So, that kind of, like, makes our goal tracking, like, the numbers month to month somewhat easy. Although those individual strategies and how they all line up to meet, that is something I think I'm curious to hear about how you facilitate those discussions with teams. How would you, like, begin an engagement with a team where you have a company like thoughtbot [laughs]? How are you going to coach us to get better at our goals?

EVAN: Well, one thing I do is I pull apart KPIs, Key Performance Indicators, from OKRs, which you actually implied. KPIs are metrics you use to judge the health of your business, when OKRs are the goals that are going to transform your business. They fit well together. But, you know, for a founding team, they're still trying to figure out, well, how do we actually measure if this is going well? What does that mean? And I have a whole technique for that.

But for a larger company, something like thoughtbot, you probably have pretty clear KPIs for the business and for each department. And you can look each month to make sure that those are in a healthy band or each week. And then, when you go to set goals, one of the things you can say is, "Hey, what's not working well? Why are the KPIs not where they should be?" And there's other ways of coming up with good goals, but I do think that's one of the starting points for goal setting.

Another one, and I'm curious if you all have this here, is, like, a sense of what's holding back your growth. So, if you have a clear goal of growing your business year over year; usually, people in different departments have a sense of what challenges they're facing in executing towards those growth goals. And, fundamentally, there's usually some sort of competitive or market conditions or customer conditions that are concerning to you as a business in terms of where you're currently at. So, do you all have that type of, I guess, angle on thoughtbot's growth at all?

VICTORIA: You know, for me, it's my first year as managing director. And experiencing how thoughtbot does planning, I appreciated our approach this year was to ask each managing director more like a retro style, like, "What should we do more of? What do we like doing? What didn't really work, and what should we do less of? And what other things do we want to start doing?"

So, it's kind of similar to start, stop, continue but, you know, just really reflecting on, like, what's working? What should we do more of? What doesn't work, and we should just stop [laughs], or change, or figure out how to improve? And then, what should we start doing? And what kind of new behaviors do we need to practice and learn to build a better system?

Which I think when you talk about what's holding people back, I think it's difficult to understand in a complex organization of 100 people how all these departments work together and how they contribute and support teams. So, I'm curious, from your experience, and you like to come in and organize and get focused, so if you have that level of complexity in an organization, how do you start to get people organized and understanding how they all work together and what's working and what's not?

EVAN: Yeah, that's a good question. I might punt that to the second half of my answer here and answer an earlier question [inaudible 17:08] how we get started. Because I think that actually comes up as, like, the second piece. I think the first piece is, like, when I start with an organization, I usually sit down with the CEO. Maybe there's a founding team. Maybe it's a leadership team.

And I try to understand their vision for where the company's going and, one, how clear and actionable it is. So, does it feel like, oh, I get exactly how they're going from point A to point B to point C, or is it a little bit murkier? And trying to nail that down. And sometimes I do, like, a strategy workshop around that.

But the next piece is understanding if they have a clear plan for the next quarter, next year. When I come into companies, I'm doing OKRs quarterly. So, even if they don't have a clear strategy, we still need to set goals for the next quarter. I then have them just kind of draft goals with not that much guidance here. I might do some sort of training so everybody, like, understands what OKRs are. And then, you know, I do...and this is a common thing, I think, like, my background is in product, is trying to understand the root cause of things.

So, usually, there's some goal that I can ask. And, usually, there's a goal that's, like, something that seems very strategic, like a new offering, or changing how the business is organized, or it's very growth revenue-oriented. Those are, like, the two types of goals that people usually come up with.

So, there's a lot of just, like, asking why this is valuable, and kind of going up the ladder, down the ladder asking why it's valuable, and understanding what their root motivation is for doing this. And then going the other direction and saying, "Oh, if we did this, then what would happen?" And trying to just understand how they're thinking of this goal and how it fits in a longer chain of events.

And, usually, through that process, we shift the focus point. So, it's rare that somebody comes up with, like, exactly the right goal. I think when they start understanding what would the effect be of that goal, sometimes one of those things is the actual goal. Or if there's a root cause, it doesn't always mean that we go to the root cause, right?

If somebody wants to, like, fix their onboarding, and that's really, like, their whole focus point, you know, when you say, "Why?" and they talk about helping a certain customer get more focused. And then you may say, "Well, why?" And they say, "Oh, well, you know, we have this revenue model that involves helping them, and we make money." And "Why?" "So we can grow our business at a certain clip." And that's the arc that we build.

That doesn't mean we go to, oh, well, you're trying to make more money faster. That might not be really what the focus should be for the quarter. So, we have to always start just trying to, like, dial in with what the right angle is. That's both...I think you want to choose the thing that's the most fundamental to the business that still feels attainable and focusable, if that's a word, in the short term, right? That's like, oh, this is a good target for a quarter or a year, if you're doing it on an annual basis.

So, that's, like, how I usually get started with folks, which, you know, depending on how much thought there is around strategy, like, it goes in different ways. Sometimes, the company has a very, like, clear strategy, and then everything I said works pretty smoothly. And you get to a goal very quickly that you kind of orient the company around.

If the strategy is either not explicit or maybe the CEO has a different vision for it than, you know, CTO or the head of sales, then there's more negotiating between folks and getting on the same page. And I think that's a whole, like, can of worms that we can dive into, but that's, like, a different type of exploration.

VICTORIA: Yes, I love all that. I have so many follow-up things I want to ask. Just to play it back a little bit, too, I really resonated with some of what you're saying around it's kind of better to draft it; just write it. Like, the act of planning is more valuable than the plan itself. Like, get as close as you can as fast as you can [laughs]. That makes sense. Like, something that feels, like, good enough and, like, kind of go with it and, like, see how it goes.

You know, like, I think that's a mindset that can be difficult to implement in an organization, especially if there's been, like, past trauma with, like, not meeting your goals. And how does that flow down to the organization?

EVAN: That's a hard thing.

VICTORIA: And it makes me think of, like, what you started with, like, talking about getting to the root of what's happening. Like, what are the motivations of individual people? Like, what's happened in the past? Like, trying to take an approach that's...I prefer blame-aware to blameless. You can't get away from the tendency to blame people. So, you just have to accept that that happens and kind of move on and, like, quickly go past it [laughs] and just, like, really get to, like, what are the facts? What does the data say about this organization? So, anyways, I think that that was where I went to. I think --

EVAN: One thing I did...I started with a new company; I guess, two or three quarters ago around the OKR coaching. And, you know, I think there was this expectation. We've been doing OKRs. There's issues we need you to come in and solve and fix everything. And the tone I tried to set was, hey, I'm not here to set great goals for you. You're going to set the best goals you can. And I'm here to help support that process and teach you a lot about goal setting.

And we're going to do this every quarter. And after two or three quarters, things are going to start becoming a lot easier. People are going to communicate better. Everybody's going to be on the same page. And it's going to feel like, oh, we're getting really good at goal setting.

And then, like, I try to set that tone when I start working with the CEO of, like, the point here is to make your whole leadership team good at goal setting so that you have this skill as an organization, rather than set just the right goals with the right language in the right way right now, right? We want to timebox everything. So, we're moving forward using this tool to make progress throughout the quarter, and then each quarter, revisiting it and getting better.


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VICTORIA: And I'm curious if there's anything else when you're evaluating whether or not someone might be a good fit for the work that you want to do with them. Are there, like, some red flag, green flag energy that you check for with executives when you're deciding whether or not to work with them?

EVAN: Yeah, there are two flags that come up; one is, are they clear with what they're saying? I think a lot of leaders want to sound good. So, that doesn't mean that they need to be clear right off the bat. But in a conversation where someone says, "This is our vision," and you say, "Hey, I don't understand X, Y, and Z," or "This part didn't make sense to me. Can we dive into it?"

And yeah, if someone through a conversation can be really clear about what's important to the company and where they're going, I think that's, like, key. Because if someone's talking around issues all the time and when you kind of bring up things they don't really address it, it's very hard to make any progress. It's like, you know, the lack of specificity ends up being a defense towards maybe dealing with some of the difficult conversations.

But, like, at the end of the day, like, one of the major things that happens with goal setting that makes it, I think, feel exciting to people when it does—it always feels exciting to me [laughs]—when it feels exciting to other people is that they say, for the first time, "Oh, this is actually the thing holding us back. This is the problem. Yeah, we want to grow our business."

But when you say, "Well, what are all the things you do to grow your business?" All of a sudden, you start talking through things, and someone says, "Hey, this is the real problem. This is why we're struggling to grow our business." And, you know, that transforms the conversation. People who are avoiding being specific, that can be really hard. That's one thing.

And the other thing is around responding to feedback. And, you know, you can just...and this is a common interview question, right? You can ask somebody, "What do you think the weaknesses of your organization are?" And if somebody doesn't know, but they're, like, open to it, that's, I think, totally fine. But if it seems like they're constantly kind of, like, filibustering the answer there, it's like, hey, the main thing you're bringing me on to do is to make sure that you communicate the weaknesses of your organization to everybody else because that's what goals are about. They're about overcoming the weaknesses of your organization.

So, those are two areas. And they also speak to, like, I think, rapport with the people that I'll be working with.

VICTORIA: I agree. And I like that, you know, you're asking really for people, are you going to be honest about what's happening in your organization? Are you honest with yourself about where you're not doing well? And I think I also pay attention to the language people use to describe those problems. And are they really speaking with a growth mindset or a fixed mindset? Because that's a really hard thing to change [laughs]. Naturally, I think people who are good leaders and run successful companies have a growth mindset. So, I think that's usually there. But that would be some yellow-flag stuff for me.

EVAN: You know, when people are looking to hire an OKR coach, they usually already are looking for improvement. And it's not like they're hiring a product manager, right? You have to be saying to yourself, hey, I believe that if we did better around goals, our company would grow better. We'd have better focus. We'd have better alignment. Like, there's already a belief that people have that is usually pretty self-aware of the limits of both the people there and the organization where it's at today, and they're looking for help.

So, I think I come across what you brought up more in individual people on a leadership team that, like, feel more coachable or less coachable depending on how interested they are around expanding how they think about things and growing. And, you know, obviously, [inaudible 27:01] lots of opinions that are wrong, and I love the disagreement that comes up there. But you want to, you know, you want to be speaking to people that are generally open to learning through a conversational process.

VICTORIA: Right. Yeah, I think it's like a confirming thing. Like, if they're reaching out to a goals coach, they probably do have a growth mindset. And if the top leadership does, then that means that there's an opportunity for other people to come along as well. So, I like opening it up that way and getting people to get specific about their goals as well. I think that's a real challenge. Like, it's either too vague or too specific, not inspiring enough.

Some people still bring up SMART goals with me. I like to prefer HARD goals, but you probably need those. And I'm curious if you're familiar with those acronyms. I can spell them out. And I'm sure you've heard of both of these [laughs]. A lot of people are familiar with the SMART goals and the specific, measurable, actionable. I forget what the Rs and Ts are.

But then HARD goals are heartfelt and more around, like, the big vision. And it's something that you want to get people excited about, which is something that you said earlier. Like, how do you get people excited? And some people would think of a corporate goal-setting event as a level three fun [laughter]. So, how do you make it more like a two or a one?

EVAN: I don't know, a lot of what I hope I offer to folks...and I've gotten good feedback here is that I enjoy goal setting a lot. So, talking through all these problems, talking through challenges, doing workshops, having these conversations. Like, whenever I'm doing that, it's my favorite thing to be doing. So, I think, hopefully, some of my joy just rubs off on the people around me. Because I do think talking to somebody who's excited about what you're talking about is helpful.

The other thing is, usually, at a decently small company, under 100 people, I'm working with the CEO and the leadership team; you know, people are there because they care about the company. They care about the mission of the company. They care about the people in the company, and they care about the growth of the company.

So, I get why goal setting has, I think, can have a bad rap. But if you're fundamentally solving problems that people care about, there should be some, like, glee that comes in when people say, like, "Oh, yeah, I thought this was going to be about, like, how do we grow more? And that felt very generic to me." And it turns out when we actually think about how we grow more, and we talk through what's holding back our growth and what we can do to overcome that, and we have the top few ideas that we've all come up with, usually, those feel really relieving to people.

And there's a company I'm working with now that I think is struggling to shift their target market a bit because...and there's awareness that the target market needs to shift, but there isn't so much knowledge around the new target market. There's a lot more knowledge around the old target market. And so, we're doing a bunch of research and talking to folks.

And I know once we're able to say, "For this target market, we need to do X," there is going to be, like, a huge amount of excitement and relief at the organization because people will feel like, oh, we've crossed that bridge, that bridge that we were kind of in the middle of crossing and didn't really know where the other side was. We now can see that other side, and we're going there. So yeah, I think there can be a lot of excitement around this stuff when it's real, and it's important work that you're doing.

VICTORIA: Right. Like, maybe there's a good factor of, like, how do you measure if what you've done with a company is successful? Is there a glee scale that you [laughs] use to evaluate?

EVAN: You know, for me, it's still probably more subjective than I want it to be. You know, I'd love it to be like, what percentage of people's OKRs did I [laughs] hit each quarter? And when I work with them, it gets better. But I think that's, like, a pretty short-sighted view in terms of my role. So, you know, I'm looking for people who were maybe disengaged to be more engaged, people who didn't see the value of OKRs to see and be able to articulate how their daily work is different because of the OKRs we set.

Yeah, and obviously, there's excitement when we're solving real problems. And we're changing the problems each quarter, and people are seeing growth increase. You know, like, all that stuff, I guess there's, like, a tangible excitement with. But I hope folks can, like, just connect the dots between the work, which can be tedious work around goal setting and negotiating with people. And often, it pulls you out of other day-to-day work that you're doing, especially for a small company, with the excitement towards the end of the quarter of reaching these goals and moving on to the next challenge.

VICTORIA: I think that's great. I think that was a perfect answer. It's kind of not always easy to know what [laughs], sometimes there's a sense of it, like, you have a feeling, and sometimes you can get data to back that up. And other times, you know you're doing the right thing by the people's faces around you at the end of the workshop [laughs]. So, I think that's great. And so, maybe my final question would be is, like, what would be the ideal organization that you would want to work with? Like, who's your ideal customer right now?

EVAN: Yeah, I guess I have two ideal customers based on these, like, two things that I'm doing. In terms of the OKR coaching, I usually look for CEO or founding team of a company that's now, like, 20-plus people who's saying, "Oh, we have these departments," or "We have this leadership team. And we need to really get all on the same page at the beginning of the quarter because then everybody's going to consistently be talking to each other but has other people that they need to organize." That's definitely for the OKR coaching where, like, 20 to 30 people is where that starts. That probably goes up to 100 in terms of where I focus.

For the other work I do as a Techstars mentor and the coaching I do through that, that's really for founding teams. And that's more focused on how do you take your vision and make that a clear goal statement, which is around, like, behavior change, usually, in a certain population you're targeting? How do you turn that into a go-to-market plan? How do you turn that into a product roadmap? So, for that, that's just much smaller teams.

I actually think that work often needs to be done at larger organizations, too. That's, like, a common thing that comes up. And that can bleed into strategy at large organizations. But yeah, I know that's probably a pretty broad bucket, but groups of people that believe that focus is a key lever towards faster growth.

VICTORIA: Thank you for that. And I guess I said that was my final question, but I'll add two more questions. Can you share an anecdote from being a mentor at Techstars that you think will be interesting for our audience?

EVAN: I think I was struck the first time I did the mentoring. They do, like, a Mentor Madness. So, it's like, you know, six companies in a row, and every company they all have different challenges. But a lot of them, it's, like, helping them articulate what they're doing a little bit more clearly. And often, there's a question around sales and growth and maybe fundraising. So, there's just, like, a focus in that direction. And I found that every company, even though they had kind of different questions, I was giving the same answer to, which was, I don't think your goal is clear to you or to me.

And so, there's this framework that I would use with each company that there was, like, this aha moment. And I picked this up from a person named Matt Wallaert. It was a book, "Start at the End." It's called a behavioral statement. And it's when population wants to motivation, and they have limitations, they do behavior as measured by data. And the kind of conceptual version is, oh, you're trying to get some group of people to change their behavior. And that's only going to happen if you can tap into a motivation that happens to them as frequently as the behavior you want to change. So, it's like a formalization of that.

And each group, I'd like bring up the statement; we work on filling it quickly. And there was just, like, a clarity that would develop around what they were doing and how to orient themselves both on the growth and marketing side and on the product development side. I guess it just struck me how much that little framing was transformative to [laughs] accelerating both focus and alignment but, more importantly, like, getting somewhere that they wanted to get to.

VICTORIA: It sounds almost like building a mental model of what you're trying to do [laughs], right? Like, it was a mental model that you referenced in your mind that helps you make decisions every single day. So, I really appreciate that. And we are about out of time. So, let me ask you, is there anything else that you would like to promote today?

EVAN: Sure. Looking for a couple more OKR coaching clients for the new year, and just happy to chat with anybody who has questions around OKRs or goal setting for their organization.

I also do personal goals coaching, which is a little different from the OKR coaching that I help individual people with their goals. But it's also similar. It's a lot of's a lot more, like, reflection, and getting to know oneself, and coming up with goals that are really meaningful.

And then the other half of, like, I think you alluded to this earlier around systems. Like, how do you take a goal that's important to you and actually act every day in ways that move you towards that goal? So yeah, interested in talking to people about both of those. I do some workshops as well, so people can reach out to me at I can also put anybody on my mailing list. I do some workshops around both those things.

VICTORIA: Wonderful. Thank you so much, Evan, for joining us today.

You can subscribe to the show and find notes along with a complete transcript for this episode at If you have questions or comments, email us at And you can find me on Twitter @victori_ousg.

This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore.

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