The role of emotions in business

This week, we talk about a topic that Rick is researching for his book: how can emotions help and hurt business leaders?

Show Notes

In this episode as part of some research for his next book, Rick interviews Tyler about his experience with emotions in the Less Annoying CRM workplace. Here are some of the takeaways:

• There are frameworks out there for emotional intelligence, self-regulation, but there isn’t much stuff out there about how emotions impact company culture, team performance, and leadership.
  • There aren’t a ton of CEOs talking about their own experiences.
  • Most of the stories out there are from therapists about their anonymous clients.
• There isn't agreement on the definition of emotion.
  • One model is Robert Plutchik’s wheel of emotions (see image below) that defines 8 primary emotions: 
    • joy and sadness
    • anger and fear
    • trust and disgust
    • surprise and anticipation
• A leader who priorities trust may be more likely to create a safer culture where people are free to express their emotions.
  • This makes it so that the emotions that you and other people experience happen in a way that is healthy, and has a mostly positive impact on other people (and  team performance / culture).
  • It also makes it safe for everyone to inquire about clarifying the meaning of each others’ emotions (instead of making assumptions).
  • When you're in a distrusting situation, emotions are probably more violent in a negative way.
• Trust relies on character and authenticity.
  • You might experience trust when you see someone do something that's not in their own best interest, but they do it because they think it's right or some set of values.
  • Competence may also play a part.
• Distrust leads to distrust
  • If you hire and keep people who you don’t trust, it can lead to a negative cycle of distrust.
• One source of potentially negative emotion for leaders is the time between becoming aware of a problem and figuring out what to do about it
  • If you have don’t have a high-trust environment, this can be a risky time period when emotions might be misinterpreted
  • Another source of potentially negative emotion is when an employee leaves
    
    

What else would you add to this list?

Source: Wikipedia

Context

Rick: It's my week for the topic. I don't really have a critical problem per se to bring you that I want to brainstorm with you, at least not more important than what I'm bringing to you today. So taking a slightly different approach with the topic I'm bringing, and it could be a total bust, so I'm prepared for bad feedback from this from the audience. But maybe this works. I guess listeners out there, if you listen to this and you don't get value, please tell us so that we don't repeat this. But if you do like it, please tell us because we'll have more confidence covering topics like this in the future. Now that I've got my writing cadence going at RickLindquist.com, I spend two to three hours every morning before 9:00 AM researching and writing about a topic of my choice. My goal is not to just throw out content, it's primarily learning through the process of writing. And so I want to write a book about emotions, leadership, and teams, and I'm starting to outline that book in terms of what would the table of contents be so it can drive my research. Because I'm going to be learning a lot as I go because I'm not an expert on emotions by any means, I know that the specific angle I'm going to take and the specific outline is going to change over time, but I hope that by constantly revising the outline based on what I'm learning, it can drive my short-term and short-form writing on a weekly so that I'm killing two birds with one stone. I'm writing and fulfilling what I want to do at RickLindquist.com in terms of outputting content, but I'm also learning the things necessary as part of research for this larger book. It may take me a whole year to write this thing. It's just a question of putting a couple of hours in a day most days. I started this week researching emotions and building the outline. I'm stunned at how little agreement there is on how emotions work and how they impact people. Most of what I'm reading is research and academic papers. I have not been able to find a ton of CEOs talking publicly about the role of emotions in leadership and in teams. Kind of coming back to listeners out there, I personally think that this is a topic that we all need to talk about more because I hypothesize that we can become better leaders if we're more in touch with our own emotions and others' emotions because it's the basis for how we form trust with our strong relationships. And trust is the ultimate success factor for a highly functioning team. But I'm trying to do research. I'm having trouble finding like layman's explanations of the stuff with consensus. I was hoping today that I could, I don't want to say interrogate, but I kind of have a feeling that I need to ask you some tough questions. I want to ask you some tough questions about your experience with emotions, both from how they happen in your head and within your body, as a leader and CEO. Then also, how you react and observe and handle emotions of team members in the day-to-day stuff. We've talked offline I know you've, we've talked offline and made sure that was okay, but is there anything that's off limits in terms of asking you questions?

Tyler: No, I mean there might be ... I'm happy to share my own experiences and I might be a little more secretive if I feel like I'm exposing something about someone else who hasn't necessarily given permission. But for myself, now I think I'm an open book. We'll see.

Rick: Yeah. Cool. Listeners, I think that the other thing that we want to do here is I want to model talking about this openly, so I'll also jump in with my own insights on emotions. I'm a pretty, in terms of like emotional spectrum, I wear my emotions on my sleeve much more than Tyler does. Not to say that we're both not emotional people, it's just we may have very different experiences with emotions because of our personalities. I'll jump in when I can add a personal take. Would you add any anything?

Tyler: I'm curious here, so I don't hear people maybe using the word emotions a lot, but I hear people talking about mental health and self-care and stuff like that and how that should be talked about more. How much overlap do you think there is between ... Are these just different terms for the same thing or are you talking about a different thing from that stuff?

Rick: I think there's a lot of stuff out there in terms of the self-help genre of self-regulation. The buzzword is emotional intelligence. That's part of it. But I'm more interested ... I think, yes. I think mental health is a topic that's becoming more and more accepted in terms of talking about, but still, we're very private about it. All the research I've done is from therapists. The thing that you actually get exposed to is therapists talking about their clients, but their clients are anonymous and they're the CEO of this. There are frameworks out there for emotional intelligence, self-regulation, but there isn't a whole lot of people talking about their own experiences with that as a leader.

Tyler: I do hear podcasts and stuff where people say things like, "People don't talk about mental health enough. We're going to talk about it. We're going to talk about the struggles and all that. Is this different from that or just a different term? Or is it the same idea?

Rick: Yeah, so it's one part mental health, it's one part. And I would say that deeper within that there's still a lack of talking about that one part. I'm interested in that, but I'm more interested in how our different levels of mental health and responses to emotions affect the work environment, and getting shit done. Because when you build a team, you're going through this right now, right? With prioritizing the roadmap for 2020. People have different opinions, or say different things, react differently and that can cause all sorts of domino effects across the organization, some positive, some negative. Part of the role as a leader is to create an environment where those things have positive effects, not negative effects, while also maintaining your own behavior. That's essentially what I'm interested in.

Tyler: Yeah, right. That's less about my personal mental health and more about how does managing a company work when emotions are involved?

Rick: Because they always are.

Tyler: Yup. Okay, cool.

Rick: Yes, exactly.

Tyler: Let's dive in.

Rick: All right, in terms of quickly outlining the approach I want to take, so I want to start with asking you some questions about your emotions as a leader. If it makes sense to talk about emotions in other situations to draw comparisons, do so. But let's constrain ourselves to focusing on emotions in your role as CEO. We know you love Shelly.

Tyler: Yes. I was going to spend the next 40 minutes talking about that if you hadn't stopped me.

Rick: Perfect. And then after we go through you, I'd like to move into your observations on how other emotions impact you and other people, and then maybe we can wrap up with how that bubbles up to a team level or the organization level. In other words, how it impacts the culture of an organization.

Tyler: Cool.

Rick: Does that sound good?

Tyler: Sure.

What roles have emotions played in your business in the past?

Rick: I'll just start with a general question to see where it goes. What roles have emotions played in your business in the past?

Tyler: I mean, that's pretty vague. My personality is, like you said, I do not wear emotions on my sleeve. I don't think I'm bottling them up. I think I don't feel emotions as strongly as a lot of people do. And so I would say emotions have not had a ... You'll probably dive in and tell me I'm wrong, but nothing comes to mind as emotions having a major influence on things. But I think that's both positive and negative. I think I've avoided a lot of the potential pitfalls, but there's also probably, I haven't maybe praised employees as much as I could of or that type of thing. I think I'm right in the middle probably.

Rick: Have you ever noticed yourself using emotion in a situation and been like, "That was bad," or, "That was good?"

Tyler: If I think it's bad, it's almost always that I think I should have used emotion and I didn't.

Rick: Interesting. Okay. You think emotions are important and sometimes you don't use it when it should be used?

Tyler: Yeah, so everybody's a different personality and I think actually it's not just me. Also, Michael, who's the other main leader here, he manages the largest team at the company and then I'm the CEO. I think both of us are pretty similar in that we are empathetic and that we care about people, we're going to treat people well and all that. But we don't necessarily express ourselves in a super touchy feely type of way. Some employees don't need that, but maybe some do more and one, in particular, has told me that's a thing we need to be better at.

Rick: Interesting. And what do you do in response to that?

Tyler: Some combination of feel bad and try to be better at it and not be better at. I mean, yeah, I don't know. It's on my list, but I'm not sure I have any answers for that quite yet. Because I am who I am, I don't think my response should be to pretend to be someone else. I can come in in the morning and be like, "Hey everybody, it's a beautiful day. I love you all," but I shouldn't do that. I need to be authentic. I think one of the things that I do well is I'm authentic and people know they're talking to the real me, so I don't want to lose that, but I also need to meet them halfway and say, "Well, you're someone who ..." I mean, one example of this is I think with our age and younger, a lot of people are more likely to go to therapy and stuff like that than people older than us. A lot of people who work here do. I don't, maybe I should, but I think I'm maybe just not ... I need to connect with kind of, I don't know, I need to treat it like, "Okay, I get that you need certain emotional nurturing that I don't naturally give." You know what I mean?

Rick: Yeah. I think authenticity is ... I think we've talked about that in the past and if you give up authenticity, you give up a lot of yourself and you might feel unhappiness or sadness. So I see you're protecting yourself against a negative feeling, in that case.

Tyler: Yeah, and this is more general than just emotion. But I do think when that situation comes up, when it's like I need to be a certain way but that's not what I am, one option is that the quick option is fake it. The long and better option is to change who you are, to some extent. Not be a fake, but if I think there's something deficient in me, work to be a better person rather than pretend to be the person I think I should be.

What is emotion?

Rick: I like that. That's interesting. Well let's take a step back and maybe talk about what emotion is for purposes of this conversation. In my preliminary research I found an emotion wheel by, I'm going to kill this guy's name, this guy named Robert Plutchik. I'm not sure if he's still alive or not. He's was some sort of researcher, psychologist. I don't know enough about him to give him proper credit, but he concluded, and this is one of the models for emotion, that there are four [Rick meant to say eight] basic emotions or main emotions, happiness and its opposite, sadness. Surprise and its opposite, anticipation. Trust and its opposite, distrust. Anger and its opposite, fear. I'm wondering if we take up happiness and sadness, do you feel those throughout the course of your time as CEO?

Tyler: Yeah, I mean, you hear a lot about the kind of the roller coaster of a startup, and I think they're all muted for me because, once again, I think I don't feel emotions as viscerally as a lot of people do, but it's still the same thing, just lower. It's the same roller coaster, just the peaks and valleys are not as extreme, I think. But yeah, I mean happiness happens all the time. You get a sale, you have a good month, you make a hire that you really were hoping for. I think I run Less Annoying CRM in a way that minimizes sadness more than most startups because it's not like it's all on the line and this is a make or break deal or anything. We've avoided that, which I think reduces some of it. But you know, yeah. You give a job offer to someone and they decline, or someone leaves the company or something like that. Definitely sadness is a reaction to that I think.

Rick: Interesting. And it sounds like you ... What I'm kind of reading is that inside your head you maybe have the emotion, but you don't express that as much as other people, or is it the feeling inside of you isn't as strong as other people too?

Tyler: I think it's, it isn't as strong probably. I don't know how much it is. I'm going to sound like such an asshole here. I have just an amazing life across the board. Not just work, but work is part of it. And to some extent humans do get used to ... Like if they're miserable all the time, they get used to being miserable, and if they're happy all the time they get used to being happy. So I think I'm really, really happy, but I also don't think ... It's kind of background noise at this point where it's not constantly I'm just being overwhelmed by happiness.

Rick: Yup. You seemed happy when we went to St. Louis Blues hockey game though.

Tyler: Yeah. Well until they lost due to a bullshit call. Yeah.

What about trust and distrust?

Rick: What about trust and distrust? Have any of these, I read off those emotions, did any of those feel stronger for you than others, or are they all about the same in terms of how you process them?

Tyler: Yeah, some are definitely stronger than others. So happiness, sadness, surprise, anticipation, trust, distrusting or fear. For example, anger and fear are supposed to be opposites. I feel fear a lot more than I feel anger. But I feel, I think like the environment of Less Annoying CRM, there's a lot of trust. Trust, by the way, I should say is I have decided that's my one word. If I were to do yoga or whatever, I think you're supposed to say your mantra to yourself. If you just get one word, for the rest of my career my word is trust. I decided that earlier this year.

Rick: Why did you decide that?

Tyler: Just because I looked at all of the things that I feel good about and that work, and they're all kind of disparate. Some are product related, some are about hiring and employees, some are about customers, and all of it has one thing in common, which is trust. I think that's what Less Annoying CRM does well. That's what I do well, and it's what I really value and I don't want to lose. That's the one that I want the most, I think.

Rick: What does trust mean to you in that context?

Tyler: I guess trust means ... When you're interacting with other people, there's the potential for everyone to have different interests, and different goals, and there's all this you can put up barriers, and you can watch what you say and all this because you don't want to give the other person some reason to ... You don't wanna be vulnerable, basically. You don't want to cause something that is against your best interest. To me, trust is when two or more people are kind of in agreement that even if our interests aren't the same or whatever, this is someone who's got my back and I don't have to play politics with them, basically. I can tell them what I feel, they're going to tell them that they feel. If it works ... I think you and I have a lot of trust. We disagree all the time, but we both know it's not going to cause problems, which gives us more freedom to disagree rather than less.

Rick: When you're saying your mantra in your head, what action does that inspire for you? How do you express that emotion and how do you make sure that other people in your company are feeling that emotion too?

Tyler: I mean, I'll give you a recent example. We've been talking about product development and we were talking about should we launch a new product, should we raise prices, should we do all this? And at the end of the day what we ended up with was we're not going to do anything. We're going to stick at $10 and change nothing. We were pretty close to a standstill in terms of what to do, and trust was kind of the guiding light there, where it's our customers have certain expectations that if we're not sure what the right thing to do is, it'd be stupid to rock the boat here and make them go through a change cycle and they don't have to. To me, trust was the reason for that decision.

Rick: So you basically use trust as almost a core value on how you treat your customers?

Tyler: Yeah, I don't think I ... You're the type of person, you have a lot of experience formalizing this, and making it a document and sending it to people, and maybe I should do that. I don't have this formalized, but I know the word trust is important. I know the concept's important and I try to apply that when it seems relevant. Yeah.

Rick: What's another example of maybe an interpersonal relationship that you have with another coworker where you've actively built trust? What are some of the things that you've done? I would be more interested someone you didn't know before Less Annoying CRM, so someone that you met as the CEO and you have built trust with, both ways, what are the things that that person has done, and what are the things that you've done to grow that trust?

Tyler: Okay. Do you want me to name a specific person here?

Rick: If you feel comfortable doing so.

Tyler: Yeah, sure. I think he listens. So, Hey Robert, how's it going? And you met Robert at my bachelor party. Yeah, I mean we hired him and he was a CRM coach at first and did HR work, and is now kind of the lead developer. I mean, I trust everybody who works here, but he in particular, he does HR, he's got access to absolutely everything. If anyone could ruin the company, after me and my brother, it's him. He has every bank account, everything. I think that to me, well I have no idea, I didn't intentionally build trust with him, so I can't answer that. But what he did to build trust with me and what a lot of people here do, is it's when you see them do something that's not in their own best interest, but they do it because they think it's right or some set of values. If you see someone act based on values rather than personal interest, to me that's a sign, especially when they don't know you're watching. That's a sign that at least once in their life they made that hard ethical choice. I mean, it might not be that hard, but it's like they could have been lazy and cut a corner here and they didn't. That's, to me, a pretty strong trust builder.

Rick: Character.

Tyler: Mm-hmm (affirmative).

Rick: Integrity. Yeah. Interesting.

Tyler: I actually think a lot of people are much ... I think the world lacks trust, but it's not individual people, it's systems. Because everyone we've hired here, I can't name anybody where I'm like, "No, I don't trust that person," but I think you take any of us, take me and put me in some horrible corporate hell hole where the company doesn't have my back, I would become untrustworthy immediately. I'd be a mercenary, you know?

Rick: Interesting. I'm going to come back to that. This led me down another path. Have you ever given someone trust and then had them, maybe this is something you can keep anonymous, and been returned distrust, and that caused you to distrust that person back?

Tyler: I don't know exactly. I've only had one person who's no longer at the company, that we had real interpersonal conflict while working together. Definitely. I think he didn't trust me. Yeah, I think I came to not trust him to some extent. But yeah, I'm trying to think of trust was like the core problem there and I don't know that it was, I don't know. Sorry. I don't have a more conscious answer there.

Rick: No, that's, that's fine. It sounds like you do a really good job of building trust at Less Annoying CRM and make it a really safe place to work.

Tyler: Yeah. I think one reason I don't view trust as a particularly emotional thing ... Happiness and surprise and stuff like that, I'm bad at those. Trust is boring and conservative and logical, which I think I'm good at. And so it seems clear to me that that should be my strength versus surprise. I don't give people birthday presents. That's not me.

Rick: Do you value the feeling of trust? When you feel trust in someone do you know what that feels like and go, "Oh, that feels good?"

Tyler: Mm-hmm (affirmative). Yeah, absolutely.

Rick: And same thing with distrust, if you feel distrust that feels really bad?

Tyler: Yeah. Yeah, well and as CEO, I'm trying to think of a time where I felt distrust. I feel distrust towards third parties all the time, where this person's just trying to sell to me or whatever.

Rick: I felt that today.

Tyler: Yeah, you got a little cranky about a bad sales email.

Rick: Yup.

Tyler: Yeah, I like trust a lot. Being a CEO's great, because if you distrust someone you just lock them out entirely. It's nice having the power to not necessarily be the victim of it. Someone's going to be the victim of distrust, but it's not necessarily going to be me.

Rick: Yeah, I don't know how many companies, and CEOs prioritize trust like you do, but it seems like that prevents a lot of other symptomatic things from happening that could have been prevented by only hiring and keeping people that you have a high amount of mutual trust with. It's a lesson. I don't think I did a good job of that in the past.

Tyler: Yeah, I think it's super. I'm not sure I did this intentionally, but there are definitely been times where I have had, I want to say conflict, but my interests have been misaligned with an employee's. They just think something and I think we should be doing something else, or I personally am not finding this job as fulfilling as I could, or whatever. One thing I really value and I appreciate their maturity about this, no one's ever suggested I did anything wrong or they got screwed over or anything. Every employee who's left, for example, it's always been on great terms because they're just like, "This is not what I want to be doing right now, but it's no one's fault." It's always been positive.

Rick: That's cool. Do you ever have anticipation or anxiety around things?

Tyler: Yes. Probably aside from that one person I was mentioning that we had real conflict, aside from that, I'd say the main thing that causes me stress is when a potentially bad outcome starts to happen. If an employee tells me something like, "There's a potential problem." It always gets resolved and it's always fine, but that time between when I become aware of it and we figure out what to do about it, that's probably my least favorite moment running a company.

Rick: The unknown.

Tyler: Yeah. I don't know if that's anticipation, but yeah.

Rick: Yeah, I think it is. If you had to characterize the most emotional thing, it could be a most trusting thing, distrusting thing, happy thing at your 10 years as ... is it nine or 10? 10 years.

Tyler: Yeah, a little over 10 now.

Rick: 10 years at Less Annoying CRM. What would that moment be?

Tyler: The happiest I feel is generally when we're celebrating some kind of milestone or something. When it's not work hours, it's a party. Yeah, this happened while we were doing the podcast. For my 10 year anniversary everyone surprised me with a shabu-shabu night at the office. Everyone got drunk and the tradition is everyone toasts each other, and that's the type of thing. There have been a handful of parties and stuff like that where that's about as high as I've ever felt in my life. Then yeah, the worst is ... I'm trying to think. It's probably when someone leaves the company. It's always been on good terms, it's only happened a few times, but when an earlier employee who was really a core part. Every company is a combination of the culture of the first few people they hired. When one of those people leave, there's no way for a new hire to replace that. They can replace the work output, they can't replace the cultural importance that person had.

What should the role of emotions be at work?

Rick: Hmm. Another broad question. We just talked about how you feel emotions and it sounds like you feel them, but you don't express them very vividly, you're pretty neutral most of the time. What should the role of emotions be relative to where you are now?

Tyler: For me? I don't know. I don't know if there's a one ... Do you think there's a one size fits all answer to this?

Rick: I would say for your situation, based on your situation and for your company that you're building, do you feel like emotions, getting more in touch with your emotions, expressing emotions more vividly could make you a better leader in some way?

Tyler: Yeah, I'm sure.

Rick: Do you know what those are?

Tyler: I mean, I think one thing, I was kind of referencing this earlier that I could definitely be better about, is basically praising people. I feel a level of pride and happiness about everyone who works here. I don't have any kids, so I don't know what that feels like, but I think when people describe, "No, you don't get what kids are like, it’s this" and I'm like, "No. That's exactly what I feel being a boss." I think if I just laid that on heavier than I do, that would probably .... not that morale is a problem, but people would be even happier probably.

Rick: In other words, it's not a feeling thing it's an expression thing.

Tyler: Yeah, I do think I feel like that.

Rick: You feel that. You feel that it's like, "Hey, some people don't know that as much as you want them."

Tyler: Yeah, that's true. But I do think my feelings, my emotions are more muted. For example, I don't cry, not because I'm trying to be a man and meh, meh. It's been years since I've felt the emotion to cry.

When was the last time you cried?

Rick: When was the last time you cried?

Tyler: I know I cried when I watched Titanic.

Rick: Did you really?

Tyler: I mean, I as a kid, but yeah. I absolutely did.

Rick: That's the last vivid memory of crying?

Tyler: No, I've definitely cried since then, but I do think I feel the emotions and I don't show them, but I also think I'm just naturally less emotional. A lot of people who work here have told me, and I really admire them for being so open about it, they're just like, "Look, I'm pretty emotional. Sometimes shit gets real and I need to go lock myself in a room for a little bit, so fair warning."

Tyler: I don't have that.

Rick: Yeah, interesting. Last time you were in Park City, this is getting outside the business context, but I'm interested in your thoughts on it. I rediscovered your taste in music, which is what I would call highly emotional music.

Tyler: See, I disagree.

Rick: Okay, so heavy metal, Fear Factory, Killswitch Engage, which I just discovered. I mean, these are people that are playing some serious loud, aggressive guitars and screaming. Right?

Tyler: Yup.

Rick: Why is that not emotional?

Tyler: Well, I was in a bunch of bands when I was younger, so I have like very real experiences with this because I loved the music and I hate the culture of heavy metal, because it's all about like, "Oh, I'm going to fucking kill you, rawr, rawr, rawr," and I'm not an angry person, so I as up on stage with flip-flops and my water polo tee shirt on playing death metal. The reason I like it is heavy metal is the closest thing to a popular form of music that is very, very technically challenging. Classical and jazz are this way too, but no one likes the ... Kids don't, it's boring. Heavy metal, I think, brings the same level of musical technical ability, like difficulty of playing it, that you just don't get from a typical country song, or pop song or something like that. That's why I like it. I never had the anger that metal singers seem to have. I was in a heavy metal band in college and one of my classmates at WashU was the other guitarist, and we were both guitarists. We wrote all the songs. Every song was named after what we were studying in calculus. So there was like Coloplast Transform, Jacobian Coefficient, the songs were about math because we just didn't have anything that we wanted to write songs about.

Rick: But were you angry at the math?

Tyler: No, we are just like, it's all screaming. No one can tell what you're saying anyway. So if you're just screaming about an equation, like whatever.

How employees’ emotions impact culture

Rick: That's awesome. So switching gears, I want to talk about your observations of your employees expressing emotion. You just mentioned that you had an employee who said, "Sometimes I need to go lock myself in a room." What are some examples of emotional moments for a team member that you can describe, and I'd love for you to tell stories about how maybe one story of how that moment positively impacted other people, and maybe another moment where it negatively impacted another team member.

Tyler: Okay, so a positive one is pretty easy, which is, so one of these people, anyone who works at the company knows who I'm talking about based on the story I'm about to tell, but I'm not going to use their name anyway, came to me and basically said ... This was the person I mentioned earlier who said, like you saying to me like, "Tyler, you're not expressive enough. I need praise. That's something I need. I've been talking to my therapist, that's like a thing I need," and what they decided to do is as their 20% project, they were previously going in a different direction working on other stuff, and they were like, "This company needs more nurturing and praise, so I'm going to make that my 20% project." And so they started planning more company events. They started celebrating everyone's birthday, and celebrating work anniversaries. At a bigger company it's always someone's job to do this stuff, but as we've grown, just no one really took ownership of that and that was great. It's something we needed done and it filled in for my deficiencies. It almost ... I know I still need to get better, but it also gave me a little bit of relief where it's like, "Not everyone has to be good at everything. Someone else is handling the stuff that doesn't come naturally to me now."

Rick: Yeah. If you're self-aware enough to know where you're ... this is called emotionally weak, you can fill that void with someone who has a strength in that category.

Tyler: Yup, absolutely.

Rick: Interesting. What about a negative situation?

Tyler: Okay, where someone-

Rick: Were you going to say something? Sorry, I didn't mean to cut you off.

Tyler: Well, no. I didn't have a great point to make. Don't worry about it.

Rick: Okay.

Tyler: A situation where someone has expressed emotions and it's led to a negative outcome, something like that?

Rick: I'm interested in it when someone's had an emotional reaction to something that resulted in pain or slower progress in the short term.

Tyler: Yeah, so the person that I was mentioning that I had real conflict with, there's tons of examples of this. They're all isolated to me. One thing I'll give him credit for is he was the ultimately professional in that there were all these things going on in his head that were driving him crazy and no one else at the company except me was aware any of that was happening until he left. But, I'll say there was a lot of times where something happened that, to me, was very, very minor. Literally in one case it was the type of coffee that we picked for our coffee machine. I don't even drink coffee. I don't care what the coffee is, it was basically a vote. People voted and we picked that coffee. He took it as a slight. Basically, it's the opposite of trust. He thought I was not taking care of his coffee preferences, or something like that. A bunch of emotion got attached to something that really, to me, was completely unemotional and it just blew up and turned into this huge thing where it's like, "Okay, what do we got to do to make this right? I'll buy you whatever coffee you want." "No, it's not about the coffee, it's about this other stuff." I don't know, it was very vague because it was a really specific situation, but it happened a lot with him.

Rick: Interesting. What about two other people? Have any team members ever had a problem that they needed you to come in and help resolve, that got to that unhealthy emotional state?

Tyler: No, I don't think so. I think that the start of that type of thing has maybe happened before. Two people have different work styles. One's a little more shoot from the hip, "Let's just go and create a lot of work for ourselves and figure out how to do it later." The other person's more methodical like, "No, I need checklists, I need a plan," and basically they were working on a project together. It could have turned ugly, but A, both of them had trust and liked each other, and so they were giving each other the benefit of the doubt. Then, B, the person who did have a problem came to me and was not mad or anything, just like, "I think there's problems with this project," and it was very easy to fix as soon as it was said out loud, you know?

Rick: Mm-hmm (affirmative). You just helped them get everything out?

Tyler: I mean, in that case it was as simple as just being like, "Got it. Don't work on this project any more." It was fixed immediately.

Is your company’s culture unique?

Rick: Yup. Be done with it. You're really a kind of an interesting situation because it sounds like you have a really healthy culture and I don't know how unique that is, but with all the negative commentary out there, like Glassdoor, social media, about employers, it seems like you have a pretty unique situation. Do you think it's unique? Are you copying someone or are you just doing your own thing?

Tyler: I think it's unique. I'm definitely learning from people, although I think every company who ... What it really comes down to is to have a culture like this you have to have ... Maximizing money can't be your primary goal, and at most companies it is. I have thought before about this. I would like to think I'm a good leader at this company. Would I be at a different company? It's not me being falsely modest, I think the answer's actually no. I think one of the reasons is because of all the stuff we've talked about here. I would be terrible. At a big, publicly traded company, a manager's job is to represent shareholders and effectively squeeze as much labor out of the workers as possible and pay them as little as possible. I mean, that's a very cynical take on it, but it's directionally something like that. I think I would terrible at that, partially for emotional reasons. To some extent you have to be able to manipulate people. You have to be able to really be inspired. The stuff I'm bad at, if you're putting people in a shitty situation, the only way to keep them engaged is to be this rah, rah leader, get people excited, give praise. So I think the only reason I can get away with it is because we don't have ... I guess the whole thing's holistic, like the business model, our customers, it all connects and allows me and Michael to manage the way we do. But I don't think it would work everywhere.

Rick: In other words, I could be a CEO at a company, but because I don't have the cap table that you have, I don't have the same owners and the motivations are different, I might not be able to create a similar work environment that you have at Less Annoying CRM?

Tyler: I think so. I think shareholders would hate the culture we've got because there are a lot of employees here who would be willing to work 10 hours a week more, and I tell them to go home. That's stupid. And depending on what your goals are, it's a terrible way to run a business,

Rick: But you're happy?

Tyler: Yup, exactly. And that's the thing, is I think there's a difference between if the only point is to make money, that's one thing, but this is ... I spend 40, 50, 60 hours a week doing this. I'm much more interested in making the environment one that doesn't stress me out. But if the owner of the company isn't working at the company, they would have no reason to value that.

Takeaways

Rick: That's really interesting. I don't want to go any further. I think I'll just kind of move to my takeaways. Do you have anything else that you want to add?

Tyler: No. This was a more interesting discussion than I expected. It's like you said, not something people talk about a lot, so I enjoyed it. But yeah, go for it.

Rick: Yeah, so I think a couple of things stood out. One is, I actually think your emphasis on creating a safe environment, trust, prioritizing trust as the mantra actually makes it so that these other emotions that you and other people experience happen in a way that is healthy, and has mostly positive impacts on other people, on the team environment and on the culture. I guess that makes total sense. When you're in a distrusting situation, emotions are probably more violent in a negative way. Whereas if you're in a trusting environment, it's the other way. It's could be violent, but maybe less violent, but in a good way.

Tyler: Well, a word that we haven't said yet is boring. And I think the downside to a lot of what I'm talking about, a lot of people could run very, very happy companies, but it'd be a little bit more up and down because a lot of people need that for excitement. I think that the culture we have here is healthy and safe, but it's also boring.

Rick: You don't have the drama.

Tyler: Yeah.

Rick: Yeah. There may be some people who prefer the drama to happiness.

Tyler: Yeah, life needs variety, right?

Rick: Yeah.

Tyler: You need ups and downs, even if the alternatives all ups, that a lot of people aren't happy with that.

Rick: The other thing is, I appreciated your definition on trust. I think there's a big element of knowing that the other party has character, which lets you know that they have maybe interests other than their own that will drive behavior. I think there's also another thing that I was thinking of and it's along the lines of competence. When I hired a lot of people that I trusted individually as people, but I put them in roles where they were incompetent. Incompetent is probably the wrong word, but` not confident in themselves, not able to do the job up to my expectations, And that kind of led to a cycle of distrust. I guess, I wonder how thoughtful are you about not putting people in situations that stretch their competence?

Tyler: This is probably another way in which, like I was saying near the end here, that I'm not a great manager. I definitely don't push people very hard. A couple of people at the company have kind of raised their hands privately to me and said, "This is not just a nine to five, I really want to push myself," and that's been fine. But if someone doesn't do that, I don't push them, that probably hurts their personal and professional development. It means they're less productive, so that's probably a downside to this, yeah.

Rick: Well, I'm going to totally disagree with you on that. I think it's actually your secret sauce. I think one of the things I did really poorly at PeopleKeep is I would hire people for a position, that they had competence for, oftentimes. But then I would expect 10X that role and challenge them. I saw it as my job to challenge them to be the best person they could be and the most impactful employee they could be. The 1%, 2% of people were like, "This is great. I love this. This is exactly what I wanted," but most people were resentful about it, not in the moment, but just completely unhappy and distrusting is the right word. It caused so much cycles of distrust, both ways.

Tyler: I know we're hitting up against an hour her, so a comment on that. If you and I were both able to work for me now, or you at PeopleKeep, we'd both rather work for you. We would both want the person pushing us, even if it's a little more stressful and all that. And I think there's an ... you don't think so?

Rick: No, I don't.

Tyler: I think he'd be bored as hell working here.

Rick: No, because I would go to you and get the extra stuff, just like you got the people doing that at your place. It should be optional, it should be a default optional to do more than what is required of you, and that's it. That makes it safe.

Tyler: That's fair, but so the point I was getting at is a lot of people who are interested in entrepreneurship want to work at Less Annoying CRM and, generally speaking, I'm like, "A, I'm not interested and B, you should be either." This is a culture designed to hire people for a company that's going to be around for 40 years, not a company that's going to exit in five years. I think if that's your goal is to exit, I think I would do a lot of things very, very differently and that's one of them, is someone who's really trying to advance their career super, super fast, this is not a good environment for them.

Rick: I buy that if money is their long-term motivator. Yup. If money's the motivator it doesn't work.

Tyler: Yeah, yeah.

Rick: Okay, so that was really helpful. I really appreciate you diving into that. Anything else you want to add before we sign off?

Tyler: No, I don't think so.

Rick: Cool. All right, everyone, thank you for listening. You can join the conversation on this topic and review past topics by visiting StartupToLast.com. If you have questions, contact us via the website or on Twitter. We'd love to hear your thoughts and ideas. That's StartupToLast.com. Also, if you are willing, please leave us a five star review on the podcast app of your choice. It'll help us get discovered and reach more people. See you next week.

What is Startup to Last?

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.