Startup to Last

Learn how to teach yourself to code a web-based application. Start by clarifying your goals and understanding the necessary skills. Choose a simple CRUD application to build and select a server-side language. Build a static version before implementing the CRUD functionalities. Add JavaScript to improve the UI/UX, and utilize APIs for third-party functionality. Pick the right server-side technology and languages. Set up a local server to work on your application. Explore the evolution of web apps and user expectations. Focus on functionality and backend development. Use APIs to enhance functionality and consider the importance of JavaScript.

In this episode, Rick helps Tyler think through how to roll out a major product redesign for his 20,000 users. Tyler has a plan, but he’s concerned about losing customers through the transition. His biggest roadblock is figuring out how to roll this out without causing his customers to get angry and leave.After going back and forth, the following framework emerged for communicating major product changes to existing users:Why you are making the product changes in the first place?How will you measure success (i.e. the desired outcome)? What are the key messages you need users to understand?What proof points (e.g. screenshots, quotes, stats, etc.) can you provide that your key messages are true?How can you segment users and prioritize them?What mediums should you use to communicate?How often and over what time period can you communicate these key messages and proof points to each segment?Takeaways include: Start with why. Identify why you are doing this. Is it for customer acquisition, customer retention, or something else?Recognize that some users will go through change cycles, and help them through it. This starts with clear messaging.Don’t surprise your users. Give them plenty of notice and time to get through the change cycle.Treat this like a marketing funnel or sales pipeline. It’s a conversion.Segment customers by risk and value so you can prioritize outreach. This might be based on revenue, net promoter score (NPS), product usage or a new survey.Choose mediums and frequencies that support your annual contract value (ACV). If you are a low-ACV product, you probably can’t afford 1:1 phone calls for every customer. The change cycle conceptSource: changecycle.comWhat’s the product change?Tyler: The topic for this week is how to communicate major product changes to your users. This could go any number of directions, but the reason I'm bringing this up is, I've referenced the last few episodes where we're working on this big redesign of Less Annoying CRM. It's both a redesign and two major new features. It’s the biggest update we've had in at least five plus years, if not ever.Rick: Did you say two new features?Tyler: Two new features. Yeah, outlook, calendar sync. And we're completely redoing custom fields. Pretty big features, but the thing people will notice most is the redesign. And so I've been kind of thinking, "how do we communicate this to people?" The traditional way to think of this is, "how do you build hype and use it as a marketing event?", which we can talk about. But the theme of the podcast is "how do you build a business to last?" And I think a lot of companies change and eventually it leads to their downfall if they do this wrong. They forget their core audience and all that. They get too excited about the upside. Our audience is not one that loves change. And so most of the communication side that I'm thinking of is not, "how do we market this?", but instead, "how do we reveal this to people in a way that will minimize their likelihood of flipping out and leaving." Basically.Rick: In other words, a lot of companies might see this as an opportunity to wow users. You don't see that. You see this as a threat to users.Why you are making the product changes in the first place?Tyler: I think it's good for them, but if I'm being totally honest, the reason we have to do this, is to keep getting new users. The two new features will be helpful to our existing users. The redesign won't. They already know how it works. It'll look nicer, but that doesn't provide any value to them and they're not going to be excited about the fact that we redesigned.Rick: Is this true in most cases? When companies do redesigns, is it always usually for new users?Tyler: Yeah, I think so. I was just kind of thinking of this case, but if your audience is really into design or something like that, maybe they get excited about it. But for the most part, if you think of software as a tool, which CRM software certainly is. I think most B2B software is a tool. Once you know how the tool works, I can't imagine much benefit to saying, "okay, now you have to learn a new way for it to work."Rick: If it works currently?Tyler: Yeah. Yeah, true.Rick: Got it. Yeah. Okay. Man, I guess, if the redesign is valuable to new users, there's got to be some benefit to switching to the new design for old users.Tyler: Yes. And so a couple things on that. First of all, this is one reason why we're bundling it with two new features. We've done this throughout our history. You know how anytime Facebook changes anything? Everyone on Facebook's like, "oh, I hate it, I'm quitting." And then they forget about it a couple of weeks later. One way we try to minimize that reaction is saying, "there's an actual new feature for you here that you care about." And probably it doesn't have to come with the redesign, but to a user, it seems like they're a package deal.Rick: Yeah. I'm also realizing that your users are probably highly sensitive to this because this is a CRM product. They use it every minute of every hour of every workday.Tyler: And there's also a history here, which is a lot of our users are older, 40 plus years old and they've been through multiple cycles of CRM companies screwing them over. And so part of this is a lot of them, their natural reaction is, "oh, you're getting ready for an acquisition. You're getting ready to raise prices." They see the writing on the wall anytime anything changes. So I have to kind of reassure them like, "no, no, no. We hadn't redesigned the software in seven years. We need a new design here."Rick: I think we should dive into why you're doing this. Just because you need to do it for seven years doesn't resonate with me. It probably won't resonate with your users. So why do a redesign? Let's actually exclude the two new features from this conversation.Tyler: Yeah, I agree.Rick: Why are you prioritizing a redesign and what does it mean for the company?Tyler: Okay. Let's break this into two categorie...

In this episode, Tyler helps Rick evaluate how to build a new software application from scratch. Since Rick is a nontechnical founder, his biggest roadblock is figuring out how to build the application without raising money.After going back and forth, the following framework emerged for nontechnical founders trying to hire a first employee:What is the idea (i.e. problem and solution)?What type of application needs to be built to deliver on the idea (i.e. requirements)?What technical skills are required to build the application?How much are these skills going to cost?How are you going to finance these costs?Some of the takeaways include: If you're a non-technical founder, it’s very hard to bootstrap early product development without giving up equity. CRUD (Create. Read. Update. Delete) software applications require a generalist “full stack” developer while more sophisticated software applications may require a specific specialty.There are two big buckets of skills for product development: design and technical. The design bucket is made up of two categories: 1) user interface (UI) design and/or user experience (UX) design; and 2) graphic and/or visual design.The technical bucket is made up of three categories: front-end development, back-end development, and infrastructure.There are a number of ways to staff these skills ranging from finding an experienced generalist co-founder, which is most expensive, to outsourcing, to hiring entry level talent at the low-end. Each approach comes with it’s pros and cons.One downside of going with less experienced talent is “technical debt”, which can increase costs down the road. Another downside is slower progress due to the learning curve.To attract top talent, you either have to: a) have a compelling idea and be willing to give up significant equity, or 2) already have some traction and be able to pay a competitive salary and bonus. What is the idea?Tyler: In this episode, we’re going to talk about the ideal technical co-founder or first employee for a software company, and how to find them.Rick: I’m excited about the topic today because I’m not technical. For purposes of this conversation, let's assume it's a software application in the business-to-business (B2B) realm. Obviously, [what type of software you want to build] is going to be a determining factor. But for the purposes of this conversation, let's condense it to, “what's the right technical co-founder for a B2B software company.” This is on my mind because I just ran into a [technical] problem with Group Current. But, it's also on my mind because as I think about LegUp Ventures, which is my parent company that owns and operates [my startups], I'm starting to think about other types of software applications that I might want to build. For example, I'm still very interested in the employee benefits space outside of health insurance. I have an idea about education benefits where a company could give money to employees, tax-free, and let them go into a marketplace similar to the health insurance marketplace and peruse courses from all types of vendors [ranging] from Coursera to SaaStr to, even in-person events or books on Amazon, buy them, and then get reimbursed tax-free by their company. I've thrown this around with a lot of people, especially millennials who are interested in going to take advantage of these new tools, and there seems to be a solid demand for it. I cannot find anyone who's delivering on this. I know exactly how this is going to work and all the technical specs. The big roadblock for me is knowing how to go about building the application in a way that I can prove [product market fit] before I raise money.Tyler: Yeah. So it seems like there's at least two parts of this. One is what skills would the ideal technical co-founder have and all that? The other one is how do you find that person?Rick: Yeah, and I would say there's a third element. So one is, yes, skillset. Two is how do you find them, and then the third is what do you call them and how do you pay them? Is it a co-founder? Is it a contractor? Is it an [outsourced] shop? Is it an employee? And what's their title? Is it engineer? Is it co-founder? Is it CTO?Tyler: Right. Okay, so where do you want to start here?Rick: Skills.What type of software application are you building?Tyler: So you're talking about a web-based application, right? And this is something that absolutely doesn't require genius-level technical knowledge to build. Do you know the term CRUD? This is a CRUD app.Rick: CRUD sounds bad. Is CRUD bad?Tyler: No. It's Create, Read, Update, Delete. It's basically the four main database functions, and a lot of software out there is nothing more than putting stuff into a database, taking stuff out of a database, and then putting a [user interface] (UI) on top of it.Rick: Yes, and I would say that the UI for this is critical, because it's going to be a low ACV (or annual contract value) product and self service is really key.Tyler: Yeah, so the UI design might be more important than the actual technical implementation here because, with most CRUD apps, and I consider a CRM to be one as well, you don't need a Google-level genius computer science PHD to build it. Maybe you need someone who has more empathy for customers and stuff like that. Do you think the person you're talking about is going to design it, or do you think someone else is going to?What skills do you need to build the application?Rick: So, maybe I could talk about what my skills are. It sounds like this is going to be variable based on what compliments I need. I am a terrible designer from a “look and feel” standpoint. I can wireframe a usable product. I can wireframe a vision for something, but in terms of making it an exciting experience for a user, from colors to a style, to even specific placement of elements, that's not me. But in terms of writing requirements, describing the high level technical requirements, describing the user persona, the strategy around marketing this, that's all I'm really strong at. I would love someone that is as passionate about the user experience as me, but I can't do the design, I can't code the design.Tyler: So you either need a designer and a programmer, or a jack-of-all-trades who's going to be able to do both of those? A lot of companies would have two different people for these two different roles.Rick: Well, let's assume for this conversation that I'm looking for one person to fill this void, and I'm open to calling them a co-founder. I'm also open to calling them whatever is appropriate to call them. Employee. Contractor. Outsource shop. If this is going to be one person, what are all the skills that they would need to be able to design, code, and, I guess, launch?Tyler: Yeah. So where you leave off is basically a requirement doc. Maybe you could do the wireframe, but it sounds like where does stuff...

What’s an employee handbook?Tyler: The topic this week is employee handbooks. This has been on my mind because we redid our whole employee handbook this last spring leading up to hiring some new people. So I rewrote it and put a lot of thought into it, but I wanted to talk through it with you. I'd like to cover things like what should actually go into it. And one thing that I hadn't thought of prior to now is when and how should the information in an employee handbook be communicated. What we used to do is everybody would start working here, and then we'd give them the employee handbook and say, "read this." And more and more, I'm realizing a lot of this information might be relevant earlier in the [hiring] process. I'm interested in your thoughts on how this should work. Rick: Yeah. When I hear employee handbook. I associate it with zero value to employees and 100 percent cover your ass (CYA) for the company. I don't think that's what you're talking about here. So what do you mean by employee handbook?Tyler: Fair enough. Maybe there's a different term for this that at the end of this podcast we will have figured out. What I mean is that, over the years, we have amassed a lot of institutional knowledge on how we do things and our philosophy on things. Plus, there are a lot of policies and stuff like that. I've actually recently split it up into three things. One is company philosophy. One is information about how compensation and benefits work. And the third one is all of the various policies like: You want to take a vacation day? Here's how you do it. You want to use the nap room? Here's how you book it. That type of stuff.Rick: And where does the CYA, or cover your ass stuff, fit in?Tyler: We probably do that less than a lot of companies would. We do have random stuff people sign when they start like, "acknowledge that we're providing all of the benefits required by law" and stuff like that. So I think we're covering our ass to some extent, but probably not as much as some companies do. Rick: So let's call that a fourth bucket, which is different than unique policies to the company. So, one is philosophy. Second is compensation and benefits. Third, policies. And fourth, CYA. Tyler: I'm least interested in CYA because some lawyer writes that up, and no one reads it and no one cares. I'm probably more interested in the other three. What's the right information to include? And the thing that has really been on my mind is, "when?"  Should this information be made 100 percent public and used as a marketing tool for recruiting?Rick: I 100 percent think so. Yes. I'll give you my experience with employee handbooks. I'm unique in that, at my last company, I was there for twelve years. I've never experienced another employer, but we went through lots of iterations of the company as you well know. At first, I was the 13th employee of the company. Then, I was one of 35 employees. Then, we went down to four people. You, of course, were one of those four people. Then, we went up to 60 something 70 employees. Then we went back down to 35. Then, we were down to 20. Now, I don't even know how many people are there. And every time there was a big switch, someone at the board would say, "we need a new employee handbook." It wasn't until probably three years ago that I really took ownership of what an employee handbook was. Before that, and I think this is what most people think, I believed employee handbooks were CYA material. My experience as an employee getting an employee handbook was: "This is unhelpful. I can't understand the language. This seems like something that you're trying to screw me with."Tyler: Yeah. When you say CYA, it's so employees can't sue you and [claim] you didn't provide some piece of information. You'll be like, "look you signed this thing that said we gave you this document."Rick: So, over the years we had different versions of this. One was there from before I got there. Then, you know, the board was like, "we have to have an employee handbook". I was like, "why?" And they were like, "because we have to cover our asses," you know. And, I said, "OK". So we hired some third party to come in and build an employee handbook that provided no value because they had no idea about our business. So it was, again, all these new rules that I didn't even really care about honestly. It created more problems. Every time we rolled out an employee handbook, it created more problems than it solved. The last time I let someone else do this was probably four or five years ago where we had a really really smart senior vice president who knew that employee books were important.  So, she brought a third party in. I was uninvolved in the building of the handbook because I didn't care about it. I didn't think it was a priority, but I was listening to the person who was more experienced and smarter. And she was right. But, I think that an employee handbook that doesn't have your imprint on it [as the CEO] could be a really bad thing because it can send the wrong message. But the point here is that when that handbook came out, I saw it I was like, "holy crap this could provide so much value because it did touch on the philosophy stuff and it did touch on the things that employees needed to know to be successful at the company. So, I actually wrote my own handbook after that. And now the employee handbook, to me, is the most important tool of a CEO to communicate to their employees consistently and clearly. Tyler: OK. So at the beginning of this you said, "you think it's a CYA tool." You used the term employee handbook and just kind of redefined what that means to you and then thought of it as a really high priority for you. Rick: Absolutely. It went from a high company value tool with low value to employees to a very high employee value and high company value tool. Tyler: Once you decided to take ownership of it and decided this is going to be really valuable for employees, what did you put in there and did you get any feedback on it? Rick: I don't know how helpful my iterations are gonna be because I would say I learned more about what not to do than what to do. Tyler: I think those are the most valuable lessons. Rick: Well, I think you've done this well for a long time. When I started thinking about this, and I don't know if you remember this, but I said, "hey Tyler, can you send me your employee handbook?" Do you remember sending that to me? Tyler: Yeah. Rick: [Your handbook] was actually really useful. Once I realized this employee handbook thing was a good thing and not a bad thing for employees, there were a couple of companies that I looked at it [as examples]. I looked at yours. I looked at Basecamp’s [employee handbook], who shares it publicly. Tyler: Yeah, there's is on GitHub, and you can just read the whole thing.Rick: So I looked at [Basecamp's] and I thought theirs was good, but it was a little bit different than the culture I wanted to build. And then I looked at yours, and I thought yours was really useful it. It was in a Google Doc. It was twent...

Tyler: In this episode, we're gonna talk about the pros and cons of remote work, such as when does it make sense for a company to have employees altogether in an office versus fully remote or something in between.Rick: I personally get this all of the time. I've heard of four core models that . One is “single site” which means everyone works in the same office environment. Second, is “multi-site” where you have multiple locations with everyone working within the office. And then the third is “satellite”, in which most of the team is together, but a few people are remote. In other words, it's more of a hybrid model. And then at the complete other end of the spectrum is “remote-first” meaning everyone works from a separate location by default and then comes together when necessary to meet in-person. Does that cover the gamut of options in your opinion? Tyler: Yeah. It's kind of a sliding scale so everything in between is fair game. But, yeah. More and more, I think people work at a company with lots of people, but they work remotely or they work in coworking spaces or whatever. So the world is trying to figure out what makes sense for which companies here.Rick: In my most recent consulting project, I'm working remotely. It's the first time I've actually worked remotely for a company before. So, that was an interesting experience. I'm interested in what your experiences are with this. Do you feel like there's a right way to do this?“There's not a one-size-fits-all, right solution”Tyler: 100 percent, no. There's not a one-size-fits-all, right solution. I see a lot of arguments in favor of remote, but my experience is that, in practice, doing remote has a lot of challenges that I think get glossed over when people talk about it. So, I think there's there's pros and cons to both. Philosophically, I want remote to be the answer. But, in practice, I haven't seen that to be true so far. Rick: Before we go into pros and cons, tell me why you want remote to be the future. “Talent is global… if you limit yourself to a specific location, you’re limiting the talent pool”Tyler: Just to name a few people [and companies] who are advocates. Basecamp is remote-first. Doist is remote-first. If you follow the founders on Twitter, they talk about this a lot. I buy the argument that talent is global. It's spread out all over the place, and your company should be trying to hire the best people possible. And if you limit yourself to a specific location, you’re limiting the talent pool. The other [argument] is that we are all adults. There’s something that seems almost like an industrial-age assembly line about having everyone commute to the same place and sit in desks next to each other in order to get work done. The internet is a thing. It doesn't seem like we should need to be next to each other. So that's why I feel like it should work. Rick: So one [argument] is that [remote-first] allows you to attract a better breadth of talent from different locations. More diversity and people that you would never even think of hiring at a co-located place. And then on the second argument, I understand that you don't like the industrial nine-to-five feel of an office. But, what is it that you would replace it with?Tyler: Well I like the idea of if you get your work done, as the boss, it’s not my business how it happens. Historically, I feel like too many employers felt like they owned their employees. I mean historically they actually did and that was obviously terrible. Rick: Are you talking about slavery?Tyler: Yes. We haven't broken out of that fully, we're still, I think-- plutocrats exert way too much control over the people who work for them.Rick: Wait, what's a plutocrat?A plutocrat is a person whose power derives from their wealth.Tyler: Rich people who run the world, basically.Rick: Are you a plutocrat?Tyler: I'm working on it. [laughs]Rick: All right. Sorry. Keep going.Tyler: Basically, like what you and I are doing right now. You're in Utah. I'm in Missouri. This is fine. We're both adults. We're getting this thing done. Should I have to fly to you every week in order to record a podcast? Of course not. Why does everyone have to drive to the same office to get work done?Employees gain autonomy and flexibility from remote workRick: There's a lot of benefits [to co-location] that we'll go through later, but what I'm trying to get to is what is it that you gain from [remote-first] as an employee?Tyler: I think it's autonomy. You get to decide where you live, you get to decide, "Do I want a standing desk? What kind of chair do I want?" You just have total control of your work environment. Rick: Flexibility. Employee flexibility. Got it. Yes, it's the ultimate flexibility. Get the job done, work when you need to. I don't think that always applies. For some roles, you will need to be available whether you're remote or co-located at a certain time.Tyler: Yes, there is time flexibility, but that's maybe orthogonal to environment flexibility.Rick: You're killing me with these words. What's orthogonal?In statistics, orthogonal means statistically independentTyler: Perpendicular. It's like an unrelated thing.Rick: They cross over each other?Tyler: Yes, it's just that they're pointing in different directions. These are two points. Your time flexibility is almost completely independent of your location flexibility. Support needs to be on at a certain time, they don't necessarily need to be in the office to do their job.Rick: Location flexibility is really what you're arguing for here?Tyler: Yes.Rick: I like it. There's also work environment flexibility, which gives the employee choice on the desks and stuff. I get it. What's stopping us, in your opinion, from getting to where everyone's working remote?“It's very, very lonely to work remotely”Tyler: My company is not remote for the most part. We have a little bit of a hybrid model, but we’re mostly not remote. Obviously, despite my philosophical agreement with it, I think there are some real practical problems. I can just rattle off a few. One is, it's very, very lonely to work remotely, especially if that means you're working from home. Remote can also mean going to a co-working space and being around people, but those aren't the people you're working with, so I think there's still an opportunity for loneliness there. I don't know if you've ever done that type of thing.Rick: I am a little bit different in this regard. I actually like to be by myself, so I can't relate to this. In fact, when I see ...

The role of a small business or startup CEOTyler: In this episode, we're going to talk about what the role of a CEO should be at a small business or a startup. I always hesitate to call myself a CEO, depending on who I'm talking to because it seems a little pretentious. I run a 17-person company and some days, I don't do any CEO stuff: I just write code or design something. And some days I'm in meetings and brainstorming long term product vision and I feel more like a CEO. I'm a little unclear on when's the right time for a founder, especially a bootstrapped founder, where you're not representing shareholders or anything like that, when's the right time for them to let go of the individual contributor role and just really embrace, “my role is to be the boss of the company” and all the actual work that gets done is getting done by other people?Rick: I don't know exactly where to start with this. I'm very interested in the subject too. My immediate reaction is, I don't think that this is written in stone. It seems very circumstantial and honestly, subject to what the person has decided what their role is going to be, how they're going to play the CEO role, how they're going to spend their time. I guess, you keep saying CEO role. Maybe we can start with, what is uniquely the CEO role at all stages of companies?Tyler: Yeah and you probably know this better than me because I think you've experienced different stages. What I have seen myself is, there's individual contributor work. If you come from sales, go to sales. If you're a marketer, do marketing. There's management, which I feel like I've stepped into. We're big enough at this point where it's, “okay, there's a programmer who needs a manager.” We don't have a manager for that person, so I'm their manager. There's a manager of managers, where I've got someone who manages the customer service team but someone needs to talk to him and then I guess there's other stuff, right? Do you agree with those three categories at least? Those kind of evolutionary steps as a business grows?Rick: I would say that that's the different types of management but not necessarily… I know CEOs who have one report.Tyler: Yeah, absolutely. I kind of think of all three of those as not fully CEO work but I'm not sure what ... There's some fourth category which is CEO work. What do you think that is?Rick: I guess I would look at it a different way. I wouldn't look at it as, primarily a ... I wouldn't look at it from a people management standpoint, I would say there are three ... I'm going to butcher this but someone told me this once and I'll try to remember it as best I can. The role of the CEO is three or four things. The first is making sure that there's enough money in the bank. The second is making sure everyone is aligned on what the priorities are for the company. The third is building a cohesive team to ... and whatever that means retaining, training, managing, recruiting…Tyler: Just making sure it happens.Rick: … making sure you have the right people and I can't remember the fourth.Tyler: Yeah and I actually think I coincidentally saw someone retweet this today.Rick: I kind of look at a CEO's role as, either those three things are happening or they're not and if they're happening, the CEOs doing a good job, right? If you've got enough money in the bank, everyone is clear on what the priorities are, the team is cohesive and you've got a solid pipeline of talent to fill future needs, then the CEO is probably doing a pretty darn good job. How much time is it taking him to do that?Tyler: Right, maybe none-Rick: Maybe none.Tyler: -depending on the company.Rick: And if there's free time, maybe there's some opportunities to dabble as an individual contributor. If it's taking all of your time to do those three things, maybe some of those things you're doing as an individual contributor.Tyler: Yeah, I can relate to the second one, having a vision or whatever. At Less Annoying CRM, we don't have a strategy aside from the product. The whole company is about execution and then the strategy is, where is the product going? And that's my individual contributor work. Product design. So I think that's an example of what you're saying.Rick: Yup, yup and so it sounds like you do a lot of individual contributions on setting, what are the priorities for the company? And that's great. Tyler: And I love that stuff.Rick: And I guess stepping back, when you say individual ... I'm interested in why you brought this up, number one, is this something that's bothering you? And two, what do you mean by individual contribution? I understand now what you mean by CEO role but what crosses into individual contributor work versus non individual contributor work?Tyler: Yeah, so I wouldn't say this is something I'm worried about or that I have a problem or anything but what I notice in myself is, from time to time, I enjoy having periods where I'm meeting with a lot of people and having high level brainstorming and stuff like that but I really really love it when I have a day or ... I never have a full week but a good chunk of the week where I'm just not talking to anybody, on my computer, either designing or programming. When I say individual contributor work, I guess what I mean is, I'm not managing or leveraging other people's work but instead I'm saying, "The work I'm doing is directly moving the company where it's going, rather than setting a vision that other people are going to follow."Rick: Would you consider that, setting the vision, individual contributor work?Tyler: Yeah, I mean I guess it's on the border. It's half and half but so for me, I'm doing the design because I think it's cool. Oh, I really want to design this, versus, I can't wait for the rest of the team to follow this grand vision, you know?Rick: It sounds like, if we agree that the role of the CEO is to do those three things, make sure there's enough money in the bank, set the vision, make sure the priorities are clear, create clarity and then build the team, then anything outside of that, that is done as an individual contributor, on your own, would be what you're talking about.Tyler: Right, so writing code is definitely individual contributor work.Rick: Yeah, okay.Tyler: Design is ... If it's like, we need this feature and I'm designing it, that's IC work. If it's what is the-Rick: IC?Tyler: Individual contributor.Rick: Is this the new lingo? Is this an acronym?Tyler: I don't know. That's how they write it on the Twitters.Rick: The Twitters?Tyler: Yeah but if I'm designing some future project that maybe we will or won't do but it's a strategic thing, then that's probably CEO work. Okay, I buy that distinction.Rick: Okay. What types of individual contributor work do y...

Tyler: In this episode, we're going to talk about impostor syndrome. Do you want to kind of explain what you had in mind here?Rick: Yeah. So you know this. I left PeopleKeep after 11 years. For most of the time, I was the leader of the company under various titles, most recently CEO. I left in October. So it's been about nine months now.Rick: One of the big reflections I had was sometimes how I treated people. Sometimes I was super impatient with people and put certain immediate business goals over really trying to make people feel good about what we were doing or where we were going. And I regret those moments because it was so short sighted, right? And so, as I look back and analyze why did I do that? I think a lot of those situations where fear-based. I was scared of missing a short-term goal, or I was scared of what I want to talk to you today about. Feeling like I might be found out as a fraud, as a CEO. And so I want to talk to you about this because I wonder if you ever feel this way? I guess impostor syndrome could be defined as a fear of being found out as a fraud. But I would go a step further and say, do you ever feel like a fraud in your job or catch yourself making decisions not based on what's right but out of fear?Tyler: Yeah, I mean, okay. So I definitely feel like a fraud all the time. I'm of the opinion that the only people who aren't are sociopaths. Everyone I've ever talked to no matter how accomplished they are, everyone's like, “Oh, I don't belong here. Everyone's smarter than me,” and all that. I definitely feel that way just constantly, yeah. It's surprising to me to hear that you did so much.Rick: Oh, yeah. Constantly. And I think it caused me to work a lot more than I needed to. That's the fear of failure. It caused me to stress and worry about things that were outside of my control unproductively, and I think it caused me in certain situations to make the wrong decision.Tyler: Interesting. Yeah. Well, so the reason I was surprised to hear that is because on the surface maybe more than anyone I've ever met you seem like the classic CEO type.Rick: Are you calling me a sociopath?Tyler: No, no. What I mean is you're type A personality. Do you agree with that?Rick: Define a type A personality?Tyler: Like you... Well, yeah, maybe I don't have the best definition. But I interpret that to mean like, you aren't afraid of conflict. You kind of say what you mean. You're just kind of a person who's in control and likes being in control. And maybe this was me just not seeing what's beneath the surface, but you work really hard. You read a million books, you network, you make connections. To be honest, half my impostor syndrome comes from looking at you and being like, oh, no, that's what a CEO looks like. I'm not doing any of that stuff.Fear-based decisions and regretRick: The interesting thing to me isn't to discuss whether people feel this way because I think everyone does. I think what's scary is... I think what I reflected on was not necessarily that I had this, it's how I dealt with it.Tyler: Okay.Rick: And so, I think that, let's assume for purposes of this part of the conversation that everyone has some feelings of impostor syndrome or being fraud. And that's a fear thing. What I think in certain situations I did was, let that dominate my emotions. And that could have resulted in me not being thoughtful about how I was communicating with someone in a moment, or making a decision that was fear-based versus opportunistic. I hypothesize that a lot of decisions leaders make, they make out of fear and maybe those are the decisions that they regret the most. Does that resonate with you?Tyler: Yeah. I think I have a very different reaction to it than you do. I think that using kind of generic words like fear and regretting a decision, I think those still apply, but like, it takes a very different form for me. But yeah, definitely. I'm trying to think of the worst decisions that I've made.Tyler: The number one worst one was certainly made out of fear, although I'm not sure it's a fear that was rooted in feeling like an impostor. And that was that I had an employee that I needed to fire. It was obvious to me that I did but I was just like, oh, I'll make it work, this or that. And I just waited for him to quit and he did eventually, thankfully, because it could have dragged on forever. But that's by far when I look back at myself as a leader. That's my weakest moment ever. It was fear-based. I don't think it was impostor syndrome based for me.Rick: What was the fear?Tyler: Well, first of all, I just hate confrontation. I guess this is maybe a little different from impostor syndrome. Part of it is that I took a big risk hiring him and I convinced him to take a big risk accepting the offer. And you're admitting you failed is one of the things. Now, I'm normally not too afraid of failure, but when it's really impacting another person's livelihood or something like that, the pressure is really high. And I think I was just afraid to say, I'm putting an end to this. I don't know.Tyler: I've definitely had other moments though, where... The thing is, I think my reaction to impostor syndrome is to remove all of the things that I feel unconfident about. And so it's less. I think maybe it sounds like you were saying you kind of lash out almost. I do the opposite. I withdraw and say, "Oh, well. I don't think I'm good enough of a leader to do this thing. I'm just not going to do it." The company doesn't do that. That's not in our core competency.Rick: Interesting. So yeah, maybe it kind of gets into fight or flight.Tyler: Mm-hmm (affirmative).Rick: I have a fight response, while you have a flight response.Tyler: Yeah, when you were talking I was thinking exactly that. You're one of those animals that gets real violent when they're backed into a corner.Rick: Yeah, when I've been under the anesthesia for surgeries before, and I had to learn this, I always forget because I don't get surgeries very often, but I do know this now. Before I go under, I have to tell them when they bring me out of the anesthesia they have to tie me down because… Tyler: Wow.Rick: ... I come out and I come out swinging. Which isn't great when you're getting a shoulder surgery.Tyler: Yeah, seriously. Wow. I didn't even know that was a thing. But yeah, I mean, I don't want to...Rick: You probably come out going boohoohoo!Tyler: Yeah, probably crying about something awkward I did in third grade. But yeah, okay. So I think we're saying we experience the same things, but we have very different reactions to them.Rick: Yeah, but do you regret that reaction? I guess, do you feel like you're missing out on... Are you fleeing from something and making decisions for the company that are fear-based, flight-based that aren't the right decisions?Tyler: This may be taking...

In this episode, we discussed salary transparency. After some back and forth, we concluded that a company’s salary transparency policy should be based on its personnel strategy. In other words, how you handle salary transparency, whether it's no transparency, partial transparency or full transparency, entirely depends on the people you have and more importantly the people you want to attract.Before you decide on a compensation strategy, you should identify the people you need to hire to execute your business plan. This includes what the job functions are and who you want to recruit. If some version of salary transparency will help you recruit and retain those people, go for it! If not, it might be best to shy away.The philosophical idea of transparency vs application in the real worldTyler: So today we're going to talk about salary transparency and I mean, who knows where this will go. But, this has been on my mind recently. I recently gave a presentation to our company about how we think about salary and how people get raises and that type of thing. The question I'm posing here is, should companies tell everybody, “here's what every single person at the company makes” (full salary transparency), or should they not be transparent at all so that each person only knows their own salary. Or is there something in between? Rick: Yeah, so when you mentioned this is going to be the deep dive today, my initial reaction was, “I love it.” But then I started thinking about how this conversation could go and the way I look at this is that, philosophically, I believe in full transparency with most things in life, if not all things. I just don't think people can handle it. Most people are not equipped emotionally, myself included in a lot of cases, to handle the burden of transparency.Tyler: And so when you say they can't handle it, I assume what you mean is you hear that the person next to you makes 5% more. And then it's just like in the back of your mind, like, "Well, why is that person better than me?" Or something like that?Rick: The best way to summarize it is “ignorance is bliss”, right? And new information causes change cycles to happen. And when you go through a change cycle, you become an evil person. You become the worst person you are when you have to deal with change because it creates this fear and it brings out all these primal emotions and people do really crazy things when they have that type of change cycle.Rick: So from a philosophical standpoint, I love it. I want all people in the world to be able to talk about all things and have a really good conversation about it and make the best decision together without emotion being a negative factor.Tyler: Yeah. But there is emotion.Rick: That rarely plays out when I see full transparency happening. Most people take it personally.What does salary transparency accomplish for an organization?Tyler: Okay. So if I hear what you're saying, you're basically, it's philosophical belief versus what happens in reality and they kind of clash with each other. But there's a reality on the other side, which is even if you don't have transparency, in this day and age, can you actually keep it a secret? And if not, maybe the reality goes in the other direction where it's like, “I agree with all the problems you have, but if it's going to come out anyway, don't you want to control that message?”Rick: So I guess the question is what do we want to accomplish as an organization and what are we trying to do? So I would say if I had my way in the world, I would go, "Let's do full transparency with everything to cash balance.” I would start there and my main goal with that is let's have full trust, number one, so that everyone knows where they stand and two, let's provide everyone context, or the same information I have as the CEO, so that people are more empowered to make the right decisions across the organization. That's the core goal with transparency for me.Rick: Now when you start going, "Oh, well, there are all these other problems that salary transparency can solve," I'd rather talk about those problems as the topic and say, "Okay, well let's figure out how we solved that." And maybe salary transparency is a way to go about that. But when I think about salary transparency and a problem, I'm thinking about, "Okay, I'm going to increase trust with employees. I'm going to give them information to help them make better decisions."Tyler: Maybe these are subsets of what you just said, but there's definitely an element of equity and fairness in it, which statistics say basically some people are more likely to negotiate on their behalf. And so if you don't give this information to people, what you end up with is what looks like things like a gender pay gap or a racial pay gap and things like that, which is very real, but it's really because people don't even know that they should have gone to negotiate or something like that.Rick: Yeah, so that's a good example of a problem I would say that I would not first go to salary transparency to solve that problem because of the cons of salary transparency. In my opinion, the person who, and I'm interested in your opinion on this because you always have a different view on this type of stuff than me. My opinion is let's train the person how to talk about money confidently before we give them all the information about all the money people are making. If they aren't comfortable negotiating, what are they going to do with information that they don't even feel comfortable talking about their own information about? In other words, if they're uncomfortable talking about their own pay, imagine how their brain is going to discuss internally with themselves other people's pay relative to theirs.Tyler: Well, it may not be that they aren't comfortable talking about their pay. It may be that they don't even know that they need to. Like they may think they're fairly paid and they're not.Rick: Then what's the problem we're trying to solve?Tyler: Well, the company, A, might care about fairness just for personal values, setting aside business, but B, you're sitting on a landmine when they do find out. What effectively happened is you've been underpaying them for a long time and they didn't know it.Rick: Well, who's saying underpaid? I guess this is the philosophical question related to this problem: what is fairness and when you say someone is being underpaid, what does that mean?Tyler: So what I'm talking about, I'll put this in very like dollars and cents capitalist terms here. If you have two people who are providing equal value to the business, they should probably be paid the same amount. But if one went and negotiated and the other one didn't even realize that they were not paid what their full market rate was, you're creating this scenario where effectively the company's kind of taking advantage of this person because they're uninformed. Now maybe they can get away with it forever and one might argue that's fine. But to my landmine comment, as soon as it comes out, and especially if it comes out and then you find out, "Oh, there's demographic trends here," that's a real bad look for the company.Rick: I react to that as, “why does t...