The role of a small business or startup CEO

Tyler: 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...