Brian Casel: [00:00:00] Hey, it's Open Threads. It's my podcast. Welcome to it. My name is Brian Casel. And today I'm talking to my buddy, Chris Lema. Chris is a longtime friend and, uh, you know, he's been through, uh, quite a journey in his career. Uh, but in this conversation, we talk about the one thing that has been constant in his decades of working in the software and WordPress and non WordPress spaces over the many years is that Chris is a coach.

He's a professional business coach. And so I wanted to really pick his brain about what it's like to be a coach, how he balances coaching with all of his other work in this industry, his personal approach to coaching, what it means to be a coach and all the different ways that a coach can be successful in helping other people with their businesses and their problems.

It's quite an interesting field and one [00:01:00] that I'm actually really focused on and interested in learning even more about since my product ZipMessage is, it serves coaches really well, and it's turning out to be our primary use case now. So I really got a lot out of this conversation as I always do when I talk to Chris. but now let's talk coaching with Chris. Enjoy.

I've known you as so many different types. You've been in so many different roles, right? Like between like blogger, speaker, event, organizer, CTO, marketing person, like. I feel like one thing that has been constant throughout, and you mentioned it in the last episode here, is that you've been a coach, right?

And I'm super interested in that, especially right now, actually, since I'm working on ZipMessage and coaching turns out to be like the best use case for this product, as you know. I've like done a tiny bit of like dabbling and coaching over the years back when I was doing like product high service stuff with folks, but like never as a full time coach, [00:02:00] I've never considered myself a coach.

And that's one sort of like one of the fears I have right now with ZipMessage in the direction that it's going. It's focused on coaches. And that's a profession that I personally don't identify with. So I'm trying to learn more about it. And of course you've been a coach for many years. So I guess, why don't you talk a bit about that?

Like, when did you start offering coaching as a service to other people? Why is that something that you've decided to devote pretty significant portion of your time and energy over many years doing?

Chris Lema: Yeah. So I did a series of startups a long time ago and it was after, I think it was after my third.

Everyone who does one startup, especially if it's like hardcore go in, we're all running hard. We're working 20 hours a day. We got VC funding, you're just running to get product launch and then turn around and raise the next round and all that craziness. If they get any level of success, right, they get to the other side of it and they start thinking I could teach other people how to do this.

I didn't do that. I went and did my second startup and we sold that one too. And then I went and did my third startup and we [00:03:00] actually folded that one. And then I was getting ready to start the fourth, which we ended up selling fourth and fifth. But I was getting ready to do that when someone said, talk to Chris, right?

One founder talked to another founder and said, go talk to Chris. And it was after doing three of these that I realized. I still don't know that I have a handle on this, right? Like, cause each of the three were different and you've, you've lived in this world, right? As an entrepreneur building product. And some of my say, well, Brian has done this over and over again.

And you're like, yeah, but, but let me be clear. Every single one of them was different. And even when some parts were the same, other parts were different. So it's not like you can do one and done and say, I'm a CEO. I've been a founder of a startup and now I'm an expert.

Brian Casel: And a lot of ways that the next one is even harder than the previous one.

Chris Lema: Yep. And so when I started doing back then was I, if someone said, go talk to Lema and I got on a call with him and I said, I don't know if this is helpful at all, right, but here is the way I think about it. And part of who I've always been part of who I recognize I've been for a really long time [00:04:00] is someone who thinks.

In an abstract way, which means whatever it is you're going through, I'm able to pull up and look at it at one level of abstract, at least one level abstraction above it, which allows me to then summarize, systematize, shape it differently, like, oh, You're looking at a five point model. You're looking at a four point model, but I craft a model to understand.

And for me, that was always just, how do I make it easier? Cause if I know the model, when I go into the next situation, I go, okay, I need to look for these five things and then do these things. And then let's look at the output. So I introduced someone to one of my frameworks. And they were like, this changes everything.

So then they went off and did their work and they referenced me to someone else who then called me up and said, Hey, can we get a couple of calls? And I didn't choose to do a slightly different framework for something different. And then they'd be like, this changes everything. Right. And so coaching, I don't submit the coaching is for everyone.

Like, Oh, if you know how to do something, you should be a coach. Right. But I think when you are able to systematize and strategize, when you're able to abstract, [00:05:00] becomes really helpful to then take knowledge abstracted and deliver it to other people and have them go after it, it becomes really enjoyable to watch it go to work.

And it also

Brian Casel: And just the value of having a sounding board, someone to think through it at a deep level.

Chris Lema: Yeah. So I started that a long time ago now more than 20 years ago, and I would go from in certain quarters, I might coach two people in the quarter, right? Like two people consistently, like every other week or something.

And then I'd have other quarters or years where I might be coaching 15 people. And so it would fluctuate depending on what job I was in, depending on how much time I needed to give it, et cetera. But I've been doing it nonstop for more than 20 years.

Brian Casel: And I have so many questions around this, like how, around the structure and the logistics of it, especially since.

I don't think you've ever been a full time coach, right? Like you've always had your role at some company.

Chris Lema: I was a full time coach for a year when I left Crowdfavorite and I, and before I joined Liquid Web, I had a year off where I just said, I'll just keep a couple of coaching clients.

Brian Casel: So I'm sure it's [00:06:00] evolved and changed over the years, but what generally, what is the structure of?

Let's say like working with you as a coach, like what does that typically look like in terms of how long does a single call go for? How many calls in a month? How many months do you do it? Like, yeah.

Chris Lema: So what I do is I have two programs, two times a month or four times a month. So every other week or every week, the majority of people start at two times a month, because at some point you're going to make them do some homework and, and on a weekly basis, they have to be really ready and have the appetite for.

Turning stuff around and getting right back the next week, right? So two times a month and four times a month, and both of those are hour long calls. Most of the time I do my coaching before 9am or after 4pm, right? So I keep my daytime for my daytime job. And I do stuff in the morning and do stuff in the late afternoon, evening.

And I tell people that for the most part, it's about, we start with a three month commitment. And after the three month, it'll go month to month and people can decide [00:07:00] if they want to keep going or not. The average is somewhere around 12 months. I have some that are now going on three years. Others that finish off at three months and go, that's all I needed.

Right. And you go, okay. And you learn to

Brian Casel: have that, have that initial three months commitment. Right. Because I mean, I'm sure it's like, I've been many mastermind groups over the years and it doesn't start to really gel until you're in it for several months.

Chris Lema: Yeah, exactly. But here's the thing, right? If I didn't have ZipMessage and back when I didn't have ZipMessage saying to someone you also have offline asynchronous access to me in between our calls.

Didn't mean as much, right? Because what would happen is you'd say, no, no, no. If you need something, hit me up an email. Right. And one of every 10 coaching clients would send something in between. They would say, Hey, I got this contract from this vendor. Can you review it? And tell me if, if making any mistakes to sign it, but everybody else would just wait until the call because it's the call, it's the visual connection and interaction.

And by the way, when I coach founders and owners, [00:08:00] sometimes they bring their co founder. Or their executive team to the call, right? So I allow that. So I'm like, Hey, bring your whole exec team if you want. I don't care. But in doing that, right? Sometimes I'm playing referee between two people. Sometimes I'm pushing different parts of the organization to flex or change.

And in between, I would say you have access to me asynchronously, right? It's not like you can call me in the middle of the day because I have a day job. But with ZipMessage. It dramatically changed, right? Because I would send them the welcome to the asynchronous model in ZipMessage. And then they would just, Oh, I have a place to go when I want to, Hey, here's a question.

Hey, a lot of times I give assignments, right? So I say, Hey, do me a favor, go look at the flow of this work that you're doing, break it up by piece. And let's talk about who the players are and how many touch points there are, how much energy is involved, how much effort and what the cost model looks like.

So we can look at the unit economics of the service you're providing. And they would go do that. And then they would wait till our coaching call to show it to me. I'm like, you don't have to wait. Send it to me asynchronously. Walk through a [00:09:00] video showing me the whole thing. I'll reply tomorrow night on that.

And we can keep making progress. So by the time we get on the next call, we're not burning time talking about the thing that. Yeah. And so ZipMessage became, became one of the ways that we do homework back and forth and challenging each other in the midst of that in between the calls.

Brian Casel: I love it. And just in my ZipMessage, I don't mean to just focus on my product here, but like, What I find in almost all of my async conversations, I'm doing a lot of them with my team right now that the team has been growing, having that space in between each message or question and then the response or feedback and then feedback back on that and bouncing it back and forth, having space of hours or days in between those and even just the space to prepare my next message or my next response just adds such a level of.

Quality and clarity and moves the ball forward, you know, because I always find like when I'm on a live call with someone, it feels like I'm on the spot. I have to come up with my next response like right now. But if I have time to digest it and [00:10:00] think about it, even jot down a few notes before I send it off or record it and then re record it before I send it off.

Chris Lema: And that's for internal thinkers, right? For people who want to slow down and process. Transcripts Before they say something that's definitely a value for external thinkers, for people like myself who are always ready with the next answer and very comfortable with the next story and know exactly what they're going to say, there is still a value for the asynchronous messaging.

And part of that is when I have to tell you something that is hard to hear. If I'm looking at Brian and I go, Brian, your messaging is completely 100 percent wrong. You have missed the boat, right? If I do that live. It can feel like an attack and you're looking at where do I hide? I have nowhere to go, right?

But if I do that in a video message where I go, Hey, Brian, I don't know, maybe I misread it, but it feels like this is in a different direction than we talked about. And I'm not sure you're hitting the points. Like, look at this one and look at this one. I can still record all my thoughts, right? But you hearing it [00:11:00] without me being present for you to hear it.

Gives you a little bit of cover so that when you watch it, you might even flare up initially, like he's wrong, but the more you think about it, and even you can hit replay and hear it again and go, no, no, he may be right, and then you can hit your own recording and come back and say, you know what, I think on most of those, you are right.

And I'm going to go, it's so true.

Brian Casel: And like, cause I receive a lot of ZMs with like. This is broken. That's broken. The product's not working for this or that. And, uh, yeah, it's like, you know, there's always the initial like emotion of receiving it, but then I'll go take a walk. That is something we need to fix.

Chris Lema: And so much better when it's not live, right? So let me back up, let me back up for a second because we jumped right into the actual coaching and we skipped. One of the most valuable pieces of coaching, one of the hardest parts of coaching and most valuable places where ZipMessage sits is before you sign up a client.

Yeah. So, so selling any kind of knowledge or expertise is completely different than selling a shoe. When [00:12:00] you sell a shoe, you set a physical object. You're talking about the attributes of the object. Is it the right size? The right color? Does it have the right fit? And you're judging the shoe. And even if you don't like this one shoe by Nike, you don't hate Nike.

You just don't like this shoe, right? So it is abstracted already. When you sell knowledge and expertise, it feels very, very close to who you are, right? And when someone rejects you, it can feel like they're rejecting you, not your offering. And that can be painful. It's also difficult to know how do you sell, right?

How do you close a deal? When it's abstract, there's nothing to show, like you don't have the physical shoe. Right? Yeah. And my answer to that forever, right, has been you need to use story or narrative. You need to be able to tell rapid versions of case studies. Here's where they were and here's what happened at the end.

You need to be able to tell prediction stories. Here's what you're about to experience, whatever, because that makes you feel like a magician. But the [00:13:00] most important part of that. Is you're not going to close those deals on email. You're not going to close those deals on the phone. You're going to need to get on video because people are buying someone they can trust.

They're buying someone that they feel good working with.

Brian Casel: Yeah. The product is the communication is the relationship, right?

Chris Lema: And there may be a hundred coaches. And the bottom line is they got to be comfortable with you, right? They got to feel like I would like you on my team. I want you on my team. And ZipMessage.

In that pre sales environment, which allows you to use video, allows you to tell stories, but it doesn't burn up your time. I can't tell 20 minute stories when we have a 20 minute call, right? But in an asynchronous dynamic, I can throw out a story and be comfortable sending it out there and then wait for them to come back.

And then I can send them another one. And I can do this back and forth three, four times. And they'll also go, Oh, I get it. Like he tells stories, that's his way. And I'm comfortable with that. Versus someone else who goes, no, this guy talks too much. I don't want this. [00:14:00] Right. Great. Move on. Right. But that video piece, even though it's asynchronous, is what helps build the trust and lets people say yes.

Brian Casel: Yeah, totally. And again, like I've seen that in the hiring process, especially as well. Right. Like it's a way to, because I'll have like a quick zoom call to just get to know the person, like a first interview, but then to really see what it's like to go back and forth over the course of a week or two before we actually start working together.

Really, really helps a lot. So I'm curious to know, like one thing that like, it's obvious, like you've always had like the energy of, of this like extrovert conversation, like, but when I think about the number of hours that you devote to coaching and talking to people, and then you go do the role throughout the day, I'm exhausted.

Just thinking about it. Like, how are you managing? Because I have done some coaching calls. Through my productized program that I used to do years ago. And like every time I would just do one, like one hour with someone, my afternoon is like shot. I'm exhausted. Do you set like limits? Do you have like routines?

And also like, how much are you thinking about someone else's problems? Someone else's business. And you've got your own stuff going on. Like, how do [00:15:00] you kind of balance all that?

Chris Lema: Yeah. So I have a buddy of mine when he does one hour coaching, he first frets. For the first three hours before the hour, right?

You know, my buddy, Sean Hesketh, who runs WP 101, right? Three hours of stressing out. He gets on the call. He does the call. And he does amazingly on the call. And then he has another two hours of downtime of trying to recover from it because he's so exhausted. Right? And it cracks me up. Like when I invite him to Cabo Press, I joke with him that I'm only going to tell him his topic.

The morning of his session so that he can only stress between the morning and his session. Because if I give it to him in advance, he's going to stress out the whole time, right? I am not plagued with that particular. I relate to Sean.

Brian Casel: I've known him for many years. He's like a creative, like tech tweaker like me.

So yeah,

Chris Lema: totally. I am not plagued with that, but that's also because of the specific mix of who I am, is that I collect stories. Some of those stories I've lived through some of those stories I read about. So if you and I get on a coaching call and you say something that is about a problem that you [00:16:00] have, I'm likely already have a story that will make my point for me.

And now it's just fun to tell you the story. It's like you're going to see a movie and I just walk you through the story and initially you're like, where's this going? If I do it right, where's this going? And then all of a sudden it drops. About two minutes before I'm about to give you the punchline. And you're like, I know exactly where you're going now.

Now, Oh, this totally makes sense. But I also know that once you get it, you will remember it because of the story rather than if I just told you the main point, but story for me gives me life. It doesn't deprive me of anything. It doesn't take away my energy in between times when I'm not focused. I spend a lot of time thinking about.

My coaching clients, as well as thinking about my day job. So I'm always ruminating and always thinking, and I'm reading a lot. And so then I'm thinking about how would I read applies to this net. I show up to every coaching call with an agenda. I show up to every call with a, I want to poke into this area, but sometimes the person I'm coaching will come to the call with their own agenda.[00:17:00]

Brian Casel: I'm curious about that. How does that typically work? Cause like a founder or a business has things that are just going on like this quarter. How does that?

Chris Lema: Yep. What I tell them is, Hey, you come with something. Bring it, we will deal with that until it's closed off. And then if there's still time, then I'll bring up whatever I want to.

Right. And so what happens is let's say I come and I'm like, okay, I want to talk about your. Right now, your lead gen approach, you're not using an indirect lead gen approach. So I don't see any distribution channels. I don't see any partners that are pitching you to their customer. I don't see any of that happening.

So I'm prepared to come. I'm prepared with some stories, some strategies, a framework. Here's what I want for you. I get there and they go, Hey, we have an employee. Who is a problem and we need to fire them. And I swear to God, I've never fired a person in my life. And how do I do this? I go, not a problem. I'm going to give you a three step framework for firing someone.

Here's what I want you to do. Here's the three steps. Let's practice it through data. It may take [00:18:00] 45 of the hour of our hour, 45 minutes of our hour. And they'll go, Oh wait, did you have something? And I'm like, we'll deal with it next week. Right, right now, the biggest thing was. By the way, we should spend 15, our last 15 minutes talking about how we hire the right people so that you have this happen less often, right?

Brian Casel: And so we structured like long term, like, are you set, you do the initial three months, are you thinking about like long term goals, like mapping out? Is it different for every client?

Chris Lema: Yeah. How are you thinking about that? So different clients function differently. Some will come and say, I want to grow in this way, or I want to drive this specific change and then we'll go, okay, so let's break out how we do that.

And I will tell you, okay, you need to do a before B and B before C and C before D. And so that's what we're going to cover over the three months. Others will come in saying, listen, I've talked to these other people. They say that you're the most indispensable part of their team. I want you on my team.

What things can you cover? I rattle off 20 things we could cover. They go, ah, these three feel important right now. So we go [00:19:00] into those three for a period of time. And then they're like, Hey, let's talk about this other one now. And then let's talk about this other one. And we just keep moving. Right. But it's because what I promise them upfront is that they're not going to go through a coaching program.

So I am not against other people. There are other people that have very specific models, right? And that model may be. I have a coaching program in 16 weeks. And each week we're going to talk about something

Brian Casel: It's like you're asking all the questions like right before I actually asked like the one thing that I do notice with the landscape of coaches is like you said, like, there's some that are just like, bring me on it.

And like, I like how you're describing it as like, bring me on to your team. Like, I'm part of your team. We're going to work through whatever comes up, wherever you're going, we'll work through it together. Like, I like that. And then there are There's a whole lot of coaches who I have a 12 week program. If you have this specific problem, I have this solution for that.

Then you're a perfect fit. Let's run through the program. And that I think both are valid, but both are sold and like, and offered in a very, [00:20:00] they're almost two completely different things, even though both might be a coach.

Chris Lema: They're really different. And frankly, I have a signature system and it's a 12 week system.

And I'm going to walk you through my, my four frameworks. And at the end of this, you're gonna be able to do X, Y, Z. I can't do it. I just can't because every client I've ever had is nuanced and different. And so me just saying, Hey, forget about your nuances. I'm going to shove a pre made system and then you're going to like it.

That it's just not me. I cannot pull that off. And so for me, I'm like, well, let's go figure out who you are and what, what do you have on your team? What assets do you have? And so I talk about this only in my family. And now apparently on this podcast, I talk about this as human chess. And human chess is about knowing each piece, how it moves, and then how to build a strategy using all the pieces to beat the competition.

And human chess can feel in the hands of someone who is not trustworthy as manipulation, right? You're just moving piece around. You're using people. And you go, [00:21:00] no, no, no, no. My objective is not to use anyone. My objective is to say. If you have this set of resources, then your best strategy to utilize these resources to go this direction.

If you have these resources, then your best strategy is to go this direction. I don't think you can do that at 27, right? At 51, and this year I'll be 52. When you're older, and if, and if you've spent a lifetime studying this and doing this and playing this out and working through, I think this plays to my strengths.

I'm very comfortable saying every one of you needs a different strategy because you have different resources in house and your competition is different. The context you're in is different. And now let's go solve that puzzle together.

Brian Casel: It seems like it's more optimized for like direct access, whether it's asynchronous or live.

It's, it's all direct. Like you're talking to Chris when you're working with Chris, you're working with Chris, like other programs.

Chris Lema: 12 week program could be an online course.

Brian Casel: Yeah, exactly. It could be a course or it could even be scaled up with multiple coaches who just implement the program. Right. Yeah.

Yeah. Interesting. How long do you expect that you'll [00:22:00] continue? Like, is coaching going to just again, like you've just transitioned into a new job in 2022, you know, does that impact your, the amount of coaching that you're doing? Is it still something that you want to continue doing for awhile?

Chris Lema: Yeah, I'll keep coaching because I think at its core, if you went and chatted with, I think we both know Jessica Frick, who is now over at pressable.

com. I'm sure there are other people we both know. If you go talk to people that have been in my employ, who've been on my teams that I have led, every one of them will say like his first superpower strategy, his second is coaching. Like he can't help but coach even our employees in the corporate structure.

Like he's going to coach, he's going to make every person on his team better. That's who he is. And so whether it's in my day job or it's, or it's outside my day job, right? I don't think, I mean, I can't stop coaching any more than I can't stop telling a story, right? That's just who I am. And so the fact that I've generated a nice, healthy.

Revenue stream from it is [00:23:00] beneficial, but. Even if I was broke, I'd still be coaching, right?

Brian Casel: Because it's one of those things. I mean, you know, we were talking earlier about like, how do you have the energy to balance out like all these different conversations and dealing through these problems? I mean, one thing that I've found is that it's actually pretty energizing for me to dig into other friends, business problems, whether it's like when I'd go to Cabo press several times, which is amazing.

And I go to other, you know, small retreats with friends over the years, mastermind retreats. It's a break from my business, but we still get to talk about business. And it's like super energizing.

Chris Lema: Yeah, that's exactly right. So I'll keep doing it, which means that I'll be like a lifetime subscriber of ZipMessage forever.

Right. So whenever ZipMessage does a lifetime deal, that's what I'm signing up for because

Brian Casel: we're not WordPress over here. I don't expect any lifetime deals. Yeah. I mean, again, like ZipMessage it's right now I am trying to study coaches. Yeah. It's been so weird because it's like,

Chris Lema: We talked about it ages ago.

Brian Casel: That's the thing very early on, like in the first, like three [00:24:00] months or so of starting ZipMessage back in 2021, I was like, man, I really need to niche this down. Like it can't be so wide and there are some coaches that seems like an obvious use case, but then I got all this feedback and mixed messages.

Like, ah, no, it's just a horizontal product. So I let that go for a year being super horizontal. And then. And here I am a year later and it's like, you know what? It does need to go. And coaching, they do tend to be the best users. And so that's where we have the conversational piece, the async conversations piece.

And I'm starting to, it's so early stages, but I'm thinking about like how far do we double down into coaching as a product and a solution to cover like all the areas of a coaching engagement.

Chris Lema: And that's where you go, okay, so I'm using this for the communication. Do I add billing to this? Right. Do I add scheduling for synchronous calls?

Right. Do I add a synchronous somewhere sitting in here and you go, no, the synchronous thing is off brand. Right. So I'm going to close one down, but maybe yes to Billy. Right. And so this is the very nature of my [00:25:00] coaching, right. Is where you go, okay, let's talk about product strategy. Product strategy isn't just let's go build stuff.

It's about what do you say yes to and what do you say no to? More often than not saying no is what's really critical because saying no allows you the freedom to have the time to go say yes to something valuable. And then you go, okay, let's go from here. What I will tell you as a coach is right now, all of my frameworks.

So files are Dropbox links. Right, and you can imagine if you're a coach wanting to be able to load up, which makes ZipMessage stickier. If I say, Oh, I've loaded all my frameworks in here so that I can share a ZM link. But that also means, Oh gosh, I don't want to leave ZipMessage because it has all my stuff already preset in there.

Right. And so things that make it stickier, having that file archive that allows me to share my frameworks easily becomes interesting.

Brian Casel: And this is, this has been one of the challenges with me with ZipMessage at how it's evolved over the last, [00:26:00] it's only been like a year and a half. Yeah. Like technically we sort of have the ability to do that.

We have, we have message templates, you can make them text, you can have links and have those ready to go, but those look nothing like what you're trying to do. Like it doesn't actually, it's not like it doesn't solve the job to be done.

Chris Lema: And it's four and it's four steps, right? You're like, why would I jump through four hoops to do this one thing?

Right. And you're like. No in ZipMessage. I need a resource library. And then if I just load on my resource and resource library, then each one has a link and I can go, Oh, share that with this guy. Right. Anyway, I got to bounce, but this is awesome. Of course, anyone listening should hear two things. Number one, I'm a coach.

So if you need coaching, ping me. And number two, I couldn't do coaching without ZipMessage. I love ZipMessage. And if you're not using it, you should definitely check it out.

Brian Casel: Well, we're going to get Chris's Twitter and websites and everything linked up in the show notes. Chris, you're the man. Thanks for doing this.

Always. Thanks for hanging out, buddy. Catch up. Have a good one. See ya. Take care.