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Building Better Bosses (Danny Ceballos) Transcript

Course Lab – Episode 97

Building Better Bosses (Danny Ceballos)

Abe Crystal: He’s taken the stance that you really need to find ways to enjoy that sales cycle because there’s really no way around it. So thinking of it more, it’s just relationship building. It’s connecting with people and trying to have fun with that and then planting seeds that will ultimately result in a bigger sale.

Ari Iny: Hello and welcome to Course Lab, the show that teaches creators like you how to make better online courses. I’m Ari Iny, the director of growth at Mirasee and I’m here with my co-host, Abe Crystal, the co-founder of Ruzuku.

Abe: Hey, Ari.

Ari: It is nice to have you back from sabbatical, Abe.

Abe: It’s great to be back. Thank you.

Ari: Today, we welcome Danny Ceballos to the show. Danny is a leadership consultant, trainer and executive coach. He works with individuals and organizations to excel in their workplace through his company, Unleashed Consulting and his Best Boss Bootcamp, which we will talk about today. Thanks for joining us, Danny.

Danny Ceballos: Oh, you bet. I’m delighted to be here.

Ari: Awesome. So to kick things off, the question I like to ask people is kind of give us an introduction of yourself, kind of a 30,000-foot view of how you came to online courses and who you serve and kind of why you serve them.

Danny: Sure. Yeah. So the tagline for Unleashed Consulting is building better bosses. So our mission is really clean and simple. We are working on that space between people, the relationships between people, so that they can be more productive, effective and efficient in the work that they’re doing. Came to that through the work that I was doing in corporate healthcare, where I was for many, many years doing training and development and coaching for managers and leaders across the country. When I left that, I wanted to pull a course together that I thought would really capture some of the breakthrough moments, tools, insights that I had and essentially make new managers and newish managers make their jobs a lot easier in the long run.

The other thing that it’s important to note, I left the corporate world because I made good on the statistic that says that over 50% of people, when they quit their jobs, they’re not quitting their jobs, they are quitting their bosses. So I just thought that was such a waste of time and effort for everybody. Everybody. So the mission is super clear, to make things better for both bosses and/or direct reports.

Ari: Awesome. And I’m curious, when you kind of made the decision to go out and build this, what drew you to it being a course versus being a coach or being a consultant or why this format?

Danny: Yeah. So a lot of the work that I was doing when I was doing the work in my corporate job was in training and development. So I was the birth father. A series of classes called the management Mastery series. So I already had experience. It was a live course, so it was very, very different. So being the young buck entrepreneur that I was at the ripe old age of 50, whatever, it’s like, I can do this. I can just bring it all online. All the stuff that I knew that worked for me, I can bring it online. And there the path started. And that was in 2016.

Ari: Very cool. And so can you tell us a little bit more about your journey there? Kind of that process, I’m sure you learned a lot from taking it online versus kind of what you were used to doing.

Danny: That’s right. It all seems so simple. It all seemed like I could do this. So I built up a pretty rudimentary course, actually on a platform called the Coaches Console. And it was good. It was solid, it was good enough. Got everything that I wanted to get on it. I can’t look back at it fondly because it was such a challenging time, but I got it together. I said, I’m going to get 15 people in there, ran around, literally was running around in my car, going around delivering workbooks and everything to get 15 managers and leaders to sign up for. And it’s called the Best Boss Bootcamp, by the way, to sign up for this course.

So it worked fairly well. I got about 15 people in there. It was messy, like I said, I was literally driving around town the night before to deliver workbooks. I discounted it all over the place and did that maybe two or three times after that. And that was really a B2C model. It was the idea of bringing in disparate people from all sectors to be a part of this. And I did that for two or three rounds before I realized this is not what I wanted to do. So what I wanted to do was to start working with organizational cohorts instead of individuals.

From a business perspective, it made sense. Thats where I could have more impact. It was easier to manage, and for folks to be able to come together from a learning perspective and move through it together made so much sense to me. It was all in theory, but it turns out that it was the better choice. And so I started looking to organizations, relatively mid-sized to larger organizations that had cohorts of managers that they would want to send through a soup to nuts course. Again, I called the Best Boss Bootcamp. I did that a couple more times in the next few years. And so basically it was kind of a stop and start with creating this thing, this baby that I still continue to nurture and I’m super proud of. But what it is now is 100,000% different than what it was eight years ago.

Ari: And currently you are selling it, though, in that way to corporate, having cohorts of managers within one organization go through it together.

Danny: That’s exactly right. And it’s been revamped, so it’s been through three versions. The first version was the one I described for those first couple of years, bringing in people here, discounting it, not really making any money off of it, and having a lot of headaches from it. The second version, I got some feedback from a client that they would much prefer that it was more of a learning management system, an LMS. And I was like, I don’t even know what LMS is. Let me look on here.

So I figured that out. I realized I could add some details to the course, like tracking, learning, and reporting back to the sponsoring organization, and completely redid all the modules. And by the way, this is a hybrid course, so the majority of it is online. It’s housed online, and then we also meet on a bi weekly basis as a learning cohort for an hour.

Ari: In person, or also online, but just live?

Danny: It’s online, it’s all virtual and online. I tried to do the course once live. This was pre pandemic, and I’ve tried to do it in a mixed group, but I have to say, both of those are much more complicated than I thought they would be. I really don’t want to do it live anymore. I want to keep putting my effort and attention on making it the best hybrid course that it can be. It’s tricky for me when I’m bringing in some folks that are joining virtually, and I’m conducting it live, it’s just messy.

Ari: I mean, there’s that balance of, I need to focus on the people in the room without making the people who are not in the room feel like they’re missing out or they’re being ignored or something like that.

Abe: Yeah.

Ari: It can be a very tricky balance to strike.

Danny: Yeah.

Ari: And so what percentage of your business now is kind of the online course versus other endeavors?

Danny: Yeah. Yeah. So the mix of my business model is moving towards being at least 50% of the online course, if not more, 60% to 75%. Right now, we’re working on getting that going. Our tagline is building better bosses. Our course, our signature course, and it’s a high-ticket item, is the Best Boss Bootcamp. And so now, everything is pinwheeling around that. So all the work that I do in terms of messaging, outreach, I do a lot of executive coaching and leadership coaching and training around other topics, but it all kind of spins from the Best Boss Bootcamp.

That’s part of the vernacular that folks have when they work with me, is best boss and working around best boss and understand what it means to be a best boss. And oh boy, you’ve got some folks who want to be best bosses. Let me tell you about the Best Boss Bootcamp. It’s still a work in progress, but the idea is that it’s all pinwheeling around this idea of the Best Boss Bootcamp.

Ari: Interesting. And so when you do an executive coaching mandate or training or do you also sell to the same organization the Best Boss Bootcamp or vice versa, come in through the Best Boss Bootcamp and then.

Danny: Exactly. When I’m working with an individual class, they tend to be from smaller organizations. It doesn’t quite work that way. But what has happened, and I love that, is that from the Best Boss Bootcamp, folks will want to work with me in an individual coaching relationship. And of course I throw in teasers and that into the course. So there’s always an opportunity to work with me one to one with laser focused coaching sessions. In fact, I was thinking about this interview and I started thinking about all the different components that have worked and that haven’t worked. And one of the things that has worked is the opportunity and the invitation to work with me individually in a very limited way. So I’m not giving away the farm, but so folks get a taste of what it is to work with me individually.

Abe: There’s a lot of people who are interested in doing what you’re doing in terms of working with organizations. So just wondering if you have kind of insights or lessons learned from the journey of doing that that you could share with other people who are interested in doing the same thing, working with organizations in general as opposed to individuals.

Danny: Oh my God. It’s a world of difference, right? So it’s B2C versus B2B in my head, anyway. And so the lessons that I’ve learned and I’m learning is how much longer the sales arc is when you’re trying to pull this together. I’ve actually designed it and organized it, so it only takes about 20 hours of my time when the whole thing is sold. Right. But it just comes in $30 to $45,000 for each of the courses. So in an ideal world, I’m doing a bunch of those during the course of the year. At this point, we’re working on it. We’re getting one or two a year and we’re working on getting more of that.

But the sales arc is just so much longer. And one of the things that I’ve discovered recently is it’s a lot of fun. It’s a lot of fun. During that sales arc, maybe the money is not coming in, but that relationship building that you do, which is a core part of doing this B2B kind of work, can be a lot of fun if you’re somebody who likes to engage with folks and work with folks and not necessarily turn everything into a sales conversation, but know that it is absolutely supporting your sales funnel or your sales trail.

Abe: So I mean, what does that sales process look like for someone who’s new to selling into organizations?

Danny: I think it’s about, first of all, making sure that you are clear about what you have. You may not have to have the whole thing necessarily built out, but we always want to be one step ahead of whoever we’re talking to, whether always just one step ahead. So to have something in mind to really get clear on some structure. And again, this was stuff that I just pulled a bunch of things together, but it’s only recently that I’ve organized it into something that I say we focus on five best boss zones, if you will, learning zones. Here are the five and here are the modules that fall underneath that.

So to be super clear, that’s the first thing to enjoy yourself, to engage with enjoyment when you are talking about it. If it’s going to be work and problematic, then see if you can reframe it so that you can have conversations with people where you’re excited about it. And then thirdly is to be patient. Just keep leaning into this idea of building up the relationship so that you are at the forefront when the opportunity does come up. When I am an organizational leader, I’m like, oh, all of a sudden, our budget is healthy. I remember this guy Danny I was talking to about the Best Boss Bootcamp. Let’s look into it. Now is the time.

Abe: And where are those contacts coming from? Or how are those conversations starting in the first place?

Danny: Yeah, well its interesting. So just a couple of years ago I moved from the San Francisco Bay Area where I lived for 30 years and I was constantly networking and out there and building up my list. So I have to say I started off with a fairly healthy list with a few hundred people on it. I have since moved to my hometown of Binghamton, New York, which is a smaller, barely a city, but I’d gotten so used to just not really going out and talking to people anymore, but doing a lot of marketing online.

And now I’m like, no, I need to go out and talk to people because that’s how people are connecting. And it’s also how I think it makes sense in a smaller market. So for whatever it’s worth in terms of advice, lean into all the avenues that you have. Again, kind of in this pinwheel mentality that I have, I have a Best Boss Podcast. I have five-minute videos that I send out every other week called Best Boss Take Fives. Right. So it’s about networking and planting seeds.

Abe: So this combination of using a network that you built up through working in a particular area, but then also going out and establishing new contacts as well.

Danny: That’s right, exactly. And again, I can’t stress the importance of enjoying it, of making sure that I enjoy it. If I’m going to be going out there and doing this kind of in person networking, I’m going to enjoy it or else I’m not going to do it. So I always think about how am I going to enjoy this? So, yes, to your point, Abe, it gets about leaning into both ends. But I have a lot more fun when I’m doing the one-to-one engagement, this kind of talking that we’re doing now.

Abe: Yeah. Interesting. Well, I guess the other piece of it then is what have you learned in terms of the experience inside of this program? I mean, the other thing we hear from people trying to work with organizations, with managers and so on, is they’re very busy. It’s hard to in geese. They may be interested in the concept of the program, but it’s very hard to actually keep people’s attention. They have a lot to do. So, just curious what your experiences have been there.

Danny: Yeah. And it’s a work in progress in a lot of ways because we’re getting that feedback all the time. So we have distilled it down to, we say that your managers will have, over the course of 14 weeks, we have six modules, by the way. We used to have ten. We only have six now. And our meetings used to be 90 minutes long. Our in-person meetings, they’re now 60 minutes. We just keep streamlining, streamlining. Actually heard from earlier episodes of this podcast, the importance of simplify, simplify. So we’re doing more of that so that it’s easier for folks to participate.

But we say now that your folks should be aware that they need to spend an hour and a half to 2 hours a week working on this. That includes all the classes, everything else, but they need to start blocking it out. So we’re scaffolding around the requirements as best we can. We have a Best Boss Bootcamp Champion, so we’ve got the sponsor, the person who’s paying us, but they also have a champion, somebody in their organization that is willing to be the go between for me to help me rally folks, bring people, keep them centered, and also track attendance and a whole bunch of things.

We also have built in accountability learning partners. So we make sure to spend some time at the beginning of the Best Boss Bootcamp talking about what an accountability and learning partner is, which is essentially one of your colleagues in the organization that you are willing to meet with on a regular basis in a very structured way to keep engagement and application alive. We try to do some online community work. So through the platform that we’re using, it doesn’t seem to work, I think, for the reasons that you’re saying. Managers are like, no, I can barely give you this time, so can’t give you any more time. So we just make it as easy as possible for folks to engage with me, with each other, and with the material.

We also do things like at the end of each of our live sessions, I do a book drawing. So I say, this is a great book. It’s a book I recommend and I love it. And you’re going to like it so much. We’re going to give it away, but you got to be here to win. So we try to incentivize. We’re trying to gamify. We say you pass 80% of the online quizzes. You are a graduate of the Best Boss Bootcamp. And we work with the organization to make sure that they figure out a way to honor their graduates. What will they look like? So we incentivize in any way possible for folks to be engaged and to do the work. But we’re still working on it. We’re still working on it.

Abe: It sounds like that works well for a lot of people. And then for people who are not engaging as well, do you have, how do you push the people who are still dropping off despite all the effort you put into keeping them engaged?

Ari: Is there a stick along with the character?

Danny: Yes, there is. I mean, we work with the organization to build that in. That’s not from us. So there’s an accountability factor. Again, work in progress. We’re still figuring it out, but it’s at the front of the engagement where we need to be super tight with folks and where the organization needs to be super tight with their managers saying, look, we’re paying a lot of money. This is what you got. And if you don’t do that, then XYZ, I mean, it’s seriously nothing.

I think what’s not said directly is this will show up in how we evaluate your performance. Right. So if you’re saying you’re going to attend this, we’ve got all the resources. You’re super clear about what’s required. And for whatever reason, you’re dropping off and working out well, that’s on us. And just so you know, we’re noting that. So we can’t treat adults like children in my estimation. But what we can do is incentivize them to move forward, to keep with it. And you have bit of an organizational stick because people are watching. That’s the bottom line. People are watching and we are reporting back. And your manager knows that you haven’t been at the session, and your manager knows that you are not passing the quizzes.

So it’s working pretty well. It’s the stuff like the community engagement, the taking advantage of the coaching. You know, sometimes, sometimes we get some reluctant folks that engage with it, but I think it’s on us as course creators when you’re doing this kind of work to really scaffold around folks’ success as best you can by building in some of these, I don’t know what you call them, stopgaps, so that folks are not dropping off. And some of it’s also, it’s the personal, it’s the one to one.

I mean, this is essentially what we teach people, too. We can give you all the tools and the structure and the insights, but you got to bring it into your heart, too. So you bring your heart to your work so that folks want to engage with you. So I try. What’s funny, at first, I was, when I was doing the work, I was like, okay, I’m going to be professional and I’m going to. And I’m going. And that was fine. It worked out fine. But I find when I bring a little bit, when I fly my freak flag a little bit, when I’m working with people, there’s a lot more engagement, distinguish myself from other folks that are doing this work.

And it seems to me if you don’t build in an in-person component, you know, a virtual in person component, you’re taking the lazy way out and you’re missing out on one of the primed ways of engaging with your folks. So maybe it doesn’t come naturally to you. You can work on that, but figure out a way to bring your personality, your DNA, your freak flag to the conversations. It won’t work for everybody. But if you’re going to distinguish yourself in a way that adds value and brings joy to the engagement, then do that. Absolutely do that.

Abe: That’s great. Thank you.

Ari: I have a question going back a little bit to the sales process. One thing that I would expect that some course creators might bump into when they’re selling into an organization, is that okay? It’s not a $2,000 deal, it’s a 35, 40, $50,000 deal. And then the organization starts pushing back, maybe not even on the price, but on the content or about what will be taught and what they want to be taught and how they want it to be taught. So what are your thoughts on from your own experience? How flexible should you be as part of that process?

Danny: Yeah, so how I’ve scaffolded around that myself is to really lean into the hour-long sessions that we have every other week. That’s where I can start to really reflect what are the needs, the desires, the messages that the organization wants built into this course. So I’m not going to go in and change all my online content. I’ve done that three times. It’s a lot. I’m not going to do that for one client. However, that hour that I spend with folks, I used to deliver additional content. I thought, oh, that’s what they need. They need more content.

We need conversation around application, connection, all those things. And so I asked the sponsoring organization, what is it that you’re missing that you want to see in here? Let’s talk about that. We could build it into the 1-hour sessions I can add on. Oh, and by the way, you’ve got folks that aren’t able to make it, but you’re going to be hiring soon. We also have a self-study, right? You’re not going to get all of the bells and whistles, the connections, all of that that goes along with a full, robust cohort experience. But we have a self-study option as well.

So I’m trying to close all the outs for folks when they have that kind of pushback. I’m not going to switch up all the content. We’ve got five coaching zones. We’ve got all these. We got a really robust interactive workbook, by the way, which took us a long time to get together. But we are certainly able to meet your needs in terms of messaging, or specific needs that you have sponsoring organizations.

Ari: Awesome. So where can our audience go to learn more about you and the Best Boss Bootcamp?


Yes, please join us and see us at

Ari: Awesome.

Abe: Great.

Danny: Thank you. That was super fun.

Danny Iny: Now stick around for my favorite part of the show, where Abe and Ari will pull out the best takeaways for you to apply to your course.

Abe: All right, a really interesting discussion. Ari. What were some of the things that jumped out for you?

Ari: A lot of interesting things from Danny there. One thing that I found interesting, we didn’t touch on it too much, but the way that he’s focusing everything around a single brand, kind of having his best boss, whatever it is, I find that really interesting. And it is a good way for him to lead from one product to another rather seamlessly because it’s all kind of within the same bucket of, this is the kind of experience you’re going to get. This is the kind of training you’re going to get. Different formats, but it’s a really interesting way to make the upselling slightly easier, which I like.

Abe: Yeah, good positioning there. This definitely was a pretty interesting case study for people who are intrigued by the idea of serving and teaching in larger organizations, and it kind of highlighted the pros and the cons of that. I mean, on the one hand, it’s pretty exciting to think about a price point of 30, 40, $50,000 for as compared to, you might think of selling a course for $500 or maybe a couple of thousand. That’s a pretty radical leap up the price ladder that could really transform your revenue.

But it’s not necessarily easy to get clients at that price point. And so one of the big takeaways here, I think, was that the length and complexity of the sales cycle to bring on organizational clients, at least certainly at this price point, it may be different if you’re selling to a small team at a company for $5,000, let’s say. But as you go up the ladder, it becomes much more complex to get that deal signed.

Ari: Yeah. And that’s something that you really want to be thinking about for yourself, for, of course, what you teach and whether it makes sense to sell into an organization, but then the Runway that you have because, yeah, if you are able to sell into a small team for $5,000, I mean, that is great, but it might still be a longer sales process than selling to individuals. So at that point, maybe you’re better off just going the B2C route versus okay, let me find a team that I can sell 30 seats in one shot, $30,000 or whatever. But it depends on your connections, how comfortable you are nurturing those connections and having those conversations and doing the ongoing work of staying in touch and staying top of mind, like Danny was saying. So that when budget frees up, for whatever reason, hey, they’ll remember you.

Abe: Well, it’s interesting how he approached it too, that he’s taken the stance that you really need to find ways to enjoy that sales cycle because there’s really no way around it. And if it’s just a grind or you’re just doing it to try to get that big payday at the end, that’s unlikely to be sustainable. So thinking of it more is like it’s just relationship building. It’s connecting with people and trying to have fun with that and then planting seeds that will ultimately result in a bigger sale. Seem like a healthy way to approach what is a challenging process?

Ari: Absolutely. And I think it’s something worth remembering for anyone who’s trying to sell anything. I mean, if the whole sales process that you’ve built feels like pulling teeth all the time, you’re not going to do it well. So try and figure out a way that you can enjoy the process and look at what needs to change so that you do enjoy it and are able to do it on a regular basis and happily.

Abe: The final point about his approach, I thought was interesting, is emphasizing the importance of individuality and bringing his own personality and approach into his program design and how he interacts with his students so that it doesn’t feel, I guess, sort of generic or corporate, you could say in a certain context. Right. And it kind of starts at the top with branding and how its positioned and how he talks to people about the program. But it’s you really behind the scenes that he’s trying to interact with people in a way that is more genuine and it’s grounded in his personality, not just concepts like, here are some techniques you need to learn that are divorced from his own perspective.

I think that’s important and it’s something we often lose sight of. We talk about courses in this more abstract way, but at the end of the day, it’s a human interaction that you’re having with the people that you’re trying to help in your program.

Ari: Absolutely. And I think that in the B2B world, as you said, the kind of more corporate environment, it gets lost more often. And as with everything, you need to strike a balance with what people will stomach and what people will accept. And of course, once you’re in, can potentially let yourself go a little bit more. Just be conscious of it also through the sales process and make sure that you’re tailoring the way that you’re showing up to whoever you’re speaking to.

The other thing that I thought was interesting is just the how much he thought through the engagement of people within an organization and how that is different than a B2C model where people are generally, they’ve made the choice to be part of a program. The fact that they’ve done that does not necessarily mean that they’re as committed as we’d like them to be. But still, in this situation, potentially people are even less committed because it was not their choice. They were forced into a program at times.

And so the way that he’s just thought through, okay, how do I keep them engaged? How do we keep them actually participating is just something worth thinking about and remembering and just noticing where are people at as they’re coming into whatever program that you’re building and whatever program that you’re delivering so that you can meet them where they’re at, kind of keep them engaged throughout.

Abe: Yeah. And hopefully being able to track and demonstrate those results to the organization that is writing a big check for them is really critical. It’s also critical to be able to then show that to future clients that are interested in the same program.

Ari: Absolutely. And I mean, that’s a great segue into, and here’s the next thing that we could do together. Look at the great results I’ve provided for this cohort. A, is there another cohort within the organization, or b, that was in a group program? Think what I could do for you when I work with people one on one and kind of go into that kind of coaching.

Abe: Yeah.

Ari: Awesome.

Abe: Danny Ceballos is a leadership consultant, trainer, and executive coach who works with individuals and organizations to excel in their workplace. You can find out more about his company, Unleashed Consulting, and his Best Boss, Bootcamp at That’s

Thank you for listening to Course Lab. I’m Abe Crystal co-founder and CEO of Ruzuku, here with my co-host Ari Iny. Course Lab is part of the Mirasee FM podcast network, which also includes such shows as Once Upon a Business and Making It. This episode of Course Lab, was produced by Cynthia Lamb. Post production was by Marvin del Rosario. Danny Iny is our executive producer.

If you don’t want to miss the excellent episodes coming up on Course Lab, follow us on YouTube or wherever you listen to your favorite podcasts. And if you’re enjoying our show, please go ahead and leave us a starred review. It really does make a difference. Thank you, and we’ll see you next time.

All right, Ari, who have we got coming on for the next episode?

Ari: I think you’re really going to like this one, Abe. We have Ali Shapiro. She has courses around the intersection of food, adult development, psychology, and behavioral change.

Abe: That sounds right up our alley.

Ari: Absolutely.