The Dependency Fix: How to Stop Founder Dependency for Good, with Jason Henneberry

It is an honor today to have Jason Hanneberry on the podcast. Jason's the creator of the Dependency Design Framework and the author of Why Your Business Won't Let You Go. He spent more than 30 years building and operating founder-led organizations and currently serves as a senior partner in a national brokerage with over 600 professionals. Jason works with founders, practice owners, and producing team leaders who run successful businesses but still feel like everything depends on them.

His work focuses on helping leaders see where responsibility has quietly settled inside their organization and how to redesign that dependency so growth doesn't keep increasing the weight that they carry. His approach is calm, structural, and practical, challenging the common advice to simply delegate more or install better systems. Jason, I'm really glad you're here. Thanks for being on the show.

William, thanks for having me. I appreciate you inviting me on. Particularly around your journey and your development as a leader. How did you get started?

I've been I've been the whole range uh of emotions in the entrepreneurial journey. So I started off as a solo entrepreneur, uh, really as a mortgage broker uh up here in Canada, uh, just you know, hitting the pavement, drumming up referrals, and uh found some early success in the career. And, you know, one thing leads to another, you're hiring an assistant, next thing you know, you're building a team. Uh, and then uh and then and you just keep plugging away.

Uh eventually we ended up building a bunch of systems around uh the team, and that led to what is uh today Tango. And uh so we've leveraged those systems and we have we're just really fortunate we have a lot of growth happening in the industry, and uh we've got over 600, uh 600 agents now that have plugged in to to be part of the uh the ecosystem. So that's that's kind of my journey. Yeah.

Well, I mean, uh building and scaling an organization to to five billion plus a year is no small feat. Uh that's got a billion in uh funded mortgages, so that doesn't mean we make five billion, but but I do appreciate it. Sure it does. Isn't that how it works, right?

That's how that works. I wish that's how that works. Dollar for dollar. That would mean people are paying like a hundred percent interest on their mortgages, which it feels like that sometimes.

I'm sure I'm sure they line up for that, really. You know, it's not just building Tango Financial. I mean, you've also built some SaaS businesses as well. Yeah, that's right.

Uh so I'm I'm uh I head up operations uh for our company. So basically, if it has a moving part, it rolls up to me. I'm responsible for it. And along the way, we've uh you know, you build uh payroll systems, compliance systems, and and and we have some fun too.

And we've built some marketing systems and stuff like that. What our process has been to really test the market to see if uh the the thing that we're thinking of even has any merit or value. And the best way to do that, rather than making a huge investment internally to test it on, you know, inside the company, is just to put it out to the world to see if there's any third-party adoption. Uh so we've built some systems outside of Tango and made them available to the entire industry.

And usually that gives us a pretty good sense of, you know, do people like this? Uh because they're not obligated to use it. They're actually paying for the for the tool. And it gives us a revenue source that allows us to invest more into the tool.

And uh so it's so that so we've created a few things that are really just extensions of of our operations. But um, but that that's a that's been a really great process for us. That's awesome. I love the testing mentality, you know, almost like the everything is an experiment modset.

Yeah, so there's uh there's a a book I read uh while I mean every I think everybody knows it, good to great, uh Jim Collins. And I'm not gonna do this justice, but there's a section of uh one of the one of the books in the series where he talks about sort of protect the core and then expand your reach. And uh basically for us in our little world, what that's meant is if you have two or three ideas that you're thinking of investing time or energy into, make sure that those are things that if they were successful, that you could bring them into the core, but also make sure that if they fail, that they don't they don't drag down the core business.

And so that we sort of follow his methodology for that, uh, which has worked really well. And when things land and they work out, uh we sort of we we double down on that thing. Maybe, maybe you've got two or three projects on the go and you ditch the others because they're not working out, and you focus on that one thing, bring it into the core, make the core stronger, and then watch and repeat that experimental process till you find something else that works. Like that.

Your book, uh Why Your Business Won't Let You Go, is all about dependencies, founder dependency, owner dependency, even leader dependencies. Uh I'd love for you to share a little bit about that and why you wrote it. Sure. Uh I'd be handy if I knew exactly why I wrote it.

I I woke up one day thinking, I just feel like putting pen to paper. And uh it it just started sort of flowing out. And uh probably, you know, since then I've spent a lot of time on the work and and that's really I'm just looking at my own businesses and my own role in those businesses and where I feel like I am I have I'm choosing my role on purpose and I'm involved in the business in the way that I want to. But then there's other parts where you know you're involved in the business because you have to or things keep popping up and maybe it's not by choice.

And so the the at some level, if you're a founder of a business or a team lead, the the business or the team relies on you as a as a founder or as a leader in your business in ways that sometimes you plan and sometimes you don't. And it's the it's in the ways that you don't plan that that it feels heavy. And so I'm you know I'm doing that work for myself, and I thought it might be fun to share that with some others. I love it.

You know, I want to key in on a word you used just a minute ago. You get to choose the the you're choosing the environment that you're building. Uh do you believe that? Do you believe founders, business owners, leaders choose their own adventure, so to speak?

Choose their path. I think sometimes we don't know that we're choosing it. Uh and so in the book we explore the concept of uh accidental dependency. So dependency by design, which is the next name of the book, dependency design, or accidental dependency.

And uh an example of accidental dependency is, you know, as a founder, oftentimes in the early days of starting a business, you are the business. Like you have to put energy into every aspect of the business in order to make it move forward. And that's one. Um as you find success, sometimes we put people, systems, processes in place.

And we, it's very easy. I shouldn't say it's easy, but it's easier to do task assignment or to hand off tasks, scale the risk, do the things you talked about earlier. And but what's harder is sort of handing off the ownership or the responsibility for the outcomes. And what happens is when uh, let's say you've got a team of people and they're all very capable under normal situations, but something comes along and it and um maybe uh an important client is at risk or there's revenue that's on the line.

And as a founder, we the team's looking at us for like, what do I do now? Because we're outside of that range of normal operating. And as a founder, we often feel like we need to just get in there, solve the problem. And that often feels like leadership.

But what we're actually teaching the business in that moment is that we are, we are the system. And and that's where we go wrong as founders, is we are quick to jump in and solve the problem, which teaches the teaches everybody around us that when something falls outside of normal operating parameters, that they come to us either through escalation or for important decision making. And if you're not careful about it, you end up further down the line, and the business depends on you in ways that you didn't intend.

You had the best of intentions, but but it's it starts to feel heavier than more successful the businesses. Aaron Powell You know, as you describe that, I I think about so many conversations I've had with founders who would fit squarely into that category. This is not what they intended, it's an accidental thing, but it is certainly a dependency. Yeah, the dependency is not in itself is not the problem.

You want your business is going to depend on things. So in the book, we we sort of uncover that there's there's you know four major domains or areas of your business, like revenue as an example, as a whole section of the business, um, you know, fulfillment operations, and decision making, like strategic decision making. And each of those domains depends on something. Uh in the early days, all of them depend on the founder.

But as you build systems and processes and team, you're trying to, you're trying to actually hand off the responsibility for the outcomes. We move the tasks, but oftentimes we don't move the that responsibility. And so what ends up happening is in those matters that count, the the business just comes, comes, it pulls us back in. And it's that pull back in that we never really intended uh that feels annoying or heavy or frustrating or whatever number of emotions that entrepreneurs feel you know when something something should just work or something, I wish they could just handle it, or those types of things come up.

You're probably in a moment where you've taught the business that you're the solution when you really didn't want that to be. So what do you do? So what eater is in that spot. What do you do?

Okay. So um there's so there's very much you you're looking for that emotion that I'm frustrated. I wish the team could handle it. I wish they would just get it right, or I wish this thing wouldn't land back on my desk.

Those moments are when we're often very busy. We feel like, uh, okay, I'll just go and fix that. Hopefully it doesn't happen again, hopefully they learn. So we already know that we're teaching the business to rely on us.

So the next time it comes back, we become the path of least resistance. So it's in that moment where you have that negative emotion where you're a little bit frustrated, uh, that you want to take pause and look at it. And it's actually a signal that the business is telling you that look, if you really want to make sure that the thing that you want that part of the business to depend on, that it that it's strong enough to actually support or carry the weight of what's happening right now, you need to strengthen that part of the business.

So it's just you just want to pay attention to those signals. And then that's a moment to look and say, okay, what what's the outcome I'm trying to achieve? Why is it coming back at me? What is it that needs to be in place so that this doesn't happen again in the future?

We just don't we just don't go through that analytical process. Most most of the time we just jump in, fix it, move on. 100%. Often describe it as pretending like you have a cape hanging in your closet.

And you just strap it on, swoop in, save the day, and then wait for the next. We want to avoid uh rescuing the business with some kind of heroic effort. That's not a that's that's not a business. That's a job.

That's right. And and and truly I like that distinction because I think a whole lot of entrepreneurs left a job and all they did is built another one. Yeah. It's the biggest irony in the world is we build this thing which is intended to give us freedom, and we end up down the line.

If we're successful, we we probably we might have the financial success or the business success, but we but we may not feel like we have that freedom, which is probably why we set down this path in the first place for most of us. In your book, you have an assessment, uh, the dependency snapshot. Yeah. You designed this specifically to help founders.

What does that help them do exactly? It just helps them see. Uh see where their business relies on them in ways that they they probably already know. Um like, look, if you go for help of any kind in your life, you probably already know that something like something's there.

But it helps to it helps to see it and be presented with it. So there's a series of questions. It's a free snapshot on our website. You just go and fill out the questions.

And what it is, it's a reflection back, and it'll say, you know, these these are the areas of your business that are working well. This is what how your business operates in under normal conditions uh and under stress or uncertainty. This is this is what happens and this is where the business relies on you. Whether you're aware of it or not, it's just it's just surfacing that information and allows you to start to look and say, okay, I really need to focus on that.

Or there could be an area where you're like, hey, this is exactly where I want my business to depend on me. That's okay too. It's going to surface that too. But if it shows you something where you're like, you know what, I really don't want to be the thing that carries the weight in that domain, um, at least it's it's pinpointing where you might want to focus some energy.

You know, you say people uh founders probably already know. I'm not sure that they can do that. And the reason I say that is as a founder myself, like I think we all have blind spots. And I think sometimes it's very, very difficult to see the whole picture when you're in the frame.

And I think tools like this can really help us to get an outside perspective. I've had uh it's it's it's a good point. I've had mixed reviews from it uh in the sense of some people will fill it out and go, oh, okay, I didn't know. And then other people will fill it out and say, Yeah, this is kind of bringing to light what I could I kind of intuitively felt, but at least it's defining it for them.

Yeah. Yeah. And some people do have a higher self-awareness, that's to be sure. But 30 plus years of of working and coaching, working with and coaching leaders, I'll tell you, self-awareness is not a flower planted in every garden, you know?

And that's where tools like this can be helpful in surfacing these things and saying, oh, hey, this is a blonde spot. And you may not have had words for it or even a strong sense of it. Yeah. But look at what the data says.

I mean I've I've gone through it two or three times myself, and I'm always like, yeah, okay. Yeah, it's it's this is it's it's a it's an interesting experiment. It forces you to just think about things. And that's never a bad thing.

Especially when you're in the weeds and fighting the fires day in and day out. It's so easy not to not to pull back and get that broader perspective. It's also been really good from a team leader's perspective. So, like with myself, with my company.

So I so you know, I've gone through the snapshot uh and just from my own perspective and my own role. But then I've obviously I've been talking about this, the book and the work that I'm doing with people around me, and uh some of those people are inside my organization. And so they've they've gone and completed the snapshot. And so as a as a team lead, I have basically I'm able to look at that and go, uh, I have a better understanding now of what is frustrating for you, where you are in your business development, and and where you might benefit from looking at some of these elements where your business is, you know, because everybody around me is an entrepreneur as well.

So as a team lead, it's been really interesting to watch people go through it and then I'm learning a lot. That's good. That's excellent. So let's let's talk about you for a second.

You know, running this business and thinking broadly and working now with people from from a lot of different businesses, you know, more is demanded of you than was true three, four, five years ago. And more is gonna be demanded of you five years from now. So how do you stay on top of your game so that you level up with the new leadership skills that your team and your clients are gonna need you to have in the days ahead? That's a really good, uh, really good question.

Having clarity around the outcomes in my business that I wanna that I'm that I want to make sure, things that I want to make sure happen without my without my involvement. So um an example is like we all set goals, right? So a goal might be like, you know, I want to double my revenue next year, or over the next three years, I want to double my revenue. But that's so that's that's taking you from point A to point B.

It's a forward momentum type thing. I'm here, I want to get there. That's that's goals. But there's a process that you can follow, which is outcome creation.

And outcome creation starts with the end in mind and works your way backwards. So you might say, I want to double my revenue over the next three years, but an outcome for your business is more like sales happen uh regularly, like consistently without my involvement. That's an outcome. Generally, as entrepreneurs, we don't we don't design our business with outcome in mind because we're all like when you when you started the bit the journey of being an entrepreneur, you woke up and you're like, okay, I'm I'm I'm an entrepreneur.

I need to go find some clients. And so you just start like doing the thing to get to the clients. Then you get the clients and you're like, okay, I better, I better figure out my systems for fulfilling on the promise, right? And then you're doing that and you're like, wow, I'm really busy now.

I don't have time for sales, so I better hire someone to do the fulfillment part. And so we build forward always. And there's nothing wrong with that because that energy is what got you to that success in the first place. But an example of a business that builds for outcome is like an airline.

An airline doesn't wake up in the morning and go, hey, we really want to like, we really want to take people to Bermuda, so we better fire up some ads, and then okay, we got lots of people booking travel now, so maybe we should get a plane, because that's kind of part of the deal. Are we going to need a pilot? Nobody does that, right? So the airlines are like, okay, Bermuda's a destination, and we we need to we need to build for outcome.

And the most important outcome an airline builds for is the plane always lands. So regardless of what that airline's goals are in terms of like growth metrics or whatever, they have an outcome that they always design backwards from, which is that plane always lands. And then there's a whole bunch of checks and balances and systems and stuff that they they put in place. So the work that that we're doing with dependency design is around helping entrepreneurs see that it's good to have goals, it's good to have that build-forward momentum.

But if you want to if you want to really truly hone in and put in place the things that that will be that are necessary for you to not be married to your business in ways that you don't want to, you need to take a totally different perspective and start building backwards. You start designing for outcome backwards. And uh we explore that and we start exploring that a little bit in book two. Uh right now.

That's excellent. I can't wait to read that. That's gonna be great. Yeah.

Well, book book one is like a a short intro, as you know, it's available on the website. It's free to download. It's a 15-minute read. It's basically the introduction to a more complete work.

Uh, but really the work is about is about shifting your perspective to designing for outcomes. Well, and I I think that's that's brilliantly put. And I think that's something that I I know every one of our listeners could benefit from if they begin to apply that thinking to the business that they run or whatever leadership role they're in. Uh, I think that's critical to be thinking about the outcome.

Start from there. That's that's a brilliant frame. I like that. Appreciate that.

Thank you. In all of our conversations, you know, I I have noticed, Jason, that you you are a learner. You are continually learning uh from a lot of different sources. Is there a book or a podcast that has made a big difference in your journey that you'd recommend to the listeners?

I mean, outside of your podcast. Oh bonus points for Jason, right there. Bonus points. I'm a quick study, as you said.

You know, I really the podcast that I'm most interested in these days, I've been really geeking out on uh Diary of CEO. What a great one. I love that one too. The way it's presented and I learned something new.

Um I actually I don't often go watch the whole thing, but the way they the way they clip it and and so you know, it's it's in my feed all the time. I'm you know, I've got these 60-second clips where I learn something. Like they do a really good job at that. So I I just I I think they're doing a really great job.

Um book wise, uh the the one that had the most profound impact on me, and I read it years ago, was the Good to Great series. Uh I even I mentioned it earlier. I just that really shifted my perspective on um there's a lot in there that can teach you how to build a business uh better. And uh tried to apply a lot of those principles over the years.

So good. You know, people look at you from the outside, and the temptation is that that we look at any successful leader uh and we see their highlight reel. You know, the pieces that are published online, the 60-second clips. You know, and uh I think some of our listeners it could very easily be looking at you and saying, oh man, Jason, he's you know, running a five billion dollar company.

See, I just worked that in again. He's running this company. Oh, gee, there you go. There you go.

Almost six billion. There you go. You know, you're running this successful company. And I think a lot of them may be thinking, man, he doesn't struggle like Astro.

He's never had to wrestle like I do. I got it all. Right. You got it all, right?

So in in line of the fact that we know that's not true. We know every entrepreneur has challenges and Struggles as part of the journey. In light of that, I ask you this question. If I had the ability right now to snap my fingers and solve one problem in your business right this minute, what would that problem be?

In our world right now, uh there's a lot of regulatory changes. And uh, you know, you do your traditional SWOT analysis. Um we've got there's a lot of headwinds in the mortgage space. Um regulation is one of them.

Um more and it's it's all it's all in in intended around, you know, protect the consumer, more disclosure, which is all things I can get behind. But when you're when you're dealing with that at the rate that we deal with it, um it it the energy that goes into it takes you away from business development activities. So it's not good or bad. It's just that there's a there's a reallocation of resources.

Um we're also at a big pivotal shift where consumers are able to, you know, it it would be nice if this was possible. It's not today, but I think a lot of financial services and a lot of products are have been really simplified where you can just kind of download an app and you know choose your investments or buy your insurance and mortgages are a little bit more complicated than that. But we're we're probably one of the last financial services, major financial services that are going to go through that shift.

But we're in it. We're we're knocking on the door. We can feel that change coming. So, you know, when you look at building a big business, and and my role is to see the future for all of our people.

Like I mentioned mentioned, we have 600 agents. Well, those 600 agents are spread across probably 50 different teams or sub brands, you know, team leads. So they're really they're plugged into our environment because uh we we give them a we give them some tools and some resources that they can they can run their business more efficiently, but they're also part of this ecosystem because they're hoping that you know we might be able to see around the next corner and help guide that.

And that's very difficult to do. It's uh difficult to resource, and it's also difficult to um keep everybody happy and calm during these major shifts. Uh and so, man, if if you can snap my finger and say, you know, nothing's gonna change, everything's gonna be smooth, there's not gonna be a new regulation change for five years. You don't have to worry about, you know, shifting ground with technology and consumer behavior.

I could go on, man. There's a lot. So uh I would stay up at night thinking about all these things and how I can be the best support person for all the people around me and help them navigate through that. And if I get it right, we win.

If I get it wrong, my business is at risk, right? So um so those those are some pretty heavy things. I'll tell you what, to have the ability to snap my fingers and say nothing is gonna change. That would be that'd be something.

So I don't know. But you as we're playing with this concept, uh Izzos has a really good thing. He's been asked that about Amazon, right? How do you stay, how do you know, like how do you stay on the next trend?

And he's like, we actually don't. Like technology is a big part of our business, and you know, yeah, we have to be forward-thinking in all these areas, but our guiding principles are actually all the things that never change. And so, you know, in his world, it's like, I can't, I'm not gonna do this justice, but it's like people want to be able to find what they're shopping for fast, they want to they want to be able to transact quickly and they want it delivered fast, like you know, those types of things.

Those types of things are never going away. And and so then the rest of all their decisions are uh largely based around that. And so in in our world, we're fortunate, it's like, oh, people are people are gonna want to live in a home, they're gonna probably want to own that home, they're gonna want to have homes are expensive, so they're probably never gonna be able to pay cash for it. So, you know, they're gonna need financing.

And so I look to those types of things as reassuring. So no matter what happens, probably those things are never gonna change, which means there's there's probably always a world where uh our services are in demand. It's a wonderful exercise for any entrepreneur uh because it it provides some assurance in in a very turbulent environment. Um I don't know if that's helpful.

No, that's brilliant. And and I think especially in the in the landscape we're in now, no matter what your business is, you know, things are changing and shifting so quickly uh with AI. You know, I mean, that is that is changing the field for a whole lot of industries. And we are only at the beginning of that.

And so I think, you know, to to be thinking like you're talking about, determining what those core things are that are not going to change, and then saying, okay, now what does it look like to build from there? Yeah. Again, you need something to hang on to, man. Like it's stormy out there for everybody.

You define the core foundational pieces and you define the outcomes that you want. And then building a bridge from here to there. Yeah. Yeah.

If you're like, okay, I know people are always gonna uh always gonna want to have a nice home and they're always gonna need financing for it. And so then that's what's always true. Then your outcome is, well, uh, you know, sales, uh, sales happen regardless. And then with between those two things, it's like, okay, I've got my goals, and then there's a shifting technology, but what are the things that you can put in place to make sure that certain things always happen regardless?

So yeah. So good. It's not easy, but that's the exercise. Well, if it were easy, everybody would do it, right?

There you go. And Jason, this has been so great. I so appreciate your generosity in sharing from your journey today. Uh I know our listeners have benefited and they're gonna want to continue to learn from you.

Learn more about what you're doing and especially about this book and the assessment. What's the what's the best way for them to connect with you? Uh yeah, I mean they could just go to the website uh dependencydesign.com and uh I think I mentioned you just download a copy of the book.

It's a PDF, it's a 15 minute read, and the snapshot's free as well if they uh care to go through that process. About five minutes to go through the snapshot. Pretty easy. Brilliant.

We'll have that link in the show notes. Jason, thank you. Thanks.