p241 Good Leadership is Ongoing Work

Listen to the BOLD Business Podcast


Search Blogs and Podcasts

Good Leadership is Ongoing Work

Facing uncertainty can be challenging – being a business owner facing uncertainty is tougher.

Red Direction helps you [fast track and] grow your business – authentically, pragmatically, and resiliently.

Start your journey HERE!

Starting the conversation:

Good leadership is a hard subject. There is no single way to lead well, and to be a good leader, you must be consistent.

Host: Jessica Dewell
Guests: Terry “Starbucker” St. Marie, Amy Charity, Jeffry Caudle

What You Will Hear:

Leadership is too loosely defined.

Two examples of companies that have decided what their leadership looks like.

Confidence in THE area your company strives for excellence.

The way you show up to new situations and new roles.

Questions to reflect on your response in new/unusual situations.

Vulnerability is more than asking for help.

The importance of iterating forward.

Learn to shift actions to align to priorities quickly.

Take time to find the simplest answer, option, even messaging.

How we use technology to automate can take us further away from human connection.

Make a high level of connection.

The way a highly integrated team looks and sounds.

Part of transparency is a clear message.

Overwhelm limits growth.

Dimensional Leadership (TM) is holding many perspectives and viewpoints.

Reflection allows you to let go of things that have stopped creating impact.

Can you embrace uncertainty?

Trust and vulnerability go hand in hand.

It is BOLD to work on having good leadership.

Notable and Quotable:

Terry St. Marie - p241 - Good Leadership is Ongoing Work

Jeffry Caudle - p241 - Good Leadership is Ongoing Work

Amy Charity - p241 - Good Leadership is Ongoing Work


Welcome to the BOLD Business Podcast. Your business has many directions it can travel. The one true direction, toward that new exciting level, we call the red direction. In this show, Jess Dewell delves into one question that will add clarity to the big questions you face in business today including: How to stay competitive in a changing market, How to break through business plateaus, and How to respond to the changing expectations of today’s customers. 

Jess Dewell brings you a 20 year track record of business excellence where strategy and operations overlap.

The premise of this show is that leadership is elusive. And, I want to counter that premise because it does not have to be.  Let’s set the stage for how we’re actually starting though, and why it seems so difficult. If you look up what is leadership in a search engine, the millions and millions of results that you get, show that people don’t fully understand what this is. We’re all working to grapple with and understand how does leadership function, and how do I show up to leadership? Knowing there is no right way, makes me think about your uniqueness. 

What you decide to prioritize.What your personality is. Where you put your priority. How you engage with others. How you engage with yourself. That is as unique to you as it is to me, and to everybody else who might be listening with us. I’m going to share with you something from Jeffry Caudle. He’s the founder of Neurodash, a technology startup. He is a critical thinker that looks for ways to improve workflow to reach our full potential. Listen to what he says about leadership.

Jeffry Caudle: The best definition that I found for leadership was, “Leadership means to lead.” A lot of people don’t really understand what leadership is because the definitions are not clear at all. The leader determines what success looks like for the team. They’re the one who want to define success, then the team put together the objectives. You give your team autonomy.

Jess Dewell: So we don’t know what leadership is, yet we’re supposed to determine what success looks like.  And then, we’re supposed to put together objectives from that. Which, by the way, everything that Jeffry said around that is true. 

It’s up to us. The role that we are in has responsibilities, and usually the roles that we find ourselves in at this level, we do have a responsibility for the clarity and understanding and work product of people that were working alongside with, our people who are reporting into us. When we’re working with and shaping for other people, it also becomes diluted in how we do that for ourselves as well. 

There are some companies that have done great work and figured this out for themselves. Just like the types of leadership that are out there, there is no tried and true way. So please take this information and use it to assess where you are at, what you are facing, and how this might work for you. 

The first is Zappos. Think about the customer service. Think about the culture that they have created. Think about the internal infrastructure that they have put together specifically for reducing the amount of roadblocks that their team encounters. And they can have the ability to act with confidence to do the job and get the job done in a way that furthers not only the entire mission of the company, but the day to day operations and positioning in the marketplace.

What Zappos does, is think about their culture, and they’re looking at these factors, most of them intrinsic. And the needs to be established early. Okay, that’s the key. When we do something and then we reverse engineer it. Sometimes, though, we also need to think ahead. That step at the beginning, where we take time to pull information, to process that information, to evaluate it, to look at it through many different lenses, is incredibly important to understand, because those times, those thought processes, are what set your culture. Deciding where you will be excellent.

So what is your company excellent at? And what is the expectation of how that looks and sounds, and shows up in every day activities, everyday behaviors by every employee? 

That requires a commitment from you and your entire team. And for those of you that are not CEOs and executives right now, it starts with them. When you are the CEO or an executive, you have an extra weight because you’re carrying what is acceptable and how people work together on your shoulders every day. 

When you have confidence the people around you have more confidence. When you lack confidence, the people around you have less confidence. Think about that in relationship to the role that you’re in, and how this works and what leadership actually means.

Now, that’s just the first example. 

The second example is base camp. I am a big fan of Jason freed and crew. The reason I’m a big fan is because they seem to buck the system all the way around. We started our first company at the same time that Basecamp began, give or take about a year. Since then, I have had five companies while Basecamp has had one single company. Unless you know what project management software is, you may not know about Basecamp. 

They strive for excellence. They strive for excellence by ensuring people have uninterrupted time. They do not interrupt people that they work with, and people do not interrupt each other. To do good work requires the space to think. And when we have constant interruptions, the space to think quickly becomes zero. Understanding your most valuable resources, something else Base Camp articulates and lives every day in their culture, and in the way that the leadership shapes decisions that are made. 

: It’s up to you to decide what is that most valuable resource. We can probably universally agree that time is the most important resource at work. When we think about time and the amount of time we want to spend there, and then the amount of time we want for our families, or our friends, or our pets, or volunteer work, or other communities. We don’t have to be in a pattern where it’s all work and no play.

One of the best takeaways that comes from “It Doesn’t Have to be Crazy at Work” by Jason and David, the founders of Basecamp, is that, it’s more important to be effective instead of busy. And sometimes we don’t know what effective is.


JESS DEWELL: I’d like to take a few minutes to tell you why we don’t run ads on BOLD Business Podcast. We’ve chosen to rely solely on you, our listeners, for support.If you are listening to this, you probably already know what I care most about. The work I do comes from a deep curiosity about what makes business work, what makes high functioning teams, and what elements shape success.

I’ve seen first hand how information can help people make better decisions and change their results. Curating and presenting this information is not easy. The vast amount of information out there and the overwhelming amount of stuff that demands our attention makes finding useful information and first hand experiences that can inspire you on with the big problems you are grappling with hard. We do the due diligence for you. I’m fortunate to have a great team to help me research and share this information.

One example is the preparation that is done for each program. We choose a question to explore, look for people with relevant information and experience, and we do the research for what the current trends are. Then put it all together into well produced program.

We produce comprehensive show notes as well. This shows in the positive response we’ve received about how useful it is to have transcripts, links to research and resources.


Jess: Terry “Starbucker” St. Marie, who is a leadership and business consultant, writer, coach and angel investor is going to share more about that with us. He was named one of the top 100 leadership management experts by ink magazine.

Terry “Starbucker” St. Marie: I came from sort of the boss world, where it was just very internal. And you did what you were told to do. And leaders didn’t seem to be so worried about being a personal thing. It was just there was a job to do it needed to get done. You’re a cog in that wheel, you needed to get it done. If you didn’t get it down, I’m going to yell at you. If you do get it done. Maybe I’ll get a pat on the back. That was something I kind of grew up with. He sort of tried to school me in the way of that. And I remember like, the second third day I was on the job, he told me the fire like like eleven people because we acquire these companies and, and I had never even done that before. And I had to like go through a Rolodex. And I think people that I think I’m I met one of the or two of these people. And literally call people I didn’t even know and let them go.

Jess Dewell: Maybe you’ve been in a situation similar to Terry’s where you were brand new, and you were fumbling through. And maybe you were given a big responsibility, or the dirty job, the one nobody else wanted to do like what Terry did with letting people go that he didn’t even know. He had to just pick up the phone and start making calls. 

So think back to a time when you’ve been in a situation that was brand new to you, and you felt that you were fumbling through. 

I can think of one. In fact, it relates to starting the Bold Business Podcast. I was saying fumbling through. I have a great team for the podcast that includes several people. And every single person showed up and was willing to fumble through with me. Now that comes from the ability of my leadership. I made it clear, I don’t know everything that’s going to happen. I made it clear each person that was part of this team has something that was necessary to make this podcast work. And that we were going to figure it out together.

Jess Dewell: So we set some priorities. And I was very transparent in the priorities specifically around that. Let’s shift this to you. Thinking back to a situation when you felt like you were fumbling through. Looking back because the beauty of hindsight is we have way more perspective. 

Here are  some follow up questions: How clear were you in the priorities? Were you fully transparent in what the priorities were and what it was going to take to achieve them? And then how did the result align to what you thought about it? That particular thought process, that tool is something that we are not taught. We find out from trial and error. Yet, you don’t have to. You’ve got this tool now. Even look at the process that you’ve already been doing. Consistency is going to allow people to feel comfortable following you. When we know what the priorities are, and when those priorities are consistent, and they’re communicated in an ongoing fashion toward the completion goal, consistent. People know what’s expected of them. They know how to show up, and it increases their confidence. And you’re helping them develop their skills. Terry goes on to say this.

Terry “Starbucker” St. Marie: Leadership is a very external thing. It’s projection of what I would call like caring and respect. And trust, and making when I call it when I define what more human leadership is, it’s making a personal connection with other people. And you can’t do that, as a leader who typically sit on a pedestal who’s being looked up at, especially when you rise higher up in an organization, you know at one point I had like 1100 people that we’re working in my department. I made a point to try to even get to know the names of just every single one of them, or at least meeting them. Because I felt like that connection was important because people want to be connected to something bigger than themselves. That’s something that I’ve sort of found out early on. They want reasons to get out of bed and go to work every morning. And they need someone sort of set that example. So traditional leadership wasn’t going to do that. And it wasn’t going to do it. I inherited situations where people were mistrusting, they were cynical, they’ve been mistreated. They’ve been neglected by their previous owners. I walk into rooms, and you could just see on it was like, well, who are you with a suit and tie dude coming in, trying to tell us what to do. So I had to try change the narrative.

Jess Dewell: Terry situation is common. To have a need, to change the way the story was going to go. The way things were going to work. That is far from instantaneous. It takes a lot of effort. 

It takes a lot of willingness to put yourself out there for you to be vulnerable. And we hear that word a lot, vulnerable. Well, here’s the scoop. We can get in our own way. And we can think we’re being vulnerable. But are we really? There’s this book by Ryan Holliday called “Ego is the Enemy.” Every single chapter in the book talks about the importance of one aspect of our ego and where we might get in our own way. In this particular scenario, where Terry is talking about this change, and being thrown into new things, is all about the way other people think. So he showed up in a way where he was not doing all of the thinking. In fact, I’m pulling a quote from the book. One of the chapters entitled, “Get Out of Your Own Head.” And here’s a quote that was used from Alan Watts. “A person who thinks all the time has nothing to think about except dots. So he loses touch with reality, and lives in a world of illusions.” 

That is one of the things that can break down team communication. Welcome to my head and my party. I hope you can find the way in because I forgot to tell ya. By the way, that is something that I still pull out of my back pocket once in a while. And I use it as a joke because it’s like, “Oh, right. I know better.” I know better than to assume that you know what’s in my head. I know better than to count on you remembering something I said, in passing, or one time, or in a project three years ago that comes down to personal accountability. Part of my vulnerability is to turn that into a joke. Oh, look, I lack awareness here. So now I am aware. Let’s pick up from here and go forward, and remove any issues that we’re experiencing between us so that we can make forward progress. Terry goes on to say …

Terry “Starbucker” St. Marie: I opened up, I made it more personal, I asked them to trust me, I listened to what they had to say. And then through all that came this almost really became a philosophy is that this is the way I want to lead. And that’s where really more human leadership was kind of born for me. It was during that period of time where I sort of figured it all out.

Jess Dewell: Just reiterating the importance of vulnerability. The importance of the willingness to say, “I don’t know everything, and you have a lot that I can learn from you as well.” Now here is a story that Terry shares about one experience that shaped his leadership.

Terry “Starbucker” St. Marie: Where I was based in New York, most of my folks were in the Rocky Mountain West. This is the core leadership experience I had. I would fly out there, and I would get in a car and I would drive to these places. And guess what? Those drives are like two hours, to half hours. A lot of time to think. And that was a pure blessing. 

Because it did allow me to take, think through, I’m going to be meeting with these people. They’re like, hard working technicians and people working cable TV. They’re crawling through crawl spaces. It’s 95 degrees, trying to do cable, and they’re getting paid kind of a decent wage. How am I supposed to relate to this? How am I supposed to talk to these people? How am I supposed to lead them? If I had just bought them from room to room and persons person, and not really think through where I was the context of where I was on those two hour drives. 

They were critical for me. Yeah, some of it needs to be spontaneous. Some of it needs to be real authentic, and all that stuff. But I also have to absorb your context, absorb the situation, and absorb, all right, these people are doing this job. They’re thinking this way. And they’re in a situation where they’ve been maligned, you know, cable TV. People walk up to them in the streets and call names because they don’t like the service. So how am I going to do this? If I hadn’t thought that through on those drives, I probably wouldn’t have done as well as I did, because I excited arrive in these places, and then I’d be prepared mentally, emotionally.

Jess Dewell: Terry took time where he could find the time. And in fact, looking at the scenery, driving through the Midwest is a great time to be focused on the surroundings around you. You need to drive a car safely, yet also be able to not be on the telephone, to be able to not be worried about what’s next but to just be. 

So think to a time in your life. Where do you get to just be? Joe Workman, who’s also been a guest on our Bold Business Podcast, talks about where his think tank is. Where’s yours? Can you find it? And then can you use it to be more efficient, to be able to unwind and let stress go? To be able to use the stress that you have to iterate forward. To be able to have space just to think. 

At Red Direction, and that’s one of the techniques and guiding principles that we use for a program that we have called Present Retreat. And in that Present Retreat, that’s all it is. It’s space that’s carved out that is not interoperable, of course, by you having to enforce that. So that you can look at where you’ve been, you can look at where you are, and you can look at where you’re going. Find the milestones you’ve reached. Confirm the milestones that are still coming u. And being able to do the same for your team and being able to do the same for your business. Here’s what happens when we take those Present Retreats.

Jeffry Caudle : There are many systems that build up trust. Trust is simplicity. And trust is clarity. Trust, is transparency. And its proximity. Better to talk to people face to face, or even Skype than email. Because email, there’s a lot that gets lost in translation. Prioritization., that’s the biggest challenge for companies right now. Knowing what to prioritize. Because leadership is defining success, but when the customer says that they want things a certain way, then the customer often leads a lot of the organization. You run into this challenge of, what are the needs of the customer? And then also, how do we translate that to a project and meet those needs? People aren’t aware of what they need. That’s the biggest challenge I think that faces companies.

Jess Dewell: Wow, it’s true. We know what we think we need, but is it what we actually need? So when you look at companies like Apple that changed the way that we use our phones, that Zappos which changed the way we get our shoes, Amazon that started delivering books, and now we can have anything to our doorstep in hours in some places. 

They thought ahead. They looked at the things that their customers were saying and you know what they said? “Ah, they’re trying to solve the same problem with different tools. But look what we have. We can see the solution to a problem that they’re having. And that solution doesn’t exist yet.” 

It doesn’t matter if you are an electrician, or a custom development shop, or an executive for hire, or anywhere in between — scientists, teachers, you name it –in the role you’re in, the people that you’re talking to, the people that you’re hearing from, they know what problems are trying to solve with the tools that they know about. 

So that can you bring to the table that solved their problem simply and clearly? That builds relationship, not only with customers or your stakeholders, whoever you’re interfacing with, but it also ensures that the way that you think and the way that you’re ensuring your team models that thinking will allow for ongoing innovation. It’s going to be that ongoing innovation that taps into the curiosity that we all have. Some of us have lost but we all have. So what can you do to foster that curiosity? To make something that other people want to be a part of?

Terry “Starbucker” St. Marie: I think everybody again, they naturally want to be led. They naturally want to be part of something bigger. I think I had already been there. It’s like, well, I was always purpose driven, more human leadership is, is this purpose driven. You realize that there’s a link between their fulfillment, their happiness and business success. That’s it right there.

Jess Dewell: Terry is saying we want to be led. By the way, that’s incredibly true. Why does YouTube exist? Why do search engines exist? Why do we ask questions? We want to learn from the people who have learned before us so we have less learning to do. Or we can skip the learning to learn only the parts that we need to learn on our journey. You know, there’s something to be said for that. And that’s important. 

Leadership is a kind of awareness that allows you to recognize The people around you want to be led. It also allows you to recognize that you want to be led. And when is the time to follow and when is the time to lead? And whichever role you’re in, what are you going to take responsibility for, to move a project forward, to move toward a goal that results in the output for the whole purpose of doing the work in the first place?

JESS DEWELL: A question we’ve been contemplating: How do we fund the necessary work to support our effort and continue this work?

While paid advertising and sponsorship spots are common, it doesn’t fit our model. Here are just a few reasons:

1. Quality Programs are important to us: I want you to know – really know – that I’m telling you the whole story. When money is exchanged to talk to you about a product or service the quality of our content is diluted.

2. Being an Advocate is who I am: I am an advocate for your success, your team’s success, and your business’ success. If I’m focussed on numbers and listeners to generate income, my attention is split between you and tactics to increase ad revenue.

3. Fuel my Continuous Curiosity: My eagerness is dulled when I’m doing something I’m not excited about.

This led me to choose a path less traveled. Listener supported programming has been proven to work over time. This keeps my focus on the content, and my relationship with you direct and straightforward.

It’s a clear answer to our question: How do we fund the necessary work to support our effort and continue this work?

The simplicity of a listener supported model ensures clarity for you and for me. I value honesty, and honesty is a two way street. If you get something out of what I’m doing, you can become a supporter and contribute at whatever level works for you.

In exchange, you get benefits above and beyond what is available for free.

It’s my goal to ensure that you get more than you give, no matter what level you support at.


Jess Dewell: Terry is going to share with us an example of how our personal awareness and what we choose to focus on impacts the way we look at what we do and how we show up.

Terry: There’s one unique part of the situation today that I think is a little bit different, that is worth addressing. And there is this gap between the cost of living and the wages. This was not a situation that existed 20 years ago, where they had three jobs, two jobs, you know, they were working a full time job and part time job and three jobs. So what job are they more loyal to? Or they are part of, or they feel a part of it? They’re just trying to make a living, they’re just trying to pay the rent. 

I’m throwing that question that audience at myself like we are, how do you lead people that are in those situations? And I think about today, and I think about the technology today. This is another side by side challenge. First, it’s the wage to the cost of living gap. And then it’s that I would call the technology issue. And I think the technology issue is critical in some degrees, because we’ve also developed this group A.D.D driven by this little thing in your pocket, and it’s so distracting, but so critical now. I don’t know how I existed without it Jess but that’s the thing. I think about that all the time. It’s like [jeeze, who uses this thing]? Sure, I was able to [read]? Sure businesses were able to operate without this. Why is it such a crutch today? Am I missing a human connection by relying too much on technology?

Jess Dewell: His question, “Are we missing human connection by relying too much on technology,” is something to consider. It comes back to, are we taking the time to think? Are we automating as much as we can so we can do more work and in that more work, we are still scheduled so much that there is zero thing time? 

That we allow interruptions throughout our day, so we are doing work, It’s not monumental work that moves leaps and bounds forward to our goal. Now, here’s the thing. Regardless of the answers to your questions today, there are awareness questions. 

And part of this awareness that you have is going to shape the type of leadership that you embrace, which will show up in the way that you lead. We’ve already talked a little bit about vulnerability. And we’ve already talked about being open and trust. Here’s the thing, though. You may think you’re vulnerable, and you may think that you can trust. I’d like to suggest another exercise for you. And that is, who do you trust? And what does trust mean to you so you know who you can call on? when you know who you can trust, you know who you can be completely open wit, you know how to begin. 

You know how to start everything. When you get uncomfortable, you go to your place of trust. When you need to be vulnerable and share, you start with the people who have your back. Amy Charity, who at the age of 34, left the financial industry to pursue her passion and career in professional bike racing. Amy has raced all over the world and she has reached the highest level of the sport. She’s been a coach for over a decade. And here’s something that she shares about trust.

Amy Charity: There are going to be a handful of people that you really can trust, and you can trust to be a bit vulnerable. I think that’s true in a job. And that’s not everyone that’s probably not your boss on the first day to. You’ve made a mistake in hiring me, that might not be the best move, but to find that person that you can rely on, I know consistently throughout my career, I have found those people who are like, this is how it works here. And this is something that might be helpful to you and going into that network of support and finding those people who you can have that help you that has been instrumental, I would say both in my career in the corporate world as well as in bike racing.

Jess Dewell: We’ve been talking about it, vulnerability, trust, leadership, awareness. Well guess what? Dimensional Leadership is all about awareness, and the levels of awareness you, your relationship to yourself, your relationship to others, your relationship to your role, oh, and then we’ve got to put the business in there. The businesses relationship to you, and the businesses relationship to stakeholders, and ultimately customers. 

Awareness is more important today than ever before. The way we communicate with each other is impacted. And we forget, we think that we can show up and interact with each other, like we interact with our technology, which, by the way, is an appropriate shortcut that our brains have learned from the situation’s we’re in. But it is inappropriate if we want to create high functioning teams.

So what does it really mean to have that high level of connection?

No, he is not undermining the use of it. However, when we rely on it too much, we’re relying on our brain. And when we rely on our brain too much, our heart becomes stifled. What is important, the mission of our company, the reason we’re taking on the role and the responsibilitity that we have can get smothered. So using more than our brain is what Terry is digging into here.

Terry “Starbucker” St. Marie: No, he is not undermining the use of it. However, when we rely on it too much we’re relying on our brain. And when we rely on our brain too much, our heart becomes stifle. What is important, the mission of our company, The reason we’re taking on the role and the responsibility that we have can get somewhere. So using more than our brain is what Terry is digging into here. But it was this, this higher level of connection of what really is important, it did surprised me. And my principles, it’s like connecting it to a higher purpose. That was my sort of teachy way of saying what I just said about drawing a smiley face. And final principle, it’s like I connected all to a higher purpose and a higher purpose, there was a reason to go to bed every morning, enjoy what you do, and be part of a team that accomplishes something. And you know what people want that.

Jess Dewell: I know I do.

Terry “Starbucker” St. Marie: I thought having a mantra, other people call the mission statement, that I literally required all my employees to know. I didn’t realize how unifying and how pulled together that would make thing. And it was very simple for us. And I wrote that on the bulletin boards, I put up posters, I walk into him enough times I go, there he goes again. “Support my customers, support each other, serve our customers for each other.” And I look at them, and they brought down past them in the hallways and they go , Serve our customers and support each other. I serve our customers for each other.” And I went, we got it.

Jess Dewell: Yeah, they did get it. Terry took that time to figure out a simple straightforward statement that everybody could say. And once everybody could say it, when they started saying it to each other with a smile on their face, when they started to embody that and show up to meetings and provide solutions in such a way that reinforced this mantra, serve our customers and support each other. That’s when it clicked.

Terry “Starbucker” St. Marie: That eventually morphed into what I call the five things you need to know. Serve our customers was one. For each other was the other. And then it was, total customers, our net promoter score. And then what we call it our customer fall [rate], which were all a key drivers in business. Every time I walk up somebody they didn’t know what that was, and it seemed corny, seem weird. But once you sort of built this house, this framework in which everybody operates under, right, then I said, “Well, if you do all that, you’re going to get to that smiley face.” So then I connected at all. That was sort of this crystallizing moment for me.

Jess Dewell: Terry had created a structure that everybody felt psychologically safe in. I know what to do here. I know what’s expected of me here. I know what problems I can take on on my own and be supported in. He was shaping, what does an effective integrated team look like? Sound like and feel like?

Terry “Starbucker” St. Marie: Once they understand the framework, once they know if I do these things, if I try to grow the customer base, and try to make the customers happy, and I reduce errors, which is what those three numbers were. And then I serve our customers and support each other. Guess what? I’m going to be happy. I’m going to love getting out of bed in the morning and do this job. Boom. That’s it.

Jess Dewell: The simplicity of what Terry’s story are articulates, is incredibly difficult to do. It takes time. It takes energy. And there’s a tenacity of being willing to hold this container, this space, for these clear messages to be grasped, because change takes time. And in true form, as far as the time that it takes to make change, it allows us more time to think.

Jeffry Caudle: We need to change the way we think about in terms of not just being systems thinking, but also intuitive, and looking at how did the system play a part in people’s happiness, It’s really easy to just blame the person. And to start with that, but we need to look at what is the underlying system? Where’s the underlying problem? Proximity is one of the biggest aspects of trust proximity can apply to people. And it applies to solutions, it shouldn’t be 12 steps to get to the goal is to be one step two steps to accomplishing this goal.

Jess Dewell: Okay, let’s go back to base camp for a minute. They have a very clear structure, about how they take on projects, the length of those projects, the complexity of those projects, the number of people that are involved in those projects. They are reducing what’s happening to achieve more.

Jeffry Caudle: And so, when we talk about breaking down our goals and settng a objective, we need to make sure that we’re reducing the number of steps so that the goal is as clear as day. And that’s part of what simplicity is about. And that’s part of what transparency is about.

Jess Dewell: Ah, so transparency has an element of simplicity. And we can only get simple and have simplicity when we have clarity. So the shift in thinking is all about the way we’re designing the work that needs to be done. 

Now, this is an elusive skill of leadership, designing the work that needs to be done, and the way that we do it. 

It’s a big difference from okay, go do that and figure it out. It’s also a big difference from, Oh, welcome, you’re filling somebody else’s role that left. You’re going to pick up exactly where they left off, good luck. And the whole range in between and around those. So transparency has to do with how clear you message is. How straightforward the message is as much as it is about creating a place that people want to work and contribute to.

Jeffry Caudle: We’re all system designers. The way we interact with each other, the way we see what other people are doing, and what we take in, and way we understand things. We have to look at our role in this bigger picture, because it’s not just us now, there’s a lot of contractors and a lot of different things. Complexity is increasing as we go along. And so, bringing that simplicity back teams is really critical, as I see it. People tend to understand things more visually than verbally. If you ever played the game telephone, for example, you have a group of people, one person passes the message to each go through each other. And by the end point, it’s not the same thing.

Jess Dewell: Jeffry’s talking about complexity. Terry’s also been talking about complexity and the fact that we navigate that every single day. So how you show up to the complexity around you is going to allow you to see here and feel what changes could be made to reduce that complexity; which changes the way work is done. This is one of the underlying concepts that will come through as you become a Dimensional Leader.

Jeffry Caudle: If you created transparency, you build trust. And the way to build transparency is through visual representations of data. By having actual charts, actual graphs that every team can see an access, and you only put the most critical information in front of people. What they need.

Jess Dewell: Oh, you’re probably thinking to yourself, “What makes me the one to know what’s critical for somebody else’s role?” Well, that is part of being a leader, shaping the direction of a company, understanding where you want to go. Critical information is decided by your vision, mission and values. It’s decided by the way your product is positioned in the marketplace, the features and services and presentation of that product. And it’s by the perception of how your customers know how to use it. So when that becomes daunting, come back down to that awareness piece. Come back down to taking some time to think ahead. Come back down to recognizing the complexity that must be addressed. Simplicity is hard.


JESS DEWELL: As a supporter, you receive full access to expanded show notes including formatted transcripts and links to all resources, full uncut interviews with each guest, and email notifications of new resources. Supporters also receive exclusive access to a platform to ask your specific business questions, the BOLD Business supporter Podcast (that doesn’t have the supporter callout), and carefully cultivated playlists on key business and leadership topics.

The BOLD Business Podcast is a resource that helps you, and will remain free to all. I hope you find enough value in the podcast itself AND the additional exclusive benefits to become a support at a level that reflects its worth as an investment to your personal and professional growth.

The value you receive from our podcast is how we fund the necessary work and continue this work.


Jess Dewell: By getting the message that you need, the goals that you must accomplish stated in a simple straightforward way, may seem overly simple. You may feel that, or you may think that, people are going to be unhappy because it is so simple that you’re talking down to them. If that’s something that you are experiencing, that as part of your story out in the world. 

When something is simple, and when something is straightforward, sometimes overly simple, that’s where everybody can grasp an idea. Pull out a chair, and have a seat at the table, so that communication can happen from a place of connection.Now, this is how holes get found. division of work can happen, the full objectives can occur, other opportunities may be identified. That’s contribution. That’s innovation. That’s creation. And when you embrace Dimensional Leadership, and have this type of awareness, you’re enabling people. You’re empowering people to contribute. Jeff has more to say on simplicity.

Jeffry Caudle: This is where simplicity comes into play, is that you have to reduce the amount of information that you’re giving people, down to bite sized ways. If the objectives that you said require so much information that it overwhelms people, you have to pay attention to that. Because a lot of times when people get overwhelmed, they won’t admit that they’re overwhelmed. But if you build small successes with your team, that’s the most critical element, as I see it.

Jess Dewell: Let’s apply this critical element to growth.

Jeffry Caudle: Right now, every business has a problem of growth. Where they want to grow, and they want to decentralize, and they want to expand, but they can’t expand because they have trouble knowing where their people are, what their people are doing. and communicating those goal is. There’s a huge amount of barriers for a company to expand right now. But, we’re in a technological age where we can expand horizontally without increasing real estate. Without increasing costs. Where technology can actually really help us is with the decentralization of your company.

Jess Dewell: Expansion has a lot of considerations. Yet there is a solution and it is customer focused.

Jeffry Caudle: If you can deliver solutions to your customer, that allows you to be transparent with your customer, and clear. Because these goals as far as simplicity, clarity, transparency, and proximity, they apply to your customers well. And we as customers,, we pick people we trust. A lot of it is about meeting the needs of your customers, going out and working directly with them. But to do that, people need to be able to check in. And their work needs to be tracked in such a way that the team sees what’s going on.

Jess Dewell: Because when I work in a silo and when you work in a silo and when Jeffry works in a silo, we’re seeing one piece of the picture. And embodying dimensional leadership to lead effectively, you must see all of those pieces. Communication between each, data between each, removing any rose colored glasses that might be in place to be able to critically analyze what’s going on and creatively explore all opportunities, is important.

Jeffry Caudle: The growth goals are critical, because it’s about prioritization. The team has to know what the priorities are.

Jess Dewell: Priorities, priorities, priorities. We hear it, but what does that actually mean? Especially as a leader, Jeff is going to tell us.

Jeffry Caudle: A lot of times people think that leadership is having all the information. It’s not. It’s distributing the information. It’s sharing it. When you implement simplicity, clarity, transparency and proximity, you actually create an automation system just by default. That’s just what happens. When you reduce steps, you get automation, and you get a system where everybody flows together.

Jess Dewell: The work to embody Dimensional Leadership™ and use it advantageously for yourself and to create high functioning teams and companies that can grow internally and externally. is ongoing.Terry says the best.

Terry “Starbucker” St. Marie: I’m still trying to refine this craft, because I call it a craft. It’s a passion, it’s a vocation, have use all those words in my writing over the years. And you can never stop learning about this. Because just like a thumbprint, every human is different. Every situation is different. And what you learn with repetition and time is that while there is differences, there are patterns. And I’m still trying to discern the patterns of behavior, patterns of thought and patterns to refine the model. [I’ll sit and I’ll] look and go, okay, are those eight things I write about as being a principles? Are those still right? Is building a culture of accountability still, right in today’s day and age?

Jess Dewell: The elements of Terry’s reflection are something we can all use in ours. And that is asking the question, “Is it still right? Is it too rigid? Is it too complex?” He goes on to say:

Terry “Starbucker” St. Marie: Is there such a thing as being too accountable or to drill down? It’s just watching myself to see if I don’t overcompensate or create useless words, and I think they’re the wrong words are like creating blind spots. Because I’m so focused on what I think is right, I don’t want to box myself in to my own stuff. I want to keep getting exposed to different philosophies and different point of view, I don’t overcompensate.The other thing you should learn is that your way is not the only way, there’s a way to get to the more human point, that’s maybe not just following my stuff to the letter, it’s maybe somebody else’s developed another way, or you can develop your own way, that still get to the same place. Still the same core, but that’s maybe what I’m still trying to learn. It’s like, well, I might not have all the answers.

Jess Dewell: Technology changes fast. It’s already changing faster than a company like yours can create an understanding of the tool, get buy-in for the tool, implement the tool, and then get usage out of the tool. Because by the time that whole process happens, there are three or four newer things that we might have really wanted. Part of Dimensional Leadership™ is also recognizing when a decision is made. How long does the solution and the decision that was made really helped the company? And when does it stop helping us do what needs to be done? And when does it start slowing us down and we can’t get to our goals as fast? Or we’re getting too complex along the way? 

Those are the times to stop and think more. Those are the times that we’re looking for to be able to recognize adaption is here. We’re anticipating change because we know what’s coming. So what if we anticipated for our own benefit instead of reacting to them like most out there do? I’ll tell you, the answer is, your company will be positioned for the change and be able to get there faster than your competition. 

The thing is uncertainty is in the center of everything. Because we only know what’s happened in the past. We do not know what’s going to happen in the future. So we use technology to help us. Well guess what? Technology really doesn’t help us tell the future. It helps us understand what we’ve got around us that can be certain, and certain right now in this moment in time.

Jeffry Caudle: So anything that centers around certainty, it can be automated. But, where people shine is their uncertainty, when it’s problem solving. when it’s working together, when it’s setting the objectives. If you free up your people, then they can call the customer personally. And all those communication things that apply to your team, it applies to your customer. Your customer is a team member in your business. They are helping setting the objectives. Work with them. Employ your customer, and see them as a part of your company.

Jess Dewell: Ahhh. Changing the way that we think about the work that we’re doing, by the way, Zappos did that. They created a loose enough structure, that their customer service could solve problems with confidence and actually make customers that needed help, feel helped and less frustrated. They do that through technology. They also do that through allowing autonomy. So it’s the interplay of both.

Jeffry Caudle: It’s so critical in the way that we use technology, that we’ve never forget the people element. When you prune a fruit tree they found they found that when you prune a tree down to three branches, it actually produces tons more fruit than if you try to just let it grow. And companies, they try uncontrolled growth of everything from their tools, their resources to their people, they no longer can see what’s important, and they no longer can actually expand things.

Jess Dewell: Jeffry’s example of the fruit tree is very applicable to business. Over time we have accumulated processes from people who were part of the initial founding team, people who were high performers and it had some results. People who now identify part of their success and position with those past actions. And so what companies do to not rock the boat and keep talent and one way is to let those things hang around? Well, what happens when those things are actually no longer relevant? What happens when those things are starting to show the wear and tear and time, technology, customer expectations, are changing into something new. The longer it takes us to let go of what’s not working, means the farther behind will be when we finally make the decision. Ruthless is another part of decision making, which wraps up into this concept of Dimensional Leadership™.

Jeffry Caudle: It’s all about pulling back everything so they know what is important, so that you have one thing in front of you at a time,We have to remember that there isn’t always an answer. And if we can’t find the solution, there may not be a solution. That’s always the challenge is working with ambiguity, trying to find a way to build certainty, but recognizing the ambiguity is a part of the process. And it’s a really important part.

Jess Dewell: Uncertainty. The fact that we don’t know what’s going to happen. The fact that everything around us is fuzzy. The fact that all we can do is put a stake in the sand and take the next step forward that is thoughtful, that is shaped by the external conditions of your marketplace, the internal conditions of the resources and talent that you have, and the goals that you are trying to reach. It’s not easy. In fact, it’s scary.

Jeffry Caudle: To adopt anything new is terrifying, Terrifying because it makes you feel stupid. Like I’ll just say that every new technology you adopt, every user interface it makes you feel dumb. To learn anything new, you will feel dumb. To work past that, you have to be willing to accept that is part of the process. And if you’re willing to be dumb, if you’re willing to ask the questions, you will find that is when the best of you shines.

Jess Dewell: Both Terry and Jeffry are talking about Dimensional Leadership through different stories, different experiences, and the problems that they are both trying to solve and the ones that they face right now. Both Jeffry and Terry have been talking about Dimensional Leadership in their own way, from their own experience, from their own journey, and their mission to provide solutions in today’s fast changing world to recognize and utilize the uncertainty that’s around the ambiguity that’s around, but also to recognize and utilize what can be certain and being able to tell the difference. Because every decision that you make has a 50% chance of working. Yet you make the decision and you go forward. 

Think about how you’re getting to your place of business today. Whether you got out of bed and came downstairs to your home office, or you got out of bed and you walked to the bus stop and you got on to the public transportation ,or whether that you went into the garage, got in your car and left. There’s some uncertainty in that. In any case, we had a 50% chance of getting out of bed and not hitting that snooze button. We have a 50% chance of the way that we get to our desk space, our workspace is going to go according to plan. What we know. The infrastructure of the public transportation. The fact that we’re assuming our car is going to turn on when we go out into the garage or into our parking space. So we rely on things, and we assume things that we expect to be true.

Jess Dewell: Being able to recognize those assumptions, shape what’s really certain and what’s really uncertain, what can you rely on in this moment, and what must you embrace the unknowns of? Because with that discernment you can get so much more from the times that you are uncomfortable.

Amy Charity: It’s to get uncomfortable. You have to be willing to step into a place that you’ve never been. It doesn’t feel good. It’s not like you step into this new area, you try something different. You’re like, Oh, this is great. It’s usually awkward. It’s not comfortable and that’s the whole point of it is when you come out the other side, that’s when you experience like true fulfillment in my mind.

Jeffry Caudle: Tying back to what Amy had said earlier about trust and vulnerability, this is key. Those people that you trust, that you can truly be vulnerable with, are the ones you can also be awkward around. So being able to talk about the awkwardness, being able to recognize just being witnessed in this journey of being uncomfortable, facing the unknown, is a way to deepen your personal awareness and amplify the way that you show up.

Amy Charity: Like if we can all agree that living your life is about fulfillment and discovering new things when you get to the other side of having been there and uncomfortable, it’s a such a better feeling of fulfillment than you would have had having not tried.

Jess Dewell: The decision to go forward is a choice. The decision not to is also a choice. something to consider is there are times when the decision not to is the right decision. We live in a time where it’s all about trial and error, failing fast, doing as much as we can. And sometimes, especially when you’re practicing awareness, and you are working with the principles of Dimensional Leadership, the right choice is the one to take less action. Now for those choices that you do take, Amy has another thought.

Amy Charity: When you’ve gone through that situation of being that person who really needs help, and then as time passes you become the person who is helping someone else that is probably the most fulfilling emotion that you can have.

Jess Dewell: We all want to give help. Yet we see it as a weakness when we must ask for help. So practicing your awareness, when was the last time that you asked for help? And then, was it help that you really needed? Or was it help that you didn’t really need help for? Or you didn’t really need help with? But you asked for it so you could seem approachable and connected to other people? Can you go deeper than that? Can you practice Dimensional Leadership and know with clarity, what’s certain and uncertain, so that you can show up and be committed to straightforward, simple messages that allow connection with other people, and that connection with other people fosters conversations and increases the depth with which the team interacts together? And through your leadership, you’re guiding your team, to the goals that you have set.

ANNOUNCER: Thank you for listening to the BOLD Business Podcast. Your business has many directions it can travel. The one true direction, toward that new exciting level, we call the red direction. In this show, Jess Dewell delves into one question that will add clarity to the big questions you face in business today including

How to stay competitive in a changing market, 

How to break through business plateaus, 

and how to respond to the changing expectations of today’s customers. 

Jess Dewell brings you a 20 year track record of business excellence where strategy and operations overlap.

Visit reddirection.com. Remember, preparedness and the right perspective.

For more UNCHARTED, and Bold Business Podcast episodes check out and subscribe on Apple podcast

More Posts in This Category