Dr. Don Thomas, Strategy Expert, is driven by the idea that there’s always something better we can do strategically. His approach includes strategy from pirates to enhance traditional methods.
We learn about his journey from software developer to strategic leadership expert, emphasizing vision-driven leadership. Don highlights the importance of casting a vision and making it attainable. He also addresses multi-generational communication in the workplace, offering insights from his Cross-Generational Communication Framework. Additionally, he shares unique leadership lessons inspired by historical pirates from his book, The Pirate’s Guide to Strategic Leadership.
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Learn Strategy from Pirates with Dr Don Thomas
Good day, dear listeners. This is Steve Preda with the Management Blueprint Podcast. And my guest today is Dr. Don Thomas, a strategy expert who’s working with investors, software and tech-enabled companies to add value to their businesses and investments. He is also the author of The Pirate’s Guide to Strategic Leadership. Dr. Don, welcome to the show.
Well, thank you. I appreciate it, Steve. Fantastic to be here.
Well, I’m very curious about you are a strategy expert. I love strategy myself, as you can see from my background. I’m curious what prompted you to become interested in strategy in the first place?
Absolutely. Fantastic question. It kind of goes to my single motivating point of what I do as well. I started out 35 years ago and was graduating college and thought, hey, I’m just gonna be a software developer. Sounds like a good life back in those days. And I did it quite well, actually. I did it and became a very good developer, became management, became engagement lead. The one thing I noticed in life is that it was so easy to get into a repetitive space of just going through the motions. There was really nothing that took you to the next level. So I was looking at what would take someone to the next level, what really takes a strategic look at where you want to be, not just day-to-day which we call operational leadership, but it’s really how do we look at things from a strategic perspective of I want to be here from a one, three, five year perspective. So, when we do that, it’s also applicable to business, to individuals, and that’s really what got me into this whole strategic leadership space.
Very interesting. So, what is your personal “Why” and what drives you to get out of bed every morning?
What gets me out of bed every morning is the idea that there’s always something better we can do strategically. So, I used to be called the pirate entrepreneur because I started quite a few organizations, adopted a lifestyle of how do you build an organization? A pirate thing. We can talk about that later, about my thoughts on how we do strategic leadership through looking at parts of the past. But what got me out was how do we move forward? How do I help others get forward? If we look today, there’s so many people that are underemployed, unemployed, that are just not happy where they want to be. So, what gets me out is I can get out there and help people to grow them to understand that there’s so much more you can do and if you’re a leader, because all of us are leaders, we lead ourselves first of all, but when we lead others, we go out there and we help others be even better at what they do.
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Okay. So how can strategic leadership make people happy?
It makes people happy because it gives them a goal to accomplish. I believe every person secretly strives to have something they want to work on. Very few of us want, well, I have daughters, so maybe this won’t apply to them. But now most people like to get out there and know that every day they’re moving forward on what they want to do, be it, I want to finish college, I want to have a better job, I want to lead others to be as productive as they are. So how that helps is by strategically plotting these through different frameworks and methodologies that we can say, this is where we are, we have kind of a litmus test, this is where I want to be in three years, five years, six years, and it gives you that motivation to keep going. Because what happens a lot is that people will think they have a plan, but then they go to work five days a week. They do the exact same thing five days a week. They’re not improving themselves. They’re not growing from that perspective. And I think that’s really the catalyst for internal growth is the ability to, how can I make myself better? What is going to give me that motivating purpose to wake up every morning? So I think that’s what strategy does for us. It allows us to look at things and not just live it day-by-day but move forward and have a goal that we can attain. Share on X
So live life more strategically in other ways.
Exactly. That is correct.
Yeah, I love that. So that is definitely part of strategy is to figure out where we’re gonna go and how we want to get there.
Right.
This strategy in your definition, how is it different from strategic planning?
Part of what I do is strategic leadership and strategic planning is part of that. But the whole idea of strategic leadership is the concept right now when we think of day-to-day type of leadership, and I’m going to give you a bad representation because I don’t have any slides to give you here. So we think of it as a pyramid. And so in that pyramid, a lot of people think the leader is right up here on top, and then everyone else is supporting him or her. In strategic leadership and strategic planning, which is part of strategic leadership, we reverse that. We turn it upside down. Now, on the very bottom is the leader that is strategically planning for all the people they work within to help them get to where they want to be. I’ve always loved the idea that if you just give everybody what they’re looking for, you’ll get what you’re looking for. Because when you enable people to be successful, they can come back and help you be successful. So that’s part of that whole strategic. So strategic planning is part of that as well, because in order to lead people, you have to give them a vision. Part of strategic leadership is casting that vision, being able to give that plan, saying this is your part of the plan. It’s not just some big hierarchy of, we’re gonna do this and we’re gonna put logos and such on it, but not get anything done. This is where you fall into that strategic plan and why you’re important to do it.
Yeah. So everyone has a place. They all play a part in the big canvas of strategy or whatever you want to call it. And then the leader supports everyone through maybe his direct or her direct reports, the next level team, and then they, as it goes, they support all the other people so that they are effective. So how is this similar or different from servant leadership or the concept of servant leadership?
Well, servant leadership is a leadership style. And I actually think one of my leadership styles is servant leadership. But strategic leadership is a concept versus a style. So strategic leadership can be any style within there. You know, you can even some of the styles that are a little more difficult to work with. But servant leadership, I think, leads a lot to this because the idea is to serve others so that they can attain what they’re looking for. So that is one of my leadership styles as well.
So strategic leadership, is it if you compare strategic leadership with perhaps tactical leadership, would strategic leadership be more vision driven? Is there something else that differentiates?
Absolutely. So, they’re both a little tactical in what they do, but where they veer off is actually that vision. So, your strategic leader is going to cast the vision and make sure it’s attainable by others. While you’re looking from a tactical perspective, it may or may not be caught by others as well. You just have the lines on the road to follow, and if you check all the boxes you’ll probably meet where you’re going to. Strategic has a lot more hand-holding, a lot more how do we get people into the vision there so that they can continue to cast it to others.
Okay, so painting the pictures, does strategic leadership mean that people are more self-guiding as opposed to tactical? Maybe in the military you’ve got a very tactical approach. And people just execute orders, essentially down the line. Is strategic leadership more visionary where you are leading not through direct instructions, but by sharing a vision which depicts the end result that you desire for you to achieve?
And that’s an excellent analogy because I was born into a military family, so I understand technical leadership very well. But you’re pretty much on the money there. The idea between strategic leadership is the idea of casting that vision and that implementation. While many times in my background looking at tactical leadership, it wasn’t really that you agreed or disagreed, this is what you were gonna do. And many organizations do that as well. They have people that cast the vision and keep it at the C level, and then it becomes tactical below that. A true strategic leadership actually casts the entire vision out from the C-level or even a little higher sometimes and brings it down to the individual. So, you become accountable because you believe you’re a part of it versus just a cog in doing a particular task, which a lot of tactical leadership works that way.
That is very interesting. So, what you’re saying is that in strategic leadership, you are helping the whole organization be more vision-driven.
Right.
In a tactical one, it’s just essentially a cascading list of instructions for people to execute. You see it alone, perhaps, or maybe your direct reports see it, but everyone else is blindly following, whereas in strategic leadership, they are all driven by the vision and they are following the vision. It’s kind of a self-motivating, empowering leadership.
It’s also self-correcting a little bit. When you think of it from a tactical perspective, let’s say I give you 10 tasks to do. You may not know the ramifications of those tasks, nor may you agree with, but you’re gonna do those 10 tasks. So it’s a little tactical in that way. Well, if you already have the vision, you might be able to say, hey, supervisor, hey, leader, this eighth task I’m doing really pulls us away from what we’re trying to accomplish. And that way they understand the ramifications of the actions they’re doing. And it’s a little bit of that self-healing at that time, where course correction can be done without bringing it back up to the top level.
Wonderful. Okay, so that is really insightful, and you really helped me understand strategy at a deeper level, even though I thought I understood strategy, but you helped me understand it better. So, thank you for that. I’d like to switch gears here and talk about an actual framework, which is a much smaller, much smaller scale, perhaps, or maybe it’s even a bigger, bigger scale because it’s the framework of cross generational communications.
Ah, my favorite conversation topic.
Okay. So, can you share with our listeners why it’s important? Why it’s even a thing, and then how did you do it?
Absolutely. And believe it or not, the topic of multi-generational communications has been the top of everyone’s mind that I’ve talked to in the last year. Because we’re in a very unique circumstance right now. At this moment, approximately five generations are working all together in the same kind of business space. Normally, we between three and four, but recently in the last couple of decades, we’ve had people that are ranged across into five generations being traditionalist boomers, Gen X, Millennials, Gen Z. And now we have Gen Alpha coming up, but we’ll talk about them in a minute. And what’s happened is, and I actually hear from a lot of HR people, is that we want to have this organization where people understand and work together, but there seems to be challenges. And those challenges are that we are all part of different cohorts. And what I mean by that is each generation is not really time-based. We used to think, oh, well, every 20 years we have a different group of people. But really when you think about it, these generations that are now in the workplace have been basically kind of time boxed in due to the environment. You know, Gen X, which I am happily a part of Gen X, I tell everybody. By 1966 and a little bit up from there, what makes us unique and why people either love us or hate us is because we grew up in a very interesting time. We were what was called the latchkey generation. We had one of the first generations where a lot of parents, both husband and wife, were out there working. So we came home and took care of ourselves. We became very independent in that way. We also saw things like the Berlin wall falling. We saw, you know, the end of different generations. So all of these different instances, historical events caused us to become very unique. We’re not just latchkey kids. We’re actually the first generation that saw a true implementation of technology. I mean, I remember corded phones, but I also remember the phone about the size of my arm being one of the first mobile phones. So, we’re very specific in what we like to know and learn. For example, our favorite communication method is generally going to be email. So if you have Gen Xers out there, you’re going to shake your head that we love email because that was brand new to us. We actually saw the internet come alive for everybody out here. And so why this is a challenge, to go back to the original question, is that now we have generations that have had different historical events shape who they are. We’ve had millennials that they were really young and being formed during the U.S.’s 9/11 attacks and the towers falling. Or we had boomers where they were more, well, we saw the first people to land on the moon and we also had these particular wars and conflicts. So, each of these things divide what we do and they set expectations of what we’re looking for, how we like to communicate, what we define as the culture we wanna work in, what do we look out for life. Many times I’ll hear something like, last week I was talking to an HR person, it’s like, I have these Gen Xers. They won’t call anyone. They won’t respond to emails except for with one word. It’s like, it’s very easy because when they came up, they were one of the first generations to be totally digital nomads out there. They grew up with a cell phone in their hands. And so they’re used to talking with, you know, communication such as emoticons and, you know, different short methodologies within that. So we have to kind of work in a way that allows us to see how each other work. Usually what I end up telling people, depends on the size of the organization, is start pairing people such as Gen Z. They were about 1996 up to about 2010. Pair them up with a boomer. Pair them up with a traditionalist, someone who didn’t even grow up with technology and start letting them work together in pairs because what we don’t have, and I tell people if I make it, I’ll be suddenly rich, is a Rosetta Stone that says, how do I translate from talking to a Gen X to a millennial or to a boomer or the brand new generation that’s coming into the marketplace very soon are Gen Alphas. And they are a very unique bunch of people. They have grown up in this very social media platform age of TikTok and everything else, and they are expecting those types of communications in the workplace. So, I always tell people the best way is really look at it from a generational perspective of how do you put them together and how do you meet that translational piece of what they're looking for in culture. Share on X
So, Don, I’m sorry to stop you there, but how can we make it more tangible? So in our pre-call, we discussed there are four steps to take account of when you are considering or you’re trying to implement the cross-generational communication. And you talked a lot about these generations being different and shaping historical events and technological developments. So first, you need to understand what this generation and how they communicate. What do you do next? So if you understand this person’s a boomer, this person’s Gen X or Gen Z, they grew up with a telephone, and the boomer, the Gen Z, maybe grew up with the chat, text messaging, whatever. What does that mean to you when you want to communicate with them?
So now that we’ve identified that, the next step is really understanding the needs and expectations of each of those generations. Because well, first of all, being mainly in a remote environment nowadays actually adds a different level of complexity to the whole, how do I get someone living in one country and one generation working with another or even just in the United States between different states. So it’s really finding, understanding those needs and the culture. The cultural aspects will have to be something similar to, if you’ll go back to, let’s say a gen alpha, they really could care less about coming into the office space, but what they care about is getting their work done, but not really working an eight-hour day. They really believe in the concept of whatever needs to be done, I’ll get it done. And whatever’s left over, there’s no need for me to really be here doing that. So it’s under those generational needs and filling those in. Usually I end up with people like that, for example, is adding additional learning and so forth, education to grow them into the organization. So it’s understanding those needs of what they’re looking for. The next one is finding that common ground, which is probably one of the most difficult pieces is where’s the common ground besides where you work. Just because we work at the same spot doesn’t mean we have the same expectations or the same needs as well as we talked about earlier. So it’s finding that common ground as to what could be something why you’re there. Is it there because you’re looking at social understandings or maybe they support different organizations and so forth. So find that common ground. And finally, you have to start in kind of an effective manner to bring these people together. So, they’re not going to come together normally just by, if we are in a workspace walking by, you might see someone in a cube or something similar. That doesn’t happen anymore, or very rarely at least. So you have to purposely plan as a leader to bring these people together, even just virtually, doing different virtual events where I’ve even had virtual dinners where everybody kind of had dinner at the same time to have that kind of that family feeling and getting those generations together. So those kind of four steps, understanding the common ground and the needs and the desires, and then how do you effectively bring them together? Sometimes kicking and screaming, but most of the time you can bring them together and really learn from each other.
That is fascinating, because I have a Gen Z team. I have very different needs, obviously, and base of communicating, and we’ve communicated virtually. And, you know, I asked the team, how can we create more engagement? How can we get to work more effectively together? How can we bring more energy to these conversations? And they came up with the suggestion that we should do more icebreakers. I put one of them in charge of bringing the icebreaker, and she actually brought a very funny and very engaging icebreaker. So I myself find myself engaged. And actually I took one of these icebreakers, which was about emojis, I took it to my clients who tend to be more Gen Xs, like I am, and some boomers. And actually they did enjoy it as well. And for them, the enjoyment came from a different place. For them, it was more of an interesting, there was a curiosity piqued by what these Gen Zs were interested in. So, the common ground was most generations were interested or willing to engage around the emojis. But one generation, for them, it was a natural thing and they wanted it because they’re used to it and they like it, as you know, day to day. And the other generation was engaged with it because it opened their eyes to something that they didn’t understand.
Absolutely, and I’ve used similar things for like gamification when we do projects. So, the idea of gathering badges for doing certain things or educational aspects where you can put them into your, what we’ll use for me, like in our email signatures. So, gamification is the same kind of theory that you have people that maybe are a little younger in the generations here, where it makes great sense for them and it’s a way to connect with the older generations as well. So it’s those types of bonding type of experiences to bring them together in that effective manner.
Awesome. So, before we wrap this call up, let’s talk about your book, The Pirate’s Guide to Strategic Leadership. So what triggered you to write this book and why is it The Pirate’s Guide? So how are pirates strategic?
Excellent question. I’m going to give you my one liner about me and then I’ll tell you why. I always like to think of myself as kind of a one-part strategic communicator, one-part technologist, with a sprinkling of pirate thrown in just to keep it all balanced. And the pirate to me is the idea that when you think about it, back in the 1600s and so forth, they had the same problems we have today. People were dissatisfied and you had people that were hungry. You had people looking for belonging, people looking for adventure. And in my mindset and my research, pirates were probably one of the first entrepreneurs out there that we can follow historically. Now, they did some dubiously odd, maybe not moral thing. Nowadays, we generally don’t kill our competition and we don’t have certain aspects of that, but there were some things when you think about it. They actually set a great example. One of them is they were very adaptive in their leadership. Most people don’t realize on pirate ships, it was not a whatever the captain did. Everything was very democratic in most of the ships and some of the more famous pirates as well that the captains were actually elected by the crew and they could be removed by the crew as well. So. I thought that was an interesting aspect in this part of why it’s strategic as well. Now, it’s very democratic decision-making, like we said there, but it’s also clear and everything was fair in compensation. You didn’t get on, like many entrepreneurs, you knew what you were getting into most of the time. Same thing with a pirate. Maybe you were hungry, you didn’t want to be hungry anymore, you want to join an organization, you knew what the compensation was going to be, you knew what you were going to do, and everybody worked together. Some of the pirate fields don’t really show that, but I think that’s part of it. Also, they were tactical in nature. Because when you think about it, they had to be adopters of brand new naval technologies. And how do they hunt people? They also were global networkers. They were probably one of the first networking people. You had to network with not just your competition, but also with other vendors to know where these travels were going. So they did a lot of things that we look at from a strategic perspective. They planned on what they were looking for. They tried to grow their crews from the best they could in those times. They were sometimes not effective, but they always tried to have a good leadership model. They were self-organized and self-governing, that adaptability. They were resilient. They also did risk management. Should we align with some other organizations or other pirate ships before we take on this particular ship we’re looking for? So many of these things we actually crave when we try to teach people. So, it gave me the idea that through strategic leadership, because that’s my background, can we take a metaphor that people can align with, even if it’s just from a movie, and take those aspects of the leadership what a pirate did and apply it to today’s leadership model and how we can be strategic with them. So that’s where that came from.
Yeah, I love it. This is fascinating. I didn’t realize that pirates were Democrats, but I can imagine that the captain of the ship and the sailors revolt, and there’s not a lot you can do.
Exactly.
They can overpower you, so you better keep them engaged and motivated and compelled to do what you do. You can’t just force them to do what you want them to do. So that’s really fascinating. So, thank you, Don. It was very interesting conversation around strategy. How is strategic leadership different from tactical? How, with strategic leadership, you can paint the vision and engage and empower your people to see your vision and to make decisions and be much more motivated to reach your goals, as opposed to maybe in a military situation where it’s a cascading list of orders that go down, although the military is evolving as well. So I’m not trying to talk down the military here. So this is very fascinating. Thanks for sharing your knowledge here and your experience and talking about the books. So, if people would like to learn more, they would like to buy your book, talk to you, perhaps reach out to you, where can they find you?
Well, it’s on mostly online realtors such as Amazon and Barnes & Noble, but you can always go to drdonthomas.com/books and it should get you there as well.
And you’re also available on LinkedIn, so if people want to reach out to you.
Absolutely.
Dr. Don Thomas, our LinkedIn strategy expert, who’s helping businesses at the cross-section of strategy and technology. Dr. Don, thanks for coming on the show.
Thank you very much. I appreciate it. It’s been a fantastic time.
Important Links:
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- The Pirate’s Guide to Strategic Leadership by Dr. Don Thomas
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