Strategies for Thoughtful Leadership & Team Synergy with Bill Flynn

Strategies for Thoughtful Leadership & Team Synergy with Bill Flynn

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Welcome back to The Daily Mastermind. George Wright III here with your daily dose of inspiration, motivation, and education. If this is your first time listening, you're in for a treat because we've got a great interview today. I've found an individual I feel is going to bring some real value to you.

And I'm going to set him up here because I want to give you a little bit of his background. I feel like the reason we talk business so much is because we want you to have a vehicle to move forward in your life. But there are so many other aspects, right? Mind, body, money, business.

And this gentleman here has been around. He's got a lot of experience.

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Meet Bill Flynn: A Journey Through Business Success

In fact, Bill Flynn's name. I'm going to introduce him here in a second, but let me give you some of his background. He's done all kinds of things when it comes to business and success—VP of Sales eight different times.

He's twice been a CMO. He's even been a GM of a division of a $100 million IT services company. But he's had success after success—two IPOs, seven acquisitions—including a turnaround during the 2008 financial crisis that I've actually mentioned a couple of times on the show. He's got a bestselling book, and he's just an overall very successful guy—father, entrepreneur, speaker, writer.

So I'm really super glad to have you on the show today. Everybody, I want you to welcome Bill Flynn. Hey, it's good having you on the show today.

Hey, great to be here, George. Thanks for having me on.

Appreciate it. As we mentioned before the show, both of us are pretty busy guys, so it's tough to align the planets, but we did—and I'm super excited to have you here. Another thing I mentioned before we started recording is that there are so many topics you're great at and that you understand.

But I really loved how you responded when I asked about your passion. I said, “What do you focus on the most?”

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Unlocking the Secrets of Strategy with Bill Flynn

And you said, "Helping to prevent or solve preventable problems." What did you mean by that? Open up this conversation by giving our audience a little insight into what you mean when you say 'preventable problems.' We have a lot of entrepreneurs, CEOs, and business owners listening to the show.

Yeah, sure. So, I believe—and what I’ve found after researching business over the last 30 years and more intensely over the past five to eight—is that there’s a gap between what science knows and what business does.

I’ve done workshops with thousands of CEOs. I’ve been a speaker for YPO and other organizations, and I generally do the same kind of interactive presentation. I run a little experiment where I ask questions, and one of them is, “What is strategy?”

I ask everyone to write down their answer and then share what they came up with. And most of the time, their definitions are not strategy. I hear things like “a plan” or “a roadmap.” But strategy is the thinking that informs your plan.

The first strategist we really model most of this off of—since strategy is a military term—is a guy named Hannibal. Many people don’t know who he is, but Hannibal was really the first great strategist, at least that we know of. He regularly defeated the Roman army with fewer resources and less training because he had a strategy.

His strategy, in essence, could be boiled down to what I call the 4S strategy: stun, surprise, surround, and slaughter. He didn’t take prisoners. He thought ahead and asked, “How am I going to do this?” He adapted based on time of year, time of day, the opponent, geography, and topography.

Great businesses do the same thing. They understand the simplicity of what they need to do to be successful.

The most successful public company over the last 50–60 years is Southwest Airlines. Their strategy is simple: “Wheels up.” Supposedly, if you walk around anywhere at Southwest—on the tarmac, check-in counters, or the corporate office—everyone knows what the strategy is: get the plane in the air. Everything they do revolves around that because they know they make money when the plane is in the air.

I’ve got to say, I didn’t expect that little topic to resonate with me so much. It’s funny, because I deal with high-net-worth, high-level CEOs all the time—and you’re right. I think a lot of times, we think of strategy as a thing… a plan, a roadmap.

But strategy in the sense of a verb—a way of thinking—that’s key. And you’re right: I’ve seen the most successful CEOs are the ones who think a certain way.

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Exploring the Mind-Strategy Connection

Yes, exactly. When you think about strategy—if you think of it as execution—then you’re thinking of it differently than you should. It should be a heuristic, a filter you use to guide execution.

So, when you’re executing something, you ask: “Does this align with our strategy? Is this getting us closer to our vision? Does it define what success means to us?” If you don’t have those beacons to guide you, you’ll start doing things that might seem like a great idea at the time—but a few years down the road, you’ll regret them.

Great leaders—like Alan Mulally from Ford, Bob Chapman from Barry-Wehmiller, Steve Jobs—they thought in simple but elegant terms. What business are we really in? What are we trying to accomplish? And how do we stay aligned with that vision?

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The Science of Management

The science of management has been around for over 100 years. Think about thought leaders like Drucker, Deming, Schein, McGregor, Porter, Edmondson—these people have been saying the same things for decades. But we just don’t do it.

Why? Because it doesn’t feel good in the short term. It takes longer. It’s not instant gratification.

Yeah, and I think all those key components you’ve talked about—vision, strategy, decision-making, planning—we tend to think of them strictly in the business vein.

But what I love about what you’re saying is the idea that what science knows and what business actually does… There's a big gap.

That’s why I try to get people on this podcast to just think differently. Because if they did stop and look around, they’d see that successful people—people who get results and are fulfilled—think differently.

Why do you think that gap exists? Why do we keep defaulting to the wrong behavior in business, even when the right answers are available? Is it cultural? Market-driven? What is it?

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The Role of Unconscious Bias in Business Decision-Making

There are a couple of reasons. One, our brain is working against us.

Our brains haven’t had a major upgrade in 10,000 to 50,000 years. Back then, we weren’t living as we are now. We were in tribes of about 150 people. We were trying to survive in hostile environments. The people who survived weren’t the brave ones—they were the ones who ran from everything. They didn’t take risks. That mindset is what helped them survive.

And now we have brains that are still wired like that.

So when we face challenges, we default to safety. And this shows up in conventional wisdom and unconscious bias. There are reportedly around 150 unconscious biases baked into our brains, and they’re operating all the time—behind the scenes—without us realizing it.

One of the most powerful is the negativity bias. We pay more attention to negative experiences than positive ones—roughly at a 2:1 ratio. That means we tend to avoid risk even when growth or innovation requires it.

So we stick to the status quo. And we rationalize those decisions after the fact.

Yeah, I think that’s such a huge insight. A lot of people don’t realize that unless they’re consciously shaping their thinking, their brain is working against them by default. Whether it’s genetics, past experiences, or unconscious beliefs… if you’re not training your brain to work for you, it’s still running—just in the wrong direction.

So what do you feel are some ways business owners and leaders can take control and start directing their thoughts more intentionally?

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Cultivating Curiosity and Thoughtfulness in Leadership

That’s a great question. And honestly, I’ve been studying this stuff for more than a decade—and I still fall into those traps every day. Because again, it’s unconscious.

There’s a behavioral economist named Daniel Kahneman who won a Nobel Prize in economics. He wrote Thinking, Fast and Slow, and one of his main messages is that we need to slow down our thinking.

That’s one of the most important things leaders can do: slow down and stay curious. When someone disagrees with you, instead of jumping to win the argument, say: “That’s interesting. Tell me more. How did you come to that conclusion?”

That kind of curiosity slows you down, and it prevents those automatic reactions.

That’s why “count to ten” is such timeless advice. Because when you react instantly, your brain is driving—you’re not. And reportedly, over 90% of our reactions are automatic.

It’s so counterintuitive, right? Especially for leaders who feel like they need to be quick and decisive. It almost goes against the training we’re given. But I’ve noticed something similar. The most thoughtful leaders I’ve met are often the most curious—but they’re still decisive.

And I love that you said “curiosity” doesn’t mean indecision. You can be curious, slow down, and still lead with clarity.

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Leadership, Culture, and the Importance of Curiosity

Imagine this: in the West, especially in the U.S. where we both grew up, the education system doesn't reward curiosity. It rewards people who have the right answer—and the faster, the better.

So people rise through school and business believing their job is to have all the answers. But that doesn't build great leadership.

Hubert Joly, the former CEO of Best Buy, talks about this in his book. He was trained at McKinsey to be a certain kind of leader—but when he became more compassionate and thoughtful, his business results improved. So did his relationships with his team.

It’s crazy because you hit it right on the head. Curiosity and thoughtfulness don’t equal indecision. In fact, the best leaders I’ve worked with are the ones who create space for their teams and listen.

And like you said, it actually strengthens the team and the company. You can still be decisive—but thoughtful at the same time.

Exactly. There’s a great book called Turn the Ship Around by David Marquet. He was a Navy submarine captain who had to lead a ship he wasn’t trained for. He told one of the crew members, “Two-thirds ahead,” and the sailor just stood there. Marquet repeated it again, and finally, the crew member said, “Captain, we don’t have two-thirds.”

He realized he couldn’t lead by command. He had to lead through empowerment. And it worked.

And it’s such a great analogy, because a lot of new leaders go into a role thinking they have to be the authority on everything. But trying to control every decision is not only unrealistic—it’s ineffective.

And what you said earlier is important: command and control might work short-term, but it’s not sustainable.

Exactly. Over the long term, it disempowers your people. They stop thinking for themselves and just wait for orders.

But if you teach them the strategy, the vision, the two or three most important things the company is working on—then you can push decision-making closer to where the information lives. That’s where it belongs.

And now you’re not relying on one brain—you’re leveraging the thinking of dozens, even hundreds of brains.

I love that. And I want to highlight something you just said: you can still set the vision clearly, but then you step back. You allow people to contribute creatively toward that direction. That’s how great organizations grow.

Exactly. You don’t need to have every step mapped out. But you do need a clear destination.

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Empowering Teams for Organizational Success

There’s research that shows most people in an organization are on at least one team—and many are on multiple teams. Some of those teams don’t even appear on an org chart.

When I work with companies, we start by identifying the 8–12 core functions that drive the business—leadership, sales, marketing, operations, finance, IT, etc. Then we drill down into how those teams interact, especially when it comes to generating revenue.

Typically, marketing feeds sales, which feeds operations, and so on. Then we look at subfunctions. Take marketing, for example—it might include product marketing, product management, development, and demand generation. These roles require completely different skill sets, and yet they must function as a unit.

As a leader, your job is to bring together the right people, set clear standards, and then get out of their way.

That’s so powerful, because most organizations just look at an org chart. They see departments—but they don’t see how those departments work as interconnected teams.

And when you don’t think through that collaboration, you get misalignment. Sales is frustrated with marketing. Ops is frustrated with sales. It becomes a cycle.

Yes! It happens all the time. Marketing blames sales for not closing, and sales blames marketing for sending bad leads. Meanwhile, operations are left to clean up the mess.

That’s why you have to get out of siloed thinking and into system thinking.

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Leadership Training: Beyond the Basics

Unfortunately, most leadership training focuses on personal development, not team dynamics. There's team-building and leadership workshops, but they often miss the bigger picture: what’s the purpose of these teams? How do they function together to serve the larger vision?

We know how to assemble people—but we don’t know how to build real teams of people.

I completely agree. I think real leadership is about stepping back, being thoughtful, and constantly asking: is the current system even working?

And most people are just reacting—doing what they’ve always done. But innovation only comes when you stop and rethink.

Absolutely. And that’s one of the reasons I wrote my book, Further, Faster.

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Practical Advice from Further, Faster

The reason I wrote Further, Faster is because I believe it’s a shame that so many good people, ideas, and businesses fail for preventable reasons. I wanted to distill 30 years of experience into the 20% of ideas that drive 80% of results.

There are three core areas I focus on in the book:

I 100% agree. Cash is oxygen. And I love how you said: don’t start with the financials—start with your goals, then reverse-engineer the cash you’ll need to fund that vision.

Exactly. Most people do it backward. They start with the numbers. But the question should be: what’s your vision? How many people do you need? What systems, tools, or infrastructure are required?

Then you figure out the cost—and build a plan to generate the cash.

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The Role of Cash in Business Growth

There are two key purposes of cash: fuel and safety.

Since 2000, we’ve had three major financial crises: 9/11, the 2008 crash, and COVID-19. On average, these happen every 6–8 years. The companies that survive and thrive are the ones with cash reserves.

And cash is also your growth engine. You need cash to hire, to scale, to invest ahead of growth. But many leaders don’t understand the difference between cash flow and operating cash—and that’s where they get into trouble.

That’s such an overlooked distinction. So many founders think they’re in good shape because they’re profitable—but they don’t realize they’re cash poor.

Exactly. And if you’re cash poor, you can’t take risks, you can’t invest, and you can’t weather storms.

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Creating a Culture of Action and Innovation

When you have the right strategy, vision, and financial metrics in place, decision-making becomes easier. More importantly, you can push daily decision-making down into the organization.

The goal is to fire yourself from the day-to-day so you can spend more time on vision, creativity, and innovation. And your best ideas don’t come from the doing—they come from the thinking. From space. From walking, running, or being in the shower.

That reminds me of the book Birth of the Chaordic Age by Dee Hock, founder of Visa. He talks about creating order within chaos. Visa works because it’s a system of independent member organizations—but it still functions as one of the largest financial networks in the world.

And like you said, businesses are living, breathing ecosystems. The best way to grow them is not control—but vision, alignment, and empowerment.

Exactly. That’s the approach.

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Final Thoughts and Resources

All right, Bill, this has been an amazing conversation. I’m going to link to everything in the show notes, but tell our audience—where’s the best place to connect with you? And you mentioned you had a gift for our listeners?

Sure. Everything is on my website: www.catalystgrowthadvisors.com. You can download my book Further, Faster for free there. It’s also available on Amazon and Audible if you’d like to support me that way, but I wrote it to help people—not to make money.

It’s a do-it-yourself book with 10 to 20 exercises you can download and use. I also publish a short, actionable blog post every other week—so feel free to sign up for the newsletter as well.

Guys, let me pause for a second. You just heard what Bill said. This isn’t some funnel. He’s giving away the wisdom of decades working with businesses, and I encourage you to take advantage of it.

Most likely, we’ll cover this in our Academy membership group and revisit it here on the podcast. But head over to Catalyst Growth Advisors, grab the book, and send me your feedback. I’d love to hear your takeaways.

And remember—no matter your background, your current experience, or your results to date—it’s never too late to create the business and life you were meant to live. But it starts with decisions. And it starts with action.

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One Final Insight

There is one more thing I’d like to leave with your audience. If you want to be a truly great leader, remember this:

Your job is to create followers. And the best way to do that is by writing a compelling vision.

Put it in writing. Share it with everyone. Hire it. Live by it.

There’s a great book called Vivid Vision by Cameron Herold. He walks you through the process step by step—even where to sit when writing it. It’s a fantastic tool, and I highly recommend it.

That’s awesome. I haven’t read that one yet, but I’m adding it to my list. Thanks again, Bill. This was packed with insights.

To everyone listening—thank you for joining us. Be sure to follow us on Instagram, Facebook, and The Daily Mastermind website.

Have a phenomenal day. Talk to you tomorrow.