How to Make Better Decisions at Work | Lessons from 27 Years in the Army

Fernanda: Hello everyone, welcome back to the leadership development channel. Today I have the pleasure of a friend of mine joining us here, Tony Caldwell. I'm super excited to introduce him to you and to talk about a topic that a lot of people quite frankly struggle with, which is making big decisions that matter and have a big impact.

Tony and I are going to have a conversation about decision-making, and I'm super curious to see what he has to say about this. For now, I'm going to bounce it over to Tony. Tony, do you mind introducing yourself to the audience?

Tony Caldwell: Thanks, Fernanda. Look, I really appreciate the chance getting to talk to you today. I always enjoy our in-person conversations, and I feel like we don't run into each other enough when we're out in Charlotte.

My name is Tony Caldwell. I run a boutique consulting and leadership coaching firm called The 2326 Group. There are a lot of people out there who are really good at leadership coaching, team building, and all those fun things—and I call them fun because I like to do them as well.

My real focus, as you said, is on a decision-making framework. It's about understanding how to make decisions beyond just "I need to do this today to solve today's problem," and really starting to think about decisions in depth and how they matter to your business.

Even if you're not the owner, how do you make a decision that sets this business up for success 15 or 20 years from now? Some of that translates into family life as well—especially around kids and setting my family up to align with our vision, mission, and values. The same applies to business.

One of the differentiators for me, and what sets me apart from other people who do this—and I have a lot of great coaches in my Rolodex who are phenomenal people and bring really good results—is that I spent 27 years in the United States Army. I started as a private and finished as a lieutenant colonel, which is a rare journey. Only about six or seven percent of Army officers were ever enlisted as privates before they became officers.

That gives me a solid perspective not only on the decision process, but also on the outcomes of those decisions and how they affect people, because those big decisions affected me when I was on the front line of the organization.

The other differentiator is that I got to spend about a decade in and around the Pentagon. As a major, my direct boss was a two-star general. During that decade, I was exposed to how to think strategically and how to make decisions that may feel minor, but end up affecting thousands, if not tens of thousands of people.

A major and a lieutenant colonel in the Pentagon are really just middle managers in a corporation. I would go in to my boss and say, "Hey sir, hey ma'am, this is what I think," and because they were so busy, they would often take my word for it.

Fernanda: Sorry to interrupt, but that's a lot of trust.

Tony Caldwell: The trust ladder is pretty steep and hard to climb in that environment. Now, I'm not saying they took every decision at my word—they pushed back a lot and challenged me to get better at it.

That experience shaped my framework: understanding that this decision is going to change people's lives five years from now, long after I've gone on to do something else. So that's me, and I apologize for the long introduction.

Fernanda: No worries, Tony, it was very engaging and interesting. It sounded to me like that decision support in the Pentagon became a muscle that you had a lot of experience exercising. Is that right?

Tony Caldwell: Yes, and it takes a long time to develop that muscle. You and I have talked about this before: one decision has a minimum of three outcomes—positive, neutral, or negative.

You have to be prepared for each of those three outcomes. Because each of those outcomes could branch into three more, you're looking at nine potential paths from a single decision.

When you take that out to what I call fourth- and fifth-order thinking, one decision could possibly lead to 243 outcomes. So you really start to think: How do I make this decision? Who needs to know about it? Who needs to be involved, and how do we do that together?

So many people see movies where people in uniform are just barking orders. Beyond life-or-death tactical situations, it's actually deeply collaborative inside that building.

You can walk up to anybody's office and say, "I'm working on this thing, and I heard you are too." They will either collaborate with you or walk you down the hall to the right person. It's bureaucratic, but super collaborative. It is very much a muscle you teach yourself to use, and over time it becomes instinctive.

Fernanda: For the viewers who may not be as familiar with the framework, what kind of thought process did you use when advising your boss on an important decision?

Tony Caldwell: You first have to look at the options for the decision. When I learned computer programming in college, we had "if-this-then-that" statements. It's about taking that principle, but instead of anticipating a single output, you look at what happens next.

If this, then that—and when that happens, what are the next set of outcomes? How far can I walk that out, and how much can I anticipate? If I do this, here are three things that might happen: positive, negative, or neutral. Of those things, what would I need to do next?

When I take that next step, how does that affect the systems that run the organization? For example, if a company buys new bill-paying software, the immediate next step is teaching the accounting and finance team how to use it.

How is that going to affect other systems? The operations and HR teams need to interact with the finance system for travel reimbursements, payroll, and vendor payments. How does it affect those workflows, and what will they have to do differently?

Then you take it to the next layer: how does this affect the culture of our company? If this software changes our systems, does that change how we operate, who we are, or how our partners see us?

Finally, at the fifth order: does changing this software today move me closer to my 10-year vision and the 20-year heritage of the organization? It's really learning how to think about what we want to be when we grow up, and whether what we're doing today aligns with that long-term direction.

Buying a new printer for the boss's desk might not alter company heritage, but it can ripple out to the third level. If that printer doesn't play well with the network, requires specialized paper or toner, and forces changes in the supply chain to a new vendor, that small choice begins to snowball.

When you play that out over creating a Chief Revenue Officer role or staffing an HR team, it becomes critical. That is what I help people think through.

Throughout my corporate career at different banks after retiring from the Army, I saw people make decisions in silos that briefed really well—meaning the slide deck looked and sounded good—but the downstream ripples disrupted lives and made things worse.

To use an analogy about ripples: when you throw a rock into a pond, you see the surface ripples disappear. What you don't notice is the rocks piling up on the bottom.

Over time, those rocks might damage the hull of a boat, change how fish swim, or block a waterway. It's about thinking not just about the surface ripples, but about how many rocks are building up underneath.

Fernanda: Do you have recommendations for how leaders should categorize decisions—such as high-importance versus low-risk decisions?

Tony Caldwell: First, we can look at the Eisenhower Matrix of urgent versus important. Urgent means it has to be fixed right now—like a broken piece of machinery halting the production floor. But important decisions are the ones we tend to live with longer.

I encourage anyone making decisions to pause and think before acting: does this decision have the potential to impact other systems? That's what I call third-level thinking.

Allowing an individual frontline employee to leave early on a Friday probably won't disrupt company systems. But shifting an entire department to a three-day workweek definitely will.

The people on that shift will love the four-day weekend, and their morale and short-term productivity might increase. But what about the other departments that rely on that team on Thursdays and Fridays?

Other departments will wonder why they still have to work five days a week, and work stalls while waiting on the missing team. One team's morale goes up while the rest of the company suffers.

Before making a decision, consider whether it impacts all of your systems. Much of corporate America operates in silos, but running a business in silos causes it to break.

This decision-making framework forces leaders to look across silos and understand how a single choice impacts everyone else. For any important decision, ask: Who all does this impact? How far out could this linger? And let's get those stakeholders together before moving forward.

Fernanda: I completely agree with bringing people from different departments together to evaluate the impact. I've seen the alternative, and depending on the decision, it can cause serious issues.

A prime example is implementing major software essential to service delivery and revenue, like supply chain software. A decision of that magnitude requires buy-in from all impacted groups, including IT.

Tony Caldwell: Absolutely. And while IT is obvious, what about sales?

Fernanda: Exactly, sales as well.

Tony Caldwell: If sales generates your revenue, and an operational shift impedes their ability to enter orders, you take on operational and reputational risk. If your sales, operations, and logistics teams cannot coordinate smoothly to deliver your product or service, you risk losing clients. Implementing new software is notoriously difficult.

Fernanda: Yes, and technology is evolving so rapidly. A lot of companies right now are investing heavily in AI, which is understandable given the trend.

However, I recently read an article noting that some AI implementations meant to replace human labor are actually turning out to be more expensive than the labor they replaced.

Tony Caldwell: I don't doubt that at all. My philosophy is that AI is a great tool, but you still need a craftsman to use tools effectively.

Anyone can watch a YouTube video, buy lumber and nails at Home Depot, and assemble a bookshelf. But if you want a bookshelf built well enough to pass down to your children or grandchildren, you need a craftsman.

Another analogy is that, at the moment, AI acts like a rearview mirror. It is effective at analyzing what has already happened, but when it attempts to predict the future, it is largely guessing.

In a car, the windshield is significantly larger than the rearview mirror because you need to see where you are going. You check the rearview mirror to understand what's behind you, and AI should be used similarly.

It can provide insights and save time, but AI cannot reliably make complex business decisions or determine how to grow, maintain, or position a business for sale. I wouldn't rely on Claude, ChatGPT, Gemini, or any model to make high-stakes decisions for me just yet.

Fernanda: That's a great point. Thank you so much for joining us, Tony, and sharing your insights on decision-making. Where can people find you if they want to learn more about your work?

Tony Caldwell: The easiest places to find me are my YouTube channel, @The2326Group, and my website, the2326group.com. Both platforms provide direct links to reach out via email.

My YouTube channel features short, focused videos with practical takeaways. If that resonates, feel free to connect with me for a conversation; if there is a mutual fit, we can explore working together.

Fernanda: Awesome. Is that also your QR code on the video screen?

Tony Caldwell: Yes, scanning that QR code will take you straight to my website.

Fernanda: I always call it a barcode by mistake, but yes, a QR code!

Tony Caldwell: That's fine. You don't have to be completely right; you just have to be right enough to accomplish what you need to do. In leadership, you often have to get comfortable making decisions with roughly 70% of the information.

Fernanda: And that's where your coaching comes in.

Tony Caldwell: Exactly—helping leaders become comfortable making sound decisions even without absolute certainty.

Fernanda: Thank you, Tony. It was a pleasure having you on, and I look forward to collaborating again. To our viewers, if you enjoyed this video, please share it, like, and subscribe. We'll see you in the next one.

Tony Caldwell: Thanks a lot, everybody.

Fernanda Brasileiro

People Development Consultant & Strategist

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