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Trust is Built in the Field, Not in the Conference Room
Lessons from the Military, Leadership, and the Book of James Trust is one of those words that gets thrown around a lot. Every organization talks about it. Every team says it matters. Every leader claims they want it. But real trust isn’t created by slogans. It isn’t built in a staff meeting. It isn’t earned through a title. And it certainly isn’t produced by a mission statement on the wall. Trust is built somewhere else entirely. Trust is built during training, in the field,
larrywpittman
Feb 83 min read


Collaboration Starts Before the Team Ever Meets
Lessons from Rural Florida, the Backroads, and the Book of James I didn’t learn teamwork sitting around a conference table. I learned it as a teenager growing up in rural Florida, during hurricane season, when our small town took a direct hit. Back then, you didn’t wait on outside help or big plans. You prepared the best you could. My dad made sure we secured everything in the yard. We stocked up on food, water, and fuel. The house was boarded up, and when the storm came in,
larrywpittman
Feb 14 min read


Ownership in the Gray: Why Leaders Must Carry the Weight
Leadership becomes real the moment excuses stop working. Titles don’t carry weight. Authority doesn’t either. Ownership does. In the gray—when outcomes are uncertain and decisions are costly—leaders are revealed by what they’re willing to carry themselves instead of pushing onto others. Ownership Is Not Shared Responsibility One of the most common leadership myths is that shared responsibility equals shared ownership. It doesn’t. Shared responsibility often becomes diluted re
larrywpittman
Jan 252 min read


The Cost of Indecision: How Delay Quietly Damages Teams
Indecision rarely announces itself as failure. It shows up quietly—in missed opportunities, eroding trust, drifting standards, and teams that hesitate because leadership has hesitated first. In the gray, not deciding is still a decision.And it almost always carries a cost. Why Leaders Delay Most leaders don’t delay because they’re careless.They delay because they’re trying to be responsible. They want: more information, broader alignment, fewer critics, and less risk. But lea
larrywpittman
Jan 193 min read


Leadership in the Gray – Part 3. Explaining the “Why”
How Leaders Preserve Trust When Outcomes Are Uncertain Trust doesn’t disappear when leaders make hard decisions. It disappears when people don’t understand why those decisions were made. In uncertain environments, outcomes are rarely perfect. Some decisions work. Others don’t. But long before results are known, teams are already forming judgments—about intent, competence, and integrity. That judgment hinges on one thing: communication . Silence Is Not Neutral Many leaders be
larrywpittman
Jan 113 min read


Values Over Policies: What Actually Guides Decisions Under Pressure
Policies are written for clarity. Values are revealed under pressure. Most organizations have no shortage of rules, procedures, and frameworks. They exist for good reason—until they don’t. When conditions are stable, policies work. When uncertainty hits, policies collide. That’s when leadership begins. When the Rulebook Runs Out I learned early that rules can’t cover every situation. Growing up in rural Florida, work didn’t wait for instructions. Weather shifted. Equipment fa
larrywpittman
Dec 29, 20253 min read


Leadership in the Gray: Making Decisions When There Are No Perfect Answers
The business world today doesn’t suffer from a lack of information.It suffers from a lack of certainty. Leaders are expected to move fast, decide with incomplete data, balance competing priorities, and still protect people, performance, and culture. That tension isn’t new—it’s just more visible now. I learned early that most important decisions aren’t made in clean conditions. Growing up in a small Florida cattle and citrus town, there were no perfect days to work. Weather c
larrywpittman
Dec 22, 20254 min read


What Other Leadership Styles Taught Me — And Why They Fell Short
Over the course of my life — from rural Florida to the military and into civilian leadership — I’ve been led by just about every leadership style there is. Some were effective in the moment. Some were necessary in crisis. Some produced short-term results. And some taught me exactly what not to become. Each style left a mark. Each taught me something. But none of them — standing alone — consistently built strong teams and developed future leaders the way servant and paternal
larrywpittman
Dec 14, 20253 min read


Paternal Leadership — Coaching, Protecting, and Developing People
Paternal leadership isn’t about being anyone’s father. It’s about being the kind of leader who guides, protects, challenges, and develops people with the same intentionality and care that a parent invests in a child. It’s a style built on: High expectations Strong relationships Accountability wrapped in compassion Teaching, not just telling Seeing potential before others do For me, paternal leadership began at home… but it matured through mentors, coaches, military leaders,
larrywpittman
Dec 7, 20254 min read


My Leadership Journey — From the Small Florida Town to Special Operations to The Boardroom!
Growing up in a small citrus and cattle town in rural Florida, leadership wasn’t a concept anyone needed to explain — it was something you watched, something you learned through living. I didn’t hear terms like “servant leadership” or “paternal leadership” until much later in my professional life, but I was surrounded by them long before I ever put on a uniform. My father was the first leader I ever studied. He was a hard-working country man, but more importantly, he was a re
larrywpittman
Nov 30, 20253 min read


Embedding Positivity into Organizational Culture
A leader’s attitude is powerful—but when positivity becomes part of an organization’s culture , it becomes unstoppable. Skills can build a team. Strategy can guide it. But culture—especially a culture rooted in optimism, accountability, and resilience—is what sustains it through the long haul. Growing up in rural Florida, I saw this firsthand. Whether it was the way my dad approached every early morning hunt with calm confidence or the way neighbors showed up for each other d
larrywpittman
Nov 24, 20253 min read


Overcoming Challenges While Staying Positive
Positivity doesn’t mean ignoring reality—it means navigating it with clarity, courage, and conviction. Every leader eventually hits a wall. Sometimes it’s a small disruption, and sometimes it feels like the bottom drops out all at once. What sets great leaders apart isn’t whether they face adversity—it’s the mindset they bring when adversity shows up. A positive outlook isn’t naïve or unrealistic. It’s a deliberate choice to believe there’s a way forward, even when the winds
larrywpittman
Nov 16, 20253 min read


How a Can-Do Attitude Inspires Your Team
Leadership is contagious. So is attitude. Whether you’re leading a squad, a staff, or your own family, the energy you carry becomes the energy everyone else feels. I’ve seen it on flight lines, in locker rooms, and around dinner tables—when a leader believes in the mission, people believe in themselves. Your Energy Sets the Tone During my time in the 160th SOAR, I learned that leadership wasn’t about rank—it was about presence. Before every mission, there was a moment of stil
larrywpittman
Nov 10, 20253 min read


Cultivating a Can-Do Attitude in Yourself
Positivity isn’t always natural—but it can be trained. I’ve seen it tested in both muddy backroads and boardrooms, on calm waters and in combat zones. Maintaining a can-do attitude doesn’t mean pretending life is easy. It means learning how to keep your heart steady and your mind focused when things get hard. Training the Mind Like a Muscle When I was a kid, my dad used to say, “You can’t control the weather, but you can control how you work in it.” Whether we were assisting
larrywpittman
Nov 4, 20253 min read


The Science Behind Positivity and Performance
I learned early that a positive attitude doesn’t just feel better—it works better . As a boy in rural Florida, I saw it in my dad. Whether we were fixing an engine that wouldn’t start or sitting on the riverbank waiting for the sail catfish to bite, he had this quiet confidence that things would turn out if we kept at it. He’d say, “Son, getting frustrated won’t fix a thing. Keep your head right and your hands busy.” Back then, I didn’t realize how much truth was tucked in th
larrywpittman
Oct 31, 20253 min read


Leading with Light: The Power of a Can-Do Spirit
Leadership is often thought of as a measure of skill, knowledge, or experience—but I’ve learned that attitude matters even more. The way a leader shows up sets the tone for the team, the mission, and ultimately the results. A positive, can-do mindset isn’t just “feel-good” talk; it’s the foundation of leadership that inspires others to follow. Growing up in a small Florida town, my dad would take me hunting and fishing. Some days the fish wouldn’t bite, or the squirrels would
larrywpittman
Oct 20, 20252 min read


Integrity in Action
Integrity is one of those words that’s easy to say and hard to live. It doesn’t announce itself with fanfare. It shows up quietly — in the small, unseen moments when no one’s watching and the easy choice would be to cut a corner or let something slide. I learned early that integrity isn’t about perfection; it’s about consistency. Growing up in a small Florida town, my dad didn’t have to give lectures about honesty — he lived it. If he said he’d be somewhere, he showed up. If
larrywpittman
Oct 13, 20252 min read


Redefining Success
When I was younger, success looked simple. It was about winning the game, making the grade, or getting the recognition. Later, it was...
larrywpittman
Oct 6, 20252 min read


The Siren Call of the Digital Deep
The air in the Ironwood School IT room was thick with the scent of ozone and stale coffee. It was 2:00 AM. A single bead of sweat traced...
larrywpittman
Oct 2, 20253 min read


The Gift of Failure
No one likes to fail. It stings, it bruises the ego, and it makes you question whether you’re on the right path at all. But over time,...
larrywpittman
Sep 29, 20252 min read
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