Leadership Insights Gained From Military Experience

Flying close air support missions in combat taught me the critical importance of empowering a team to make decisions and take action. On each mission, the flight lead was entrusted with the authority to: 🛩 Make Independent Decisions: In critical moments, the flight lead had the power to assess the situation and make decisions on the spot. 🛩 Act with Confidence: We didn’t always know what challenges we would face, but we fully understood the rules of engagement and our commander’s intent. This clarity empowered us to act with confidence and decisiveness. 🛩 Execute the Mission: Leadership trusted us to do our job well without needing to radio back for permission. We were empowered to make time-critical decisions, which was essential for mission success. As leaders, it’s also our responsibility to empower our teams: ➡ Encourage Preparation: Challenge your team to show up prepared every day. Ensure your team has the training and resources they need. ➡ Trust Their Judgment: When we empower our team members to make decisions, we foster confidence and independence. This means encouraging their ideas, supporting their choices, and sometimes letting them solve their own problems, even if we see a different path. ➡ Allow Room for Mistakes: Empowerment includes giving your team the space to make mistakes and learn from them. This builds resilience and trust within the team. Empowering a team takes courage. It means releasing control, but it also expedites decision-making and frees up the leader to focus on the bigger picture. #leadership #leadershipdevelopment #FlyingInTheFaceOfFear

What Combat Taught Me About the Boardroom I was in my early 20s when I first took a seat at a leadership table—only it wasn’t a boardroom, it was a dirt-floor room in a remote district of Afghanistan. I sat across from Afghan elders, tasked with earning their trust and building stability for their people, knowing my unit of 39 men would only be there for a year. These meetings weren’t about optics. They were about survival, trust, and leadership with real stakes. Years later, in business, I still carry the same mindset into every meeting. Here’s what I’ve learned, and what I’m still working to perfect: ✶Every meeting must matter. Time is precious. Don’t gather people unless there’s a clear purpose, an agenda with action items, and accountability. ✶Presence sets the tone. How you enter a room—your posture, your tone, your confidence—shapes the urgency and energy of everyone around you. ✶Deliver truth without flinching. Good news and bad news should come the same way: eye contact, directness, and a focus on action—scaling what works and fixing what doesn’t. ✶Connection transcends barriers. Language, background, title—they’re secondary. People respond to authenticity, curiosity, and clarity. Sometimes it’s a firm voice. Sometimes it’s a simple smile. ✶Be consistent, not just charismatic. Likability fades. Consistency, accountability, and results build trust. Real leaders own their team’s failures with humility and zero excuses—and they respond with care, not ego. Whether you’re in combat boots or dress shoes, leadership is about clarity, courage, and care. The table may look different, but the stakes are always high. Let’s make every meeting count—with intention, with integrity, and with impact. #Leadership #VeteranLeadership #BusinessMindset #MeetingCulture #LeadWithPurpose #MilitaryToBusiness #RichardGroup

After spending nearly two decades in the Army National Guard, climbing from SOC Analyst to VP of Information Security, and now working with DHS, leading a cyber intelligence and insider threat team—I've learned some crucial things about leadership. If you are a leader... It's not about you. It never was. It never will be. It never should be. I've seen dozens of people chase leadership roles for all the wrong reasons. The title. The "power." The validation. The escape from technical work. And at one point, this was me. Who doesn't want to feel important? But when you finally get there unprepared, reality hits hard. The first time a team member suffers a family tragedy. When someone shows up distracted because their child is sick or they're facing a personal crisis. When your star performer is burning out but won't admit it. When executives demand impossible results that would break your team. These moments reveal what leadership truly means. How you handle these situations shows your team who you really are as a leader—often in stark contrast to how you might see yourself. Outstanding leadership isn't born from authority or technical prowess—it's forged in vulnerability. It's having the courage to say "I don't know" or "I screwed up" before asking others to do the same. It's creating environments where people feel safe bringing their whole selves to work. There's a balance to strike, but expecting people to behave like robots inevitably leads to turnover, broken trust, and operational failure. If my experience has taught me anything, it's that leadership means bearing responsibility for supporting your fellow humans, who have entire lives beyond the workplace. It's providing cover when things get chaotic and ensuring your team knows you have their back—even during the bad times, even when they make mistakes. The Army has a saying for this: "One Team, One Fight." Sounds cheesy, but it makes sense when you break it down. My strongest teams weren't built on having the smartest people or the most advanced tools. While helpful, even underrated teams can overcome tremendous challenges when built on deep trust—the kind that only forms when your team sees you as human and knows they're valued as humans first, employees second. If you're aspiring to leadership, ask yourself honestly: Are you ready to put others before yourself? Can you absorb blame and distribute credit? Will you make unpopular decisions to protect your people? Because that's the work. Not the corner office. Not the decision-making authority. Not the salary. The real reward isn't what leadership gives to you—it's what it allows you to give others: the opportunity to remove obstacles, develop talent, and create space where people can do their best work while having lives worth living. If that calls to you—this messy, human-centered approach to building teams—then leadership might be your path. But if you're just looking for the next career step, there are easier ways to climb.

93% of people in the U.S. will never learn leadership lessons from military service. They also won't learn how to make ramen soup in a canteen cup, how to stockpile the little bottles of Tabasco from MREs or how to sleep on the floor of a C-130. But those aside, it's the leadership lessons that I learned in the military that truly transformed my life. Here are 7 of mine: 💪 Serve people first. Above all else, they are your winning strategy and what makes all of this worthwhile. When mistakes happen, when you're pulling an all nighter, when success does not look likely, the incredible power of having people to rally with absolutely makes or breaks it. Devote your whole self in service to your team. Find every way possible to make them successful. 💪 Training matters. Skill is achieved through knowledge and practice. When the chips are down, the work is hard and the time is short, you want people who have absolute command of their craft. Lack of knowledge doesn't indicate lack of ability. Between schools, training plans, tests, informal trainings, we committed 100% to increasing the skill of our teams. 💪 Disagree but commit. We have a word in the military "HUA", which stands for Heard. Understood. Acknowledged. It does not mean "I agree with you". You object. And then you commit to the decision made. You support the top. You support the unit. You support the team. 💪 Change is always possible. Just because you failed that one thing - that PT test, that NCO exam - does not mean that you've failed the job. You get to keep trying. And so does the guy next to you who failed his PT test 5 times & turns out to be the Sergeant Major 10 years down the line. None of us have to be static. Growth is always possible. 💪 Lead with empathy. You get to know your fellow platoon members real well when you’re stuck in a tent for 6 months with them. You learn how the guy who is late has a mom sick with cancer, the girl who is always on her phone is struggling not to get divorced, etc. Everyone has a story of struggle. Everyone deserves grace. 💪 Purpose connects us. We signed up for the college money, or because everyone in our family served, or to get out of our small town. All different backgrounds, all different values, all different motivations - thrust together. Give a team like that purpose and you can pull out operational excellence. Trust and a belief that the work we do matters is incredibly powerful. 💪 Everything is figureoutable. Need to fix brakes on your humvee with a Leatherman tool? I'll figure it out. Discharge from the military and trying to figure out how to go from combat medic to the corporate world? I'll figure it out. There’s always a path, we just have to find it or make it. I'm sure I've missed some lessons. But for now, I'll leave you with this. You find the veterans who learned some of these lessons and they will be the best hires you've ever made. Service to others matters. #cmo #jessgmarketing #veteran

In the rugged terrains of Afghanistan, amidst the grit and gravity of military service, I learned the most profound lessons on leadership from my brother, Sam, whose bravery and heart knew no bounds.   Leadership is often pictured as the hand that steers the ship, commanding and strategizing. Yet, the true essence of leadership, I believe, is empathy. It's the ability to not just understand but to feel the needs, fears, and hopes of those you lead.   Sam's story exemplifies this beautifully. He wasn't just an Officer; he was a guardian to his Marines, a man of strength and compassion. His empathy was his compass, guiding every decision, every action.   One day, Sam and another Marine witnessed a harrowing scene — an Afghan father and child, injured and in despair. Without a second thought, Sam was there, rendering aid with the utmost care. He saw no enemy, no stranger. He saw human beings in need and responded with an unwavering sense of shared humanity. Sam and his Marine saved this father’s life and no doubt, the child, now a man, remembers the American Marines who saved his father.   In leadership, it's easy to get lost in the bottom line, the strategies, and the day-to-day operations. But the leaders who leave a lasting impact, who inspire loyalty and courage, are those like Sam. They lead with empathy. They see the person behind the role and understand that at the core of every decision is a human experience.   As we navigate the complexities of leadership in our own lives, let us remember Sam's legacy. Let us strive to be leaders who not only make a difference in the outcomes but who touch lives, heal wounds, and bridge divides with the power of empathy.   Sam's ultimate sacrifice is a reminder that the greatest leaders don't just lead; they love. They empathize. They serve.   In his memory, and in honor of all who serve with such heart, let's commit to leading with empathy. For it's not just a soft skill — it's the very soul of leadership.   #Leadership #Empathy #MilitaryStories #InMemory #ServantLeadership