The General Beyond the Headlines: Michael Flynn and the Making of a Leader
.jpg/v1/fill/w_320,h_320/file.jpg)
Updated: Sep 10
In a rare, personal conversation, the former national security advisor reveals how family, mentors, military service and mission shaped his leadership—and asks every successful American one uncomfortable question: How are you serving?
On a Saturday, I received a call asking whether I could bring a group of Iowa leaders together to meet Lieutenant General Michael Flynn the following afternoon.
I sent out what I jokingly call the bat signal.
Less than 24 hours later, roughly 30 men gathered in a room in West Des Moines: business owners, community builders, grassroots organizers, public servants, a former member of Congress and four state legislators. They came from different professions and different corners of Iowa. Some had spent years in public life; others had built companies, led organizations or quietly done the work that holds a community together.
They had one thing in common: they believed the country needs capable men to step forward—and they wanted to know what that should look like in practice.
The meeting was supposed to last about 90 minutes. It ran closer to two hours. The reaction moved in both directions. Flynn later told me that what he saw in the room was leadership.
The men who attended left energized. My phone filled with calls and texts from people asking the same question: What can we do next?
That question became the starting point for my podcast conversation with Flynn.
It also became the real subject of the interview. Not Donald Trump. Not Washington intrigue. Not the partisan conflict that has made Flynn one of the most recognizable—and polarizing—figures in American public life. Those subjects belong to his story, but they were not the story I wanted to tell.
I wanted to understand the man behind the headlines: what formed him, what he learned about leadership under pressure and why, after nearly 34 years in the Army, he still speaks about service as if the assignment is unfinished.
A question more important than politics
Flynn’s central question is disarmingly simple:
How are you serving?
That question lands differently when directed at people who have already achieved conventional success. Many of the men in the room had built businesses, raised families, created jobs and accumulated decades of experience. Flynn’s argument was not that those accomplishments were unimportant. It was that success creates a second obligation.
Once you have built something, what will you do with what you have learned? Once you have influence, where will you spend it? Once your own household is secure, what responsibility do you have to the school, church, city or county beyond your front door?
“Service is something that everybody has a civic responsibility to do,” Flynn told me.
He was not telling every listener to run for Congress. In fact, much of his message pointed in the opposite direction. Washington is remote, slow and frequently beyond the control of any one citizen. A school board, city council, county commission, nonprofit, church ministry or neighborhood effort is close enough to touch. That is where experience can become action.
Flynn put it plainly: great leaders do not merely identify what is wrong. They accept the challenge and begin looking for a solution.
That distinction—between complaint and responsibility—runs through his entire story.
Leadership was first learned at home
Flynn was the sixth of nine children in a working-class Rhode Island family shaped by military service. Both grandfathers served during World War I. His father served in Europe during World War II and later in Korea before retiring from the Army as a master sergeant. Flynn was born at Fort Meade and spent part of his childhood in Germany before the family returned to Rhode Island.
There was little glamour in the family’s version of service. It meant deployments, uncertainty, work, discipline and shared responsibility. Eleven people eventually occupied a small house where everyone had a job. A large family, Flynn recalled, had to function as a team.
His father taught humility and the Golden Rule. He also demonstrated that leadership does not depend on title. After leaving the Army, the combat veteran took a job as a bank teller, far below the level of responsibility he had carried in uniform. Flynn remembers watching his father offer thoughtful advice to the bank manager—not to show him up, but in a way that helped him learn. The manager recognized the talent in front of him, moved him into lending, and Flynn’s father soon became a bank vice president.
The lesson was not about climbing a corporate ladder. It was about seeing people clearly. Flynn’s father taught his children not to be dazzled by status or possessions, but to judge people by their conduct: what they do, how they respond and how they treat others.
His mother supplied the other half of his formation.
According to Flynn, she had been valedictorian of her high-school class and received a full scholarship to an Ivy League college during World War II. She turned it down to marry Flynn’s father and begin a family. Later, while raising nine children, she returned to school and earned two bachelor’s degrees and a law degree.
Education in that household was not optional. Flynn remembers her saying that each child would get an education and put it in a back pocket, because one day it would be needed. She also became a leader in the pro-life movement, bringing conviction out of the home and into public life.
From his father came humility, teamwork and the obligation to treat people well. From his mother came intellectual discipline, moral courage and the refusal to stop learning. Those influences help explain Flynn better than any cable-news segment ever could.
The mentor who saw a different future
One of the strongest leadership lessons in our conversation began with a path Flynn did not take.
As a young man, he enlisted in the Marine Corps through a delayed-entry program. His father, an Army man, had other ideas. An Army ROTC officer from the University of Rhode Island visited the family home and offered Flynn a three-year scholarship—provided he recommitted himself to his grades. The Marines even came to the house to persuade him to stay with them. Flynn chose Army ROTC.
At Rhode Island, another mentor, Lieutenant Colonel O’Grady, watched Flynn closely. Flynn expected to pursue the infantry. O’Grady saw something else. He encouraged him to enter the emerging field of electronic warfare and signals intelligence and helped him reach the 82nd Airborne Division.
That intervention redirected a life. Flynn would eventually become the senior military intelligence officer in the Department of Defense, command the Defense Intelligence Agency, rise to three-star general and serve as national security advisor.
His takeaway was not that young people should wait for a powerful sponsor. It was that leaders have a duty to notice potential before it becomes obvious.
Flynn calls such people “diamonds in the rough.” They are not always the loudest voice or the first to volunteer for command. Often, he said, the person worth watching is the quiet one—the person who listens, performs and leads by example rather than trying to appear like the smartest person in the room.
Good leaders find those people. Great leaders help them become more than they currently imagine.
That idea deserves attention far beyond the military. Every company, campaign, church and civic organization has overlooked people whose ability exceeds their confidence or position. Leadership is not only directing the people already at the table. It is developing the people who do not yet know they belong there.
What building teams looks like when the stakes are life and death
Flynn’s most compelling management lesson came from his time at Joint Special Operations Command during the wars in Iraq and Afghanistan.
When he arrived, intelligence and operations were not moving together fast enough. The United States possessed enormous amounts of information, yet enemy networks adapted quickly and American lives remained at risk. Flynn saw that the problem was not simply a shortage of data. It was fragmentation.
The intelligence professionals and operational teams needed to stop functioning like separate departments. They needed to live, plan, learn and act as one network.
Under the approach Flynn described, a raid was no longer judged only by whether a target had been captured or killed. Phones, computers, documents and thumb drives recovered on a mission could generate the next operation within hours. Intelligence became action; action produced new intelligence. A force conducting roughly six raids in a 24-hour period eventually demonstrated the capacity to conduct 36.
Flynn illustrated the principle with a mission centered on one thumb drive believed to contain command-and-control information for al-Qaeda in Iraq. Operators did not find it on the target. They stayed at the site, searched the house and eventually recovered it from the rafters. The information revealed communications methods and elements of the organization’s hierarchy.
The broader lesson was not about raid counts. It was about alignment.
In business terms, Flynn compared the challenge to manufacturing, production and sales. If those functions operate as separate tribes, the company eventually fails. A team becomes powerful when every part understands the mission, shares information quickly and measures success by the same outcome.
At the end of the day, it’s about working together. It’s about solving problems.
That is leadership stripped of theatrics. Define the mission. Break down the silos. Put the right people in the room. Move information to the point of action. Give talented people responsibility. Then make sure ego never becomes more important than the outcome.
Conviction is where leadership stops being comfortable
A serious profile of Flynn cannot separate leadership from conviction, because he certainly does not.
Late in our conversation, we turned to abortion and a Massachusetts law that had recently caught his attention. Chapter 188, signed August 10, 2026, made a dramatic change to the state’s law governing abortions after 24 weeks. The previous statute limited those abortions to circumstances involving the life or physical or mental health of the patient, a lethal fetal diagnosis, or a grave diagnosis incompatible with sustained life outside the womb. The new law removed those specific conditions and instead states that an abortion may be performed by a physician based on the physician’s professional judgment. It further provides that a medical review process may not override the judgment of the treating physician and patient or health care proxy.
Flynn did not mince words about what he believed that change meant. He described it as allowing abortion up to birth.
And I did not push back on him. I shared his concern.
The conversation became even more pointed when I brought it home to Iowa. I noted that Rob Sand, now a candidate for governor, had previously been described by his own 2018 campaign manager as arguing that biblical passages indicate that life begins “at breath, not conception.”
For Flynn, this was not an abstract policy discussion. His mother had been active in the right-to-life movement and had taken him to an early national March for Life. His response came from a conviction formed long before Washington politics entered his life.
That exchange captured something important about the kind of leadership we had been discussing for more than an hour. Conviction has very little meaning when nothing is at stake. It matters when saying what you believe may cost you approval, relationships, votes, influence or reputation.
Flynn’s view was unmistakable: decide what you believe is true, say it plainly, and be willing to accept the consequences.
That is where leadership stops being comfortable.
Honoring Charlie Kirk {See the Post}
Put something at risk
The most powerful moment in the interview arrived when Flynn connected the sacrifice of service members overseas to the obligations of citizens at home.
Men and women in uniform, he observed, are still willing to place their lives at risk for a mission larger than themselves. He was not asking an Iowa business owner or grandfather to reproduce that sacrifice. He was asking why civic life should require no sacrifice at all.
His challenge was simple:
PUT YOUR TIME AT RISK.
PUT YOUR RESOURCES AT RISK.
PUT YOUR REPUTATION AT RISK
That last demand may be the hardest. Time can be scheduled. Money can be replaced. Reputation touches identity. It is the fear of being labeled, misunderstood or attacked that keeps many otherwise capable people silent.
Flynn’s response was concise:
I know who I am. You know who you are.
This is where his challenge reaches beyond any single political constituency. You do not have to share every one of Flynn’s conclusions to recognize the problem he identifies. America has no shortage of accomplished people with opinions. It has a shortage of people willing to convert experience into service when doing so may cost them comfort, status or approval.
Leadership is not outrage posted from a safe distance. It is responsibility accepted at close range.
It may mean mentoring a young person whom everyone else overlooks. It may mean helping a local organization build a competent board. It may mean running for office—or helping a better person run. It may mean bringing business discipline to a nonprofit, insisting on higher standards in a school district, serving through a church or convening 30 people on a Sunday because the opportunity appeared on Saturday.
That is the idea behind Kairos Nexus: kairos is the critical moment, the opening that must be recognized and acted upon. The important door rarely announces how much depends on walking through it. Flynn’s own career turned on several such moments—and on mentors who helped him see them.
Why this felt familiar
Maybe that is why this conversation with Flynn stuck with me.
For years, through Iowans for Freedom, I have tried to operate from much the same premise: citizens cannot simply watch what is happening around them and complain about it.
At some point, somebody has to step forward.
For us, that has meant interviewing legislators and giving people a chance to hear directly from them. It has meant researching issues, sending calls to action, emailing lawmakers, showing up at public hearings, testifying and organizing rallies that brought hundreds of Iowans to the Capitol. During COVID, when many people felt unheard and isolated, we helped create places for them to show up together, meet lawmakers face-to-face and turn frustration into action.
More recently, I have tried to bring that same philosophy into my role with the Dallas County Republican Party: identify people with something to contribute, give them opportunities to lead, build stronger relationships within the community and create a culture in which serving is something we expect of ourselves—not simply something we expect from elected officials.
That is why Flynn’s question struck me so deeply.
How are you serving?
For years, a quieter version of that question has been running in the background for me in almost every situation:
How can I serve?
What can I do here? Who can I connect? Where can I help? What needs to move forward?
I realized I had been asking different versions of Flynn’s question for years.
When the Headlines Fall Away
The evening after the episode was released, I sat around a campfire with one of my brothers, who is a Democrat. He had been especially close to our father, a Marine and Korean War veteran who fought at the Chosin Reservoir, and I think that part of Flynn’s story struck a familiar chord with him.
I played part of the interview on my phone, expecting he might listen for a few minutes.
Ten or 15 minutes later, he looked at me and said, “I’d like to meet him. Send me the interview.”
Another listener told me the episode did not feel political at all. It felt inspirational.
That does not mean Flynn suddenly became nonpolitical, or that viewers will agree with everything he says. It means a genuine human story can reach places an argument cannot. Before he was a national controversy, Michael Flynn was a boy in a crowded military household, a son watching two very different parents lead, an athlete learning how a team wins, a young man redirected by mentors and an intelligence officer trying to make an institution move faster because lives depended on it.
The headlines might tell us what side someone occupies. A conversation can reveal what made him.
Flynn closed our interview with a warning against fear: do not let it overcome what you know to be right. But the line that stayed with me came much earlier, in the form of a question.
How are you serving?
It is not a question reserved for generals, politicians or people with national platforms. It belongs to anyone who has acquired experience, influence, resources or wisdom and must now decide whether to protect them—or spend them on something larger.
The answer will not be the same for every person. The obligation to answer belongs to all of us.
