Now Go, Lead

Brandon Pinkerton

5.0 (1)
Business
Updated Weekly

Welcome to Now Go, Lead! Tune in each week for fresh insights, inspiring stories, and actionable tips to elevate your leadership. Whether you're a seasoned pro or just beginning your journey, there's always room to grow. Hit play and start leading at your next level!

6d ago

Outsourcing Your Integrity

Every leader eventually places a piece of their reputation into someone else's hands, and this leadership development episode explores what that really means. The moment you build a team, you are no longer the only person representing your standards to the world. You feel this most sharply when someone on your team drops the ball, disappoints a customer, or stops being responsive, because the mistake becomes yours to answer for even though you didn't make it. Brandon illustrates this with the story of Michael Jordan and Nike at the 1992 Barcelona Olympics. Nike's rival, Reebok, had paid to put its logo on the medal ceremony jackets, putting Jordan in a position where wearing it would have damaged the brand he represented. Rather than refuse outright, Jordan draped an American flag over his shoulder, covering the rival logo entirely. It was a quiet, decisive act that showed he understood exactly whose name he was carrying. That same responsibility falls on every leader who delegates real authority to a team. Brandon lays out four commitments for leaders who want their people to carry their standards well: set a clear vision for each person, watch the words you use about their abilities, embrace the awkward conversations that build trust, and be the place your team can retreat to when things go wrong. The challenge for leaders is direct. You cannot control every interaction your team has, but you can shape how prepared they are to represent you when you're not in the room. That preparation is not a one-time conversation. It is a standing commitment. KEY TAKEAWAYS - You outsource your integrity the moment you build a team, whether you intend to or not. - Leaders must set a clear vision for each person they lead, not just for the organization as a whole. - The words you use about someone's abilities can become self-fulfilling, so choose them with care. - You cannot build trust without embracing the awkward conversations your team is avoiding. - Your team will only represent you well in public if they know you protect them in private. CLOSING REFLECTION So take five minutes and think about this. What does it mean to have others represent me in the world? What values must I impart to others so that they represent me well? FINAL THOUGHT Integrity is not something you get to keep entirely to yourself once you lead others. It travels through your team, carried by the vision, the words, the honesty, and the protection you give them. It's time to now go lead.
Aug 25

Shallow Roots

Every leader eventually invests years in someone, only to watch that person walk away the moment the ground gets unstable. This episode of Now Go Lead is about that exact experience, and about a piece of leadership development that rarely gets talked about directly: the difference between influence that spreads wide and roots that actually run deep. Brandon Pinkerton shares the story of a leader he personally mentored for five years, someone he considered a true disciple of his leadership philosophy and believed was ready for real responsibility. When the organization approached a major, course-altering event, Brandon did what he always does before a crisis: he had honest, individual conversations with his team and asked for their trust to help shepherd everyone through it. Within days, this leader told him they weren't on board and left for an opportunity with more certainty. The storm had barely started, and Brandon discovered the roots he thought were deep were far shallower than he realized. The insight he draws from it cuts against a common leadership habit: handing someone real influence before they've actually put anything down into the ground. Brandon reflects on his own long-held belief that ownership shouldn't be a requirement for leadership, and how that generosity sometimes left key leaders with enormous influence and very little at stake. He's also honest about what a departure like this does and doesn't mean. Losing a trusted leader isn't automatically a personal indictment, but it is always worth a hard look inward first. The challenge for leaders is to stop mistaking someone's reach for their roots. Influence that spreads wide can look impressive on the surface while running dangerously shallow underneath, and the only way to find out which one you're dealing with is before the storm, not during it. Key Takeaways - Everyone has a limit to what they're willing to sacrifice, and you cannot force someone past theirs. - Asking someone for a hard commitment is fair. Using guilt or obligation to get it is not. - Influence without ownership or a real stake in the outcome often has shallower roots than it appears. - A trusted leader's departure is not automatically a verdict on your leadership, but it always deserves an honest look at yourself first. - Pay attention to the roots you're allowing to grow around real influence, not just the reach. Closing Reflection Take five minutes and consider. Who has some shallow roots that need to be deepened? Where is my organization at risk because of leaders with too much influence but not enough roots? Final Thought Today's a reminder to pay attention to the roots, more than just what you see on the surface. There comes a moment when the growing leader must make a greater sacrifice than simply working more hours or taking on more responsibility, and the only way to know who's ready for that moment is to check the roots before the storm arrives. It's time to now go lead.
Aug 18

The Other Option

Every leader eventually has to confront a hard question about their own leadership development: are you actually leading your team, or just finding new ways to make them move? Brandon opens this episode by pointing out how much time leaders spend debating the stick or the carrot, all while missing that both approaches still put the leader in the position of pushing someone else forward rather than leading them. He illustrates this with the story of a department manager who built his leadership style entirely around the carrot and the stick, feigning interest in his team only to learn what he could dangle in front of them, and resorting to veiled threats when that didn't work. It produced short-term performance, but people began to see him as more of a tyrant than a leader, and his best people started leaving. When he finally came to Brandon for advice, he realized mid-sentence the difference between the leader he wanted to be and the one he had actually been delivering to his team. Brandon offers a different path: leading with kindness. He's careful to frame kindness as demanding, not soft. It requires total empathy, genuine humility, and a willingness to get out of the comfortable chair and share the load rather than manage from a distance. The challenge Brandon leaves leaders with is to notice where they've defaulted to carrot-or-stick thinking without realizing it, and to consider how much untapped potential in their team is waiting for a leader willing to unleash it instead of extract it. KEY TAKEAWAYS - Leading with the stick or the carrot still means you are pushing, not leading. - You cannot fake interest in your team long enough to build real trust. - People will tolerate a tough leader, but not one they believe doesn't have their best interests at heart. - Kindness is demanding, not soft. It requires empathy, humility, and sharing the load. - You must stop making promises you cannot guarantee and start carrying the outcome together with your team. CLOSING REFLECTION Take five minutes and think about this. Where have I developed a carrot or stick approach to leadership? What untapped potential is available in others if I can simply find a way to unleash it? FINAL THOUGHT Motivating a team isn't about which lever to pull. It's about whether you're willing to lead beside them instead of above them. It's time to now go lead.
Aug 11

A Good Plan

A plan means nothing until someone is willing to act on it, and this episode of Now Go Lead looks at what separates leaders who talk about progress from leaders who actually deliver it. This is leadership development at its most practical: the discipline of execution, not the sophistication of the plan itself. Brandon Pinkerton grounds the lesson in the Army Corps of Engineers' four-decade effort to rebuild the flood walls protecting New Orleans after Hurricane Betsy struck in 1965. Though Congress authorized and funded the project under the Flood Control Act of 1965, the Corps spent years unable to agree on which flood models to use, ultimately rejecting updated data from the newly formed National Oceanic and Atmospheric Administration in favor of older, more familiar methods. A project originally scoped for thirteen years dragged on for forty. It was still only seventy percent complete, and still built on flood models from the 1950s, when Hurricane Katrina made landfall in 2005. The failure that followed was not a failure of planning. It was a failure of leaders, one after another, choosing to defer hard decisions, protect familiar processes, and mistake meetings and reviews for real progress. Brandon is direct about what this costs: when leaders avoid the hard call, the people who depend on them are the ones who pay the price. The challenge for every leader listening is the same one the Corps never answered in time. A plan you never execute is only an idea, and the excuses that feel reasonable today are the same excuses that leave you exposed the day the storm actually arrives. Key Takeaways - A plan without execution is only an idea, no matter how good it looks on paper. - Leaders who defer hard decisions are not avoiding risk. They are relocating it to the people they lead. - Comfortable, familiar processes are not the same as sound processes, and clinging to them can be costly. - Meetings, reviews, and activity are not evidence of progress. - You will not always get a warning before the cost of inaction comes due. Closing Reflection Take five minutes and think about this. Where am I deferring hard decisions that I know need to be made right now? What excuses am I hiding behind that are keeping me from doing the hard things I already know need to be done? Final Thought The Army Corps did not fail for lack of a plan. It failed because for forty years, no single leader was willing to make the hard call and see it through. The same choice sits in front of every leader today, long before any hurricane makes it unavoidable. It's time to now go lead.
Aug 4

The Epigone

Every leader eventually asks a version of the same question: am I becoming who I actually am, or who the world has told me I need to be to count as successful? This episode of Now Go Lead centers on that exact tension as a foundational piece of leadership development, the pull between necessary growth and quietly trading your identity for the approval, money, or recognition our culture uses to measure success. Brandon Pinkerton grounds this question in his own experience. In the year after selling his business, he faced an identity crisis, the loss of important relationships, and no shortage of advice on what to do next with the leadership platform he had built. Nearly everyone told him to grow it through social media and public speaking, the same path other recognized leaders in his space had taken. The advice made sense on paper. It also ran straight into his genuine dislike of social media and real anxiety around public speaking. He turns to George Washington's story to work through what to do when good advice and personal conviction pull in opposite directions. At 57, having already given the country the best years of his life, Washington wanted nothing more than to retire to his farm. Instead, a deep sense of duty pulled him into two demanding terms as president, years that cost him the retirement he had earned and exposed him to accusations he never wanted to face. Washington did not resolve that tension perfectly, and Brandon is direct about the fact that no leader will. What made Washington's example worth studying was that he resolved it faithfully. He held two unbreakable commitments at once: he would not sacrifice his integrity, and he would not ignore a legitimate call to lead. Every leader operates inside that same narrow space, choosing again and again between service to others and preservation of self. The episode's challenge is a personal one. It is easy to become what Brandon calls the epigone, a pale imitation of someone else's success, quietly shaped by expectations that were never truly your own. The real work of leadership is deciding, in that narrow space between duty and desire, who you are willing to remain. KEY TAKEAWAYS - Leadership demands a choice between the version of success the world defines and the version of yourself you refuse to abandon. - You cannot build a lasting leadership identity by measuring yourself against someone else's definition of arrival. - Discomfort is not proof you are on the wrong path. It is often the cost of growth worth paying. - Duty and desire will not always agree, and you must learn to act faithfully within that tension rather than waiting for it to resolve. - The choice between service and self-preservation will outlast your time in leadership and shape the legacy you leave behind. CLOSING REFLECTION So think about this for five minutes. Where have I compromised my authenticity or integrity to become something that only others want me to be? Where am I retreating into complacency because I'm afraid to take on a new challenge? FINAL THOUGHT Washington did not resolve the tension between what he wanted for himself and what was asked of him perfectly, and neither will you. He resolved it faithfully, and that is the standard worth pursuing. It's time to now go lead.
Jul 28

Progeny

The people who leave your leadership are not the end of your story — they are the continuation of it. In this episode of Now Go Lead, Brandon Pinkerton explores the leadership principle of progeny: the idea that the most enduring measure of your influence is not how long people stay, but how far they carry what you gave them. This is leadership development at its deepest level. Brandon opens with a scene many leaders know well — sitting with the quiet ache of watching people walk out the door. He describes scrolling through the career profiles of people who once worked under his direct influence, tracing the varied and distant paths they have taken since leaving his company. Where he once felt loss, he began to feel something more powerful: the recognition that each of those paths carried a thread of what they had learned, developed, and grown into under his leadership. The image of a deck on a spring morning becomes the backdrop for a fundamental shift in perspective. The leadership insight is straightforward and demanding at the same time. You cannot control how long someone chooses to stay with you. Trying to do so makes life miserable for everyone. What you can do — what you are responsible for — is take seriously the work of developing people while they are with you. When you instill values and vision deeply enough, those things travel with a person wherever they go. The vision extends beyond your direct reach. That is what Brandon calls true multiplication. The episode closes with the concept that gives it its title. When the progeny of your leadership carries your vision to places you have never been and to people you will never meet, you have done the most important work a leader can do. Your legacy is not measured by retention — it is measured by what takes root in the people who once sat across from you. KEY TAKEAWAYS • You cannot control how long someone will stay under your leadership — attempting to do so only causes damage to yourself and those around you. • Your true measure as a leader is not retention — it is the values and vision you instill in people before they go. • The most powerful form of multiplication is not growing your own team, but seeing your influence continue through the paths of those who have moved on. • Leaders who develop others with intentionality will one day see their vision living in places they have never been and among people they will never know. • Departure is not failure. In most cases, it is the beginning of someone carrying your work further than you ever could. CLOSING REFLECTION Take five minutes and think about this. Where have I gotten sidetracked or angry over people leaving my sphere of influence? What is my plan to intentionally develop others so that my vision lives beyond my reach? FINAL THOUGHT The leaders who leave the deepest marks are not the ones who held people the longest — they are the ones who sent people forward with something worth carrying. Your vision does not have to end where your influence stops. It's time to now go lead.
Jul 28

Progeny

The people who leave your leadership are not the end of your story — they are the continuation of it. In this episode of Now Go Lead, Brandon Pinkerton explores the leadership principle of progeny: the idea that the most enduring measure of your influence is not how long people stay, but how far they carry what you gave them. This is leadership development at its deepest level. Brandon opens with a scene many leaders know well — sitting with the quiet ache of watching people walk out the door. He describes scrolling through the career profiles of people who once worked under his direct influence, tracing the varied and distant paths they have taken since leaving his company. Where he once felt loss, he began to feel something more powerful: the recognition that each of those paths carried a thread of what they had learned, developed, and grown into under his leadership. The image of a deck on a spring morning becomes the backdrop for a fundamental shift in perspective. The leadership insight is straightforward and demanding at the same time. You cannot control how long someone chooses to stay with you. Trying to do so makes life miserable for everyone. What you can do — what you are responsible for — is take seriously the work of developing people while they are with you. When you instill values and vision deeply enough, those things travel with a person wherever they go. The vision extends beyond your direct reach. That is what Brandon calls true multiplication. The episode closes with the concept that gives it its title. When the progeny of your leadership carries your vision to places you have never been and to people you will never meet, you have done the most important work a leader can do. Your legacy is not measured by retention — it is measured by what takes root in the people who once sat across from you. KEY TAKEAWAYS • You cannot control how long someone will stay under your leadership — attempting to do so only causes damage to yourself and those around you. • Your true measure as a leader is not retention — it is the values and vision you instill in people before they go. • The most powerful form of multiplication is not growing your own team, but seeing your influence continue through the paths of those who have moved on. • Leaders who develop others with intentionality will one day see their vision living in places they have never been and among people they will never know. • Departure is not failure. In most cases, it is the beginning of someone carrying your work further than you ever could. CLOSING REFLECTION Take five minutes and think about this. Where have I gotten sidetracked or angry over people leaving my sphere of influence? What is my plan to intentionally develop others so that my vision lives beyond my reach? FINAL THOUGHT The leaders who leave the deepest marks are not the ones who held people the longest — they are the ones who sent people forward with something worth carrying. Your vision does not have to end where your influence stops. It's time to now go lead.
Jul 21

The Troglodyte

Failure leaves a mark. The scars from your worst leadership moments do not disappear once the situation is resolved. They stay with you as a constant reminder, and your brain, doing exactly what it is designed to do, will work hard to make sure you never find yourself in the same painful place again. That protective instinct is a reasonable response to trauma. It is also one of the most dangerous forces a leader can allow to go unchecked. This episode of Now Go Lead asks a direct question: what are you hiding from? Brandon Pinkerton draws on the story of Luke Skywalker in the Star Wars sequel trilogy to give the pattern a name and a face. After the fall of the Empire, Luke attempted to train a new generation of Jedi. His most gifted student, Ben Solo, had so much potential that Luke was afraid of it. Rather than teaching Ben how to channel and develop that talent, Luke let his fear drive his approach, and Ben felt so much betrayal that he turned to the dark side and became the leader of the First Order. The weight of that failure was more than Luke could carry. So he vanished, retreating to a remote planet and living in isolation while the galaxy slipped back into darkness. He was not absent without reason. The reason was completely understandable. But the people who needed him bore the consequences of his disappearance regardless of how justified his retreat felt to him. Brandon frames this as a choice every leader will face after their worst moments: learn from the failure and force yourself back into the difficult places, or run from the weight of it and go into hiding. No one will fault you for stepping back. The pain is real and the logic of self-protection makes complete sense. But leadership does not stop needing to happen simply because the leader has been hurt. The people in your sphere will feel your absence whether they understand its cause or not. The call in this episode is not to pretend the failure did not happen or to minimize the weight of it. It is to recognize that the next stage of your leadership journey may be waiting on the other side of the very thing you have been unwilling to face. Staying hidden is always an option. Staying hidden always has a cost. KEY TAKEAWAYS Trauma is a natural protective response. Left unchecked, that same protection becomes the wall that keeps you from leading effectively. Your leadership philosophy should not change based on how painful your circumstances have been. Your commitment to show up is what separates leaders from former leaders. Retreating from leadership after failure is understandable. The people who needed you will bear the consequences of your absence either way. The dark places you have been avoiding may be exactly where your next season of leadership growth is waiting. Facing past failure is not about re-living the pain. It is about refusing to let the pain make your decisions for you. CLOSING REFLECTION Take five minutes and consider, what are some past failures you've been unwilling to revisit? Where have you become a recluse instead of staying engaged in the journey? FINAL THOUGHT You can learn from your worst moments and force yourself back into the scary places, or you can run and hide. No one will blame you for running. But everyone will bear the consequences of your absence. Stand up and face the things you do not want to face. The next great stage of your journey may be waiting on the other side. It's time to now go lead.

Welcome to Now Go, Lead! Tune in each week for fresh insights, inspiring stories, and actionable tips to elevate your leadership. Whether you're a seasoned pro or just beginning your journey, there's always room to grow. Hit play and start leading at your next level!

Creator

Brandon Pinkerton
Years Active

2024 - 2026
Episodes

109
Rating

Clean
Copyright

© 2026 Now Go, Lead
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Now Go, Lead