Now Go, Lead

Brandon Pinkerton

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!

  1. 5d ago

    The Past

    Your past failures shape your name as a leader, but they do not have to write the final chapter of your leadership legacy. In this leadership development episode, Brandon Pinkerton explores why a leader's mistakes carry more weight than a private person's, and why dramatic change is still possible. Every decision you make as a leader becomes another page in the story of your life, and because leadership magnifies everything, a moral failure that might seem inconsequential for a private individual can look unforgivable in the eyes of others. Brandon tells the story of Charles "Chuck" Colson, special counsel to President Nixon in the early 1970s. Colson was called an "evil genius" and "the president's hatchet man" by the press. He kept a list of political enemies and used his influence to keep them under his thumb. After the Watergate scandal, a close friend gave him C.S. Lewis's Mere Christianity, and it became the catalyst for a dramatic change of heart. He was still convicted and sent to prison for his part in the crimes. For many, that would have been the fitting end to a bitter legacy. For Colson, it was the beginning. He went on to start the largest prison ministry of its kind in America and worked to bridge theological divides between Catholics and Protestants. Brandon then turns the lens on himself. He once stole candy from his third grade teacher's desk. He once sabotaged a friend's trumpet before a chair test. As a college building caretaker, he once left the doors unlocked to go on a date, and the building was burglarized. Viewed in isolation, those moments could label him a thief, a saboteur, and an unreliable person. The full story of his life paints a different picture, and that is the point: Colson's story is not unique. It is a template. The challenge for you as a leader is to take your decisions seriously while refusing to let past failure cement itself as your legacy. You will make mistakes. Some may get you into real trouble. But your story is still being written, and often the greatest chapter of your leadership is the one you write as you emerge from the ashes of failure. KEY TAKEAWAYS -Your past does define your name, but your past is not complete. -Leadership magnifies every decision, so you must understand the gravity of your choices before you make them. -A single failure viewed in isolation distorts the picture of a life. Leaders are defined by the full story, not the worst page. -Dramatic change is possible, no matter how public or serious the failure. -The greatest chapter of your leadership is often the one you write as you emerge from failure. Closing Reflection "So think about this for five minutes. Where have I let failure in my past define my future? And what changes do I need to make today to correct the course that I am on?" FINAL THOUGHT Your worst moments are real, and as a leader they will be seen. But they are pages, not the whole book. Wherever you are in your leadership, don't despair, because the next chapter is still yours to write. It's time to now go lead.

  2. Oct 20

    Pardon Me

    The tension between accountability and grace is one of the most difficult a leader will ever navigate, and how you handle it shapes the loyalty of everyone you lead. As a leader, you set the destination, make the rules, and set the tone of accountability for your organization. When someone on your team falls short, it is your responsibility to address it and protect the integrity of the vision. But enforcing the rules is only part of the job. Brandon Pinkerton turns to a remarkable story from the Civil War. William Scott was twenty-two when he volunteered for the Union Army alongside his four brothers. Stationed at Chain Bridge in Virginia under General W. F. Smith, he guarded an important water supply eight miles from the capital, under a strict rule: sleeping at your post was punishable by death. After a long march, William volunteered to cover a night shift for a sick fellow soldier, then accepted the same shift again the next day. After nearly 48 hours without sleep, he dozed off before dawn and was found by his morning relief. He was sentenced to death. Hundreds of officers and privates signed a petition on his behalf, and it reached President Lincoln. Having heard the full story and the extenuating circumstances, Lincoln granted the pardon. To impress upon the men the seriousness of the offense, the firing squad was still assembled, and the pardon was read aloud before the entire company. William pledged never to fail in his duty again. A few months later he kept that pledge with his life, killed while carrying a wounded soldier up the bank of the Warwick River after saving several men from drowning. The lesson for leaders is direct. It is too easy to let the rules do the work for you. Leaders who look past the surface circumstances and into the hearts of their people will find the grace of fierce loyalty waiting for them when the toughest moments arrive. KEY TAKEAWAYS Accountability protects the vision, and leaders must still address it when someone falls short. Rules tell you what happened. Understanding the circumstances tells you why. It is too easy to let the rules do the work for you. Leadership requires looking at the heart of the person. Grace does not erase the seriousness of a mistake. It can be extended while still making the stakes clear. Leaders who extend grace wisely earn fierce loyalty that shows up when the toughest moments arrive. Closing Reflection So take five minutes and consider. Have I used accountability as an excuse to dismiss people instead of taking time to grow them? How do I handle forgiveness in the wake of serious mistakes? FINAL THOUGHT William Scott's legacy could have been one of failure and shame. Instead, a leader who looked beyond the circumstances gave him the chance to become a hero. Hold the standard, and never stop looking at the heart of the person who missed it. It's time to now go lead.

  3. Oct 13

    Shallow Leadership

    Episode Summary A shallow leader is someone who looks the part of a leader on the surface but lacks the depth to carry real responsibility, and learning to spot them is one of the most important leadership development skills a senior leader can build. Shallow leaders interview well. They know the language of leadership, and many hold an advanced degree like an MBA to strengthen their case. Left unchecked in positions of influence, they can become a cancer in your organization. Brandon Pinkerton speaks from hard experience. One of his greatest regrets from his years of building a company was allowing a shallow leader to keep running a regional office for several years after he recognized the problem. The office eventually imploded almost entirely, and Brandon lost significant respect within his organization. In the aftermath, he resolved to be much tougher and more proactive with those who had the privilege to lead under his watch. The first lesson he took away: you have to know what you are looking for before you can act on it. Brandon identifies two of the clearest signs. Shallow leaders are sticklers for rules, leaning on structure and process instead of instinct and visionary thinking, which leaves them stuck when a challenge falls outside the rule book. They also avoid pain and run from difficulty, enjoying the privileges of leadership while making excuses when sacrifice is required. Often, someone they respected told them they were already a finished product. Pride keeps them from asking for help, and insecurity turns into a facade of bravado and overcompensation. The challenge for every leader with influence over hiring and promotion is clear. Promote, elevate, and hire only those individuals with the depth of leadership to support your vision. And if shallow leaders already hold positions of influence in your organization, do yourself a favor and have the hard conversations today. KEY TAKEAWAYS Looking the part is not the same as having depth. Credentials and a strong interview can mask shallow leadership. You have to know what you are looking for before you can act on it. Leaders who lean on rules instead of judgment get stuck when a challenge falls outside the rule book, and the problem festers. Leaders who enjoy the privileges but avoid the sacrifice believe only in the easy parts of leadership. Every season you allow a shallow leader to keep influence, your organization and your own credibility pay the price. Closing Reflection So take five minutes and consider. Who are the shallow leaders in my organization that I've given too much influence? Am I willing to have honest conversations with my shallow leaders about taking a step back to work on growth? FINAL THOUGHT Shallow leaders rarely set out to be shallow. Someone told them they had arrived before the real work had begun. Your job is to look beneath the surface, have the hard conversation, and reserve the privilege of leading for those with the depth to carry it. It's time to now go lead.

  4. Oct 6

    Final Destination

    Leadership development includes a question most leaders never ask out loud: who do you want standing beside you when you reach the destination your vision points toward? Every leader carries a vision, and its realization is a destination, the culmination of all the steps, the tears, and the toil. You probably have at least a vague picture of who is there celebrating with you. The harder question is whether those people know it. Leaders often operate on assumptions. You assume the people closest to you will always be there. You rely on tacit understandings and never say out loud what motivates you, what you expect, or what you hope for them. Unless you want to arrive at the finish line alone, those assumptions have to give way to an intentional invitation. Brandon Pinkerton learned this firsthand in his late twenties. He was a new father in a dead-end job, and he had secured a role with a major corporation that offered good pay, excellent benefits, and reasonable security, with a start date a few months away. When he told the vice president he trusted that he would be leaving, the VP supported the decision. A couple of days later, that same VP came into Brandon's office, laid out the vision he had been developing for his future, and personally invited Brandon to help build it. He did not have to bring Brandon along. He chose to, because he wanted to share the destination with someone he trusted. That small invitation changed Brandon's life in ways he could never have imagined. The challenge for you is direct. Share your vision with the people most important to you. Tell them why you cannot imagine reaching your destination without them. Make clear that they are integral to your success and that the rewards at the end are meant to be shared. When you dream together, you succeed together. KEY TAKEAWAYS Your vision is a destination, and you should know who you want with you when you arrive. Leaders who rely on assumptions about the people closest to them risk reaching the finish line alone. A tacit understanding is not an invitation. The people who matter to you need to hear it from you directly. One intentional invitation can change the direction of someone's life, even when it feels small in the moment. When you share the vision, you share the rewards. Leaders who dream together succeed together. Closing Reflection So take five minutes and think about this. Who do I want with me when I reach my destination? And what intentional conversations do I need to have today with those closest to me? FINAL THOUGHT The people you want at the finish line will not get there by assumption. They get there because you invited them, told them why they matter, and made room for them in the vision. It's time to now go lead.

  5. Sep 29

    Give not Take

    Every leader operates under expectations set by someone else, and how you respond to the tension between those expectations and the people who depend on you is at the heart of leadership development. Everyone answers to someone, whether that's a manager up the chain, a customer, a child, or simply a person counting on you to follow through each day, and when you fail to meet what's expected of you, the people relying on you are the ones who suffer. Add in your own daily, weekly, and quarterly goals, and you're left balancing what benefits you in the moment against the tasks whose absence will eventually cause real damage. That tension, between protecting your own priorities and giving your team what they actually need, is where this episode lives. Brandon illustrates this with the film Mr. Holland's Opus, the story of Glenn Holland, a young musician who dreams of composing his own masterpiece and takes a temporary job teaching high school music to make ends meet. Over the course of the film, Mr. Holland gives up more and more of that dream to help his students succeed. In one memorable scene, a student is struggling with the clarinet. She has heart and effort, but something isn't clicking, and Mr. Holland has every right to move on and protect his own time. Instead, he reluctantly offers to give up part of his mornings to help her, and she responds with visible gratitude. Meanwhile, his own symphony keeps waiting. Brandon frames Mr. Holland's reluctant sacrifice as a template every leader should follow, built on three commitments. First, give of yourself without stopping. Not a few scheduled minutes a week, but your best time, thought, and resources, given generously enough that leading actually feels sacrificial. That said, sacrifice only works if it's sustainable. You cannot pour from an empty vessel, and a leader who burns out helps no one, so the goal is to give from a place of genuine strength, not depletion. Second, give grace at every turn. As a leader, you often know more and have more experience than the people you're developing, and it's easy to forget what it felt like to struggle with something you've since mastered. Third, be profoundly patient. Growth requires a developmental period you cannot shortcut or dictate on someone else's timeline, and pushing people into roles before they're ready puts the whole team at risk. Brandon's challenge to leaders is personal: someone once invested time in you when they could have focused entirely on their own goals, and that investment changed the direction of your life. The same opportunity now sits in front of you, and it starts with noticing who in your sphere of influence needs your time and where your own priorities might be crowding out someone else's growth. KEY TAKEAWAYS - You cannot lead others well while treating their development as an interruption to your real priorities. - Leadership should feel sacrificial; if giving to your team costs you nothing, you are likely holding something back. - Sacrifice without self-care is not sustainable, you cannot pour from an empty vessel, and a burned-out leader serves no one. - Grace toward a struggling team member is not weakness, it builds the trust that holds a team together. - You cannot dictate someone else's developmental timeline, and impatience risks pushing people into roles they are not ready for. Closing Reflection Think about this for five minutes. Who are the people in my sphere of influence that need additional time and resources from me? Where have I been so focused on my own goals that I'm neglecting to develop others? FINAL THOUGHT Every leader is already answering to someone, the real choice is what you do with the time in between. Give generously, give patiently, and give without keeping score, because the people you invest in today will be the leaders someone else depends on tomorrow. It's time to now go lead.

  6. Sep 22

    Process to Prepare

    Leadership development stalls the moment a leader tries to carry more weight instead of putting more of it down. If you are working longer hours every year and your organization still is not growing, the problem is rarely your effort. It is what you have refused to hand off. Brandon Pinkerton points to a pattern he has watched play out again and again in small businesses: a founder in their seventies finally has to close the doors because no one ever came along who was ready, or willing, to take over. It is not just a sad ending. It is value lost to the founder that never had to be lost, and it starts years earlier with a leader who decided training a successor was less urgent than getting today's work done. Brandon shares the two decisions he made about two years into his own time as CEO that he still counts among the best of his career. First, he carved off the parts of the role he did not love and built a new position around them, then found someone eager to take it. Second, he built a multi-year training program for his top performers, opening up the most sensitive parts of the business to them and including them in every strategic decision. Years later, when it came time to sell the company, that investment had produced a genuine bench of internal leaders, ready for what came next and free to move Brandon into his own next chapter. Naming a successor is not the same as preparing one. Succession is a process, carried out week by week, long before the handoff ever happens. Brandon's challenge to every leader is to measure their success not by how much they are still carrying, but by how ready the people around them are to carry it instead. KEY TAKEAWAYS - Leaders who keep adding responsibility instead of giving it away are treating a leadership problem like a workload problem. - Your unwillingness or inability to develop your team is often the real reason you cannot get out from under the work. - Talented, ambitious people do not stay long in organizations where no one ever hands them real responsibility. - Succession is not naming someone. It is the ongoing process of preparing them. - You will know your leadership development worked when you can hand off what you built and trust it will keep moving forward. CLOSING REFLECTION So take five minutes and think about this. What is my current succession plan? What intentional steps am I making each week to prepare others to lead in my place? What do I need to give up to move forward? FINAL THOUGHT Succession is not a single decision. It is years of small, intentional handoffs that determine whether your leadership outlasts your time at the top. The leaders who take this seriously build organizations that do not just survive their exit, they are ready for it. It's time to now go lead.

  7. Sep 15

    Those Wounds

    Have you ever been hurt? The old proverb says that "wounds from a friend can be trusted, but an enemy multiplies kisses… [Proverbs 27:6]" I've known this for a long time, but recently it hit me like it was brand new. This concept is wrapped up in the idea of "hard conversations," which is difficult enough on its own. Maybe the most important part of this concept is not the hard conversation, but who is qualified to deliver it. If you are a leader, I bet you want to grow your people, there are things about them that need to change, and you wish you could be honest about what those things are. But you probably have been putting off the conversation because you aren't sure how it would be received. I remember one of the deepest wounds I ever received. I am certainly open to occasional critical feedback from my team, but like anyone, there are certain areas of my life where I take genuine pride. It may come as no surprise to you that I take pride in my leadership. It is the area where I put in the most time and effort almost daily. So, it caught me completely off guard one day when I got a message from one of my direct reports telling me they could "no longer work under this type of leadership." My world crumbled beneath me in that moment because the words came from someone I trusted. I knew the person was being honest, but it was a towering indictment against my very identity. I needed to hear the words, but I could only receive them because the other person was qualified to deliver them. The idea of friendship between leaders and followers is more complicated than it first appears. If you look a little deeper into the word "friend," what you discover is that "friend" can also mean "loved one," or more colloquially, someone who cares a great deal about you. This matters because it reframes the entire dynamic. The leader is not waiting for the relationship to be good enough to have hard conversations — the leader is the one responsible for building it. That means the onus falls entirely on the leader to develop and cultivate the right relationship and circumstances to allow the wounds to be not only given but received as the gift they are. So, do you want to grow your people? Then you must first love them. They must know it; they must understand it. Only then can your leadership be trusted, real change can begin, and your words will carry the weight of someone who can be trusted, landing as the gift they were always meant to be. Five-Minute Exercise: What is a hard conversation that I have been putting off? What relationships must I strengthen so that I can have the privilege to deliver difficult words when they are needed? Now Go Lead

  8. Sep 1

    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.

    Outsourcing Your Integrity

About

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!