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!

Now Go, Lead is a business podcast hosted by Brandon Pinkerton, with 40 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Brandon Pinkerton hosts Now Go, Lead, a business show with 40 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #88

  Those Wounds

  Sep 15, 20265 minS1

  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

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  Episode #89

  Process to Prepare

  Sep 15, 20266 minS1

  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.

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  Episode #89

  Outsourcing Your Integrity

  Sep 1, 20266 minS1

  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.

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  Episode #88

  Shallow Roots

  Aug 25, 20268 minS1

  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.

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  Episode #87

  The Other Option

  Aug 18, 20265 minS1

  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.

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