When Does Giving Someone Another Chance Become a Failure of Leadership?

Most leaders have been in one of these moments. You've caught yourself thinking something you'd never say out loud. You've sat across from someone who was crying and had no idea what to do with that. You've kept giving someone more time because you cared about them. You've backed out of a commitment you'd already made, and felt guilty about it even though it was the right call. These aren't the big, dramatic leadership failures. They're the quiet ones. The ones that happen in real time, with real people, when nobody's watching and there's no playbook for what comes next. This compilation pulls together five moments from past episodes that keep coming up in the conversations I'm having with other leaders. My new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Most leaders have been in this situation. You made your case, you pushed back, and then the decision went another way. Now you've got a team looking at you trying to figure out what you think. What happens next is where it gets hard. When you leave the meeting and find someone who agrees with you. When part of you is quietly hoping the decision fails so you can say you were right. When someone asks you directly and you say “well, I didn't agree with it, but that's what they decided”. That moment is one of the more expensive moves you can make as a leader. This episode is about what you do with a decision once it's been made, and why that part is harder and more important than the debate that came before it. My new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Most leaders I know have someone on their team right now that they know is not working out. I just went through this. And the reason I recorded this episode is because I think we talk about accountability in the abstract far more than we talk about what it actually feels like to sit with a decision you know you need to make but keep not making. I cared about this person. I believed in them. I kept giving it more time. And while I was doing that, other people on my team were quietly absorbing the consequences — fixing mistakes, picking up work that wasn't theirs, and watching me not deal with something they could all see clearly. That's where this one started for me. Not with a framework for accountability. With the specific discomfort of realizing that my compassion toward one person had a real cost for everyone else, and that I'd been calling it leadership when part of it was just avoidance. The episode works through the questions I ask myself to tell the difference: am I still trying to understand this situation, or am I looking for another reason not to do what I already know needs to happen? Where has my belief in someone started interfering with my ability to see what's actually there? And who's absorbing the cost of my hesitation while I figure it out? I don't have a clean answer. But I do have a question I try to end with: where are you waiting for more evidence because you don't like what the evidence you already have is asking you to do? My new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

My company is being hit right now. A war in Iran is affecting oil prices, customer behavior is shifting, and my employees are asking me questions I do not have answers to. How long will this last? Are there going to be more changes? Am I going to be okay? That last one is the one underneath all the others. And as the CEO, people expect me to have the answer. What I keep wrestling with is how easy it is to slide from optimism into false reassurance. You want your people to sleep at night. You want them focused on their work, not sitting in anxiety. And so you say things you are not fully certain of, and eventually you have made a promise reality may not allow you to keep. I have done this. I am talking about it because I think most leaders have, and the pressure to perform certainty is real and almost never discussed honestly. What has helped me is a distinction I keep coming back to. Certainty says I know what is going to happen. Confidence says whatever happens, we will face reality and respond to it. The first one I cannot offer my team right now. The second one I can. And that, I think, is what talking with trust actually looks like when there is no clean answer. Just telling the truth about what you know, what you do not know, and what you will do when things change. My new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Something I keep seeing in my company, in the situations leaders bring to me, and honestly in my own life, is that the argument on the surface is almost never the actual conflict. Someone gets left out of a meeting and suddenly they are furious. Someone's idea gets overruled and now there is tension that feels personal. Someone misses a commitment and now they cannot be trusted with anything. None of those responses are really about the original event. They are about what the person decided the event meant. I caught myself in this not long ago. Someone questioned a decision I made, and I had a thought I would not say out loud: I'm the CEO. Just do what I say. I did not act on it. But that instinct was real, and it was useful information, not about the other person, but about me. About what I was afraid would happen if I lost control of that situation. That is what this episode is about. Not conflict resolution as a skill set, but conflict as information. What does it reveal about what you are protecting? Underneath most emotionally charged conflict, I have found a threat to one of three things, control, trust, or respect. Sometimes all three at once, stacking on top of each other until what started as a simple disagreement feels like a personal attack. My new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Something I keep seeing in my own company, in conversations with leaders I know, and honestly in my own life is that almost every conflict has the same thing underneath it. Someone needs to be right. Not because the facts require it. Because something in their identity requires it. I had an employee recently who was frustrated that he was not being heard. And the more I watched how he showed up in meetings, the more I could see that his need to be right was the very thing making people stop listening to him. He would get angry, people would pull back, he would get disinvited to meetings, and then feel even less heard. A loop. Not caused by the people around him. Caused by the question he was never asking himself: do I want to be right, or do I want influence? That question is what this episode is about. Not as a simple call to be agreeable or let things go. There are facts worth defending, values worth holding, positions worth taking. But before any of that, there is a more honest question: what am I actually trying to accomplish here? Kerry’s new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Kerry has been making high-stakes decisions and leading people through difficult situations for years. And even when she considers herself open to feedback and emotionally grounded, there are still moments when something hits a nerve and she can feel herself defending against things that have not even been said. That moment happened the same day Kerry recorded this episode. And it became the starting point for a deeper conversation about what emotional intelligence actually looks like under pressure. Not as an abstract leadership concept, but in the seconds after something triggers you. Kerry explores what happens when leaders misread comments, react to stories they have created, or let their emotions take over the conversation. Because when a leader cannot manage themselves, their team starts managing them instead. Kerry’s new book, Talk With Trust, is now available: https://a.co/d/05mNRnJH To learn more, visit http://kerrysiggins.com Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

In her twenties, Kerry was struggling in a sales role when her manager sat her down and told her she was not getting in front of the right people. He asked her to come back with a plan. Her immediate reaction was: she already knew that was the problem. What she did not know was how to solve it. Rather than asking questions, understanding what she had already tried, or offering support, her manager handed the problem back to her without helping her build the skills or confidence to work through it. Already navigating a difficult period in her life, Kerry left that conversation feeling more discouraged than before, and eventually decided to leave the company. Years later, she found herself repeating that same pattern with the person who is now her COO. When he came to her with questions, she responded by asking why he was asking her to do his job for him. He had the experience to find his way, but Kerry realized she had not helped him think through the challenge. She had simply handed the problem back instead of creating a path forward. In this episode, the fifth installment of a six-part series on the SHARES model, Kerry explores the “E”: Endorse a Path Forward. Endorsing a path forward is not about solving someone else’s problem or giving them an answer disguised as collaboration. It is about creating enough clarity and support for someone to take ownership of the next step. To learn more, visit http://kerrysiggins.com Her new book, Talk With Trust, is available for pre-order now. Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Kerry runs a company. People are constantly reading into things she does: a look she gives in a meeting, a question she asks, even her silence. And most of the time, what they conclude has nothing to do with what she was actually thinking. Kerry has learned over many years of leading that the most damaging relationship problems inside an organization rarely start with bad intentions. They start with a story someone told themselves that nobody ever thought to check. This episode covers the R in the SHARES model: Reflect with Questions and Dialogue. It follows directly from last week, when Kerry talked about articulating your experience. That step says: Here is what I experienced. This one says: Now help me understand what you experienced. Without that second part, articulating your experience becomes a speech. And nobody wants to receive feedback as a speech. The most important relationship problems do not start with bad intentions. They start with stories we told ourselves that we never bothered to check. And dialogue is the only thing that interrupts those stories before they become someone's reality. To learn more, visit http://kerrysiggins.com Her new book, Talk With Trust, is available for pre-order now. Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins

Most leaders assume that when someone gets defensive during a feedback conversation, it means they cannot handle feedback. Kerry used to think that too. Years of leading as a CEO have taught her that defensiveness almost always has the same cause. The person sitting across from you has just been handed a conclusion about their intentions instead of a description of what you actually experienced. Those are two very different things to receive. Kerry is not sharing this as someone observing leadership from the outside. She runs a company and has these conversations every week, sometimes in situations where she does not know walking in whether someone will still have a job when the conversation ends. This is work she lives every day, not just something she teaches. In this third installment of the SHARES series, Kerry explores the A: Articulate Your Experience. She also shares a story about someone who repeatedly canceled meetings with her and the assumptions she built around why it was happening. What she discovered was a powerful reminder for every leader: your experience can be real while your interpretation can still be wrong. When you stop presenting your assumptions as facts, you create space for curiosity, understanding, and trust. Because that is where better leadership conversations begin. To learn more, visit http://kerrysiggins.com Her new book, Talk With Trust, is available for pre-order now. Let’s connect on LinkedIn, Instagram, or TikTok! LinkedIn: https://www.linkedin.com/in/kerry-siggins-166b66/ Instagram: https://www.instagram.com/kerry.siggins/ TikTok:https://www.tiktok.com/@kerry.siggins