The Decision Gap: Why Great Leaders Struggle To Decide

Episode 225 June 17, 2026 00:24:01
The Decision Gap: Why Great Leaders Struggle To Decide
Let's Be Diverse: Solutions for HR Leaders, Managers and the Workforce
The Decision Gap: Why Great Leaders Struggle To Decide

Jun 17 2026 | 00:24:01

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Hosted By

Andrew Stoute

Show Notes

In this episode, we explore The Decision Gap, the space between knowing what needs to happen and actually taking action. We dive into why capable leaders sometimes hesitate, overthink, seek perfect answers, or get stuck weighing every possible outcome. Our Guest today is Lindsay William.

If you would like to reach out or connect with Lindsay Williams:

linkedin.com/in/lindsay-williams-msw-lsw-72321571

Thank you again to our Sponsors Nicole Donnelly, with Hello Moxie, and Alexandra Bowden, Will Kruer with PEOPLEfirst Talent & Retention Consulting and The Wellness Universe Corporate, Erika R. Taylor Beck with Authentic Foundations, Ashley Cox with AshleyCox.co, Lauren Bencekovich with Lauren Recruiting Group LLC, Ari Degrote with Upward and Inward, Kaitlyn Rios with Faced With Grace, Jennfer Gomez with The Joyful Strategist, Melissa Marie Maltais and Melanie with ConnectHers + Co. Thank you all very much for your support.

Hi, I’m Andrew Stoute, host of Let’s Be Diverse, an HR podcast where I share motivational posts, insights on HR and leadership topics, and personal anecdotes. As an empathetic and innovative HR professional, my goal is to inspire like-minded individuals who believe that the workplace should be a safe place to succeed and grow. Together, let’s explore different perspectives and create meaningful conversation.

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Episode Transcript

[00:00:00] Speaker A: Before we dive in today's episode, I want to take a moment to share something that's been on my heart, something I've been working on behind the scenes [00:00:07] Speaker B: for a while now. [00:00:08] Speaker A: I'm officially writing a book. This book is called let's Be A Practical Guide to Leading Through Change. And it's deeply personal to me. It's built from real experiences. The uncertainty, the challenges, the moments where I didn't have the answers but had to lead. This isn't just a leadership book filled with theory. It's about navigating uncertainty when there's no clear direction, building internal clarity when everything around us feels unclear, having courageous conversations, [00:00:36] Speaker B: even when they're uncomfortable, and leading with [00:00:38] Speaker A: value, especially when it's the hardest to do so. I'm also going into topics that don't get talked about enough, like what it feels like to be challenged, overlooked, and even bullied as an adult in a workplace. And how those moments shape the kind [00:00:53] Speaker B: of leader you become. [00:00:55] Speaker A: This book is for anyone who's ever thought, how do I lead when I don't feel ready? How do I show up when I don't have all the answers? And how do I stay true to myself in environments that challenge me? If this is you, this book is for you. I'll be sharing more about the journey behind the scenes moments, and opportunities for you to be part of it as we go. So stay tuned, because this is more than just a book. It's a movement around how we lead through change together. All right, let's get to today's episode. [00:01:25] Speaker C: Opinions expressed in this episode are personal. They do not necessarily reflect the views of this streaming platform. [00:01:35] Speaker B: Good day, wonderful people. Welcome to another edition of let's Be Diverse. I am your host, Andrew Stout. This episode is dedicated to all my loved ones who've supported me through this journey. Those who have left us will always be in our hearts and will never be forgotten. Our topic today is the decision gap, why great leaders still struggle to decide. Our guest today is one extraordinary human. Her name is Lindsay Williams. Lindsay, welcome to the show, and thank you so much for joining us today. [00:02:04] Speaker D: Hi, Andrew. Thank you for having me. [00:02:06] Speaker B: Very welcome. What's been energizing you these days? Give us the tea, give us the deets. Give us it all. What's going on? [00:02:12] Speaker D: Yeah. What's energizing me? It's summertime. So summer is my favorite time of year. I am in Ohio, in the. In the United States. So we have all four seasons. But I love the summertime. Being able to get out during the Day in between clients and take walks with my dog. And we have four active kids. We actually have a swim meet we're going to tonight. So all, all of the fun summer activities. [00:02:37] Speaker B: Sounds amazing. Those swim meets are always so fun to be at. There's so much energy, so much excitement. The kids that are involved in it, they're just so into it and excited and they want to do well and they want to do well for their pool. So, yeah, it's super exciting, super cool. Well, I'm sure it's going to be a great time, so. Well, you'll have to let me know how, how the meat went today in the future conversation. [00:02:59] Speaker D: Yeah, we, we've got two good swimmers, my stepson and my stepdaughter. So they, they're little fish, they love the pool. So really excited to see them swim tonight. [00:03:07] Speaker B: That's awesome. Well, thanks so much for sharing that. And like I said, you'll have to let me know or let us know how the meets went for sure. Before we begin, I always have a fun, thought provoking question that I ask all my guests to get things going. Are you ready for yours today, Lindsay? [00:03:22] Speaker D: I am. [00:03:23] Speaker B: Okay, wonderful. So my question to you is, what is your definition of happiness? [00:03:28] Speaker D: Of happiness. My definition of happiness, honestly, for me it's freedom. I have been able through the work I do now to create freedom and flexibility in my life so that I can have amazing work, life balance. Family is very important to me as a mother of three of my own kids and three steps, three step kids, we've got four kids at home. Having that work life balance is so important and being able to have fulfillment and in both my career and my family life, that that makes me truly happy. [00:04:05] Speaker B: I love that. [00:04:06] Speaker A: I love that. [00:04:07] Speaker B: Such a great answer. And the freedom and flexibility, those words really stick with me because a lot of us are trying to do that. We're all learning to have freedom. We're looking to have flexibility in our personal and our professional lives. So when you can get that, I think it is absolutely the definition of happiness for sure. Well, thanks so much for having some fun with us to get us started here. Who are you and what really drives you to do the work that you do? [00:04:32] Speaker D: Yeah. Well, I'm Lindsay Williams. I am an msw, which means I have a master's degree in social work. I'm a licensed social worker, an ICF trained coach. I do some speaking and I'm the author of a book called the life you're allowed to want. For over 20 years, I worked in the Human services, child welfare space, over 10 years in leadership, leading teams, managing large systems, really helping people navigate change. And the second part of that was what drives me. What drives me is seeing how many people who are incredibly capable leaders, how they can feel stuck when they hit a major crossroads in their lives or in their career. And it's not always that they need more information. It's not always that they need, you know, another certification or a way to optimize their calendar. It's really that they need to get clarity, learn to trust themselves, and give themselves permission to make decision about that, really, I guess, align with the person that they're becoming. And so. So that's the work I get to do now. I left that corporate job about a year ago, and I work with people who are in that decision gap through my grounded pivot framework. And I get to. I get the privilege of doing that work every day with amazing people. [00:06:00] Speaker B: First off, I love what you just said at the end there. There's so many people that have said that, and I just love those words. I get to. And that's such a big mindset shift on that as far as, like, I want to or I have to instead of I get to. And that just motivates you and keeps you going for sure. And then the other thing that you mentioned, too, is the life you're allowed to want that stuck with me as well, Lindsay, because a lot of us are stuck, and I know we're going to talk about this, as this conversation goes, but a lot of us do feel stuck, and they don't know what to do or where to turn or who to talk to or who they can trust. You're absolutely right. There is a way out, and there is a way that you can figure stuff out. And you just have to, I think, have the passion and the want to do it. [00:06:47] Speaker D: Yeah. There's a calling. You get to a certain point in your career, and you have a calling to want to do more and have more impact. And, you know, like I said earlier when you asked me about the definition of happiness, it's really being able to have that time, freedom, and flexibility so that you can have true balance in your life. [00:07:07] Speaker B: Absolutely. So, Lindsay, when you hear the phrase the decision gap, why do great leaders still struggle to decide? And what does that decision gap actually look like in real leadership moments? [00:07:18] Speaker D: Yeah, sure. So the way I kind of frame the decision gap is that space between recognizing that something needs to change and feeling ready to act on that knowledge. And so for leaders, this can show up in A variety of different ways. Maybe if they are considering taking on a new role or leaving a, a role they've been in a while, maybe if they are considering restructuring their team, having a difficult conversation, setting some boundaries, delegation, all of those type of things could be a decision gap for those leaders. And what I find interesting is that a lot of times they know the answer intellectually, like something in them, they know. And so the struggle isn't always so much a lack of information. It's being able to do the emotional work and the identity work that's required to become the person that has the capacity to make that decision and hold [00:08:19] Speaker B: that decision, do the emotional work. I would like you to dig into that a little bit deeper here. Doing the emotional work. What does that look like? [00:08:27] Speaker D: Yeah, so many leaders might be carrying old beliefs. Like, you know, one belief that a lot of leaders will carry is, hey, I'm the leader. I have to have all the answers or I don't want to disappoint my team, or I don't want to disappoint, you know, my boss, or if I slow down and take time for myself and have balance in my life, then everything is going to fall apart. For a big one. And one that, you know, I personally struggled with for a long time was my value comes from how much I produce, from how much I do, how much I create. And those beliefs, you know, can cause people to hesitate on making the decision even when that path forward for them on some level is really clear. [00:09:12] Speaker B: I love that. Yes. And that totally makes sense to me. And when you say that they, they have old beliefs and that they, they should have all the answers, it's that uncertainty, I would say, as far as what to do, and I am seeing a lot more. Leaders are very uncertain as far as certain situations and what to do. And they're afraid to seek help or to ask for help because they don't want to seem like they are inferior, unable to do the job or to lead teams. So they're, they don't want to ask that question, when in reality it's probably better for them to ask that question and get the help because we're not going to know everything. So that's. Once we realize that, and once we get that in our noggins, that we're not going to know all the answers and we're not going to know everything, it's going to be so much easier for you, for sure. Yeah. [00:10:07] Speaker D: That's what I call leading in the gray. Because as leaders, you can't know Everything about everything. And sometimes you have to make decisions that aren't 100% black and white, that aren't crystal clear. And you have to be able to navigate with your staff and with your team in those gray places. And being able to do that is, I think, a true hallmark of a leader. Being able to take your team through that place of uncertainty, like you were saying, Andrew, and to the other side, even when you don't know what that outcome is going to look like at the moment. [00:10:43] Speaker B: How much of a struggle comes from overthinking versus a lack of trust in their own judgment or their team? [00:10:49] Speaker D: Yeah, I think oftentimes overthinking shows up as a symptom versus, you know, the root cause of the problem with leaders. So most of the leaders I work with, like, they're not lacking intelligence. Like, to be a leader, you. You are usually incredibly smart. The real issue is the trust, right? So a lot of times, leaders have spent their whole lives, their whole careers being rewarded for being the responsible, the capable, the prepared one, you know, the one that everybody can lean on. And so when they're faced with times of uncertainty, you know, they try to really think their way through that uncertainty, right? To think their way to certainty, to be logical. But being a leader often requires being able to make decisions without having perfect information, without having all the information. And so I think when leaders lose trust in themselves, you know, a lot of times they want to overcompensate by looking at the data again or seeking more data, seeking more opinions. Sometimes they'll delay action. And that can look like overthinking. Right. But underneath that is really maybe a fear of making the wrong decision. [00:12:03] Speaker B: That overthinking symptom, very interesting to me. I don't know about yourself, but in my past, in my career, I've felt that I've gone through the overthinking process of whether something was done and it didn't work out, and then you kind of overthink, well, maybe we should have done it this way. Or you get home and you're relaxing and you have this thought of, oh, I probably should have put this in that project, or I should have done it this way. And I know what I've learned through that process is once it's done, it's done. You can't go back. You can't turn back the clock on it. The one thing that I have been working on doing is making a little bit of a mental note to say, okay, this is what we did the last time, or this is What I wrote the last time or this is in this situation, this is what I did, what could I do the next time that's a little bit differently and that's kind of helped a lot, Lindsay. [00:12:56] Speaker D: Yeah, yeah, that makes sense. I mean, I think it really comes back to trusting yourself. Right. So the leaders who can navigate uncertainty the best, they aren't always the one that has the perfect answers, but they trust themselves to move forward before they have certainty. And you can always pivot. And you know, that's what I have always told teams that I'm like, we're making a decision, we're going this way, but I'm not too proud to pivot if, if we go down this path and we realize this isn't working for us. So I think it's really about that self trust and the over overthinking can be a symptom of that. [00:13:32] Speaker B: Yeah, the communication part is key there. Right. So as long as you have good communication between everything, everybody that's working on a particular project and you say, hey, this is, you know, why don't we, you know, do a little shift or to this. I thinking of doing it a little bit differently during the project and if you have that good communication, that's going to be easy to fix for sure. [00:13:54] Speaker D: Yeah, absolutely. I think I, I think that's why it's really important that the leader can navigate through that uncertainty. Because if not, you can kind of get bogged down in that and you can lose momentum on a pro a project, you know, so you're working along on a project, you don't know what the next right decision is. And so if you spin in that analysis paralysis for a while, then you're not moving forward. So, you know, you really need to, as a leader be able to say, I'm not sure if this is the right decision, but we're going to make this decision and we're going to go down this path and then if we [00:14:25] Speaker B: need to, we will pivot for sure. What does this gap cost teams in terms of momentum, morale, or even trust in leadership? [00:14:33] Speaker D: That is a great question. So I think this is really important because when you, when leaders have that indecision, it doesn't just impact the leader. Sometimes the leaders think, you know, this is just impacting my life, but really it ripples. It can ripple through the team, it can ripple through the organization and teams. I have found that teams and employees and staff, you know, they, they do a better job of being able to handle and manage a decision that they maybe don't love better than they can handle that prolonged uncertainty of kind of being in the gap. So I think when leaders get stuck in that place, it can slow down momentum. People will start creating their own narratives about what that means, and that can impact workplace culture. Anxiety can rise. And if you're a high performer, you're going to get frustrated because you know things are slowing down and you're like, come on, we just need to move. We just need to move. And so innovation can. Can decrease too, because people aren't willing to. To take risk if they don't think it's going to go anywhere. And it can also erode trust between a team. [00:15:42] Speaker B: Yeah, I definitely think that it can cause a ripple effect as well. When you think about the fact that when you're making these decisions and you're trying to put like, these processes or trying to get a project done, it can definitely have a ripple effect because I think that people are watching. You talked about it before. People are watching what the leader is doing. It's almost like the game followed a leader. You're following what they're doing. If they are easygoing, cool, calm, collective, then yeah, it's gonna be easy. But if there's chaos and you are acting in the chaos, everyone's gonna follow and they're gonna see that. They're gonna go, I wonder, you're not really good under pressure. How can we follow someone who is not? And I'm not saying that you have to be perfect, but I think we just have to be mindful of who is watching and what people are actually watching. [00:16:31] Speaker D: Yeah, and when you said you don't necessarily need to be perfect, I think you hit it right on the nose there, because teams don't need perfect leadership, but they need clear leadership. And one, I think, of the most overlooked costs, you know, when you're talking about that decision gap, is that teams end up carrying the weight of the leader's uncertainty. And that is when momentum can really slow. [00:16:55] Speaker B: How does diversity and inclusion show up in real decision making, not just in policy or intention, but in who actually gets heard when important choices are being made? [00:17:05] Speaker D: Yeah, that is a great question. So I really think inclusion needs to be a key part of decision making practice. It's easy for you to say, yes, we value diverse perspectives, but the harder question is, okay, so whose voices are influencing that final decision? Right. So a lot of times, if leaders are feeling stress, burnout under pressure, you know, they will default to listening to familiar voices or the loudest voices, because that's a human tendency so they might be listening to their own boss, they might be listening to the high performer on the team. And you can miss valuable perspectives when you do that. So truly, truly being able to create an inclusive decision making environment, it requires, it requires intentionality. It requires slowing down enough to create a space of psychological safety, which essentially means that you're creating the emotional comfort for people to be able to express opinions and make mistakes and challenge each other in a respectful, curious way. Right. So I think as leaders, when you're talking about making sure that you have diversity and inclusion in your decision making, like, you need to ask yourself, okay, who hasn't been part of this conversation? Who, who am I missing? Right. What perspectives am I missing from all of the information I have here? And who might experience this decision differently than I do? Because I think when leaders have the humility to recognize that their viewpoint is, is not everything, it's incomplete. Right. Then they can create that space, space for others to be able to contribute and that will give them a full picture of the decision that they are making. [00:18:55] Speaker B: And all the conversation I've been having, everyone is trying to get a seat at the table. And when you not don't let people have a seat at that table, you're going to lose their engagement and they're going to try to find another table to sit at. We don't want that. Especially if there's somebody who is innovative, creative, hard working. Like you said, we just don't know what their thought process are on certain things or ideas until we ask them. And if we ask them, we're going to be very surprised sometimes of what those people can come up with. But also I will say, if you're going to ask people stuff and they give their ideas, then there are some times that you're going to have to do some of those things that they're suggesting. We can't say no to people all the time because then you're going to lose the engagement fully because they're going to say, well, I've come to them with like 10 things and they've said no to every time, so why am I bothering? Right. We don't want them to just come to work and focus on their job and then leave. We want them to be involved in the company because they're going to be engaged and they're going to stay longer. [00:20:00] Speaker D: Yeah. I don't know if you've ever read any Daniel Pink, but he talks about autonomy, mastery and purpose and that employees will stay when they feel like they have autonomy in the roles they feel like they've mastered the roles and they feel like the roles are purposeful. And so when that bleeds into the decision making process. Right. So something, you know, I used to do a lot when people would come to me with an idea, I'd be like, hey, you know, let's flesh this out into a one or two page proposal. And then, you know, if it's something, if it's an idea that then they can be involved in and spearhead kind of what, you know, what they're coming to you with. Like I've had people that will come to me maybe with like a teaming idea or how to improve culture, you know, and so I'll say, okay, well, you know, put that together, get it all on paper for me. And then you give them the autonomy to kind of run with it and be a leader in their own right. And then that's when, you know, one, you're developing new leaders, but two, you're creating, you know, a culture where people feel safe to bring ideas forward and they know that their ideas are going to be recognized and valued. Yeah. [00:21:06] Speaker B: And not every idea is going to be great. There's some parts of it that would [00:21:09] Speaker A: work or some are, parts of it [00:21:10] Speaker B: are good and some parts of it that is not. So you're absolutely right. Coming to the, to the person and the leader and saying, hey, this idea. And then the leader would say, you know what, I do like some things or some things that I would reframe. So let's look at this, let's reframe this and then come back and see me once you've redone it all. So it kind of gives them a little bit of like, okay, well, you know, they're, they're listening. I just need to reframe it a little bit. [00:21:37] Speaker A: So. [00:21:37] Speaker B: And I think that would work as well. [00:21:39] Speaker D: Yeah, absolutely. Or what else do we need to consider here? Or how might this play out, you know, in the day to day, giving them those thought provoking questions so that they can come to their own conclusion. [00:21:50] Speaker B: Yeah. And what's the time constraints? What's the cost of it? How many people do we need to do that? Is this a single project? Do we need to grab people from the teams? These are all things we got to consider as well. But again, communication, having these conversations and being open to being, having those conversations as a leader are super important. [00:22:07] Speaker D: Yeah, absolutely. [00:22:08] Speaker B: Before we wrap up here today, what is one key takeaway that you'd like our listeners to remember from this episode? [00:22:14] Speaker D: I would say if you are a leader and you are struggling to make a decision. It doesn't, it doesn't automatically mean that you're confused. It usually means you're standing on the edge of growth. The decisions that matter the most rarely have to do with our intelligence. They rarely challenge our ability to accomplish the thing. But what they challenge is our identity. Right? So you gather the information, weighed options, but you still might be stuck. And so the next step isn't necessarily more analysis. It's it's really this. And so this would be my key takeaway. Ask yourself, who do I need to become in order to trust the answer that I already know. [00:23:08] Speaker B: So well said. I couldn't have said it any better there, Lindsay. My call to action would be to like, share and follow this episode. Lindsay, I want to take the time to thank you for coming on today. What I admire about you is your ability to connect, your ability to make people feel special, your strength, your energy and your passion. It has been an absolute pleasure to connect with you and to have you on as a guest today. Thank you so much for joining us. [00:23:34] Speaker D: Yes, it's been a pleasure to be part of your podcast, Andrew. I've really enjoyed it. [00:23:39] Speaker B: Thank you so much. On behalf of myself and my guest Lindsay, I'd like to thank you all for listening today and until next time, be safe. And remember everyone, that if we all work together, we can accomplish anything you [00:23:53] Speaker C: have been listening to let's Be Diverse with Andrew Stout to stay up to date with future content. Hit Subscribe.

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