Encore: When Bad Teams Happen to Great Leaders: Why Smart Executive Teams Underperform

Enjoy this encore release of an early season episode, that is just as valuable to listen to for a second time!

Strong leadership teams do not happen by accident. In this episode of Executiveland, Elizabeth Freedman focuses on why even smart, experienced senior leaders can find themselves on teams that underperform, and what it actually takes to build teams that deliver real enterprise value. 

With teams under extraordinary pressure in 2026, Elizabeth explains why old meeting habits, misaligned agendas, and unclear accountability are quietly eroding performance, engagement, and results.From rethinking team meetings as engines for decision making, to replacing low value updates with real dialogue, to designing agendas that create space for strategic thinking, this episode offers clear guidance for leaders who want better outcomes without adding more complexity. 

You’ll learn:

• Why leadership teams struggle even when individual leaders are strong
• How meeting design directly shapes team performance and accountability
• What separates productive dialogue from time wasting discussion
• How to prepare teams for decisions that actually stick after the meeting ends
• Why enterprise value, not activity, is the real measure of team effectiveness

This episode offers a clear, grounded approach to improving performance where it matters most, while within a team or leading one yourself. Tune in to learn how to strengthen your team, increase impact across the organization, and create a leadership environment that supports both results and careers.

For more tools, insights, and strategies to lead with clarity and credibility, visit Elizabeth’s website, take the C-Suite Readiness Assessment, and subscribe to Executiveland on  Apple Podcasts and Spotify and so you never miss a new chapter of the unwritten playbook!

• Free C-Suite Readiness Assessment
• Website: https://esuiteleader.com/
• Forbes Column: https://www.forbes.com/sites/elizabethfreedman/
• LinkedIn: https://www.linkedin.com/in/elizabethfreedman
• Twitter X: @‌esuiteleader

Transcript

SPEAKER_00 0:05

Hi, and welcome to Executive Land. I'm Elizabeth Friedman, and this is where top leaders go off script to share straight talk and the unwritten playbook about life in the C-Suite. For more ideas, visit East SuiteLeader.com. Now let's dive into today's episode. Hi, everybody. Welcome back to Executive Land. And today we're talking about one of my favorite chapters in the Unwritten Playbook, leadership teams. You know, you cannot have a great organization without great teams in it. Teams really are the backbone of great companies. And, you know, what I've learned after years of working with senior leaders and teams is that even very, very smart, talented, capable leaders can easily become part of teams that are not nearly as good as they could be. And why does this happen? I mean, I think teams are really just very complex systems. They're not simple things. And so being able to work well in a setting like that, it is not something that they teach in executive school. I just don't think most teams are really ever taught explicitly how to operate like a high-performing team. And so let's talk about that today. And what I want to share with you are the patterns that I have seen working with teams for really over a couple of decades. But, you know, something new that I'm seeing right now is that teams are really under extraordinary pressure in 2026. I am finding the teams I'm working with, they are being asked to do some very, very big things inside their companies. Things like driving a level of transformation that might take out billions in cost. I'm seeing teams needing to launch some must-succeed offerings and new nascent areas, let's say related to aspects of AI. I'm seeing leaders have to restructure major parts of organizations, really accelerate performance in the meantime while we've got a new leader and a new mandate. And I mean, I could go on, and you're probably thinking, yeah, but like, isn't that the job, Elizabeth? Isn't that what senior leadership is? And of course, yes, but that doesn't mean it's easy for teams, because I do see that teams are working hard to do these things in environments that just don't naturally create a lot of optimism. So, for example, I'm seeing a lot of tension between teams and their corporate leadership, where teams are saying things like, hey, you keep changing the goals, you're adding priorities, we don't have the resources to actually achieve these things. Teams will talk about the matrix structures they're in, the level of complexity that they add, and they'll say, you know, it's just impossible to get alignment and really get work done around here. And even within the teams themselves, you'll hear leaders talk about how they also are not necessarily aligned or unified, how they don't feel like they have the real conversation often enough. You know, nothing changes on the team. So it can feel rough for teams right now. And listen, if that's not your reality, I'm happy for you. I mean, that's a great thing. But, you know, just consider this might be the case for some of the folks you work with, other teams that you may be interacting with, and maybe it is true for others on your team. And so I want you to just start with a couple of obvious places to look if you're wondering about your own team. And the first place to begin, I always say, are your own leadership team meetings? I, you know, if you want to understand a company, its culture, just check out how teams have meetings. I'm talking about any kind of meeting, your weekly, touch-base, update meeting, the kinds of meetings where strategies get developed, where decisions are supposed to happen. You know, so again, you want to improve how a team leads or how a team communicates, improve the meetings. So, what I've found is that even really good teams can fall into some pretty predictable traps when it comes to their meetings. And when that happens, it's just so frustrating for teams. Like the conversations never get to the right level of dialogue. Teams leave without feeling like we have no clarity, we didn't make any decisions. And so the result for everybody feels like a big waste of time. And this is a common thing that I see. So I'm not just talking about your once-a-year big type of, I don't know, leadership team off-site. I'm talking about the kinds of meetings that teams have routinely. And so no wonder I'm hearing about these kinds of frustrations. And I have to tell you, I hear a lot about this from very senior leaders. They'll tell me how they're involved in team meetings where honestly they're virtual. These meetings are not engaging. Many leaders are multitasking, they're checking email, they're working on stuff, they're slacking their other team members, thinking, oh my God, like, can you believe what this person just said? And you and I know none of that is the kind of, shall I say, mature behavior we'd expect or want to see from a senior leader. But bad meetings drive teams crazy. They really do. And uh allow me to say, dear executive land listeners, not in any world would I want to lead a meeting like that. And certainly in the meetings I facilitate, those are not the kinds of experiences that certainly I create. But I want to tell you, right? Any team can quickly elevate in this area. You can absolutely go from good to great, or I would say great to amazing. It is possible. And so I want to share some ideas, whether you're on a team, you're leading a team that you can easily adopt. And these are the kinds of things that make a big, big difference in terms of the performance and really just the engagement you're gonna see across a leadership team, starting with idea number one. Really want you to be careful about any kind of meeting that is about team building. Now, I am not saying that team building is a negative thing and the kinds of things we associate with team building meetings, you know, growing trust, candor, they don't matter. They matter deeply. But the best teams do not get better by sitting around talking about trust. They get better when they work on real things together in a structured, guided, safe way. So instead of holding a meeting where maybe the goal is we're going to improve trust, make the goal, we're going to actually work on a real business challenge, something substantive, real things that make a material difference in our business. You know, we're going to work on things where we have to make real decisions and real trade-offs because what happens along the way when you do that? Trust actually is built. That's where things like trust, candor, accountability can improve. And it's not because you demanded it or you created some sort of contrived exercise around it. You actually built it through real work. Second idea I want you to consider when it comes to the way you and your team meet and interact is really think about your agenda in a strategic way because your agenda becomes really a mirror for the performance of the business, meaning what? You know, often agendas are copy and paste, right? We kind of repeat or recycle the same agenda or we overload our meeting agendas. We say, well, we don't meet often enough, we've got a lot to do, but we all know you try to do too much in too little time, what happens? We rush, we never get past a surface level of dialogue. And so the rule is, right, if you want to kill productivity, just try to do too much in a meeting. If you want strategic thinking and real outcomes, we have to create some space. We have to let the ideas in the dialogue be productive and breathe. So this is really fewer better in action. Fewer better, less is more when it comes to that agenda. But I want to say one thing. Yes, less is more, but I caution you against what I call over talking in the spirit of wanting to have a deeper conversation. I have to tell you, if you're a team that's worked with me, you know who you are, you know that at a certain point, chances are I'm going to interrupt you. I will cut off the conversation. Now, I really try to be gracious about this, but you know, there are always people on a team who really want to keep discussing an issue, even after we understand the problem, we've aligned on a solution, we're done discussing. And you know, on senior teams, this happens a lot because we all want to say, and leaders want their voices heard. But you know what? Leaders also want to weigh in on and influence other people's decisions. But you know what? Sometimes on a team you don't get to weigh in. Sometimes you have to trust the other people on your team to make decisions that best serve the team, and you just got to move on. The third idea: great meetings require great preparation, but I see a lot of prep that we do for meetings is wasted. Now, I'm talking in particular about maybe your less frequent meetings where we spend a lot of time building pre-read materials that may or may not get read by members of the team. Maybe they'll skim them. And it's not because people don't care, but you know, team, team members are overloaded. You are too, probably. And you know what happens is we get a lot of information from our colleagues, but people aren't clear about what is the purpose of this pre-read. How does the information in the preread connect to what we're trying to accomplish in the meeting? So, what actually matters here? And you know, because that doesn't happen, because we really don't absorb or retain those prereads, so many meetings start with are you ready? A retelling of the preread. It's so ridiculous. I mean, we have to ask ourselves, why do we even bother with pre-reads at all if we're just going to review them again in the meeting? So make that preparation purposeful. I always like to say reward the right kind of activity in advance of a meeting, not necessarily a lot of pre-read material. One more aspect of how we prepare for a good meeting is we collect the right type of information and data in advance. And when it comes to team performance, we have to collect that kind of information because even good teams have blind spots. And the best teams always take time to evaluate their own performance. But the mistake that I often see, teams evaluate themselves without that outside in perspective. Because, you know, getting the team to think about, hey, what's our trust like on the team? How are we communicating? How do we handle conflict? That's important. But honestly, I think we're missing the point. The point is that if you're on a leadership team at a senior level, you exist to serve the company and create value for your company. I mean, that's the that's the reality. And so part of the pre-work has to be about assessing the degree to which the team is in fact creating and delivering that value. So when we look at collecting data on the team, it's not just does this team believe they communicate well with each other? We have to look at is this team actually producing results? Did they achieve the commitments that they signed on to? What does the CEO think about this team's performance? What do stakeholders have to say? So if you're gonna meet and you're gonna evaluate your performance, your work in any way, assess that performance through the lens of value, and then bring that data into the meeting and of course share and discuss it together. Idea number four, when we talk about meetings, and remember, meetings are where we create teams. We've got to be able to get to the right level of dialogue. And that means, one of my pet peeves, is we cannot have reporting out and updating meetings. We've got to eliminate those or do our best to minimize updating. Why? It's just such low value. If all we're going to do in a meeting is update each other on what we're working on, we don't need a meeting. Just email me. Right? So that updating environment creates really a passive culture. It allows for you to have a team that has a lot of passengers where we just spend time sort of engaging with each other, talking about what we're working on, talking about activity, and really that's not important. It's how that activity translates into performance, value, and results. Senior teams are really there to debate, to discuss, to make decisions. That's really what they're there to do. And then finally, when we talk about helping teams, we have to not just create a great meeting, great agenda, strong dialogue, thoughtful, insightful pre-reads, but really we have to think about what happens after that meeting too. And so I want to suggest you think about your off-ramp. Create an off-ramp. You know, one of the biggest reasons why I see teams struggle with accountability and sustaining commitments is what happens? A team has a good meeting. And then, you know, it's just back to work, real life hits. And so we have these sort of abrupt transitions. And so all of that good work, those decisions, those commitments that we made in the meeting might evaporate. At a minimum, they're certainly difficult to sustain because there's no off-ramp or structure when it comes to implementation. And actually, we need to start to build that off-ramp, of course, while we're still in the room. And I think this goes beyond just deciding, hey, what are the actions we're going to take after this meeting? That's fine. But for instance, if you're going to create a strategic plan, it's not just about agreeing to it or agreeing to a set of activities. I always like to say start pressure testing that plan when you're in the room. Practice selling it, run a mock QA with each other, right? Really kind of put each other in the hot seat. And yes, of course, build that simple, that practical 30, 60, 90-day plan. Yes, with owners, with timing, with a measure, but also, right, who are you going to have to communicate this plan with? You know, what does that kind of rollout or engagement look at? All of these things are aspects of an off-ramp plan that you can create so that you can sustain progress. Now, look, we all know if you're on a great team, it makes a huge difference, not just in the performance of a company, but in your own career. It's really one of the biggest reasons that keep people in roles and that they say creates the most happiness for them at work. It's those relationships. And that's why companies simply can't leave team performance to chance. I mean, the do-it-yourself teams will figure it out approach, it's such a waste and it leaves money on the table. And then, of course, organizations can be surprised when not a lot changes when it comes to team performance. So I want to give you just a couple of other things to think about. When you think about simple things that you can do to make your own experience on a team even better, first thing, and I want to go back to everything we've been saying, you've got to evaluate your meetings, the meetings that you sit in and the meetings that you're part of. And for those of you that are leading meetings routinely, again, I just want to ask you, are they effective in the ways we've been discussing? If you work with me, you know I love the term car wash. As in, give your meetings a car wash, clean them up, get rid of the meetings where no one's showing up prepared or where everybody's checked out in multitasking, change the format, create more accountability, leverage information, data pre-work differently. So this leads to a more productive conversation and ultimately better outcomes. The other thing I want to say is if you're on a high-performing team, you really have to think about the impact to the company. What is the enterprise impact that you're having? Many of you know I teach a course called E-Suite Impact, and we spend a lot of time talking about this idea because it's easy to be on a team where you're generating ideas, you're looking at activities that serve your team, your business unit, but not necessarily the broader company. And, you know, this makes a lot of sense because teams are expected to produce results, you know, and so they have to really be thoughtful about what are the things we're gonna do to achieve those results. But, you know, I've worked with the team, you know, who needed his organization, a leader, to really come up with the types of strategic imperatives that are gonna create enterprise value. And so the leader asked the team to create this, and the team came back with a list, but a lot of these initiatives weren't enterprise priorities. So the leader asked a question. He said, you know, what would the CEO say about where you're focusing our time, our energy, and resources? You know, if the CEO looked at this plan, would that CEO say, yeah, this is this is exactly what we need right now? Would they say, I can see how these actions are going to create value for us? Or would they say, why are you spending time on this? Last point I want to make is that sometimes, and maybe you've been there, you're on a team, and the team is struggling. And it's not because necessarily the team is weak, but maybe the conditions are weak. And by that I mean the leader of the team. The biggest factor, you know, connected to the performance of the team is the leader of the team. And sometimes you might have a leader who is indecisive, who may not be experienced at this level. Maybe this team is bringing in some legacy behaviors that don't work on the team. Maybe they're not assimilating well, they're not respected by the team. But you know, you might have one or two members of the team who have been around forever. They've been in the same role for ages, and maybe they resist new ideas. They're not including maybe new ways of thinking. And so all to say no team is perfect. As I said before, teams have blind spots, and so the best teams always take time to take a step back. They get input so they can take an objective look at their own performance and really have the courageous conversations. And so, if you're on a team, I gotta tell you, this is just so important because the organization is only as strong as the team that's leading it. And so I want to encourage you to make sure that you're regularly taking a step back, whether you're a member of a team or you're leading a team, and really listen to that feedback. Be willing to hear it and make changes to improve your performance and your leadership. Because, you know, I have to tell you, the best leaders I've worked with, they really do have the best teams. It just does not happen by accident, though. Great teams don't just happen on their own. I find the leaders that are leading them, they're not waiting. They're not waiting for the right time. They really build a great team and they build it often before they even need it. So I want to encourage you to really improve your team experience in 2026. Support the team you have. And by the way, get a team that's gonna support you too, not just inside your organization, but a strong external team, a team of people that care about your success, mentors, coaches, advisors. And if I can support your success and be a member of your team, I'd love to do it. And so with that, I want to encourage you to go visit me online, see how I work with leaders and teams. And if you're at a senior level, you're stepping into the C suite soon, and you want to test your own readiness for what 2026 is going to demand of you. I want to encourage you to take my C suite readiness. Assessment. It's quick, it's practical, and it's going to give you a lot of clarity right now on where you're strong, maybe where you have some opportunities to improve and what to focus on next to increase your own performance over your team and over your own impact. You'll find it linked in the show notes. Thanks for listening, everyone. I'll see you next time in Executive Land. Well, that's all for today in Executive Land. Thanks for listening. And if you're looking for more, check out my website, esweetleader.com, where you'll see all kinds of free resources and take the free executive readiness assessment. It shows you exactly where you're strong and where to focus next in your own leadership. And don't forget, subscribe to this podcast so you never miss an episode. I'll see you next time in Executive Land.