Define What Winning Looks Like to Improve Team Performance & Leadership Success

Welcome back to the show where we have real conversations about leadership growth and what it actually takes to rise to the next level in today's workplace. Our guest, Jackson Lynch of Talent Sherpa, has spent years working with CEOs, executive teams, and high-performing organizations, helping leaders understand why success isn't only driven by mindset, skill or ambition. It's also shaped by clarity, decision rights, accountability, and the architecture that supports performance. If you've ever stepped into a big role and felt like expectations were unclear, or you've wondered why talented people sometimes struggle to thrive, this conversation is going to challenge the way you think about leadership development. Stay with us.

Welcome to Shedding the Corporate Bitch, the podcast that transforms today's managers into tomorrow's powerhouse leaders. Your host Bernadette Boas, executive coach and author, brings you into a world where the corporate grind meets personal growth and success in each and every episode.

Jackson, how are you? Welcome.

It's so great to be here. Thanks for inviting me.

Oh, you are absolutely welcome, and I am grateful that you're here. I love these topics around leadership. I love these topics around how to handle rising, and not necessarily to the top, just getting on that next level and really ensuring that the leader has all the tools and all the resources and the mindset that they need in order to be successful, right?

Yeah, mindset's really important.

Yes. And we're gonna get into it because you've worked with so many CEOs and so many executive teams for years. What have you found to be the biggest misconception of leadership as someone goes from one position, middle, maybe middle manager, to a more senior role?

Yeah, I think this might be an unusual way of framing it. So give me a second to unpack it. But I actually think the biggest misconception is that leadership is about the person, not the system around them. And if you were to go back to W. Edwards Deming and take a look at some of the work that he did, he talked about a talent problem being 94% the system and 6% the person. And yet, in human capital and broadly across most businesses, we focus way more than 6% on the actual talent involved. And I think the architecture is below that. So that's where I try to focus in on with people that I work with and providing the mandate and understanding the clarity and focusing on that element of it. And I think that's an understated and under-referenced element of professional development is making sure you have the right architecture around you. Okay.

So for those, because we are talking about rising and what you need to arm yourself with in order to be successful, help our listeners and viewers understand what you mean by the architecture.

So in any particular role, as I'm looking for a new assignment, whether it's inside my current organization or as I'm looking more broadly into new organizations, We spend a lot of time, no matter the role, of defining what it is that I would be able to bring to the table. We spend a little bit less time talking with the hiring manager about what it is that they want us to deliver. We spend almost no time focusing in on how do we create the architecture around it. So what is the clarity in terms of outcomes of what those, what this job is supposed to do? And do you understand what winning really looks like? Can you talk about the 5 to 7 outcomes where if whoever's in that role does those things and only those things, that they would be considered successful? Do you understand the decision rights tied to the accountabilities that are with it? With people that I've worked with over the years, one of the biggest challenges you have is you have accountability, but you don't have decision rights that are linked to that level of accountability, which of course puts the person in a position where no matter how talented they are, they may not be in a position to thrive because there's a disconnect there and you're held accountable for things that are beyond your scope of impact. And then finally, I think one of the elements that is uniquely missing is the understanding of the boundary conditions within which people can operate. And what I have found over the years is The individual talent is important, but it's the architecture around that individual talent, which has a much higher degree of influence. So whether someone thrives or someone stubs their toe.

So you're talking about the architecture of leadership. Would that be a fair assessment?

I would even say it's closer to the role architecture because it starts with the clarity of the role that allows the leadership stuff to, to put within. For example, if you have a lot of very tactical folks in there, I'll use an example from our friends in finance. You can have a role that's in accounts payable. And one person is going to say, that role is all around collecting cash. That's a tactical-based role clarity. It's very limited. It's very narrow. And you know what you do. You don't know whether you do it well or what winning looks like. You have the same job and you can focus in on the efficiency of the cash collection process. You can put actual numbers against that. Now, what does that framing of the role clarity do for you? It tells you what the winning position looks like. You understand the conditions through which you're going to be seen as successful at role. It gives you a great deal of agency on what you do underneath of that. And you can in fact be in a position where even if you do the tasks, By defining it in terms of outcomes, you have increased the ability, the person's ability to win within a set of boundary conditions. We don't do that consistently throughout organizations. And then we say, oh, this talent, boy, they just didn't own their work. And yet, as leaders, we haven't defined what the winning outcome looks like in the majority of the cases.

Would you say that It's almost like a chicken and egg. Is that the accountability of the organization as a whole, or even that leader, that individual?

Yeah. So you should always start with what you can control. And so as a leader somewhere in the organization, I can't control anywhere outside of my accountability boundaries. And let me pause on even that word accountability. We talk about accountability a lot in leadership. I would argue it's usually after the fact, and it usually includes some sort of blame condition.

Yeah.

So as I work with folks, what I try to help them think through is how do we reframe that as reliability? So what's the impact of that? If you are focusing on reliability, you start asking questions, what must be true for this to work? It's very forward-looking. It is, again, you start thinking about the design architecture around the task or around the person. Accountability is almost always backwards looking. It's always, who screwed this up? Whose fault is this, right? So as you think more holistically about what a leader is delivered, is supposed to do, I would contend that the first order of business is to set the boundary conditions for winning and provide the clarity that allows everyone to know what winning looks like. And then you can start working on the tactical application of leadership within the context that's necessary. I believe 95% of the people come to work every day trying to do the absolute best job they can. And yet 7% of the workforce feels engaged. So what's the, what's the breakdown of that? I would argue that it is a matter of we haven't defined what winning looks like. And we haven't defined what winning looks like in terms of outcomes, which gives people the agency to own their stuff. And we're now entering this world with artificial intelligence where we have, we are starting to think about how do we automate tasks. But when AI hits fog, it scales the fog. In most of our organizations, from my view, at least, they're just sitting in fog. It's San Francisco Bay on a Saturday morning. You're not getting the plane to land. You can't see the runway. And yet now we're auto— now we're using speed and scale at a increased clip. I think it's gonna be challenging.

Because without even having that from the beginning, and we're not also— are you finding that we're not reskilling them with these more strategic, with these more, not necessarily leadership roles, but more so the mindset of impact and the business outcomes, then they will be lost.

1000% agree completely with that assessment. Let's maybe distill it into a real-life scenario. If I have defined, we'll come back to the accounts payable clerk. If I have defined winning for that person as doing cash collection activities, what leadership can I provide other than do the task? I might be able to describe doing the task faster. I could say, do it more effectively. I could talk about doing that task more reliably, consistent in terms of whatever that, But I am limited in what I can reach into my toolbox to deliver to build that employee up. On the flip side, if I am talking with an employee about the outcomes, I want to reduce the cash collection cycle. Now that person has the ability to come up with better ways of handling things. We can think about how we design the work, not just automating the work. We can think about in this kind of future world, what's the right labor model between human, agentic, and short-term intermittent work, project-based work. And now I have an entire portfolio of leadership things I can do that build up not only the output for what that person is bringing, but I can build up their skills that make them much more employable in this future world. I can't do that until I've defined outcomes rather than tasks.

And what have you seen to be the impact or the cost to a business if they don't do that? So we can make sure that our listeners and viewers understand why this is so important.

Where I think we are finding the real cost is not as much in the direct cost as in the opportunity cost. The opportunity cost of what we could be doing differently in the organization as a result of it. I'll give you a real-life example. I was working with a CEO recently, and he said, "I don't know really what to do with this talent stuff. What would be the one move that we could do that will radically transform the throughput of our business. I said, how many people can answer the question, I know what is expected of me at work? And there are two elements of that. And it's the old Gallup Q12 question, it's the first question they ask. One of them is, are my leader and I aligned on what good looks like? And the second piece is, are the people up and downstream from whatever process I'm a part of aligned with what my role in that process is? Historically, that number is unbelievably low. If you can put that where 80% of the people know what is expected of them at work, what do you think the outcome of the business is? And they're like, holy cow! That's the opportunity cost between what you're delivering today without clarity of outcome with what you can with clarity of outcome. And that is the most meaningful lever I think you can pull in a business today and oh, by the way, it has all of the benefits that come with better employees, more engaged employees, and all of those metrics where people can bring their whole selves to work. We can thrive. All the things that we would like to go do, but we can't do it until you've defined what winning looks like in a way that is beyond the task. Think about the accounts payable clerk in a world where all I have done is say, do cash collection. That job's going to be very replaceable if that's how I've defined it. You know why? Because I have not given that person the ability to think more broadly and define processes in a way that expands the scope and allows the intellectual horsepower of whoever's in that role, who knows it way better than anybody else. How can I allow myself to have a more meaningful impact on our broader organizational outcome. If I've done that poorly, I have created a role that is imminently replaceable with an agentic solution. However, it's the judgment, it's the discernment, it's the things beyond mere pattern recognition that will open up if you focus on the outcome. So as a result, I think the opportunity cost is you have jobs that sustain in this future world we're moving into, rather than being replaced with agentic solutions.

Opportunity loss.

Yeah.

Opportunity loss would hit harder for me than opportunity cost, but you're absolutely right. And, but I had to touch on what you were saying about accountability because we need it, right? And yet we need it to not be blame. So how do we change that? With our leaders? How do we get them to look at accountability differently and to execute accountability differently than what they do?

First off, the mirror— and I'm going to nudge on this just a little bit. So sorry if I get a little spicy on it. The here notion that accountability is something that a leader does to somebody else, I think is a challenged frame. And yet it's the most, it's the modal one. It's the one we talk about all the time.

That's fair.

I would argue that the most important thing a leader can do to drive accountability is provide the upfront clarity. And if we had leaders across the organizations that were good at providing that clarity, providing regular feedback against those expectations, and then hopefully with some help from their human capital partners, provide the right incentive structure with both positive and negative consequences relative to that performance. Life gets a ton easier. But accountability, what you're really looking for is ownership. And can you own a task easier than you can own an outcome? I think you can own an outcome easier. So then the question is, how do you design for that? And that's where I think focus on reliability versus accountability is better. Number 1, it's a lot less scary. Yes.

Yes. Yeah, certainly.

I want you to help me make sure that we are reliably doing delivering this outcome time after time.

Right.

What can get in the way? We can use red teams to say, OK, what's going to break if we do this? And let's go work on those solutions. You build the ownership of the output so much more easily when you're focused on the outcomes rather than the tasks.

Yeah.

And so I think that's ultimately, you focus on the design, what must be true for us to reliably execute, and it's a game changer. So I would do those two things to drive the leadership behaviors. Because I think those are upstream of everything else that we do.

So on that note, what is it that either the organization or the leader struggling with so much that they aren't taking that time to really understand their desired business outcomes, the boundaries, and getting that clarity communicated out downstream? So then we can see a major change in how they operate.

So I think there's, I love that question. I think there are two possible explanations. And I didn't, I'm not a scientist, but I have previously stayed at a Holiday Inn. So I'm going to lean on that skill set. The first is dopamine. We end up having a much stronger reaction to tasks than we, in the moment than we do outcomes in the future. And if you believe what I think we're starting to learn with social media and the impact that it has on the kind of internal bodily reward systems, we are fighting our chemistry by focusing too much on, on, on tasks. That's what we end up doing. The broader reason why we struggle with providing that upfront clarity is we just get so darn busy. And the reality is, as much as I want to do it for, provide appropriate leadership and set the organizational context and boundary conditions and clarity for my direct reports, I probably have to also negotiate that same set of standards with the people that I work for. Because life's busy. And especially in this public world, public company world, SMB has a whole different set of expectations around cash flow and runways that also create a very now boundary condition. What I found is when you can think and get the organization focused in on the things that are outcome-based and down the road as well, all of this becomes a little easier. But it's really hard when you're moving from crisis to crisis. You don't fully appreciate that you might also be an arsonist. I might be good at firefighting, but I might be the arsonist.

And that's a, that's a Fabulous analogy, and I'm gonna use it. And what percentage, let's just put some numbers to it, what percentage of leaders do you see are arsonists?

I think Gallup did a survey a couple years ago, and they broadly assessed the entirety of the US employment market and said roughly 10% of people have the innate skill to be good leaders.

Yeah. Oh yes.

So I'm gonna, I'll go with their number. It is very challenging because again, one of the things as you grow up in organizations, and I started on factory floor and I've been leaders in public companies. One of the things that you don't fully appreciate is the reward structure shifts as you move through organizations. And you get rewarded for task much more tactical performance earlier in your career. And then you end up being judged professionally as to whether you can get work done through others. And then ultimately, you get built around the purpose and building an organizational zeitgeist and architecture that allows the entire organization to thrive. Those are different skill sets, and you don't move from one to the next. You actually have to build, expand, build, expand, build, expand. And that is just a very challenging growth pattern to do. And sometimes we just promote people because they were good at the last job. We should be equally as good at saying, whoops, and moving it back where they can be successful and probably happier too.

At the same time, instead of having to say oops and moving them, moving them backwards, what should they be doing up upfront to ensure that person that they're putting into a different role, let alone a very influential role, is actually the right move for them?

Yeah, I love the question because I work with a lot of my clients on answering that very question. And the approach that I call it a talent portfolio optimization. Here's what it is. You would define what winning looks like for those roles in terms of outcomes. You then evaluate the individual relative to those outcomes if they are incumbent in it. And if that person can, and if you are in an organization that is growing, then you can look down the road 3 years, not much farther than that, because it's really hard to figure out what the world's gonna look like in 3 years. Might be hard to do it in 18 months at this point. But you then evaluate the incumbent relative to those outcomes. And if there are things that are gaps, then you have to ask yourself, do you have a gap? That I can close in the next 6 months? If so, great. If not, you should think about where I can reallocate that person inside the organization where they can thrive. And then the last thing that we end up working on is how do you sequence the changes? And what I would recommend is we think about a graph where you have high reward, low risk associated with making a change, all the way to low reward, high risk in making a change. And you sequence it out timing-wise. And so if you think about that broad portfolio approach to it, that is a performance lens that business hasn't really gotten. So think about it in, if you're a sports fan, if you have a, if you have a junior on the basketball team that is really good, but the freshman shows up and they are better. Who plays? The freshman. In business, the answer is we probably are going to wait for the junior to graduate and then we'll move somebody up. That's a problem.

That's a problem.

It's a business logic problem.

Because I love the whole sequencing. How early would you say should that be identified and implemented when it comes to, you said that talent progression, how, what should they be really thinking about and/or when they should be thinking about it?

So if I've done that work upfront, it opens up something that, that I don't think we do enough of. And that is to evaluate the person relative to the outcomes of the job we're considering them for. And if I have defined the outcomes clearly, and I can look, I can have a confidence level in which these 5 to 7 outcomes I can go deliver. And then candidly, we need to understand how fast I can make an adjustment if I need to. There may be things that I can do rather quickly. I can teach skills rather quickly. If it's cognitive or behavioral, it's, those are much longer time horizons. And it probably means we need to be either building that skill well in advance of making that adjustment, so you're just applying it in a different context. Or you have to say, I need to have a different sourcing system that brings in talent from the outside if I can't build that. Or I buy that talent much earlier, knowing that throughout my entire organizational career track, I'm going to have to have people who are, hypothetically, I just want to hire a lot more smart people than less smart people, because Smart people tend to outperform over time. It's actually one of the, the R-squared on that is much higher than almost any other evaluation that the companies do.

And so since we're talking about people and talent progression, how do, how should leaders be partnering with their HR or with the HR function to really ensure that, that the business is looking at business outcomes even as early on as looking at that talent pool and how they need to create that succession plan or progression plan going forward. What is that partnership that is needed?

So I've spent 25 years in human capital and I've grown up in it. And I'd like to think I'm OK at it. And I think we do it wrong. We apply it in a compliance way. And we should rethink about how we do that into a constraint way. So what do I mean by that? We think about processes and programs. And largely, largely, that's built because when HR people grew up, that was the area of their career that was very compliance-based. The higher you get in organizations, you're not a compliance person; you're an enterprise business operator. And not everyone makes that jump. So what could we do? If I'm a leader and I'm partnering with my HR community, I'm wanting to make sure we are both looking at the business outcome. And then we start looking at constraints. What is getting in the way? The good news is the HR team probably put a lot of those constraints in. So they ought to be pretty good at pulling them out as long as they have the appropriate mindset to it.

Right.

Succession planning, by the way, I'm going to be a little bit contrarian on that one too. I don't like succession planning outside of some very small number of critical roles, usually at the top of the house. Fair.

And here's why.

There's, there's no forcing function. I need to have something that says I must act as a result of this work. The amount of time we put in, Certainly, it would suggest that we're going to do something with this work. That's why I think the talent portfolio optimization makes more sense, which is asking a different question. It's not, what should I do if someone leaves? The right question is, how do I ensure I have the best possible people fit for the most important jobs that have an outsized impact on the business? And just doing that mental model flip, I think changes the way leaders are going to partner with their HR communities. And I hope that the HR folks are able to pull it forward.

And would you say that the majority of your clients have moved to that thinking? Because the succession planning was very traditional, very old-school traditional. And are they open? And do they see that to be strategic and to be impactful as the approach to take when it comes to their people.

Yeah.

And let's think about the base level assumptions around succession planning. I know what the job is supposed to do. I know the context in which it will happen. And I, and there's very little forecast inaccuracy on either. Now bounce that up against the way the world works today. We move too fast. And the fact that we have all of our processes around performance tied to an agrarian calendar is part of the challenge. And especially, sorry to go off on a tangent here, but especially as you have the incumbents who are growing up, coming into the organization today. I'm Generation X. What did that mean? I was raised on hose water and neglect, and I had to be home by dark. We just figured it out.

Right.

That and all of our systems are built around that. We'll talk to you twice a year. Look, I'm doing a great job and I'll give you feedback. These folks grew up on same-day shipping, instant shopping, likes on whatever social media platform they had. They're, we mocked them a little bit for disconnecting. That's us. That's a challenge of leadership. Because the system doesn't meet the moment. What my clients that are leaning towards this do is it changes the nature of the conversation. Most of my folks are at senior levels. It changes the conversations with the board because ultimately, the business wants to know, am I going to be able to execute the strategy? The question, what happens if someone leaves, is a part of that risk scenario. But it is a combination of what would, what's the likelihood of it happening and what's the magnitude of it happening. The magnitude would be high. The likelihood is low. So we should spend the majority of our time making sure we have the right people fit for the outcomes defined for the 5 to 10% of jobs that have an outsized impact on our organization. And that has an immediate forcing function to put the best people in a position to drive business performance. Performance. And I think where you put that in place, it changes the nature of enterprise altitude from a human capital perspective. But more importantly, it drives business outcomes at a level succession planning would never will.

Absolutely. Abs— and would you say too, that's how they're also going to get to a point where their team moves from just being busy and even themselves, from just being busy to being not only effective, that's nice, right? But impactful. They need to create impact, not just a checklist of things that they've accomplished in the day.

Yeah. And look, whether you're a human capital person or you're a business leader that has humans working for them, the work is the same. I tend to think the HR folks ought to be really good at this. And it ought to be our singular focus area because business leaders have other things to do with different timelines, horizons. What is that thing? We need to be able to look at the business through a talent lens, predict what's going to happen, identify the root cause, which is constraint-based modeling, and then prescribe what needs to happen to relax that constraint. And if we get really good at doing that from a human capital perspective, we will in fact unlock business. So what does that look like? I have an entire new product launch in the west part of the country. And my entire compensation plan supports care and feeding for my current products. Now identified a constraint. I've looked at that and said, unless I change the way I deliver rewards for my salespeople, I will kill my new product launch on the vine because the incentive structures have reverse gravity towards what I want them to be doing. Now, what do I go do about it? Root cause is the comp plan. And now I can prescribe some things that we can adjust. And that's where it's a lot more fun as a human capital leader to figure out what's the right way to engineer the architecture that drives the behaviors.

Yeah.

We don't do that very often. By the way, if we were to do that, We're in the upfront part of the process. We are in the design of the new product launch, not after the meeting where we're talking about how to implement the new product launch. And that is the critical point back to your partnership question. How do we pull these two groups together? Bring your human capital partners into the discussion and force them to have an opinion on the talent executability of what you're trying to do. If you really think about how to make a material impact on the business, it is to understand what is likely to happen, forcing someone to have that perspective in the design meeting, and including the relaxation of that constraint in the execution plan, not as a result of it. And more often than not today, the plan was never going to succeed because you never had a red team. Those are the ones that look at the, look at a strategy and say, why could this fail? And give them the permission structure to say, I think that's a bad idea and here's why. Or I think this, we believe this must be true for this to succeed, but I don't think it's true. And have that psychological safety that you can put that uncomfortable truth on the table and still feel like you belong to the team. There are things that we can build around that can increase our ability to deliver outcomes. But you've got to focus up front on the clarity and include the talent constraint as part of the work up front. And that is where you have high-altitude work that gets done, and it moves you beyond the busyness that you're talking about.

And it gives you sanity and some breath and some white space and just overall success, right?

Yeah. Nobody, nobody I don't know very many people that get overwhelmed because they know exactly what winning looks like. I know 1,000 people that are overwhelmed because they're working their tail off and they don't know whether they're winning.

And yeah, and they don't know why they're doing the work that they're doing.

Yeah, it's not connected to purpose. It's, it's—

Is there one thing, and maybe you just ended on it, But is, and if so, then just say so, but is there one thing that if our leaders listening and watching today ended this podcast and they went off to execute, what would you suggest they do?

This is gonna be really unpopular. I think they should audit their calendar. And when they think about where they spend their time, calendar is your strategy. What I have my clients do is I ask them to take a look whether they're talking about executing whether they're coordinating the execution, some might say managing the execution, and then whether they're changing the work. And in this world that is moving at an alarmingly high pace, it is finding time in your calendar that allows you to do the change of the work piece that will ultimately allow you to have an outsized impact on your organization. Most important thing is you're going through there is First step is to admit you have a problem. And then you have to do something about it, right? And understanding, once I've gone into my calendar, you got to be very disciplined about where you invest your time. Because as an executive, throughout the organization, but especially as an executive, it is the most valuable resource you have is where you're paying attention. And if you're in meetings that you don't have a unique perspective or decision authority to the meeting, Move out of that and start working, take that same time and reallocate it to something that moves the business forward by changing the work.

But that's a great focus. Let's get them focused on one thing that they could be doing. And that is a fantastic one is to audit your calendar. Fantastic. Jackson, this has been super. I want to mention to everyone, please check out the work that Jackson's doing. You could do that at mytalentsherpa.com. At the same time, LinkedIn with him. You can do that @jxnlynch. Is there anything in particular they could be looking for on your website to learn more?

Yeah, I think if you wanna dive deeper into how I think about these things, I put out a weekly Substack. We have 6,000+ folks that read it. And it just, I started writing it because it helped me think through things. So if you wanna see the musings of some of the things that human capital is at the orchestration level that's missing and wanna think about it systematically and how to improve business outputs, I encourage you to, to go read more about what we do there.

Fantastic. So go to mytalentsherpa.com and look for that Substack. Thank you so much, Jackson. This has been wonderful.

It's so much fun to be with you and I appreciate the invitation.

What a conversation, a powerhouse conversation. One of the biggest takeaways from today's episode is that leadership success isn't built in isolation. It's built through clarity, alignment, accountability, and creating the right environment for people to actually succeed. Jackson reminded us that even the most talented leaders can struggle when the system around them isn't designed to support performance. And that's a perspective that every organization needs to hear. If this episode gave you something valuable, make sure that you subscribe, follow, and share this episode with a colleague, manager, or leader in your network who needs to hear it. You can also find more leadership insights, episode clips, and full episodes on our YouTube Shed the Corporate Bitch TV channel, or go to ballofirecoaching.com/podcast. Thanks again for listening. And remember, great leadership isn't just about becoming better individually. It's about building systems where people can truly thrive. I'll see you next time.

Thank you for tuning in to today's episode of Shedding the Corporate Bitch. Every journey taken together is another step towards unleashing the powerhouse leader within you. Don't miss any of our weekly episodes. Subscribe to our podcast on Apple Podcasts, Spotify, or wherever you love to listen. And for those who thrive on visual content, catch us on our Shedding the Bitch YouTube channel. Want to dive deeper with Bernadette on becoming a powerhouse leader? Visit balloffirecoaching.com to learn more about how she helps professionals, HR executives, and team leaders elevate overall team performance. You've been listening to Shedding the Corporate Bitch with Bernadette Boas. Until next time, keep shedding, keep growing, and keep leading.