In this episode, Jackson Sprayberry, Anderson Williams, and Cynthia Hiskes kick off Season 2 of Raw Talent with one of the bluntest questions leaders face: when do you invest in the talent you have, and when is it time to move on? They explore why most leaders answer that question too quickly, driven by frustration or loyalty rather than real diagnosis. The conversation unpacks how high-growth environments amplify the pressure, why the “messy middle” performers are the hardest to evaluate, and how a lack of role clarity often masquerades as a people problem. The episode makes a clear case that this decision should never be a gut call. It depends on how critical the role is, how urgent the need is, and whether the person has the coachability to close the gap in time.

Introduction

Jackson Sprayberry: Welcome to Raw Talent, a podcast from Shore Capital Partners focused on the real work of developing people and building stronger organizations.

In this series, members of our talent development team have candid conversations about what it really takes to grow leaders and strengthen teams. Talent development is not just a program. It’s the everyday work of coaching, feedback, stretch opportunities, and accountability that shapes performance over time.

Each episode explores the real challenges companies face when developing people and the lessons learned along the way

All right, great.

Cynthia Hiskes: Let’s go.

Anderson Williams: Let’s do it.

Jackson Sprayberry: All right. Welcome to the second season of Raw Talent.

I’m excited to have two of my colleagues here. before we get them introduced, this second season is titled Build, Buy, or Both. I’m Jackson Sprayberry, I’m the Director of Talent Development here at Shore. and I’m here with Cynthia and Anderson.

Anderson Williams: You wanna start?

Cynthia Hiskes: I do. I do. I’m Cynthia Hiskus. I am the Head of the Human Capital Center of Excellence at Shore Capital Partners.

Anderson Williams: And I’m Anderson Williams. I lead talent development. I’m the Principal of Talent Development here at Shore Capital.

Jackson Sprayberry: All so we’re gonna start with one of the, bluntest questions that I think leaders grapple with, inside of, their business. when do you invest in the talent that you have? And when do you decide it’s actually just time to move on?

and the real issue that we’ve talked about, in preparation for this, is that most leaders answer that question too quickly. They answer that question before they have a firm grasp on what that diagnosis is.

Cynthia Hiskes: For sure.

Jackson Sprayberry: And maybe jump to conclusions.

So the honest answer to that question is based on what your diagnosis is.

Anderson Williams: Say, hang on a second.

Cynthia Hiskes: Absolutely. Yeah. Absolutely.

Why This Question Keeps Surfacing

Jackson Sprayberry: So let’s actually start with that. why is it that this question keeps surfacing for leaders in the first place?

Cynthia Hiskes: I think it surfaces for them, especially in our environment, because you need to make decisions quickly.

pressure to deliver results are there. And you also, just by the nature of our business, have a number of people on your team who you’ve been working with for a while. So you’ve seen them grow, and you’re looking to what’s next, and you’re not really sure if they are going to grow along with you or not, or what you may need to do to get them there.

Anderson Williams: And I think that sense of urgency and so many competing priorities, and often with, a new executive team or a first-time CEO, it’s hard to keep your eye on all the things. It… What you, sense or what you know is something’s not working the way you want it to work.

Cynthia Hiskes: Right.

Anderson Williams: And you tell somebody, and then it still doesn’t work the… and so it becomes this, almost emotional spiral that as you get more frustrated, you’re probably more likely to fire because of frustration, not because of any real analysis. It’s just the pressure of the, environment.

Cynthia Hiskes: Yep. Yep, which then gets back to slow down, pause, and understand why. what’s really happening?

diagnose the problem. is it the individual? are they, not a fit? Is it the environment around them? We, we don’t necessarily know until you pause and start to think about that and ask that question.

Jackson Sprayberry: And Anderson, you mentioned, y- you both touched on it, but most recently, that high-growth kind of environment.

That’s obviously one potential reason why leaders default to one side or the other. And when I say one side or the other, I just mean, loyalty, or development. or moving on, And so what are some other reasons why leaders default so quickly to either keep or move on?

Anderson Williams: I go back to that emotional response to things, right?

so in the loyalty conversation, people wanna generally be good to other people. And they wanna give them a chance, especially if they came up and had worked with them for a while, they know them, they know their family. All of that makes that loyalty, weight that much- heavier. and that loyalty is important, but when you think about your role as the CEO or as an executive and you’re thinking about building this business, you’ve gotta balance that with what the business needs, what is expected of you and your role, and that’s tough.

But loyalty is, feels a lot stronger than, the alternative, right? Like it, it’s, that the, thought of letting someone go who means something to you, or, even sometimes having a difficult conversation with somebody who means something to you, kinda outweighs the other things because of the emotional weight.

Cynthia Hiskes: Wholeheartedly agree. And what I have found to be really helpful when you’re in any kind of emotionally charged or human, dynamic, if you can take the emotion out of it and approach it in a more, methodical, systemic way and asking the question, and this is where you get to the diagnosis. you’re like, if, this has always been fine, what changed?

Did the person start doing something different or, not? And then what do I need them to do different, and did I tell them that they need to do something different?” so it helps you when you slow down and start asking those questions, really start to chip away, ’cause it’s usually not one thing, right?

It start to chip, you chip away at what the potential causes are, and then you address those one by one.

Jackson Sprayberry: Yes. and, that’s something I know we’re gonna get to, and we’re, it’s a tease a bit, but-

Cynthia Hiskes: Yes …

High-Growth Pressure on People Decisions

Jackson Sprayberry: A strong performance management system and cadence- should make this decision much easier.

It shouldn’t feel like it’s coming out of the blue. Let’s actually dig in a bit, though, on, on this high-growth environment- and the way that kind of changes the way we approach this. One thing that Shore often talks about is your business can’t grow faster than your people do.

Cynthia Hiskes: Sure.

Jackson Sprayberry: or y- if your business grows faster than your people, the business breaks.

Cynthia Hiskes: Yeah.

Jackson Sprayberry: How does that play out in the decisions and the way that leaders approach their talent?

Cynthia Hiskes: I think there’s a couple things. When you talk about what does someone need to do different or what does the business need now from a skill standpoint, I think that’s the question is- How quickly do you need someone to be able to do something different, and can they get there that c- that fast?

So when you, do I find someone else, or do I try to develop the person I have? I think a lot of the times it de- it depends upon how much time you have and how quickly can they, how quickly can then, can they change or perform. And two things to think about there. One, is it a skills gap that they have that they need to close?

How quickly can you get them the skills? And then the other question is, or is it a behavioral gap? Which are usually a little bit more difficult to change, for people. So I think that plays into the environment also is how quickly can you actually make it happen based upon what the environment needs.

Anderson Williams: Yeah. I think the other thing, and I know we’ll dig into this a little bit later in another episode, is that in the rapid growth environment, if we’re doing … If a business is really doing well, y- your job description is out of date by the time the ink dries, right? For sure. And so you have this mix of talent on your team, some of whom embrace and run into the void, that are your more entrepreneurial, they’re, naturally wired that way for whatever reason. They’re great early stage, what Shore calls athletes.

And so for those people, you don’t often have to rewrite the job description. They rewrite it for you, and then you write it based on their performance, just as these things. And in other cases, you’ve got somebody who’s a good, steady performer, but then when you start to evaluate their position or what their position needs now at three, four, 5X what that title was before, you’ve got to do the work to redefine the new standard.

Goes back to your conversation. I know we’ll d- dive more into performance management, but there’s the performance of the individual in a rapidly changing environment, and then there’s the evolution of the environment to set the expectation for the ind- individual.

Cynthia Hiskes: One other piece I think that plays into this is, the, individual is maybe performing, maybe not performing, so you’ll have that scenario. It … When you said you have the athlete that’s driving- driving and creating the job description as they are moving down the road, which that’s fantastic.

You usually just stay out of the way of those people, honestly, right? And then you have people who are N- maybe not even not performing, but behavior is just bad. And that’s easy to identify. So those two ends of the spectrum are easy to m- to manage. You know what to do. What’s hard is the ones that are in the middle.

Anderson Williams: Yeah. ‘

Cynthia Hiskes: Cause you’re like, I don’t know. are they gonna get there? Are they not gonna get there? What do I need to do different?” And, and I think that is something that also is amplified in our, environment- when things are moving quickly. Because those decisions don’t come just once a year.

They come, every quarter.

Anderson Williams: Yeah. With every

Jackson Sprayberry: add-on.

Cynthia Hiskes: Exa- Yeah.

Anderson Williams: Yeah …

Cynthia Hiskes: absolutely. Absolutely. and again. You’re like, “So let’s systemi- systemically solve it.”

Anderson Williams: Yeah. Yeah. The other wrinkle just to, to, since this is the first episode, I’ll just keep adding wrinkles and hopefully- … we’ll iron those out as we go on.

But, the other part about that, Jackson, and I think this is true in any environment, is perhaps more challenging in a hypergrowth environment. But let’s, say you’ve got a really good biz dev person, a really good salesperson. and they’re, they have with your company, your small company, been the chief and the only.

and they’ve largely operated independently, and they’ve built your business because they’re really good at doing that, and now you’ve grown, and you have a team, and they really suck at being a team member. So now in a rapid growth environment, you have the tension of the person who on one side has driven and can still drive a form of growth.

But on the other side is undermining what you’re actually trying to build. So which, which do you value and when? How can you rationalize, y- letting go or top grading your top salesperson because of the impact they’re having in not being able to build a scalable sales team?

That’s a, that’s just a difficult tension. when, there, when your performance, your financial performance is under a microscope.

The Founder Dynamic

Jackson Sprayberry: One thing that comes to mind is, that, founder dynamic, and I think that you, touched on it a bit. it’s a different slant though. another phrase that we often use is what got you here won’t get you there.

Cynthia Hiskes: Yeah.

Jackson Sprayberry: And so it’s this weird kind of, as you all have talked about, this tension of, they’ve done really well for the company as it was-

Cynthia Hiskes: but

Jackson Sprayberry: strategic leaders are looking one year out, two years out, three years out, and having to make these really tough calls initially-

Cynthia Hiskes: Yeah

Jackson Sprayberry: Do we keep this person or not?

Yeah And it’s that kind of messy middle.

Cynthia Hiskes: Absolutely, messy middle. and I really think this is where the, the diagnosing conversations can be super, super helpful. Because what got you here, let’s, say in most cases, CEOs are wearing multiple hats.

And now to get to there, there’s probably some focus that is required, or maybe there’s one place or a couple places where they’re more uniquely qualified to contribute.

Sometimes I think it really comes down to role clarity. So what is it that we need you to do, or the business needs you to do in order to carry us forward? And it’s not a matter of you, you got us here, but you’re not gonna get us there. But what gets us there is a little different version of you.

Performance Management and Clarity

Jackson Sprayberry: Let’s actually use that as a transition then to touch on performance management.

Cynthia Hiskes: Okay.

Jackson Sprayberry: Cause you brought it up, and I think there’s, this fine line between- Bringing new people on- and thinking about that. And then with those folks in the middle that you need maybe some time to figure out-

how does the performance management system or conversation shape the conversation a leader has when they have- to make that decision to move on or not? And what does that look like leading up to it?

Anderson Williams: I just think that the challenge goes back to something Cynthia’s already said, it’s clarity. And it’s hard to keep clarity in such rapid change.

but if you, get swept up by the current and don’t keep building that clarity, then you’re creating more noise and more chaos- and more difficult performance kinds of conversations. In this, environment, your, roles may be slightly out of date, but they shouldn’t be a lot out of date, or else it’s gonna be really har- hard to have these conversations.

You, you… even if it’s a founder or an executive from a company that has joined a larger Shore platform, clarifying how that founder, who’s done all the things- built a great business, is now clear in how they’re gonna contribute to the building of the platform, where they don’t have to do all of those things.

Is an important conversation. And if that convers- that simple conversation, that simple clarifying conversation, is overlooked, then you create grind and tension between, what, do you want me to do?”

Cynthia Hiskes: Absolutely.

Anderson Williams: “This has always been my thing. What do you want me to do now?” Yeah. And so I just come back to that.

Performance management to me, and I, again, I know we’ll start, we’ll dig into it even more, it’s, it starts with clarity.

Cynthia Hiskes: E- exactly. When you sit down with someone, you’re like, did you do what you were supposed to do?” “What was

I supposed to do?” Yes. Exactly. “I thought it was this, so I thought I’m great.” Yeah. “I didn’t know it was that.” Or it changed halfway along. But… And I think that is something, I hadn’t thought of this before, but is really important when we think about, I don’t know, the competencies of folks that we, or mindset competencies of folks that we’re, hiring in and bringing into the environment is your job is also about changing.

It’s about- Getting your thing done that you’re accountable for right now, but if you’re trying to get it so it isn’t gonna be different next month or the month after that, it’s not gonna… You’re not gonna be happy, ’cause that’s just part of the environment. So I think there’s a little bit of that, too, when we not only share expectations, but clarity around this is gonna continue to change and evolve, and if that’s not comfortable for you, it really may not be a good fit.

Jackson Sprayberry: All right, with that in mind, I, just wanna explicitly… I think we’ve hit on it, and I may have missed it. One of you may have said it explicitly already. But typically, a people problem starts as a leader or a system problem upstream somewhere.

Cynthia Hiskes: Yes.

Jackson Sprayberry: And so it’s our responsibility as leaders to make sure that we’re diagnosing that well.

and so the headline I’m taking away from this is that this decision on keeping or moving is never just a gut call.

Cynthia Hiskes: Never.

Jackson Sprayberry: It’s never just a gut call. It really depends on how critical is the role? How urgent is this? What is their coachability? What is the business need both now, and do we have the time?

It’s this triangulation of can I coach by when?

And if not, then what? The earlier that performance management system and conversation happens, the easier it is for these conversations to take place, and for a leader to move with more conviction- in, in the way that they move, i- instead of some sort of, last-minute, almost disciplinary conversation.

Cynthia Hiskes: Yeah.

Jackson Sprayberry: and so when you’re moving into a fast-moving business, we often don’t wanna slow down to do, a root cause analysis- for where our people are.

but that’s what we have to do, and that’s what we’re gonna talk about episode two.

Cynthia Hiskes: Excellent.

Jackson Sprayberry: Yeah.

Anderson Williams: Great.

Jackson Sprayberry: so we’re gonna slow this down in, in the next episode.

and before you decide that the person’s the problem, what else should we be looking at?

Anderson Williams: Cool.

Cynthia Hiskes: Sounds great. Fantastic. I’ll be ready.

Jackson Sprayberry: If you enjoyed this episode, check out other Raw Talent episodes at www.shorecp.university/podcasts or anywhere you get your podcasts. Here, you will find our Bigger. Stronger. Faster., Microcap Moments, and Everyday Heroes series, each highlighting the people and stories that make investing in the lower middle market unique.

This podcast was narrated by Jackson Sprayberry. Created and produced by Austin Johnson. Editing by PodHouse Productions.