Skill, Will, or System? Diagnosing Underperformance in Customer Success

In this episode, we’re tackling one of the toughest challenges Customer Success leaders face: underperformance. When a team member isn’t meeting expectations, it can be hard to pinpoint the root cause. Is it a skill gap? A motivation issue? Or is the system itself setting them up for failure?

You’ll learn:
 ✔ How to diagnose whether the issue is skill, will, or system
 ✔ Why the traditional “skill and will” framework falls short in CS
 ✔ How to evaluate if your team’s underperformance is linked to organizational or process issues
 ✔ How to handle underperformance without jumping to conclusions or making assumptions

Whether you’re facing challenges with your team’s performance or you’re looking for tools to help guide those tough conversations, this episode provides a clear framework to help you lead with clarity, empathy, and intention.

Ways I Can Help You Level Up Customer Success:

1. Value Realization Framework Online Course:  Install a repeatable system your team can run: deliver value, prove outcomes, and drive retention and expansion. Self-paced with ready-to-use templates. Learn more.
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3. 1:1 Coaching: Hands-on guidance to roll out value realization in your org. Book a free consult call.

For more information, visit my website: Explore more resources and insights. CS RevSpeak

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Until next time, keep driving success and speaking the language of revenue!

Transcript

Angeline Gavino 0:40

As custom success leaders, we've all come across team members who are underperforming. Maybe they're not hitting their KPIs, they're not showing up how we expected, they're not making the impact we need. And as a people leader, it's one of the toughest challenges to navigate. Because underperformance isn't always about someone being bad at their job. More often than not, it's a signal, a symptom, something deeper we need to unpack. That's what we're talking about today: how to diagnose underperformance. Because if you misdiagnose the problem, you're going to prescribe the wrong solution. And that's where trust erodes, motivation drops, and performance issues linger longer than they need to. Let's dive in. Welcome to the CS RevSpeak Podcast, where we talk about practical insights, strategies, and frameworks that will help customer success leaders who carry a revenue number, drive sustainable growth, maximize customer lifetime value, and crush their numbers. So let's start by talking about the classic skill and will framework. This model has been around since the 1970s. It was popularized by Max Landsberg and his coaching work and became widely adopted in leadership circles through his book, The Tau of Coaching, in the mid-1990s. The idea is pretty straightforward. If someone's underperforming, you ask yourself two questions. Do they have the skill and do they have the will? And it makes sense, right? Skill is about whether they have the knowledge, the experience, or the technical ability to do the job. Will is about whether they're motivated. Do they care? Are they brought in? If someone has the skill but not the will, you're likely dealing with an attitude, burnout, or engagement issue. If they have the will but not the skill, that's a coaching moment. Maybe they're new or they haven't been properly trained. It's been a useful tool for decades because it gives managers a quick mental model to understand why someone isn't performing. And in a lot of cases, it works. It gives you a path forward. Do I need to train them, inspire them, move them into a better fitting role? But here's the thing, and this is where I started to feel the gap as a customer success leader. The skill will model assumes that performance is purely an individual thing. It assumes that the issue lives entirely within the person. But in customer success, that's really true. CS doesn't operate in a vacuum. It's one of the most interconnected, cross-functional roles in the business. I've had high-skill, high-wheel CSMs who were still struggling, not because they were doing anything wrong, but because the system around them was broken. The processes didn't make sense. The tech stack created more work than it solved. They were spread across way too many accounts, or the expectations weren't clear, or they were constantly pulled into last-minute fire drills. And that's when it hit me. There's a third element missing from the traditional model, the system. Because if your team is operating inside a chaotic or unclear system, even your top performers will start to falter. Scale and will matter, but without the right system, which means the right structure, tools, and support, is just not enough. So in today's episode, we're going to reframe how you look at underperformance. We're going to talk about skill, will, and system. And more importantly, how to know which one is actually the root cause so you can solve the right problem instead of just guessing. Let's dive into the first one, skill. When someone in your team isn't performing the way you expect, it's easy to assume is a motivation issue. But more often than not, it's actually a skill gap. And I don't just mean product knowledge or technical expertise. Although, of course, those matter too. I'm talking about the full range of competencies needed to be successful in a customer success role. Think about it. CS is a complex job. A great CSM needs to know how to manage customers, run strategic conversations, handle tricky escalations, understand renewal mechanics, drive adoption, tell a compelling value story, align stakeholders internally, and sometimes even debug scripts or talk API integrations, right? That's a wide spectrum. So when I say skill gap, I don't mean incompetence. I mean that person may be missing a specific skill that's critical for this role right now at this stage of the company. Here's an example. I once had a CSM who was great at building relationships. Customers love them, but they weren't confident in renewal conversations. They tiptoed around commercial topics and deferred everything to the AM, even when it was within their scope. At first glance, it looked like a motivation issue. But when we dug deeper, I realized they'd never been coached or trained on how to lead a commercial conversation. No one had shown them how to position value or speak to business outcomes. So it wasn't a will problem, it was a skill problem. So how do you diagnose it? You observe, you listen to their calls, you read their notes, you look at how they prep for a customer meeting or respond to an escalation. You get curious. Are they struggling with discovery? Do they default to feature dumping? Are they avoiding certain types of conversations? That's where the clues are. And here's the key. When you're diagnosing skill, you have to be specific. Vague feedback, like you're not strategic enough, or they need to step up, doesn't really help anyone. What exactly are they doing or not doing that's holding them back? Because once you know that, you can coach to it. You can give them training, shadowing, templates, feedback, you can create a plan. But if you skip the step, or worse, assume it's a motivation issue, you risk losing a great person simply because they didn't get the support they needed to level up a skill. Okay, let's talk about what happens when the issue isn't skill, but will. This is the one that gets tricky because it's less about what someone can do and more about what they're willing to do. Will is about attitude, ownership, drive, and follow through. It's about whether someone is showing up with intention, whether they care enough to put in the work, to get better, to stay accountable. And here's where it often gets murky in customer success. You've got someone who technically knows the job. They can run the calls, update the CRM, manage customer issues, but they're just not stepping up. They're not proactive, they're not rallying cross-functional teams, they're not pushing for value. You're constantly nudging them to follow up with customers or escalate risks. So you start wondering, do they even want to be here? That's a real problem. But again, we have to be careful because sometimes what looks like low motivation is actually something else entirely. Maybe they're burned out, maybe they don't feel safe speaking up, maybe they don't know what good looks like because expectations haven't been made clear. Or maybe, this is a big one, they do want to do better, but they've stopped trying because nothing they do seems to move the needle. So when you're diagnosing for will, the first thing to do is listen, check in, get curious, ask questions like, How are you feeling about your accounts? What's been draining your energy lately? Is anything unclear about your role or what's expected? Basically, you're looking for signs of disengagement. Yes, but also signs of misalignment, confusion, or frustration. Because motivation can look like low motivation, but are actually fixable with the right support. On the flip side, if someone is consistently checked out, misses deadlines, avoids ownership, deflects feedback, or refuses to engage despite repeated coaching, that's a will issue that may not be coachable. And that's where tough decisions come in. Because you can coach skill, you can even change the system, which we'll talk about next, but you can't coach someone to care. Okay, let's move into the third piece of the puzzle. And the one that often gets overlooked, the system itself. Because sometimes it's not about the person at all, it's about the environment they're operating in. You can have a CSM who's got all the right skills, they're motivated, they care deeply about their customers, but they're stuck. And not because they're underperforming, but because the system is broken. Maybe they're buried under too many accounts. Maybe the handoff from sales is chaotic, so they're constantly starting at a disadvantage. Maybe the tools don't give them the data they need, or they're spending more time chasing internal support than actually helping customers succeed. That's not a scale problem. That's not a will problem, that's a system problem. And it's really important as a CS leader to look at performance through this lens. Ask yourself, have we set this person up for success? Do they have the resources, the structure, the clarity, and the support they need to do their best work? Because if the answer is no, then no amount of coaching is going to fix it. You're trying to coach around a broken system. I've seen this happen so often. A leader pulls someone into a performance conversation when what that CSM really needed was fewer accounts, a better onboarding process, or alignment with product and support. We end up blaming the person when the real issue is the operating model. And that's why I added system to the traditional scale world framework. Because in customer success, performance doesn't exist in a vacuum. It's connected to structure, process, and enablement. So if you're seeing inconsistent performance across the team, don't just look at the individuals. Zoom out and look at the system they're in. Sometimes the best lever you can pull is operational. Now that we've walked through scale, will and system, how do you actually use this in practice? The first step is to pause before jumping to conclusions. Let's say a CSM is missing deadlines or customers are escalating more than usual. It's easy to assume they're not putting in the effort or they're not just the right fit. That before you make that call, take a step back and run through the framework. Ask yourself, number one, is this a skill issue? Do they receive the right training? Do they know how to do what's expected of them? Do they have the core competencies for their role, like value storytelling, stakeholder management, or commercial acumen? If the answer is no, then your solution is enablement. You coach, you train, you support. Number two, is this a will issue? Are they motivated? Do they take ownership? Are they engaged and showing initiative? If the skills are there, but the drive is missing, you've got to go deeper. What's affecting their engagement? Are they burned out, misaligned with the role? This is where you step in as a coach and try to understand what's blocking them. And number three, is this a system issue? Even if they've got the skill and the will, are they working inside a structure that actually lets them succeed? Do they have the right tools, clear processes, reasonable expectations, and cross-functional support? If not, you've got a systems problem. And that's on you to fix it, not them. The moment you start using this framework consistently, you'll find that performance conversations become less emotional and more diagnostic. It removes blame and brings clarity. It also gives you a roadmap. If it's a skill, invest in development. If it's will, invest in coaching. If it's system, invest in fixing the org. And sometimes it's all three. But now you're no longer guessing. You're leading with clarity, and that's what your team needs from you most. So the next time you feel like someone's underperforming, ask yourself, is it skill, is it will, or is it the system? Because the answer will tell you exactly what to do next. Okay, if this resonated with you, I want you to take one action this week. Think of a team member who's struggling or just not performing at the level you need them to. Instead of jumping to conclusions, walk through the skill will system lens. Get curious, diagnose before you decide. Because the best CS leaders aren't just great strategists, they're great coaches. And this framework will help you lead with more clarity, empathy, and intention. And hey, if you want support in applying this inside your team, this is the kind of work I do with customer success leaders every day. Whether it's helping you coach your team more effectively, redesigning your org for performance, or simply getting out of the weeds and back to strategy, I'm here for it. You can learn more about coaching and consulting support at csrevspeak.com or just shoot me a message on LinkedIn. I'd love to hear what this episode unlocked for you. Thanks for tuning in. I'll catch you in the next one. If you enjoyed today's episode and you want to learn more about CS RevSpeak's coaching and training services, head on over to www.csrevspeak.com. I specialize in working with customer success leaders who carry your revenue number, and I look forward to helping you confidently run a revenue generating customer success team. Don't forget to connect with us on LinkedIn and join our Customer Success Leaders Hub for more discussions, resources, and networking opportunities. You can access the links on the show notes. See you next episode.