A CHRO’s Playbook For Naming Dysfunction

You've been in the role eight to twelve months. You've done the diagnostic. You know where the talent gaps are, where the succession risk lives, which functions are underperforming and why. But there's another part of the picture — harder to name, harder to act on. Two leaders undercut each other after every meeting. The CEO consistently leaves the room with a different takeaway than everyone else. A business unit has been managing up for years while the numbers underneath them tell a different story. None of it shows up in a succession tool or a talent scorecard. And you're sitting on it.

This episode is about the conversation most CHROs find an excuse not to have. Not because they can't see the problem — they can — but because they don't have a frame that makes the conversation survivable. Jackson walks through the two traps CHROs fall into when executive team dysfunction is in the room: speaking without the right frame (and becoming part of the dynamic), or staying quiet while the damage compounds one level down. Then he gives you four concrete plays for bringing this to the CEO in a way that actually opens the door.

The CHRO is the only person in the C-suite whose job requires holding the full picture of how the talent system operates — including the team at the top. This episode makes the case that the obligation to clarity doesn't stop at the C-suite door, and shows you exactly how to act on it.

What You'll Learn

• Why naming executive team dysfunction without the right frame turns the CHRO into part of the problem — and how to avoid it
• How to describe organizational dysfunction in observable, verifiable terms that the CEO can check against their own experience — without naming individuals as the problem
• The specific technique for translating a leadership team pattern into a business cost before you walk into the room
• Why this conversation must happen privately with the CEO before it ever touches the broader leadership team — and what goes wrong when it doesn't
• How to end the CEO conversation with a clear ask so both people leave with direction rather than a polite nod and no follow-through
• How your best performers are already drawing conclusions about the culture from what they see
• The concept of the "Watching" component of the CEO-CHRO one-on-one and how it creates a natural container for these observations over time

Key Quotes

• "Dysfunction at the top doesn't stay at the top. It teaches itself down."
• "This is the trap of having the right observation and the wrong delivery. The observation doesn't survive the delivery."
• "The CHRO who stays silent about executive team dysfunction is making a choice. And the organization pays the compounding cost of that choice."
• "The CHRO's obligation to clarity does not stop at the door of the C-suite."

Transcript

Hey there, senior leader, and welcome to the Talent Sherpa Podcast, where senior leaders come to rethink how human capital really works. I'm your host, Jackson Lynch, and today we're going to be talking about the assignment that nobody — nobody — prepares you for.

You're brought in to support the executive team, to optimize it, to help it perform at the level the business really needs. And then you sit in the room long enough to see it clearly. The team itself is the problem. Not one person — the entire dynamic. The way decisions don't get made. Commitments that evaporate after the meeting ends. And accountability? It dissolves at the top before it ever reaches the next layer down.

You can see it. You can name it. The question is, what do you do with that clarity?

So before we get started, let me ask you for a quick favor. If you find value in these conversations — and I hope you do — please take a moment to like, subscribe, and leave a review for the Talent Sherpa Podcast. It helps more senior leaders find the show, and it helps us keep doing this work for the larger HR community.

And this week I want to tell you about the CHRO Chronicles. If you're a sitting CHRO, this is a weekly paid newsletter written exclusively for you. It covers the things that don't make it into the job descriptions — the political dynamics, the altitude adjustments, the moments where the role gets really, really hard in ways that nobody ever prepared you for. It's $30 a month, and you can subscribe at mytalentsherpa.com.

All right, let's dive into this. Here's how this actually shows up from my view.

The CHRO has been in the role eight to twelve months. They have done the diagnostic work. They know where the talent gaps are, where succession risk lives, which functions are underperforming, and probably why. They have a really good, clear picture of what's going on.

And part of that picture is harder to name. Two members of the leadership team don't align in meetings and actively undercut each other once they get outside the room. The CEO is consistently leaving senior team conversations with a different takeaway than everyone else in the room — and nobody corrects it. A business unit has been managing up effectively for years, while the performance numbers underneath them tell a completely different story.

Now none of this shows up in a succession tool or an iDebox or a talent scorecard. But it is the most material risk in the talent system, because it is sitting at the very top of the house. The CHRO sees it, they can articulate it, and they're sitting on it.

What normally happens next is one of two things.

The CHRO manages around the dysfunction — rounding decisions differently, absorbing the friction that the team should be resolving itself, filling the gaps that the leadership team dynamic keeps creating. Or alternatively, they wait. They wait for the problem to become undeniable enough that somebody else names it first.

Both of those paths have a cost. And the organization today is already paying it.

So I think there are two traps here. And the hard thing is they pull in completely opposite directions.

The first trap is speaking without the right frame. The CHRO sees the misalignment and they name it — maybe in a leadership meeting, maybe to the wrong person first, maybe with more heat than precision. And it lands as accusation. The CHRO becomes part of the dynamic they were actually trying to describe. Their credibility takes a hit, the CEO gets defensive, and the actual problem gets buried under the friction the naming created. This is the trap of having the right observation and the wrong delivery. The observation doesn't survive the delivery.

Here's the second trap: staying quiet while the dysfunction compounds. The misalignment continues. It runs through every major decision the leadership team is touching — budget conversations, resource allocations, strategic planning. The business absorbs the cost in the form of slower decisions, weaker execution, and a leadership team that's quietly stopped trusting each other.

Now the damage compounds one level below. High performers are watching how the senior team operates and drawing their own conclusions about what kind of organization this really is. Because your best performers are always auditing your culture.

What I mean is: dysfunction at the top doesn't stay at the top. It teaches itself down. And the CHRO who stays quiet to preserve their standing is watching the organization pay a price that compounds with time.

So here's what changes when you shift the frame.

The CHRO is the only person in the C-suite whose role requires holding the full picture of how the organization actually runs. The CFO sees the numbers. The CRO sees operations. Every business unit head sees their little slice. The CHRO is the one person whose job it is to see how the talent system functions across all of it — including the team at the top. That is a diagnostic capability. It belongs at the center of the role.

When the CHRO brings an observation about executive team dynamics to the CEO, the framing determines everything. A conversation that names individuals as the problem puts the CEO in a protective position within the first three sentences. The actual problem becomes impossible to address. But if you bring the same concern framed as a pattern with a cost attached, that conversation opens up.

Here's what I'm observing. Here is what it is costing the business. Here's what I think needs to change.

That's a diagnostic conversation. The CEO can hear it, and they can act on it. That framing puts the CHRO exactly in the role they were hired to fill. The CEO brought on someone into the CHRO role who can see the talent system clearly and speak about it directly.

Most CHROs interpret the talent system as succession pipelines, development programs, and individual contributor performance. But the executive team is also a part of that talent system. I'd argue it's the most consequential part. The CHRO's obligation to clarity does not stop at the door of the C-suite.

So how do you actually bring this conversation to the CEO? Let me give you a few plays.

Play number one: build the observation before the conversation. Before you say anything, write down what you're actually seeing. Describe the pattern in observable terms, without the narrative about who is at fault. Something like: "In the last three leadership team conversations about this initiative, the decision has been deferred. And after each meeting, I've heard different accounts of what was decided from different members of the team. The result is that the team leading this work has no clear direction and the timeline is slipping." It's all verifiable. The CEO can check it against their own experience. It opens up a conversation.

And historically, we've talked about having a part of the CEO-CHRO one-on-one called "Watching." This is a great place to introduce that concept.

Play number two: translate the pattern into a business cost before you walk out the door. Every observation about executive team dysfunction has a business translation — you've got to find it. Decisions that get deferred twice mean implementation timelines slip by this many weeks. Misalignment between two business unit heads means the integration carries execution risk that the current plan doesn't account for. Leadership team members who've stopped trusting each other stop sharing information freely, and that information gap shows up as poor resource allocation decisions.

When you bring the observation with the cost attached, you are speaking in the language of the room. You are giving the CEO something very specific to act on.

Play number three: take it to the CEO directly, and importantly, privately. This belongs in a one-on-one conversation with the CEO before it ever touches the broader leadership team. That distinction matters more than most CHROs realize. When you surface an observation about the leadership team's dynamics in a group that includes the people involved, you've created a public confrontation that is almost never productive — fun as it might be. The CEO needs to hear what you're seeing privately, with enough space to sit with it before responding, and with enough context to decide what to do about it.

If the CEO is ready to hear it, this conversation will move really quickly. But if they're not ready, at least the observation is on the table. The door is open. That's part of the job.

Play number four: end with a clear ask. One of the most common failures I see is this conversation gets wrapped up without a direction. The CHRO names the pattern, the CEO nods, and both people leave without any clarity on what happens next. Before you go into the conversation, you need to decide: what are you asking for? A direct conversation between the CEO and a specific leader? A leadership team process that creates more visible accountability? A third-party facilitation of a specific tension? Whatever it is — know your ask, and end the conversation there.

Now, I'm going to share this honestly: none of this gets easier with experience. The most seasoned CHROs I've worked with still find these conversations really hard. The willingness to have them anyway is what marks the role.

And if there's one thing I'd like you to carry out of this episode, it's this: the CHRO who stays silent about executive team dysfunction is making a choice. And the organization pays the compounding cost of that choice.

And that's it for today. Thank you for spending some time with me, and I really do appreciate you being a part of this community of senior leaders who want to rethink how human capital really works. Shout out this week to David from Greeley, Colorado — and thank you for listening, whether you're tuning in from Austin, Texas or Amsterdam in the Netherlands. This community keeps growing, and that is because of you.

Now, if you're thinking about how to apply this in your own situation, let me point you to a couple of resources. If role clarity is where you want to start — and it usually is — check out getpropulsion.ai. They have AI teammates that enable your leadership to focus on the work that actually drives business outcomes.

And if you're a first-time CHRO or you're prepping to step into the role, I'd love to work with you. I have some availability right now. We've built practical tools to help you make an impact from day one, and you can find everything you need over at mytalentsherpa.com.

So until next time — keep raising the bar, keep naming what you see at the top, and keep on climbing.