Your AI Questions, On the Record

Most AI rollouts skip the one step that makes everything else work: redesigning the work itself. This episode puts your questions on the record — about AI strategy, your CHRO seat, and whether leadership development is actually doing anything.

Jackson Lynch and Scott Morris answer alongside Rihanna Barr, a two-time Chief People Officer now fractional CHRO at Pinnacle Peak HR. She's been in the seat. She knows when an answer is complete and when it just sounds that way.

What You'll Learn

• Why starting with vendors before mapping your work is the single biggest AI rollout mistake — and what to do first instead.
• How to reframe the AI headcount conversation with your CFO before it becomes a pure cost-out exercise.
• Why "strategic HR" has become a self-description and what real CHRO influence looks like instead.
• What separates CHROs who get pulled into decisions early from those briefed after the fact.
• Why "accountability" as a frame suppresses your best performers — and what to use instead.

Key Quotes

• "Strategic has become a self-description and a posture. How the hell do you measure it?"
• "Authority follows demonstrated impact on the business — not an org chart fight. It's about usefulness."
• "Your best performers are auditing your culture every day. When they go quiet, they're self-censoring judgment while maintaining effort."

Sources for Statistics Cited

• ~5% of AI implementations show positive ROI (Jackson stated this inversely — the actual MIT finding: 95% fail) — MIT GenAI Divide Report 2025
• Less than 5% of 2025 layoffs were AI-driven — Challenger, Gray & Christmas 2025 Year-End Report
• 55% of companies regret their AI-driven layoffs — Forrester via HR Executive
• 47% of the working population can't confirm they know what's expected — Gallup
• ~50% of HR people don't see their business as a force for good (Marc Effron / Talent Strategy Group) — Source not independently verified
• Companies benefiting from AI focus on growth, not cost-cutting — a16z Big Ideas 2026 (specific article referenced not located)

Transcript

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You know, sometimes the conversations that matter most inside of an organization happen off the record. But today, the questions that you actually sent us are going on the record. Let's see if our answers hold up.

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 I am joined by my co-host. His name is Scott Morris. He's a former CHRO with all the playbooks and scar tissue to prove it. But today we have a third person in the room, and she is the reason this format works. Rihanna Barr is a friend of mine. She's a two-time Chief People Officer and now works at Pinnacle Peak HR as a fractional CHRO and an executive coach. She happens to have worked with me back at Nestlé in Clearwater. So all of this that you're going to see today or listen to, I've had a front row seat for this for years. And she's here because this episode's different. You have over the last several months sent in the questions through the number in the show notes — or sometimes just tracking us down in real life. Either way, the right person to ask them is someone who's actually lived them. So, Rihanna, welcome to the Talent Sherpa Podcast.

Well, thank you, Jackson. I'm so happy to be here. I have been a long-time listener of this show. And I know you guys don't do easy answers, and that is why I said yes.

I love that you're here. I've had a great time meeting you. I'm glad you're doing this with us. And I think to the audience — I think Rihanna is actually going to hold us to it. And let me tell you why I think that matters. She has an operating history. She's been a CHRO. She knows when an answer is incomplete and when it is operationally complete. She's been in those rooms. And that's the differentiator between what a real answer is and what a polished answer sounds like. And before we get into it, Rihanna, we do a shout-out every week to people that have written in or asked us questions. And this week's shout-out isn't just for one person — it's for everybody. And I'm really excited about this, Jackson, and I know you're really excited about it too. We've been named a top 100 management podcast in May for several different countries. The US, obviously, but that list also includes — and I'm sorry, I'm going to have to read it because there are so many: Cyprus, France, Taiwan, Sweden, Germany, Canada, Australia, and Austria. And we were, if I've got this right, Jackson, top 200 in Malaysia, Ghana, Singapore, and Hong Kong. And I think that's interesting because when Jackson and I started doing this, we had no idea if anybody was going to listen. So a genuine, heartfelt thank you and a shout-out to everyone who is listening around the world. You are proving that the conversation about how human capital actually works matters — not just across industries, but across every market around the world.

And Scott, you forgot Norway, where we're the number one management podcast, top 20 in business, and top 40 overall — which is absolutely mind-blowing. We are unbelievably grateful. And that list of countries is proof that what we're doing here matters and that you are really serious about the work. And I can also tell that based on the questions that you sent in. I think you are here for a real conversation.

I would agree with that. And that includes every person who sent in a question. I've read through all of them. You asked the right things, so let's get into it.

Before we get into the listener questions, there are two things I wanted to ask that I think everyone listening could be curious about. So, Jackson, what were you doing before this? And what was the moment that told you this was the work you were supposed to be doing?

The honest answer is that I've spent most of my career inside organizations watching the same problem show up in different configurations. And what I mean by that is: mandate clarity is so unbelievably important. And yet the numbers would suggest that we have serious issues with management, CEOs, boards, and HR aligning on what this function is supposed to do. If you look back a few months, we had Scott Botempo on the podcast, and one of the things he talked about is the dramatic difference in what CEOs expect from one CEO-CHRO relationship to the next. And I was trying to figure out why that was. I think it comes down to two things. The first is a low-altitude mandate — a very functional mandate and one that feels right in the moment. And the second is an identity vacuum, where most first-time CHROs — and sometimes even into your second run — don't realize that a CHRO job is not the more senior version of every job you've had up to that point. It's uniquely different. So I wanted to really start focusing in on that mandate and helping people figure out what that is. Because I think it's the ultimate road to helping us figure out how human capital should really work — which is why we talk about that every time on the pod. The decision to build Talent Sherpa was just a decision to change that conversation at scale.

Jackson, if I can add one thing just by observation — for the year and something that you and I have been doing this together — the learning that you have had in the context you've been in is really expensive learning. You only get that when you're inside the room and something goes wrong. What I appreciate about what you bring, and certainly what you have taught me, are those expensive lessons distilled down into practical terms. And I think that's a hallmark of what you've done.

I appreciate that. And I've stubbed my toe. Earlier in my career — and Rihanna might actually acknowledge this for me as a proof point — I had a hard time saying that I made mistakes, but I was making them left and right. And watching that same failure mode in enough organizations stops at some point from being a curiosity and becomes an obligation to do something about it. So the podcast, the Substack, the coaching work — all of it's an attempt to name the pattern clearly enough so that the next person in the room can see it before it becomes the crisis that they, in fact, are managing themselves.

And I think that's what makes the show different from most of the HR content out there. It's pattern recognition from inside the work. It's not aspirational HR.

That's great. So, Scott, we've heard from Jackson on why he built Talent Sherpa. I would love to hear from you — what made you walk away from your CHRO seat? And how in the world do the two of you end up in a room together?

So that's two questions. I'll take them one at a time. I don't think I've walked away from a CHRO role per se, because I still feel really invested in that. But I walked away from actively being a CHRO because of timing and technology. I'm on my third entrepreneurial venture — Propulsion AI is my third. And it happened because I was an early adopter of AI back in 2018, when we weren't commercially talking about AI being integrated into the workforce. I was working in Silicon Valley, and we were using artificial intelligence to market-price jobs. I didn't have any comp team, and yet I needed to deliver really thoughtful analysis because we were competing for really top talent. And we used artificial intelligence to do it. I worked for an organization called Singularity that really focused on disruptive technologies. Those technologies started to progress to the point where I said, I have got to go try and do something with tech to really serve the workforce, or I'm just going to miss the opportunity. And so I founded Propulsion AI. Jackson and I wound up in the same room because I cold-called him about our platform. I was persistent. And he did turn me down — and in part it was his company situation, less than my platform. At least that's the story he tells me that I'm going to choose to believe. But that persistence in trying to sell became a friendship. And then we had a recognition that we saw workforce dynamics pretty similarly. One of us said, we should probably record these. And the other one said, who would be interested? And here we are with a top 100 podcast.

But we still want to bring that raw, this-is-the-way-it-should-work perspective to everyone who's serious about this function so that we can do something significantly different. And that's really why we focus in on constraint-based HR, the focus on clarity, and the use of work redesign around tools — because I think that's where the future of the function is going to go.

That's amazing. Thank you both for sharing. One more thing before we hop into these awesome listener questions. I've taken the liberty of rewriting some of your questions to help sharpen the discussion. So I want to apologize in advance to anyone who hears their name and says, hey, that's not exactly what I wrote. What is she doing? Possibly you were a little too polite. Some of these needed a little more edge. I like a little spice. So are we ready to do this?

Let's do it.

Okay, this first question is a version I'm also hearing from several of my clients right now. Ryan from Atlanta has written in and said: my firm just announced a major AI rollout. Leadership is obsessed with the technology side — new tools, new vendors, new dashboards. But no one's really talking about whether people know how to use any of it, or what changes when they do. Is this just how every company's doing it right now? Or are we actually behind? Jackson, do you have any thoughts on this?

First off — are you behind? That really depends on the paradigm you're looking at. The companies that are on the right track and getting results today don't start with, okay, what tool can I give people and how can I map adoption? They actually start one step backwards, and that's mapping the work. From my experience working with different companies, that sequencing is the whole game. We've talked about this on the pod before, but start with a work map. Don't start with the vendor. You actually have to interview the vendor because if they're not being curious about what problems you're trying to solve — and they're just talking about the features and benefits of what they bring — it's not going to work. The tool decision has to be downstream of understanding how the work itself needs to change.

And the one really simple question that's going to open up the understanding of what's going on in the company: ask the CEO why they're adding the technology. What is this important for? The answer tells you everything — and may reveal the absence of a plan, in which case you now have an idea of how you can steer it toward a positive result.

Yeah, because this is the key point. Up to this moment, all the technology adoptions have been bolted onto whatever foundation was there before. No one really looked underneath. No one ever really asked, should we even be doing this work? No one really asked, where's the high-value-added work versus the low-value-added work? No one asked whether we have high-value talent stuck on low-value activities. This moment allows us to redesign the work in a way that has the ability to automate the tasks that no one gets joy from doing anyway, figure out a way to get people in and above the loop where human judgment matters most — and then there's a third part, which is an interim or elastic talent model, which we're going to talk about in a few weeks with Jamie Jacobs from Geek Talent. This is just at such a different moment.

Well, thank you both. Along the AI talk track, there have been so many questions submitted. Jennifer from Dallas is one step further down the road. Scott, I'll be interested to get your insights here. She says: I keep hearing that AI makes individual contributors 30 to 40% more productive. My CEO is already doing the math on the headcount. How do you have an honest conversation with the leadership team on what this actually means for our people without it turning into strictly a cost-cutting exercise dressed up as transformation?

There are so many things in that question. The first thing I would do is challenge the assumption. The 30 to 40% more productive stat — just adding the technology is not going to make you more productive. If you have a system for mapping out what the outcome is, backing it up through the work, and then understanding the steps you need to take to enable with technology, that's different. But if you're just adding tech, I don't think a 30 to 40% bump on anything is practical. The second piece — and I think it's really the heart of the question — is how do I have the conversation? The right answer there is get ahead of it. Start looking at your own team and start looking at the things that are holding them back. Jackson and I talk a lot about constraints. And normally when the subject comes up, we're talking about business constraints. But as a CHRO, if you can find the constraint and figure out what relaxes it and then work backward into a program, that's the right move. I would take the same logic and apply it to your own team. What's holding your team back? How much of that is rules-driven? How much of that could be enabled with technology? Then do a scan for tech — but a scan with a purpose. You're not looking for AI generically. You're looking for a way to enable, without the people, that portion of the work that's constraining your team. Once you've done that, you have a way of saying, I'm going to take that headcount and transfer it into something that we can do. And if you're able to do that, that's the entrée to the conversation with your CEO. Because you've created a small-scale model of what can operate at a larger scale. In introducing your own example, you're showing your CEO that there's a real opportunity — not cost cutting, which is a short-term gain, but productivity growth, which is a long-term growth strategy.

MIT actually published something — I think it was March — that roughly 5% of AI implementations have led to a positive ROI. And I think the root cause is that we haven't treated it as a work redesign. Part of the work redesign approach is you actually need to step back and say, if I'm going to free up this capacity, let me tell people what I want them to be doing with that freed-up capacity. If you don't do that, finance is going to say, let's go take the heads out. But we're not seeing that productivity today because we haven't defined it. And that's why you see some of the results that you do.

And I want to double-click on it for the audience. It's because nobody redesigned the work. The thing that's different about AI from any other technology is that it forces us to fundamentally reconsider the distribution of work between people and machines. And in the absence of that redesigned work, we're going to apply it to the tasks that exist today. You've got to think about it as work redesign.

And Andreessen Horowitz wrote something — I think it was about four or five weeks ago — and they said the companies that benefit from AI are not thinking about it as a cost out. They're instead focusing on how to use this as a growth and innovation lever. And I think that's an outfit that has done some pretty good stuff with companies over the years. We should pay attention.

The next question comes in from Marcus from Washington, D.C. Marcus, I gotta tell you, I felt this one — it hit me right in the heart. Here's the question. It feels like HR is getting handed the AI problem without the authority to actually solve it. We're supposed to own the strategy, but the decisions really are being made within IT and finance. Jackson, how do you get real ownership out of this when no one's really willing to give up that control?

I think you need to start upstream and define what kind of technology this is supposed to be. If you lose that initial argument, you are going to lose all the subsequent arguments, and it will turn into a cost-out technology implementation. As a result, you may find some short-term wins, but you're not going to turn that into a growth and innovation engine. But I'd also note that ownership isn't granted by what function is in your title. It comes from being the person in that room with the most useful answer to a question that matters — like: how does this capability change what our people can do? What does that work look like on the other side? There's no one else in the room who's going to be able to have that conversation. IT can't. Finance can't. But we can. And I think it's really important to do the upfront homework so that you have that perspective — and then lean into discomfort, even at some personal risk, to make sure that conversation is being had at a C-suite and board level. Otherwise, it just turns into a cost out. And that's going to hurt the company long term.

What I wanted to contribute has nothing to do with technology — but it has to do with a bunch of prior episodes that you and I have done together. Because if you look at the themes that run throughout this show, we're talking about altitude, we're talking about mandate, we're talking about voice in the debate. And those are not things that you just wake up one day and decide, okay, I'm going to have a voice in the debate, and then you have it. You're working toward that. And Marcus's question is really why you're working toward it. Because when these existential-crisis moments come, you have got to have built the capital already that sustains it. Every head in the room has got to turn toward you. So if you're not thinking about mandate or altitude or voice in the debate and how you sit at that table with a perspective on the business — plant the tree today. Best time to plant it was 20 years ago. Next best time is right now. Go back and find those old episodes, because that's where the heads are going to turn to you — and you're going to have something to say that includes some cost out, but also some productivity growth and new enablement that leads to higher engagement.

And just be practical about it. Find something you can insert yourself in now. Insert that work design lens and then keep doing that. Whether you're invited or not, it doesn't matter. That's the voice in the debate that needs to be heard. And if you do it sufficiently, with unique value-added perspectives, I think that dynamic ultimately starts shifting. Authority is going to follow the demonstrated impact on the business — not an org chart fight. You can't win an org chart fight because no one really cares about that. It's about usefulness.

Yep, completely agreed.

Elena from Chicago is eight months into her AI rollout, and her dashboards are looking great — congratulations, Elena. But nothing in the business has actually moved. Scott, what did she miss?

What were you trying to do? What was the business constraint? What change did you need to see when you brought in this technology and started measuring these things? There's an old paradigm — largely we work with people, we hire them, we assign them tasks, we give them tools — and that just doesn't translate to AI. AI is really about the redistribution. I think the opportunity for the workforce with AI is the redistribution of work. So what was it that you were trying to move in the business? How did you expect to see that? Where did you apply the technology to do it? Those are all predecessor questions. I hate to not have a direct and practical answer for you, but that's where I would point you, Elena.

Maybe here's the question I would ask to put a fine point on what you said, Scott — which I agree with completely. Just ask: what in the business is different because of the rollout? Spend a little bit more time focused on that question. And if you can't answer it, that's why the business isn't moving. If the answer is we have a dashboard — okay, time out, do over. You've got to define the clarity of outcomes up front. When it comes to individual roles, it's equally true when it comes to this kind of organizational, chaos-inducing technology. What are you solving for?

Jackson, let me double-click on that — there were two parts to what you said. Asking what's different as a result of the rollout is a trailing metric. There may be value in that. But I think you're asking a better question, which is: what did we want to be different? And are we actually seeing that? And did we apply the technology to that leading indicator question in the right way?

Yeah, I think that's right.

Yeah, it's all about figuring out what we're measuring, how we do it with the business, and whether we have cross-functional partnership from the leaders. It really starts with that preliminary conversation that you guys have already identified for Elena.

Moving on — we heard from Jennifer. Her question was more about her CEO doing the math. Tyler from San Diego wants to get ahead of the math. You keep hearing about AI taking work off of people's plates, but nobody's talking about what you do with those people once the work is gone. How do you have that redeployment conversation with finance before it becomes a headcount decision?

When you do the work redesign engagement, it follows a very clear set of methods. You define what the process is supposed to deliver. You then look at the tasks associated with that process and identify whether they're high-value-added or low-value-added. You redesign human work around the high-value-added tasks, and use AI to automate as much of the low-value-added work as possible. But then you have to figure out on the back side of it what the opportunity cost is from your previous life — what you can apply these newfound capacity hours toward. It's really funny — early on in this evolution, you heard this is going to be the end of coders as we know them. But I've been in technology for the last several years — we had about 10% capacity of people who actually know how to do that work. And the backlog of coding that needed to get done, all that did was pull forward. That same model holds true in almost any work redesign effort. For example, if you can figure out in the human capital space how to take your HR business partner and get them out of "did you do the performance review?" and turn them into "what was the quality level of that performance review?" — that has a value add that we've never been able to get to. And that's the lens you need to pull in when you do the ROI. You need to make sure that math is included before the savings math starts.

And Jackson, I would add one thing. It's not just the transference of the business partner activity that matters — but if performance management, if performance coaching, gets more effective, what's the net business impact? Where's the margin improvement? Where's the productivity gain? That's what the HR leader should be looking for. Because then when you're speaking to that CFO, you're saying: look, we need to improve performance management because this is the impact it's going to have on the business. To do that, I have to get my people out of these transactional activities. I'm going to use technology to do that. Here's where I'm going to put their effort. That's language the CFO can understand. And it's about the application of technology and the redesign of the work. Tyler, don't miss in Jackson's answer that key piece — you have to redesign the human's work.

And I am so embarrassed that you actually caught me failing to add the "so that" after all the times I talk about it. But thank you for the addition. You are 100% right.

Stephanie from Houston is in a unique situation. Her CEO wants her to lead the company's AI transformation. Her concern is that her HR function is three years behind. Do I fix my own house first before I lead the broader initiative? My experience is that there is not a clean sequence. But Jackson, I'm curious to hear what you think.

My gut feel is you can't credibly advise others through a transformation that you are visibly exempt from. That credibility gap will be real, and I think people will see it. So I don't think it's fix HR first and then go do something else. And I don't think it's do something else without fixing HR. You've got to demonstrate some form of transformation in your own house. Pick something that changes fast and is visible, give it a name, and then talk about it at the enterprise level the same way you're doing it as part of the broader initiative. So it's not two separate tracks. And then I think you need to be really focused on transparency about where you are — being very, very clear on here's where we're headed, here's what we've learned, here's what we've gotten right, here are the areas where we stubbed our toe. I think that becomes really important, especially in your own house as you're talking broadly to the enterprise. It signals honesty, not incompetence.

I want to build on Jackson's answer. The transformation's never done, Stephanie. You're always going to find something. So don't wait until the transformation's done — and that's the point Jackson is making. But where I would take this answer in a slightly different direction is: you need to set up for a hard conversation. Go to your boss and understand the altitude. He or she wants you to lead the company's AI transformation — why? What's the business impact? What is in their head? Why does that CEO want AI in this organization? What are they seeing? If you're not clear on that, no matter who is in the leadership seat for an initiative, you're going to step off in the wrong direction.

Completely agree.

Ingrid from Bergen — we're on the AI track, talking about roles and teams. Her team continues to ask her what AI means for their roles. She has a team of recruiting coordinators, HR business partners, analysts. And Ingrid is being vulnerable and transparent. She's told her team she doesn't have the honest answer — which is great. So, Jackson and Scott — what does our HR function look like in three years? And how do we prepare people for it when we ourselves don't yet know what it's going to look like?

Jackson, can I lead on this one? So, Ingrid, I wrote an article you can find in the Perspectives page of our website. The article is titled "While You Make Incremental Improvements, Your Competitors Are Rebuilding Everything." If you read that article, you're going to see my practical prescription for the future of HR. And I love the fact that you said to your team, I don't have an honest answer. If I were there whispering in your ear in that moment, I would have said: make sure you tell them that you're going to find it together. Because the key to unlocking this is really understanding from their perspective where the work that can be transformed actually is. Then you can find an answer to what AI means — or doesn't mean — because AI is not the right application for every single problem in the world right now. Your people on the front line are going to understand, because they do it every day, the stuff that's holding them back. Similarly to the way Jackson and I push heads of HR to look for business constraints — you need to be looking for the people constraints. Where are your people spending an inordinate amount of time that is not contributing an inordinate amount of value? Once you understand that, and once you understand where they think they could contribute more value, you have a way to redesign their role. The pieces that are designed out of their future roles are the candidates for technological innovation. I would go back to them and say, let's do an exercise together. Let's start to work this out. And along the way — read my article. Because what I'm arguing is take all the transactional stuff out, and then focus on what you should be focused on: workforce development.

You should read my articles too. But the one Scott mentioned is a really, really good one. The headline from what I heard Scott say, summarized, is: you need to be honest with a plan. And that's a really important piece. But I also want to go in a slightly different direction here — because this one is so unknown, it's harder for us to ingest, internalize, and bring forward in a confident way. I totally get that. But there are examples in my own personal life that I think are really useful here. If you've ever seen an emergency room doctor — that is the metaphor for what I think we're about to be going through if we haven't started yet. There is a ton of tactical training that these people go through. There are protocols that they use and build around to do the right thing in the moment that matters. And yet every moment that matters has something that isn't perfect. And so you have to improvise. You have to apply those skills in a hardened way, but in a very unclear fog of war. We have to be comfortable dealing in the ambiguity from a position of strength. That's different from: I'm used to having firm answers, and I will not rest until I have firm answers about the future. The whole world is going to pass us by if we take that approach. Don't do it. Be comfortable leaning into that discomfort. Honesty with a plan — we'll figure it out together. That's as good as we're going to get.

Yeah, that's spot on. Thank you both.

Michelle from Philadelphia says strategic workforce planning used to be a top three priority for CHROs, but now it's dropped to fifth. Meanwhile, AI is eliminating roles faster than anybody can rebuild them. Is the field just getting fatigued with planning exercises that never go anywhere? Or are we actually taking our eye off of something critical right now? Jackson, curious to get your thoughts here.

Well, first off, I think it's unclear that AI is eliminating roles faster than anyone's rebuilding them. I push back on that one. I think there's a lot of talk about people making changes as a result of AI, but that isn't square with the data we've seen on AI deployment. There are times — and I've been inside companies, and I wish this wasn't true, but it is — if you were going to do something anyway and there's a nice way to tuck it underneath a broader umbrella, you're going to tuck it in. And this one — especially in the public-facing markets and probably in the private ones as well — gives you enough cover. And the people who own your shares are pretty comfortable because it feels like you're moving forward. So I would not necessarily believe that AI is eliminating roles at the rate being claimed. I think it is absolutely true that you are going to be in a world where there are two distinct roads. One road is somebody who fights it — says, I'm not going to engage in it, I'm going to push back on the changes. And then there is a different road: I'm going to use this as a vehicle to learn everything I possibly can about what I do, what I want to do, and what brings me joy. And I have a 140 IQ tutor sitting in my pocket at all times. I have the ability to use this to improve my personal productivity, and I also have it as a thought partner to help shape things. Those two paths are going to produce remarkably different outcomes. And that's not going to happen in the future. That's happening now.

Let me toss in a couple of stats because they support what you're saying. Challenger Gray & Christmas says that less than 5% of 2025 layoffs were genuinely AI-driven. That is not what you hear in popular press, it's not what you read online — but that's their work looking back at 2025. Forrester in a 2026 report said 55% of companies regret their AI layoffs. And we're starting to hear this term more: boomerang hires. So CEOs have a constituency — it's their board — and they have to say, hey, we're moving, we're cutting edge, we're doing this. And they're also rehiring those people for a variety of reasons, in a variety of locations.

Yeah, there are companies that were planning to do a remarkably deep cut. This has been in the works for 12 months. And in the last month, they decided to put it all under the umbrella of AI enablement. It has nothing to do with it. They were offshoring jobs. That's what they were doing. So inside your own business, what matters is what you're telling your employees and your stakeholders. And that's where you need to be courageous and focused on the clarity that matters. Because if you don't do that, you want to have enough credibility for the next time you go through this — because there will be a next time. Don't use all of your credibility capital in your first run.

We do want to move into questions more around programs and the CHRO seat itself. Catherine from Minneapolis — my firm just did a big investment in leadership development. They brought in a major firm, they did 360s, ran cohorts, the whole thing. Two years later, has anything really changed? How do you know the leadership development program is working? And when do you pull the plug? Scott, what do you have for us?

It's a great question, Catherine. Let me do the simple answer first, and then I'll give you the deeper answer. How do you know it's not working? Well, you're not sure anything changed — so it's not working. How you start a leadership development initiative — I think this is where a lot of HR people trip themselves up. And I will speak about myself because I'm confident I've done it. I came out of learning and development, and I have made some sublime programs that did absolutely nothing. Back to the constraint logic. I think you've first got to get down to root cause. And if you've listened to the previous episodes that Jackson and I have done, we think there are a couple of things that leaders need to be focused on. And until they are demonstrating capability in those areas, the rest of the leadership agenda probably matters less. Here are the two things. First: do you know what you are expected to do every single day? Not the tasks — the outcomes you're expected to generate. If the answer to that question is no, there's your leadership development program. Your leader is not delivering that layer of clarity, and your people need it. Gallup tells us 47% of the working population can't answer yes to that question — that they understand what's expected. Second: do you have the support you need in order to do it? If the answer to that question isn't yes, there's your leadership development program. Until you can prove that your leaders are delivering at that level, the rest of the agenda — put it to the side. And it's easy to deliver, quick to make, and easy to measure.

Two quick points on that. First, 10 points for Scott for using the word "sublime" in a management podcast on learning and development — that was amazing. The second piece is — listen to our podcast from a couple months ago on leadership development. What we said in that episode was that a lot of leadership development comes out of a lack of clarity about what a manager is supposed to be doing. If your leadership development is focused on a broad swath of expectations that may or may not have a "so that" leading to a business result — stop. Focus on the clarity that Scott talked about, and then figure out where you have talent density and where you have incumbents in roles that need radical improvement. Take those same resources and dedicate them to making the people in the roles that matter most the best they can be. That's how you turn it into outcomes really quickly.

Rihanna, can I just have one 30-second addition? To try and marry these two tracks of questions — we can give our people AI tools. If they don't know how to use them, and if their boss doesn't know how to think about those tools in the context of their work, it's not going to generate anything. No productivity, no headcount savings — none of it. So your leadership development, coming back to clarity — are you clear about how to use the new tech tools we're trying to give you? No, I'm not. Well, there's a part of your leadership development. How are the managers thinking about tech?

Yeah, that's spot on. Thanks, Scott.

Sandra from Chicago has a question for you, Jackson. And she's quoting you. Jackson, you said the CHRO influence problem is partly structural and partly self-inflicted. I'm a CHRO at a mid-market company. My CEO likes me, but I don't think he sees me the same way he sees the CFO. What is one thing — just one thing — that I can do to change that dynamic?

I can't believe you would accuse me of this, but I'll try. One thing: walk into the next conversation carrying a point of view on a business problem through a talent lens — not an HR problem. Period. If you do that consistently, the way you think about those conversations will change. And if you want help doing that, I do have something called the Mandate Protocol, which is available on my website for $297 — and it can get you right where you need to be around the mandate, with either your CEO or your business leader, in five days.

So, why do you think the CFO and the CEO have a different relationship? I know I said one question — you answered brilliantly. But I want people to understand that CHRO-to-CFO dynamic.

Not to be overly generous to my colleagues in the finance world, but their view changes how the CEO thinks about decisions. And when you have a CHRO who is at enterprise altitude, they have an organizational visibility that no one else has. They can help you figure out where execution is failing, where a leadership gap is costing the company, where a structural decision isn't producing. And if you look at the business strategy through a talent lens, you predict what's going to happen, why it's going to happen, and then prescribe actions — that's how you get involved in the same dynamic. It works not just because you're showing business acumen, although that's critically important, but because you're actually answering a question the CEO is already sitting with. Most of the time, HR people show up with HR problems, solutions, and programs — and that adds to the CEO's worry list rather than resolving something that's already there.

Patricia from Phoenix is on a search committee looking for a CHRO. Half of the finalists have deep HR backgrounds, half have business backgrounds with some HR experience. Every time they debate it internally, they go in circles. How do you actually make that call? And what do you do if you get it wrong?

Patricia, first thing I would say: congratulations to your talent acquisition team for not screening out based on a really limited profile for CHRO. I'll also tell you — I came out of learning and development, and my first official HR job was as a head of HR. And I had very little HR experience. In that assignment, I was really, really lucky. And this is part of what I want to give you in the answer: I had people reporting to me who were absolute experts at what they did. If there's one thing I do really, really well, it's that I bring people together, get their opinions out, listen very intently, and find ways to connect different points of view into a comprehensive answer. And I did that with this group. Along the way, they taught me the HR stuff I was missing. And what I brought was a business lens that they didn't have. And so it worked. Personally, I think the head of HR is just a completely different job. I would go as far to say it's not even an HR job anymore. And if you come up through the HR ladder, you have a big obstacle that I didn't have. I never had the HR training to lose. I had the business training, and that carried me, and I learned the HR things I needed along the way. But if you are coming out of HR through the traditional ladder, you've got to really work to divorce yourself from that — because it's just a different job. So I would look at who you have on the ground, look at the skill sets in the organization, and ask: do those skills serve the compliance and regulatory aspects of HR? If yes, I'd put a business person at the head. If the situation's different, the HR skill sets may become more important. But that's how I would go about making the choice.

Yeah, let me push back on this a little. And this might come across as odd because I've been so vocal on the need for business acumen in the CHRO spot. By the way, we agree completely — it's not an HR job, it's a business job. That said, there are things that growing up in the function provides you the opportunity to do and see that are hard to capture if you didn't grow up there. So I don't think it's a matter of business background versus HR background. You need both. But what you need is someone who can look at business strategy through a talent lens, predict what's going to happen, identify why it's going to happen, and then figure out in the moment that matters — what do you do about it? So my selection framework would actually be to put a business problem in front of your finalists and see how they attack it. Whether you have an HR background or a business background, you both have the opportunity to win in that battle. And that's the cage match I would set up to see who wins.

I love that. I think that's absolutely smart.

Carlos from Madrid writes in and says: I've had the "HR needs to be more strategic" conversation at four different companies over 18 years. Same words, same outcome every single time. Is strategic HR a real destination or just a story the function keeps telling itself? And Carlos, I hear you. I've been there. So, Jackson, give us the candid honest answer.

First off, hello Carlos — really appreciate you listening. Thanks for being an early editor of the book I'm writing. Let me try to be blunt on this.

Please, Jackson. I want you to be blunt. This one hit us.

This one hurts. Because 25 years-plus of "HR needs to be more strategic" with almost no movement — maybe some limited movement in actual influence. That's a data point. It's not a perception problem. And as I've mentioned, my family has a long line of alcoholics — the first step is to admit that you have a problem. "Strategic," by the way, has become a self-description and a posture. But how the hell do you measure it? It drives me nuts. So I try not to use the word strategic at all — because if you have five CEOs and five CHROs and you say "define strategic," you're going to get 25 different answers. The CHROs with real influence stopped asking to be seen as strategic. They just started doing the work. Same thing goes for a seat at the table. That's a passive activity. It's a participation trophy in corporate form. Don't worry about getting a seat at the table. Show up with a voice in the debate, with a perspective that changes what the CEO does next. If you do that, you don't have to worry about these labels.

Pick your metrics. Here's what I would do if I want to be seen as strategic: I pick units of output, and I pick revenue per employee. I'm looking at what I can do with the workforce that is going to move those numbers. Because that's exactly what the CFO does. The CFO is thinking about deployment of capital and what measures will show that the capital is being deployed in the best possible way. We need to be thinking about the workforce in the same terms. We're just using the wrong measures. Engagement is a means to an end. Satisfaction is a means to an end. Time to hire is a means to an end. Those aren't business metrics. They're the ones we've been focused on that keep us feeling as if we are not contributing something to strategy. But start talking about: if we're going to move revenue per employee, we're going to have to move these three rocks. That's the essence of strategy. It's a lever that moves a big rock that's meaningful somewhere.

And I would double down on that and say — I think one of the underserved focus areas for HR people is decision rights and the definitions around them. Because the drag on how things get done and get decided will automatically have a positive effect if you do that work well. I would also throw talent density on there. It's the only one I've been able to find that actually has a forward-looking view of future performance. And I think that's important too. But yeah, all of our measures are in the rearview mirror. Stop using them.

I want to congratulate Kinsey from Chicago, who's spent the last three years learning the business from finance, operations, and strategy. Her CEO still brings her in after decisions are made — not before. What is different about CHROs who do get to be part of that decision-making process? Scott, what insights do you have for us?

Where I would start is: what's the conversation you're having? Go back and audit your last five meetings with your boss. Look at what was on the agenda — not what you came in with, but what you actually talked about. And if the nature of those last five meetings is all transactional, or all HR programs — that's signal. But if what you're talking about in those meetings is: here's revenue per employee today, here's where we want it to be, this is how I'm going to get it there, here's where our output differs across facilities, here's what I think accounts for those differences, here's what I'm going to change — that's a completely different conversation with your boss. And the CHROs who are getting brought in ahead of time are the ones who have invested the time to have that kind of conversation. Here's the business constraint, this is how I think we can relax it, this is what I'm going to do with the people in order to do it. It's just that simple of a formula.

With the folks I coach who are sitting CHROs, this is something we talk about a lot. So it's not just you, Kinsey. Don't worry about that. Here's how I approach it. I love the audit of the last five meeting agendas — that's important. I also think you need to look at your calendar and figure out: what are you doing to execute, and what are you doing to change the work? You need to find a way to spend a lot more of your time on the latter. Right now we spend very little time changing the work. You also spend very little time thinking about how the work needs to change. So I would find time in your calendar to go do that. And then the play is you go into the senior team meetings and bring something that they needed and couldn't get anywhere else. Do that once — people will look at you funny. Do it a second time — they will start to notice. Do it consistently, three times — three data points makes a trend — and they will start inviting you to the meetings because you're adding incremental value. That's how you do it.

Fantastic. Thank you. We're down to our last two questions, and they are connected — both about accountability, but from opposite ends of the same problem.

Michael from New York says: an accountability reset was necessary. Now my best people have gone quiet. When does that become something that I can fix? Jackson, curious to get your thoughts on accountability.

I don't like accountability. I don't like it because it looks backwards and it tends to be blame-oriented. I like reliability — and focusing on reliability — because it asks the question: what has to be true for us to do what we need to do? So I think the first step is to change your frame of reference. Because the orientation, even the word "accountability," pulls you into a place that quiets people down — if that's what you're worried about. Second — your best performers are auditing your culture every day. And when they go quiet, it's not necessarily disengagement. They're concerned about psychological safety. As a result of that, they're self-censoring judgment while maintaining effort. Performance kind of looks fine, but the organizational thinking atrophies because they're no longer sharing it. How do you fix that? You need to create an environment where people believe they can put an uncomfortable truth on the table, argue it vehemently, maybe even be wrong — and still belong to the team. There are lots of different ways to get to that point. But that environment allows your top performers, who are auditing the culture, to feel psychologically safe — to be uncomfortable, to share the hard truths the organization needs to hear.

I'm not sure I have a lot to add on that one. Michael, I would love it if you would write more to us. Give us more than what you gave us in that question — tell us a little more about the context, and maybe we can work it into another episode and help you differently.

Christopher from Frankfurt writes in: I've watched organizations swing from "nobody gets held accountable for anything" to "the only thing that matters is hitting the number." Both feel broken. Is there a version of high performance that doesn't eventually produce one of these two outcomes? Scott, what are your thoughts?

First of all, I think that's a false choice — those are not diametrically opposite things. I'll also tell you how I've coached managers on one-on-one meetings, because the interaction you have in your one-on-one is going to determine what your people actually do. A really solid one-on-one starts with a review of your numbers. But to start there, it means you as the boss had to articulate those numbers first. So clarity is job one for every single manager, in every single industry, in every single context. If you are not delivering clarity about the outcomes your people need to produce, about how you're going to measure their success, and about the targets you need them to hit — if you aren't speaking repeatedly about that, you're not doing your first job. And the rest of it is going to matter less. Jack Welch in his book Straight from the Gut talked about taking over at GE. He said all he talked about for 24 months was two things: number one and number two in every industry, and Six Sigma. He said by the end of 24 months he was so tired of talking about those things, he didn't think he could do another investor meeting or another company meeting. He couldn't talk about it any more than he had. And they were just starting to get it. That's a big job — delivering that clarity. But if you've delivered it, then now your one-on-one can start with: how are you doing to the numbers? Because you defined them, you measured the pre-state, and you can now observe the movement. How are you showing up against the competencies we said were important — and I think it's important for every manager to pick those with their people, not seven, just one or two. How are you doing on the skills we said you were going to work toward? How are you feeling? Where can I get some obstacles out of your path? Tell me anything else we need to talk about. I think that five-point formula is the right way to hold a one-on-one. When you do that, you start inculcating this idea that the numbers absolutely matter — because we're not paying you for activity, we're paying you for results — but how you get there matters too. And if you model that behavior, that becomes a multiplier.

The only thing I would add is — focus on the why the numbers matter. It's got to have some purpose-driven element to it. Especially with folks earlier in their careers these days, that is increasingly important.

And Jackson — if you can't do the why that you're suggesting, you might have the wrong numbers.

Also true. Because at the end of the day, you want to be able to say: we are accountable to these results because these results make these other things happen. I feel confident that the purpose of our business matters. Marc Effron just did something at the Talent Strategy Group that found roughly 50% of HR people don't think their business is a force for good in the world. And that is screaming a problem — we're putting in accountability without explaining why it matters. Maybe there are some companies where it doesn't connect easily, but I've never actually sat in one where I can't say we're doing this because of that. When I was in solar energy, it was pretty easy. When I was trying to help people find their forever homes, it was pretty easy. When we were bringing people ice cream and pizza, that was really easy. And when I made toilet paper — it was still easy. It was a crappier job, but still.

I knew you were going to do that.

It doesn't always have to be some greater social good. Everybody wants to be part of an enterprise that's succeeding. And mapping back — this is what your work enables us to do — it's the number two driver of employee loyalty, right behind a relationship of trust with your boss.

Amen. And the CHRO — you guys are the right people to name that distinction. And if you're a CEO or an operating partner, listen — really focus in on that, because that is how you drive the culture. It is decision residue.

Wonderful. Thank you both. This feels like the right place to stop.

If there's one thread through all of this, it's that the frameworks have never really been the problem. The follow-through is.

And I want those listening and those who sent in questions to know that you got the real answers. So thank you both.

And it wasn't as scary as I was originally thinking. It's exactly how the show is supposed to go. So thank you so much for joining us. Where can people follow your work?

Well, it's my pleasure to join you and Scott — thank you again. You can follow me at pinnaclepeakhr.com.

Yeah, and let me just put my full-throated endorsement behind Rihanna and the work. I've known her for 20 years — which for her meant, I think, she might have been five. But this is a person who has the ability to work with senior leaders across multiple functions and industries. She's been in the seat. She gets the joke. And if you need help, please reach out. I want you to know why I trust her with this work — because I literally have seen her do it. So please go find her, and let her know you heard her on our podcast.

And Rihanna, it's been a real pleasure getting to know you. You've been really sharp in our prep sessions, and I'm happy that you're here. I would love it if you would come back — I like this format. We'll see what the audience reaction is.

Well, I hope the audience agrees. I'd love to come back.

It's all up to you, audience. Write a comment and a review, and make sure we hear from you. But regardless — it's time to wrap up. Thank you so much for tuning into the Talent Sherpa Podcast, where senior leaders come to rethink how human capital really works. And we do this because it is so much fun to do with all of you. Episodes like today just demonstrate that with enthusiasm.

We're trying to experiment with this episode, and I say it every week — but I think I mean it even more today. If you liked this episode, hit the like button, because that gives us signal that we can lean into. Better yet, subscribe, because that activates the algorithm and helps spread the pod to other senior leaders who may benefit from the content. You can leave us a review on your favorite platform — whether that's Apple Podcasts, Spotify, or YouTube. We are on all of those. It's free to you, it benefits us immensely, and it might help other senior leaders.

And I want to take just a second to talk about Scott's company. Propulsion AI is workforce intelligence for private equity. Their AI teammate surfaces workforce risk before close, and helps leadership teams drive execution after. They're translating strategy into individual accountability. They're coaching managers to define roles by outcomes — something most companies really need to focus on more than we do. And they give every employee a clear line of sight into what actually matters — which is the foundation for an engaged workforce. It's all really, really good stuff. And it's all done through artificial intelligence, because he's been doing this since machine learning. You can learn more at the very cleverly named getpropulsion.ai.

And Jackson, you know what we're finding — we originally were very focused on the diligence phase of private equity. But every private equity transaction that closes spawns a company that needs to execute. And increasingly, we're hearing from CEOs who need the same power we're putting into diligence in the early stages of their execution for their company. So if you have an interest, head over to the website. And if you are a new CHRO, or if you're aspiring to be a CHRO, or if you've got the job and you're preparing to step into it — all three of those use cases — Jackson has built all of the tools you need to help you operate exactly where we keep trying to drive you: at the altitude the role demands. Personal coaching, the CHRO Ascent Academy, even his best-selling Substack. You can find everything at mytalentsherpa.com.

Well, thank you, Scott, and thank you, Rihanna. And thanks to everyone who's listening. Until next time — keep raising the bar, name the gap before it becomes the crisis, and keep on climbing.