The Talent Sherpa Podcast
Where Senior Leaders Come to Rethink How Human Capital Really Works
This podcast is built for executives who are done with HR theater and ready to run talent like a business system. The conversations focus on decisions that show up in revenue, margin, speed, and accountability. No recycled frameworks. No vanity metrics. No performative culture talk.
Each episode breaks down how real organizations build talent density, set clear expectations, reward the right outcomes, and fix what quietly kills performance. The tone is direct. The thinking is operational. The guidance is usable on Monday morning.
If you are a CEO, CHRO, or senior operator who wants fewer activities and more results from your people strategy, you are in the right place.
Keep Climbing.
The Talent Sherpa Podcast
Your Work System Has No Owner
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
The HRBP model is 30 years old. Most organizations changed the title without changing the work — service logic stayed, compliance logic stayed. PwC research shows only 60% of CEOs call their CHRO highly effective, despite years of transformation investment. The capability problem is real. But it's downstream of a design problem most organizations keep skipping.
This episode names what's actually broken and builds a frame for what fixes it. Jackson, Scott, and guest Phil Kirshner make the case for the Chief of Work — designed to own what no current role does: the combined output of how work is actually designed and experienced.
What You'll Learn
- You can put excellent people in a broken role and still get broken outcomes.
- HR has two fundamentally different jobs — run the business and change the business — and giving both to the same function guarantees one never gets done.
- IT, HR, and real estate each optimize their own lane; the combined output of all three has no owner, and that accountability gap has a measurable cost.
- Freeing up calendar time through AI doesn't produce strategic capability — it produces more of the same kind of work without design changes.
- The Chief of Work only works if it sits outside the functions it's reading — independence isn't a preference, it's the design requirement.
Key Quotes
"You can put excellent people into a role structurally designed to produce a service outcome, and they will produce a service outcome."
"I want to do it with you, not to you."
Sources for Statistics Cited
- 60% of CEOs describe their CHRO as highly effective — PwC Pulse Survey, 2024
- Employee engagement cited as dropping, — Gallup Global Workplace
- 41% of CHROs want greater depth in data analytics — Mercer 2024
- 39% of HR functions have adopted AI — SHRM 2026
- Workers using AI tools report 346% increase in time on certain tasks — NBER/Duke
Connect with Phil Kirschner
Because Jackson Would Want You to Have This
- "You keep using that word. I do not think it means what you think it means." — The Princess Bride (1987)
If this episode landed, the next move is yours.
Coaching is where it closes fastest — Jackson has developed CHROs from both sides of the table, as their leader and as their coach. The CHRO Ascent Academy, CHRO Chronicles, and the best-selling Substack are there too.
All at mytalentsherpa.com.
In private equity: Propulsion AI surfaces workforce risk before the close and translates strategy into individual accountability after it. Before AI automation - drive outcome clarity with digital teammates to do the work fast and at scale.
All at getpropulsion.ai.
Scott: Your HR function is organized to run the business. But the problem is that stopped being the hard part. What nobody has built yet is the function that changes it.
Jackson: Hey there, senior leader, and welcome to the Talent Sherpa Podcast. This is where senior leaders come to rethink how human capital really works. I'm your host, Jackson Lynch, and today I'm joined by my co-host Scott Morris — a former CHRO with all the scar tissue to prove it, the man who has reviewed enough HR transformation decks to know they all end the same way: a re-org, a new title, and the exact same work — and the founder of Propulsion AI.
Now, Scott, here is the situation we're going to talk about. Every CEO I talk to wants their HR function to be more strategic. And every CHRO we've talked with is trying to be more strategic. And yet, PwC's most recent research shows only 60% of CEOs describe their CHRO as highly effective at being a business partner today. The investment's there, the ambition is there, the outcome keeps coming up short. So today we're going to name why, and we're going to build a frame for what actually fixes it.
Scott: Before we get into it — the organizations that I've seen who get this right didn't get there by making HR better at what they were already doing. They got there by making a deliberate decision about what HR was for and what it's not for. And that distinction sounds really simple, but it's not. Most organizations keep avoiding that subject because the conversation that follows it is really uncomfortable.
[Shout-Out and Ascent Academy Plug]
Jackson: It really is. And we brought someone into this conversation today who has been thinking about that discomfort for quite some time. In fact, he's built a framework for what comes out the other side. More on that at the end — that's what we call, in the business, a teaser.
Scott: A teaser. But let's also do what they call in the business a shout-out. This week's shout-out is to Marissa in Atlanta, Georgia. Marissa, thank you so much for being a part of this community — it means more to us than you know that you're here. And to everybody listening in, whether you're joining us from Comsaz, Austria, or from Mansfield, Texas — we're really glad that you showed up today.
Jackson: Yeah, we're glad you're here. Very, very grateful. And we're going to make it absolutely worth your time.
Scott: We're going to do one more thing, Jackson, because I want to talk about the Ascent Academy for a second. I want everybody to take 30 seconds and think about the performance problem you're most focused on right now. And now ask yourself: is that about a person, or is it about how the system around that person was designed?
Jackson's CHRO Ascent Academy teaches CHROs to read the difference between one and the other before they act. And I know — because I've looked at it — there's a lot of strong feedback from graduates: material that's immediately relevant, participants able to apply the ideas the very same week they're in the program. Seats are limited, folks. Check it out at mytalentsherpa.com.
[The 30-Year HRBP Hangover]
Jackson: Yep, starting May 15th. Okay, let's dive in. Here's where we are. The HR business partner model is roughly 30 years old — 1996, I think. Dave Ulrich designed a function that would sit inside the business and translate talent decisions into business outcomes. That mandate made great sense on paper. The problem is that most organizations took that model and changed the title without actually changing the work. The service orientation stayed. The compliance orientation stayed. And the reporting structures that kept HR one step removed from real capital decisions stayed. And then we spent three decades wondering why the function couldn't operate at enterprise altitude.
Scott: The framing that keeps surfacing is that HR needs to be more strategic. The CEO wants it. The CHRO wants it. The CHRO wants a strategic team. The HR business partner wants a strategic role. And PwC's research shows only 60% of CEOs actually describe their CHRO as a highly effective business partner — even now, even today, after 30 years. That number has moved really slowly despite years of investment in different types of transformation.
In 2024, Mercer's Voice of the CHRO report found that 41% of CHROs want greater depth in data analytics — which means that even at the top of the function, the diagnostic capability for strategic work is still being built. The capability problem is real, but it's downstream of a design problem that most organizations just keep skipping past.
Jackson: And here's where that design problem becomes visible. Hybrid work is fragmenting how and where work happens. AI — I don't know if you've heard of it — is changing what work requires for humans and everything else. Skill-based resourcing is reshaping how talent moves inside organizations. And real estate decisions — which we never talk about — are shaping collaboration patterns in ways that HR, IT, and facilities are each addressing from their own lane, but not together.
Gallup's 2024 State of the Global Workforce report found that employee engagement dropped from 23 to 21%, costing an estimated $438 billion in lost productivity globally. That's the second decline in over a decade. And the dominant response has been more manager training, better benefits, improved communication — which is treating work design problems as people problems.
Scott: What I think is going on is that every function optimizes its own slice and nobody really owns the whole system. IT deploys a collaboration platform. HR designs the onboarding program. Real estate configures the workspace. The person actually doing the work is navigating three independently designed systems that were never reconciled together. That's not a talent problem. That's an organizational design problem, and it doesn't have an assigned owner. Until you name who's accountable for that whole system, you're going to keep throwing capable people at a structural problem and calling the results a performance gap.
[Meet Phil Kirshner and the Gap]
Jackson: That's exactly the frame for today's conversation. And it's a frame that led me to reach out to our guest. Phil Kirshner is someone I met when he was already a listener of the show, and he had very strong opinions about where the org design conversation needed to go. I'm grateful he reached out. He's done this work from every angle — across Credit Suisse, JLL, WeWork, McKinsey. He's been sitting exactly at this intersection for over 20 years. For the past several years, he's been building the intellectual architecture for the function that does not yet exist in most organizations — and he calls it the Chief of Work. Phil, welcome to the Talent Sherpa Podcast. Before we get into the assumptions, what's your read on what Scott and I just laid out?
Phil: Thank you so much for having me. I'm really excited to go from being a listener to being a guest — especially as someone who has identified myself as a Sherpa. I love that you have that name.
What you said resonates absolutely. As someone who comes from outside of core HR, just hearing you lean into the business partner as the anchor role for this — and thinking about the half of my career spent on the practitioner side in three different groups internally — if you had asked me whether I had a business partner involved in "change the work / design the work" kind of conversations, I absolutely cannot think of a single example. And that was at large financial services companies where business partners were present in at least three, if not four, of the core shared services functions: HR business partner, IT business partner, finance business partner, maybe operations. But all of them I think of as handlers, really. They're translating how the sausage gets made for the business. They're passing information back and forth — but we were never in the weeds of: this feels clunky, this is broken, this is full of friction — how do we do it differently? That's not the memory I have.
[Assumption One: Better HRBPs Fix It]
Jackson: So let's get into what's keeping organizations from closing that gap today. The first assumption is one I've held for a long time, and I think most senior HR leaders would recognize it. It sounds like this: if we can get the HRBP to be more strategic, we've solved the problem. Find better talent, reduce the administrative noise, tighten the mandate so expectations are explicit. But I challenge the assumption underneath that. It's the right vehicle — but we're running a talent problem inside of it. What it misses is that you can put excellent people into a role structurally designed to produce a service outcome, and they are going to produce a service outcome. That design does not care about the capability of the person in it.
Scott: Let me name why that assumption feels right — because it's not careless thinking. When you're inside a large HR organization, the visible evidence is about execution. What did you do today? Did the onboarding happen? Did the performance review cycle close? Did the benefits renewal go smoothly? Those deliverables require capable people. And the assumption that better people produce better outcomes is a rational conclusion — but it's from the wrong data set. Phil, when you've walked into organizations going through this kind of transformation, what does that assumption look like when it's running at full speed?
Phil: Right. And I like your point, Jackson, that if you take even a highly capable, strategic, motivated, sleeves-up business partner — someone really trying to know more about the business of the business — and the business they're in is still service-oriented, then the reputation of the function they represent is nine times out of ten going to be: you're slowing me down. Like, "oh, that process is coming back around" — it's happening to me, or it's taking longer than I want to hire that new person. The whole aura of the function — the fog from which this business partner emerges saying "I'm here to help, I want to be strategic" — strictly from a change management perspective, the client is already carrying the burden of being burned or slowed down by the thousand people behind that one business partner. Which means they're walking into an unfair fight. Plus it's designed for repetition — for running the company, as we'll get into — and not for helping me and my people work faster, better, smarter.
Jackson: I think part of that, Phil, is that you grow up in organizations as a younger HR person and you are asked to look at the business through a compliance lens. And then you end up as an HRBP running all these programs. And what is the primary thing you're asked to do? Make sure that people are complying with the program as intended. So you have business logic absent and compliance logic instead. One of the challenges with the CHROs I work with is that as you get more advanced in the organization and your enterprise scope expands, you still have all the people you're interacting with who think of you as the compliance person they grew up learning to work around. And now we have a structural problem. And it kind of doesn't matter who's in the chair — but it also really matters who's in the chair. What are your thoughts?
Phil: That resonates directly. While I may not have been a business partner, I started my career in information security — so it was always "hi, I'm here because you're building something and we have questions, because I work for a regulated company." It was always smiles and polite. But you're not here for fun. You're here because of the kind of company we are. The leader was always: how do I get through this as quickly and reasonably as possible? And no matter how many good ideas you bring — help us close the risk landscape, help us avoid an audit, do anything positive — I can maybe remember one time where a group came back proactively and said, "we want you here to help us think about how to do this differently from scratch," instead of waiting until we set off the alarm somewhere. It's just so difficult to show up representing a process orientation, a compliance orientation — even if you're charismatic and excited — and still be seen as: how do I get through this form?
Jackson: There's a corporate version of the old Ronald Reagan joke. What are the scariest words in the English language? "I'm from the government and I'm here to help." So, Phil — what's the concrete cost when you don't change that base assumption?
Phil: At minimum, you're in a negative-reinforcing cycle of lost credibility. You're losing a seat at the table. To the extent that your client ever expected the work might change — that you might actually help — I think their patience for that happening is very small. So you lose your window.
And you mentioned real estate. I come from the built environment, and we saw a version of this in COVID. A lot of real estate teams were thrust into the spotlight — health and safety, touchless entry, social distancing. In that moment, maybe 5% of real estate and workplace leaders were able to demonstrate real value. The others were sent back down the chain. I used to work for the CFO; now I report to procurement, who reports to the CFO. What happened? It's an erosion. And with the pace of change now, the laser just moves on. You can't get that second at-bat in the way you're structured today.
[Assumption Two: AI Creates Strategy Time]
Scott: You talk about pace of change — let me push us to the next assumption. It's one that AI is reinforcing right now, and it goes something like this: once we automate all the administrative work HR has to do, then HR is going to have the capacity for the strategic work they've always wanted to do. If you remove the burden from the people, the strategic capability will somehow just emerge.
SHRM research shows only about 39% of HR functions have adopted AI at all today in any capacity. So this is mostly a future promise being used to justify a current structure. The problem is that capability and capacity aren't the same thing. Just removing work from someone's calendar doesn't produce the skills. And it doesn't create a mandate to do different work. It just opens the calendar.
Jackson: Which is not bad in itself. But the deeper problem, Scott, is that the work we're describing — work design, organizational friction, reliability architecture — requires a different operating orientation than what HR was built for. Running payroll demands reliability at scale. Diagnosing why a high-performing team is losing executional reliability demands structural acuity and the authority to intervene in how work is designed. Those aren't the same. And when you put both mandates on the same person, my experience is it always defaults to the lower altitude. Someone used to operating at high altitude is going to have a hard time downshifting fast enough. Phil, where do organizations discover that gap most painfully?
Phil: Most organizations just assume freeing up time will magically create new pockets of productivity. I just looked it up — the NBER National Bureau of Economic Research and Duke University did a CFO survey that found workers using AI tools report time spent on certain tasks increased by 346%. There's a concept called Parkinson's Law: effort expands to fill the time. If I have an extra hour because my AI assistant helped me write an email, I'm more likely to write 20 more emails than to look at some higher-order North Star for the work I've always wanted to do. My own article published today is about this kind of white-knuckled feeling of: I've got AI, we're doing everything, we have more meetings, we're recording transcripts, we're sharing documents — but very few companies have actually let go and put themselves into the void where things may very well get worse before they get better. That's the design work. How do we let go of something we don't do anymore and grab onto something we were never able to do without this capability — instead of just writing more emails faster?
Scott: Phil, what do you say to the CHRO who hears all this and responds: you're telling me there's just going to be more of the same kind of work, not less?
Phil: Look, if you're measuring adoption, you're going to get people leaning into adoption — the same as if you prioritize on-site presence, you get coffee-badging: "yeah, I'm here." People will lean into the input and not the output. If instead you say: it is intolerable that it takes 10 days to make a widget — can we put all the problems on the table and figure out why? These technologies are really good at piloting and experimenting. But you have to lean into the world where the names in the boxes may change, where the system you always loved may change. IBM famously shut off all the ways to talk to HR that weren't through a chatbot. And hearing their CHRO tell that story — a lot of the fear was: if I'm a business partner, my value is derived from when my client picks up the phone and calls me. That's a painful realization. So you have to do a pre-mortem on the human resistance to the technological change and set a durable, galvanizing North Star for the bigger change you're trying to see — not just individual experiments, because some of those are going to go sideways.
Scott: The unsaid thing — I want to call it out directly — is that the work has to get redesigned. It's one of the reasons we build actual teammates, not just platforms, and put them on the org chart. So the CHRO can say: that work doesn't belong to you anymore. It belongs to this digital teammate. Your work is now something else. The smart CHRO right now is thinking about how to redesign around that.
Phil: Yes. Name the workflows, name the work. I came from a Swiss bank that loved a good process map. But even looking at clients across different industries — I honestly don't see evidence of that happening the way it was years ago. I didn't see it before COVID. I don't see it now. Who just walks around and documents "this is the way things happen — period, today" — so that if you want to redesign around pain or friction or attrition, there's at least a precedent to start from?
[Assumption Three: Engagement as the Signal]
Jackson: That's an entirely different podcast — and we might pull some all-stars back for that one, because there is a skill inside of HR that is necessary and not there today. I've posted about it, and it's included in the Ascent Academy.
But let me push us into the third assumption. This one might make some people uncomfortable because it's pretty diagnostic — and I also think it's the one that closes the conversation before it can start. We end up in organizations reading engagement scores, looking at attrition rates, and talking about productivity metrics as if those are leading indicators of work system health. I fundamentally disagree with that. By the time engagement drops two points and shows up in a survey, the work system has been producing that outcome for six, nine, twelve, eighteen, twenty-four months. Those are the results of a design problem. So when the C-suite reads a declining number and says "HR, go fix this part of the culture" — they're asking the function responsible for people outcomes to diagnose and repair a system it doesn't own. Culture is decision residue. If you want to know what your culture is, go back and look at your last hundred decisions. You'll find it. And yet HR gets told: go fix the engagement scores. That's ultimately where the conversation breaks down every time.
Scott: It doesn't just break down the conversation — it produces the wrong interventions. If engagement is a work design problem presenting as a people problem, then more manager training, better recognition programs, and improved communication cadence treat the symptoms and leave the system that produced the outcome alone. Organizations cycle through those interventions again and again. They see modest improvements and then watch the numbers drift back because the underlying work was never changed. Phil, what does that diagnostic error cost organizations in concrete terms?
Phil: I'm on my fourth year in a row of seeing Gallup release its major workplace study — the graph always stops on the y-axis at 40% as long as I've been looking at this report. And I post the same thing every year: what happens if you move it to 100%? You notice these little blips don't matter. We haven't changed the system.
I don't come from the world of engagement surveys, but I've come to appreciate the stark difference between the kind of survey most companies send — where employees agree or disagree that "we make good decisions" — and something that actually illuminates the system. When I got to McKinsey and first started learning about the Organizational Health Index, I assumed it was an engagement survey. They were very clear: no, this is different. And it is, because it asks questions about observable leadership behaviors. Do you see leaders giving feedback publicly about how to improve a process? That's scary for leaders, because suddenly the light is shining up instead of down. The real cost is: the longer you keep running a survey oriented toward whether every branch of your tree is happy, the longer you're prolonging the fact that it may very well be your own behaviors that are connected to the outcomes you're trying to change. The people who make the decisions are the catalyst of the culture — and they don't get a lot of feedback.
Jackson: So what's the signal that would allow a CEO or CHRO to address the root cause better?
Phil: Even just a willingness to measure feedback regularly — like a pulse. Something I was impressed by at McKinsey was a willingness to send regular weekly pulses and share the good and the bad. Even when there were contractions or pressures, you'd see it immediately. It gave the entire organization a regular heartbeat that didn't feel biased toward some predetermined outcome.
And from the workplace side — I've tried to add questions to those surveys with many clients and been told by HR: "no, we have our way of doing it, we can't possibly add more questions." So you're burying the feelings people have, and they'll take them somewhere else.
[Local Optimization With No System Owner]
Jackson: That's a Pandora's box we can open. I'm a strong advocate for more frequent, almost zero-question check-ins. But that's a debate for a different time.
I want to build on something you shared, because there's a mechanism underneath all this. The natural inclination is to treat symptoms, not the loop that produces them. Every function that touches the work system optimizes for its own outcomes — which is fine if you only care about your own outcomes. IT deploys the collaboration stack to reduce ticket volume and improve adoption — probably not to improve actual collaboration. Real estate designs the workplace to maximize utilization and reduce cost per square foot. HR measures onboarding completion rates and engagement scores. Each of those might be a legitimate metric inside its own lane. But none of them are metrics for whether work is designed well for the people doing it. And because each function is accountable only to its own lane, no one is accountable for the combined output of all of it.
Scott: That's exactly the point — and it's hard to see from the inside because everybody is doing their job. IT isn't failing. HR isn't failing. Real estate isn't failing. The individual functions are executing. But the system those functions collectively produce is the thing that's not working. And the reason nobody fixes it is that there's no role in the organization whose mandate is to read the combined output and intervene when it's producing friction.
Phil, that's one of the things that immediately resonated for me about your work. You've been the person in the room at McKinsey, at WeWork, at JLL — working at the intersection of people, place, and technology. Tell us what it looks like on the ground. What are the visible signs that nobody owns the whole system? And what do you do about it?
Phil: Two easy examples.
One: you can see it in the digital layer. If an employee encounters a problem in their day and has to go to more than one place — or even has to think for a heartbeat: where do I submit this? — you've put the burden on them. And the odds are they won't bother. The more fluid and chaotic the day gets, the more likely someone is to physically move away from a problem rather than report it.
Two: the empty chair. I experienced this at Credit Suisse. We built an environment that was highly oversubscribed — more people than places to sit — so you want every spot humming. But there would be times when a spot would just sit empty, and depending on who you asked, you'd get a different answer. IT would assume it's cabling, monitors, power. Real estate would assume something about the built environment — the desk doesn't go up, an arm is broken, something spilled. And it may actually turn out to be a people problem — not an HR policy, but: the local senior-ranking person has made a sub-culture where only Bob is allowed to sit there. Everyone else is just terrified. But there's no group that can show up without bias or fear and say the truth. The person in HR in that group doesn't want to say that the senior managing director has created a shadow system that's breaking the environment for hundreds of other people. They don't feel safe saying it.
[Split: Run the Business From Change]
Jackson: Yeah — and you're speaking my language, because when I'd walk into a senior leader meeting on Monday morning and someone was sitting in my chair, it was awful. But what you're really describing is where the reframe lives.
Here's where I think the structural shift is. The HR function was designed to do two different jobs and was never designed to do them separately. First: run the business — payroll, compliance, benefits, onboarding logistics, HRIS, staffing, running core programs that grow as the company matures. Those things have to happen. They have to happen reliably, at scale, with minimal variance. Then there's the change the business work — work design, organizational effectiveness, role clarity, understanding where the friction is, the systems that shape how people actually produce outcomes.
Those two jobs require different people, different incentives, and completely different outcome measures. But we put both under the mandate of one HR business partner and wonder why we get one and not the other. When you ask the same function to do both, you get a function that does neither at the level the business needs. And if one gets done, it's going to be the tactical one. Whether that's because we chase the dopamine hits, or because of capability, or mandate — we can unpack it. But Phil, does that framing match what you've seen?
Phil: Yes, absolutely. It holds across HR, IT, and real estate. There's a very hard feeling of most of the energy going to run the place, and an episodic feeling of excitement when the people who run the place even think they're doing something that's changing the place. Sticking with real estate: renewing a lease or moving across town feels like change, and it is in a way. But it's not a step change. It's moving the current state to where someone told you to go — not a change you're being deliberate about.
And the people buried under the weight of that run-the-place organization tend to be the most progressive, the most interested in aligning outside of functions. Someone I know in digital workplace used the phrase "trauma-bonded peers" with me recently, and I just loved it. Because you feel this shared pain. But the second even one person leaves that network of misfits, the body rejects the organ. Everyone shuts back to: we run the thing, and life goes on like there was no change.
Jackson: Yeah. That's how you end up with an organizational black eye, don't you think, Scott?
Scott: Well, I'll tell you what — for anybody watching on YouTube, you can see I have a black eye. It's from my 177-pound Great Dane slamming into my face. Anybody listening on Spotify was spared that — until right now.
I ran HR for an organization of 15,000 people. We successfully split the urgent from the strategic. And from the practitioner side — it's not that the day-to-day run-the-trains job isn't important. It's critically important. We ran four payrolls. You don't get payroll wrong; there are consequences. But splitting the work is really important — and you can't split it and leave it unfilled. That's one of the reasons I really like your Chief of Work concept. To be successful, all of the tactical work has to go to the people with the skills to do the tactical work. It's a different skill set. And what's left over, you have to think deliberately: have I hired the person with the knowledge, skills, abilities, attitude, and belief system to handle the strategic work? But you still need someone looking over the top, thinking about how things integrate — whether that's the two sides of HR, or whether that's IT, HR, and real estate together. Phil, where does that show up in your experience?
Phil: Where does it show up today, or where should it be?
Scott: Where have you seen good examples of it actually happening?
[Early Models for a Chief of Work]
Phil: I think it's important, as you said, to split run from strategy. I'd even say within strategy and change the place, there's a divider between change that 95% of employees will never explicitly see — entering a new market, onboarding a new kind of employee — and the Chief of Work construct, or what I sometimes call a human COO or the head of what it feels like to work here. That's the human side of change: the adoption of AI, the rhythms, the moments, the journeys that affect all employees in some way — and that no one is thinking about in business as usual.
The points of light I'm starting to see are companies that have created employee experience product managers, using product-related language instead of just journey design language. One approach is a one-and-done: we made journeys and personas, that's cool. The other is: I own the impact. A single workflow, a single journey — say, onboarding — where you pull someone from HR and someone from IT, put them together, and say: you own this end-to-end.
Dropbox is a great example. They have a program called Virtual First and a head of Virtual First that sits in the CHRO organization. Not only does that person look after employee experience and workplace, but they pick up gathering design — gathering becomes a function. They help you plan it, run it, execute, and measure outcome. When you see work design showing up in a title — employee experience product owner — it shows me this is starting to be a recognized problem.
Jackson: Double-click on that for a second. I had not heard "Chief of Work" until you and I started talking. The product framing is really important — it changes the entire frame of reference for who you're solving problems for. It's not solving for compliance; you have to make things actually work better. But one thing you mentioned in our pre-meeting: the Chief of Work has to sit outside the function it's reading. Can you help us understand why?
[Why the Role Must Sit Outside]
Phil: I'm not precious about the title or about reporting structure. But I do believe this bucket of energy — which you could probably seed with some of those trauma-bonded misfits who are already there — needs to be placed somewhere independent. COO, chief of staff, office of the CEO, office of productivity — anything. Because you need them to be able to monitor and speak truth. Why is this process running poorly? Maybe because the leader of that function is still enforcing things to be done the old way. And they can't say that if they report to the head of HR or the head of real estate or the person who rolled out the chatbot that's creating negative implications for the work.
I've called it an organizational Fitbit, or an F1 pit crew. We can phone into the driver: here's everything we're seeing from the telemetry of the car. But you're still driving. It's your choice — your group, your team, your outcomes. I can tell you the way you're taking a turn is negatively impacting your performance.
And then — hopefully — when they have an aha moment about something like onboarding: oh, this affects everybody, we're all really bad at this — they can go get central funding to fix these work design problems quickly. Instead of waiting months for IT to do something, then HR to approve a policy, then real estate to renew a lease. Just: buckle up, let's try something. Don't worry about it.
Jackson: That's really interesting. Let me take a different lens on it. What you're describing is a function that treats organizational friction as a diagnostic signal rather than a management failure. That is a very core shift. Because the old model presumes friction is a talent problem — so the solution is always an intervention around the people involved. Send you to finishing school, teach you how to give good feedback, some broader learning intervention. But the model you're describing assumes friction is a design problem — so the solution is always a systems intervention, not a people one. And the person doing the diagnosis has to be positioned outside the system to read it clearly.
That's what separates your Chief of Work idea from a really talented HRBP. The HRBP is inside the system. In fact, we put "partner" in the title — which I think is a ceiling. It places a limit on what you can do, and it reinforces that you're in a service environment. The Chief of Work reads the system from outside, with accountability for what the combined output produces. Do I have that right?
Phil: Yes. And the people I think of — curious, data-oriented, human-centered, experimentation-friendly, low ego, willing to say "I think I know a better way, will you come with me on this, and if I'm wrong I will not hide from it" — if you put those people independently, give them a data scientist, a human-centered researcher, someone with a Six Sigma black belt — we've done work design for years on the operational side, building cars, down to a science. We just don't apply shop floor logic to office work. Where maybe it is training in the end. Maybe there is something you don't know that you should know. But that shouldn't be the leading assumption. The leading assumption should be: there's something here, we're going to find it, and I want to do it with you, not to you.
Scott: Those are the qualities of it being a systems problem, not a people problem. The system isn't working, so we're going to tweak something and see if it makes the system work better. That's fundamentally different from how we fix people problems.
Phil: And with AI today, you can actually get people engaged in the redesign of their own work. If framed with curiosity, that's exciting. I'll help take away my own toil. But you can't lead with: there's something you don't know, and you have to know it. We're sending you to ChatGPT finishing school to learn how to prompt better.
Jackson: And you mentioned pre-mortems earlier — that's such a critical component of the red team concept we've talked about on this podcast numerous times. You have to be curious about whether what you've designed will reliably deliver the outcome you're designing for. And that requires a permission structure that says, "I don't think this is going to work the way you think it is." To quote one of my favorites — "Inconceivable."
Phil: "You keep using that word. I don't think you know what it means."
[Four Plays Leaders Can Start Monday]
Jackson: "Prepare to die." For those under 40 — we'll put that in the show notes.
This is the part of the podcast where we talk about what to do with this. Concrete actions someone in a leadership position can take starting next Monday. Phil, before Scott and I get into ours — what's the one thing you'd tell a CHRO to do starting Monday?
Phil: Pick some journey, experience, or cross-functional moment. It could be big — like onboarding, which is gnarly. Every company onboards somebody into something; that's somewhat universal. Or it could be as small as meetings. Meeting culture is awful. We were bad at it before COVID; we're worse at it now. There are excellent books about how to make meetings better, and they're usually multi-function in their recommendations. But there's no one person you can hand it to at a company to just fix it. So it's a good example of a thing to test. Pretend you have that little team. Go out, eyes open, do a study. What is good about meetings? What is not? Let them come to your senior group and tell you the truth.
Scott: Diagnosis has to come before design, every time. We're in such a hurry to go fix things, and we don't spend enough time really diagnosing. Great starting point.
Phil: And then lead by example. When McKinsey was exploring how to make hybrid meetings better — they tried 3D cameras that pick up multiple faces in one room. It was the executive team that tried it first. And they were clear: "this is better than it was, but it's still a little weird, and we're humans too, we're figuring it out." Dog-fooding that immediately got everybody on board. We can do this. This isn't you telling me you figured it out — you're going through the motions too.
Jackson: Play number two. Pull your HR headcount budget and look at every role. Next to each line item, put one word: run or change. That exercise is diagnostic, and you don't have to restructure anything to complete it.
Phil: Though "not sure" might be the worst answer of all.
Jackson: What I think you'll find in most organizations is that the large majority of the function sits in the run column. That's not inherently wrong. The problem is when that distribution is invisible, or when you're trying to have the same person accountable for both. My experience is it will always default to run if given a dual mandate. So that exercise opens the ability to have a real conversation with your CEO about what needs to change — and it starts with a shared picture of what actually exists today.
Scott: Here's mine. Find a manager whose team is underperforming. And please — don't send them to training. Instead, sit with them for an hour and ask one question, and probe the heck out of it: what about how the work is structured is getting in your people's way? Not culture, not attitude, not skill gaps — the structure of the work itself. That conversation is going to tell you more about your organization's work design than any engagement survey. And it gives you a concrete entry point. You don't have to have the complete Chief of Work function from day one to do it. You can do that small piece yourself, and it leads you to understand how you'd structure it at scale.
Phil: Just try it. And you may find out that the reason some group thinks something is clunky is because of something they perceive they can't control that's upstream or downstream. "We wait forever for this one thing and it kills the vibe." You never know until you ask.
Jackson: Play four. Under the headline: you only live once. If you're bold — take the accountability gap question directly to your CEO and ask: who in this organization is accountable for how work is designed and executed across HR, IT, and real estate? Not who touches it — who actually owns that combined outcome? My guess is, unless you're working with Phil, the answer is going to be unclear or distributed. And you've now identified part of the mandate gap. That conversation can lead into the opening for a Chief of Work type role.
Phil — close us out. What's the play most organizations skip?
Phil: Treat work like a product. The same trends driving hybrid, AI, and skills-based work are also creating massive leaps in our personal lives — how we personalize everything. I can talk to my house and it does all sorts of things. And yet I go to work and everything feels clunky and I'm filling out paper forms. We're bringing our consumer preferences to work. So we have to think of the work experience as a product where your employees consistently resubscribe — Dropbox actually uses that language: you're always resubscribing to the job. Think about employees the way you think about customer experience, and it becomes much more obvious. But name it.
Jackson: How does a CHRO know if they've actually moved forward on that, Phil?
Phil: I think the hardest challenge — maybe just emotionally — is: are you the run CHRO or are you the change CHRO? If your skill set is being a brutally effective operator for the function, know that, name that, and offer that this small part of your org that is thinking differently should probably be somewhere else. Protect it somehow, whatever the baby step is. Be willing to lead with vulnerability: "I have something in my organization that is not best suited here. We will be better if it is somewhere else." Instead of just assuming you're sending people to finishing school — or holding on to it because the old way said you had to.
[Talent Sherpa Summary and Takeaways]
Jackson: That's brilliant. Okay, senior leaders — your favorite part of the podcast, every week. The Talent Sherpa Summary. Phil, I know you heard Scott say this earlier: the best HR transformation is a cross-functional task force, a 45-day charter, and a slide that recommends renaming the HR business partner.
Scott: They literally never said that, and nobody should listen to Jackson characterize it that way. Oh my God.
Okay, here comes the summary. Phil, keep me honest.
One: the HR mandate hasn't really changed in 30 years, but the work it needs to produce really has. PwC research shows only 60% of CEOs view their CHRO as a highly effective partner today, despite consistent investment in transformation. The reason it keeps stalling: we're aiming at capability inside, but the design hasn't changed. The design problem has to be named before the capability investment can land.
Two: there are two fundamentally different jobs inside any current function — using HR as an example. Run the business handles payroll, compliance, logistics. Change the business handles work design, org effectiveness, friction identification. Asking the same function to do both under one mandate produces a function that does neither.
Three: the loop sustaining the current model is local optimization without cross-functional accountability. IT, HR, and real estate each have their own metrics and optimize to them. The combined output — the actual experience of work for the people doing it — doesn't have an owner. Gallup's data puts employee engagement at 21%, down from 23%, costing a lot every year. But it's not always a people intervention that will solve it. It's a structural problem.
And last: the Chief of Work function fills the accountability gap. It's independent of HR, IT, and real estate. It's product-oriented, focused on high-value journeys like onboarding, and it reads the work system the way a diagnostic tool reads the body. It doesn't work if housed inside one of the functions — it needs to be outside and independent.
Phil, how did I do?
Phil: That's excellent. And it's all going to be even more important the less predictable our days get — org structures are getting blurrier. How are you going to know if any one team is doing the right thing for them if power pushes further and further from the center?
Scott: Do a close-out for us, Phil. If there was one thing you wanted people to walk away with, what would it be?
Phil: Walk the work line — my website and my newsletter, walktheworkline.com — and have the conviction that we can do this. You have to be change-positive and curious, and look for every possible chance to iterate and test faster. That's easier in IT. Trickier with HR and culture, things that move slower. And dead last in real estate, where we've built things for 20 years. But we have to try. That's the only way we'll know if we're making progress.
Jackson: Speed is going to be the currency of the future. There's no doubt.
Phil: Speed, and willingness to hit a few bumps along the way. Speed and safety.
Jackson: Which is hard. Everyone talks about failing fast — until you actually fail. And then how you respond in that moment becomes really important. I've seen people say "fail fast" and then turn around and ask "how could we let this happen?" It's one thing if it's an irrevocable mistake. It's another if it's an area that has to be perfect. But outside of those things — screw up, stub your toe. That's how we all learn.
Phil: And to bring it full circle — I used to have a boss who said when you get a black eye in corporate real estate, it lasts for a decade. Which is why when you say "fail fast" to a facilities person, they'll have a heart attack on the spot. In IT, some people can move a little quicker. But we've all got to move faster and be okay with it — have short toes, so we don't get stepped on as much.
Jackson: Ten extra points for the black eye reference.
[Closing and Where to Learn More]
Jackson: I've got a fly in my studio — I'm having a Mike Pence moment. Please ignore that. We'll leave it in because everyone needs to understand this is real life.
But where I keep coming back to is this: the accountability gap concept. Every organization we described today has capable people in functions that touch the work system. The problem isn't the people. The problem is that no one — in most organizations today — is accountable for the whole. And there's a specific kind of organizational courage required to name that gap. Because naming it means admitting that a structure is not producing what the business needs, that someone new has to own the problem, and that feels like loss — but it's not. The leaders who take that step, who bring the work system question to their CEO rather than waiting for the performance numbers to force the conversation — because you're going to have the conversation, it's just a matter of whether you're choosing it or the business is choosing it for you — those are the ones who are going to stop solving the same problem every two years with a different label on the solution.
Okay, everyone — thank you so much for tuning into the Talent Sherpa Podcast. This is where senior leaders come to rethink how human capital really works. And this is so much fun to do with y'all.
Scott: If you liked today's episode, hit the like button, or better yet, subscribe so episodes get delivered to you. Write us a review on Apple Podcasts, Spotify, or YouTube — it really benefits the community and helps us reach more senior leaders. And if you want more reading, I wrote an article on this subject at Propulsion AI's Perspective page at getpropulsion.ai — called "While You Make Incremental Changes, Your Competitors Are Reinventing Everything."
Jackson: That's a good article — I got a preview and I can tell you it's good. And since we're on the topic, Scott's company Propulsion AI is a workforce intelligence company for private equity. They have AI teammates that surface workforce risk before it closes and help leadership teams drive execution afterward. They translate strategy into individual accountability, coach managers to define roles by outcomes, and give every employee a clear line of sight to what actually matters. Learn more at getpropulsion.ai.
Scott: And if you are a CHRO new to your role, or preparing to step into a CHRO role, Jackson has built tools to help you operate at the altitude that role demands. Personal coaching, the CHRO Ascent Academy, his best-selling Substack — everything you need is at mytalentsherpa.com.
Jackson: Phil — before we close, I just want to thank you so much for being here.
Phil: Thank you so much.
Jackson: The work you're doing on the Chief of Work is exactly the conversation this field needs to be having. For anyone listening who wants to learn more or get in touch — where should they find you?
Phil: Very active on LinkedIn — look for me there. And my website and newsletter are at walktheworkline.com.
Jackson: We'll have all that in the show notes. Thanks again, Phil. And thanks to everyone who's listening. Until next time — keep raising the bar. Separate what runs the business from what changes it. And keep on climbing.
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