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.
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The Talent Sherpa Podcast
The Question That Opens Power and Trust
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There's a specific moment that defines CHRO careers — and it has nothing to do with strategy, credentials, or knowing your P&L.
It's the moment when something important is heading the wrong direction in a senior room, and you have to decide what to do. You either swallow it and stay quiet, or you come in so hard that the room goes cold. And in both cases, the decision keeps moving without you.
Most of the CHROs this happens to aren't lacking knowledge or confidence. They're losing influence because of how they challenge — not whether they challenge.
This episode is about the third path: challenging with curiosity. If you've ever been right in a room and still watched the decision go sideways, this one is for you.
What You'll Learn
- Why the gap between "knowing the answer" and "influencing the outcome" is behavioral, not analytical
- The four faulty assumptions that keep confident CHROs excluded from key decisions — including why directness and being right aren't the strategies you think they are
- A three-move framework — slow the certainty, name the data not the conclusion, seek what you might be missing — for challenging without triggering defensiveness
- Why asking questions is not soft: how precise inquiry surfaces the assumption underneath the metric while letting the other person own the insight
- A six-step weekly practice for building the "challenging with curiosity" muscle, from auditing your behavioral default to debriefing one challenge conversation per week
- The bridge phrases that signal inquiry without signaling uncertainty — and why they only work in your authentic voice
Key Quotes
- "If you don't challenge, you're not adding value. And if you challenge badly, you lose access."
- "Do you want to be right, or do you want to be effective? Directness is a delivery mode — it's not a strategy."
- "Silence isn't neutral. It's a choice. And 'later' is often never."
- "The skill that keeps CHROs in the room is the ability to raise a hard thing in a way that opens the conversation rather than closes it."
Sources for Statistics Cited
- 89% of CEOs believe their CHROs should have a central role in driving long-term growth — Accenture, "The CHRO as a Growth Executive" (2023)
- Only 45% of those same CEOs are creating the conditions to let the CHRO have that impact — Accenture, "The CHRO as a Growth Executive" (2023)
- New hires enter feeling optimistic, then over time feel less safe speaking up — Edmondson, Bransby & Kerrissey, HBR (July 2024)
- 93% of executives report the highest level of psychological safety — Wiley Workplace Intelligence, 2023
- 76% of executives say they feel safe taking interpersonal risk — Wiley Workplace Intelligence, 2023
- 50% of employees
Resources
- CHRO Ascent Academy — Jackson's cohort-based program for sitting CHROs and leaders actively preparing to step into the role. A practical, peer-driven experience designed to build altitude, mandate clarity, and the strategic relationships the role requires. Currently building the next cohort — sign up for the wait list at mytalentsherpa.com
- getpropulsion.ai — AI teammates that enable leadership to focus on the work that actually drives business outcomes. Recommended for organizations where role clarity is the starting constraint.
- Talent Sherpa Substack — Jackson's newsletter on human capital, CHRO altitude, and enterprise leadership at talentsherpa.substack.com
Jackson Lynch: 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. He's a former CHRO with the scar tissue to prove it, the alleged owner of a coffee mug that just says culture, and the founder of Propulsion AI.
Now, Scott, nobody talks about this one openly, but I think it's one of the most career-defining moments that shows up in the CHRO role. And I've watched really talented HR leaders lose influence in rooms that they deserve to keep. Not because they didn't know their stuff. Not because the CEO was unreachable. Because when the moment came to push back on something really important, they either swallowed it and kept quiet, or they came in so hard that the room went cold. And once that happens, the decisions keep moving — but without you.
Scott Morris: Yeah, so today we are going to talk about what it actually takes to challenge something in a senior room and come out the other side with more trust than you walked in with. But before we dive in, do us a favor, folks — please subscribe to the podcast, leave us a comment, or drop us a quick review on your preferred platform. It's how we grow the pod, how we keep the content sharp for senior leaders. It's a small favor for us, but it's potentially a big favor for somebody else.
Jackson: Okay, Scott, every CHRO has been told some version of this: earn your influence. Be credible, speak the language of business, be strategic not tactical. And most of the CHROs that I know and work with have done that work. They understand the P&L, they can talk margin and risk, they see the constraint impacting business performance and work to relax it. They know where the talent gaps are before the CEO does.
But what we're going to talk about today is the difference between knowing the answer and being able to influence the outcome — because those are two completely different skills. And the gap between them is not analytical, it is behavioral.
Scott: You know, the gap has a name, actually — and it's not confidence. I've met plenty of confident CHROs who were systematically excluded from key decisions. What it really comes down to is how you challenge. Because if you don't challenge, you're not adding value. And if you challenge badly, you lose access.
Jackson: That's right. And here's what makes this so interesting. Accenture published research showing that 89% of CEOs believe their CHROs should have a central role in driving long-term growth. 89%. That is not a small minority — that is near-universal belief. But here's the number that actually matters: only 45% of those same CEOs are creating the conditions to let the CHRO have that impact. So the belief is there, but the access isn't. And I would argue that a big chunk of that access gap is a behavioral pattern problem, not a structural one.
Scott: Walk us through what you mean. Because I think a lot of CHROs might hear that and think it's a politics problem or a power problem — not something they can actually move.
Jackson: Well, maybe think about it this way. We know from Amy Edmondson's research at Harvard that new hires enter organizations feeling super optimistic and confident — and that over time they feel less and less safe speaking up. And that decay happens at every level, including the C-suite. No one thinks we're immune to this, but people think we might be. We're not. It happens at every level.
But here's what is really interesting. The Wiley research on psychological safety shows that executives report the highest level of psychological safety — 93%. But 76% of executives say they feel safe taking interpersonal risk. So think about that gap: the gap between feeling safe and actually acting on that safety and taking risks. That's the behavioral gap I'm talking about.
And for CHROs, to be honest, the risk calculus is real. If you speak up wrong, you're going to get cut out of conversations where your input actually matters. Or you can go silent and become irrelevant. So what we're really talking about today is a third path — and it requires a very specific skill. Scott, can you name it?
Scott: Yeah. It's challenging with curiosity. It's not the absence of a challenge, and it's not a challenge delivered as an indictment. It's a challenge delivered as a question that opens thinking rather than closes it. It's a skill that determines whether CHROs become strategic voices or get quietly relegated to process management with a decent salary. And it's not just the CHRO's career that's on the line. When CHROs go silent, the organization starts to run into risks it can't see. When the CHRO challenges badly, the same thing happens — they stop getting pulled into conversations early.
Jackson: Let's call out a few of the faulty assumptions that get leaders stuck.
The first one: If I speak up more clearly and directly, people will respect me more. I'll be honest — I'm a reformed smoker on this one. I'm a direct communicator. And I thought as long as I'm saying the thing, life will be good. Think about it like the CHRO who goes into the AI deployment meeting and says, "This model is biased," instead of, "I'm looking at the pass-through rates across candidate groups — what are we seeing here?" Same concern, completely different outcomes based on how you deliver it.
The assumption is that being clear and direct is always a virtue. Bluntness is honesty. If someone is uncomfortable, that's their problem, not mine. I've grown since then. How you say it determines whether you were heard or tolerated. I had a coach who once helped shape this for me: Do you want to be right, or do you want to be effective? Directness is a delivery mode. It's not a strategy. When a challenge lands as an accusation or a conclusion, it triggers defensiveness. The other person stops processing and starts shielding. So what happens? Your brilliant insight — completely ignored.
Scott: You said that one applied to you. I gotta tell you — it applies to me too. I get an exponent because I'm passionate about things, and that passion multiplies the directness. It's one I wish I could say was in my past, but it's not. It's one I constantly have to watch.
Here's a second one, and it's the other side of what you just painted: Going silent is the safe move when the room gets charged. The research shows that 50% of employees believe their ideas are not going to get taken seriously. And I think sometimes we — CHROs, people broadly — are not immune to that. We're people just like everybody else. Sometimes the stakes are just higher because of who we influence.
The assumption here is that staying quiet avoids conflict and preserves the relationships you need for later — that you can raise concerns through the right channels eventually. But the reality is that silence isn't neutral. It's a choice. And it has consequences on both sides. "Later" is often never. And when the thing you saw earlier surfaces as a crisis, you're not just credited — you're often implicated for not saying anything.
Jackson: Yeah, that's a really interesting one, Scott. I've had people who worked for me go into meetings, know the right answer, say nothing, and then bring it to me afterward like I'm supposed to solve the problem. You were in the meeting. That's why you get paid a lot of money.
The third one is a correlate to my first: My credibility comes from being right. When's the last time you changed your mind in a meeting because someone told you definitively that you were wrong? Never — you dig in. Now think about the last time a question made you see something you missed. That happens all the time. The second experience is the currency of senior influence. The first one just shuts things down.
The faulty assumption is: if I have the data and the analysis, my position will prevail on the merits. The substance will win. Back to the question: do you want to be right, or do you want to be effective? The reality is that credibility in the room comes from how you show up in the conversation, not just whether your conclusions are correct. Being right is table stakes — you should be right more than you're wrong. But being useful in real time is the differentiator. People who make the people around them think better earn access. People who make the people around them defensive lose access — regardless of whether they were right to begin with.
Scott: Let me hit the next one. It's that challenging with questions is somehow soft — that it lacks conviction. I think this is the move that separates CHROs who get called in early from CHROs who get briefed on what already got decided.
The assumption is that asking questions rather than stating positions signals uncertainty or passivity — that strong leaders take positions. But the reality is that questioning is one of the highest-leverage leadership moves available to anyone. The question: If overall accuracy looks strong, but certain groups advance at a much lower rate, what might that be telling us? That's not soft. It's precise. It surfaces the assumption underneath the metric without assigning blame. The question can change a deployment decision. A statement can't — because a defensive response shuts the door. The question opens it.
Jackson: Yeah, I think that fourth one is the one that costs people the most. The instinct is to demonstrate conviction by stating positions — we're wired to do it that way. And let's be honest, you get promoted by having answers. Then you get in the room where the skill you need isn't to have the right answer — it's to have the right question. And no one ever told you that the rules changed.
Scott: Yeah. The job changed the day you walked into that room. You're not there to be the smartest person with the data. You're there to help the room make better decisions. And those aren't always the same thing.
So, how do we move from challenge as conclusion to challenge as discovery? Let's think of it as a three-move framework — three moves a CHRO can make in any charged conversation to stay in the room, stay useful, and actually shift the outcome.
Jackson: All right, Scott, why don't you take Move One? You're naturally way better at this than I am.
Scott: I'm always nervous when you say that. But I'll take the first one: slow the certainty.
Most bad challenges happen at speed — when the energy is running, when the passion is there. Someone says something that feels wrong and the instinct is to correct it immediately. But speed here is the enemy. When you slow down in a charged moment, you signal confidence rather than reactivity. You have time to choose your entry point. You move from reacting to responding.
Practically, that means building two or three seconds into your pattern before you speak. It means noticing when your body is moving into correction mode and deliberately shifting into inquiry mode. That's not passive — it's the opposite. You're choosing how to engage rather than letting the moment choose for you.
The question to ask yourself in that moment is: what's the assumption underneath what was just said? And how do I get that assumption into the conversation without triggering the room?
Here's where I see it in myself. When I start to lean in — when the passion moves — I know I'm moving on emotion rather than listening to the underlying assumption. And I have to sit back and force myself into that more intellectual mode rather than emotional.
Jackson: And there's maybe a little story time on what that looks like in real time. The former CHRO that I replaced was put in one of those positions in front of the board. The CEO said something that was inherently inaccurate — but also one of those moments you sometimes need to manage through. My predecessor decided to correct the boss in front of his bosses, in real time. He was right. Did I mention he was my predecessor? He didn't make it through the week.
And candidly, it wasn't even a big deal. It was: did we do step one before step two, or step two before step one? No ethical component whatsoever. But he wanted to be right. So what the boss said made him look a little bad. You take one for the team in that moment, and then you have the conversation afterward: "Hey, I wasn't going to correct you in the room — but I want to make sure you and I are thinking about this the same way. Here's my view. Do you have a different one?" Those are the right conversations to have.
Okay. Here's Move Two: name the data, not the conclusion.
There's a moment in every charged conversation where a CHRO has two choices. They state what they believe — which closes the loop — or they name what they're observing. Naming the data sounds something like: "I was looking at the pass-through rates across candidate groups and I noticed some differences. How did we evaluate those in the model design?" That's not a soft question. It's precise — aimed at the assumption underneath the metric. But you're asking how. It invites the other person to surface the issue themselves.
When they surface it themselves, they own it. They're not defensive. If you raise it as a conclusion, you put them on the defensive immediately. Contrast that with: "The model is biased and we should not deploy it." That might be true — but you just closed the door. The tech team is now defending their work instead of examining it. You were right. Congratulations. Now you're irrelevant.
Scott: But Jackson, let me push back for a second — because I'm worried some people might hear that and think it's political softness. Isn't there a time to just say the thing directly?
Jackson: Of course there is. When the stakes are legal or ethical. When you've exhausted the inquiry path. When you need to escalate. Over 30 years of doing this, it happens occasionally — but it's not every conversation. And when it does, that's a different conversation entirely.
But most of the moments CHROs face in any given week aren't that. It's: this decision is heading in a direction I see differently than the room, and I need to redirect it. You do that better by naming the data without the conclusion. That is the most powerful move available.
Scott: Let me go to Move Three: seek what you might be missing.
I borrowed this from what I've taught other HR leaders and managers for years in performance management. Start with the assumption that you don't know — and get an inquiry going that uncovers the truth as if you didn't know it was there.
When you challenge with curiosity, the stated purpose is discovery — not victory. And you have to do it genuinely, including the possibility that the other person knows something you might not know. By using this approach, either the other person discovers something they were missing, or you discover what you were missing. Both outcomes are wins. Both outcomes improve the decision.
When people realize you were asking because you genuinely wanted to understand — not because you were building a case against them — it shifts the dynamic in the room entirely. And I think CHROs who master this get called in early because their questions are known to make things better, not harder. That reputation — and I know you and I resist the "seat at the table" analogy — but that reputation is the seat at the table that no org chart and no title will ever give you.
Jackson: Two words I want to double-click on: genuine and authentic. Because you can ask a question in a non-genuine or inauthentic way and come across as a real problem.
Scott: It's worse.
Jackson: That's not what I'm suggesting. I had a situation — a real story — where we were making a decision around an employment practice that I found to be wrong. It moved into ethically risky, legally questionable territory. And I still took the approach of: "Have we considered what would happen when...?" and "The data would suggest that 35 to 37 percent of the time, this isn't doing what we think it will. Have we calculated the potential cost when...?" I could have asked that same question as a challenge — "Have you really thought through what would happen if this happened?" — and completely torpedoed the conversation.
How you deliver it matters tremendously. So for me, Scott, the real question is: are CHROs willing to stop leading with their conclusions and start leading with the questions? That's not soft. It requires a level of confidence that's actually harder than being direct — and this is coming from a direct guy. It requires you to trust that the question is more powerful than the answer. And I have absolutely found that to be true.
Scott: I think we've named it, called out the elements, and exposed the assumptions. Let's make this practical — let's turn this into a playbook.
Jackson: What I would do first is audit your last three weeks of meetings. Go into your notes, look at the moments where you had a concern, and then evaluate: Did you say something? Did you come in too hard? Did you ask questions? Did you provide definitive answers? Don't judge the outcome — just use it to identify the pattern. Most CHROs have a consistent behavioral default. As I've mentioned, I come from a long line of people who know this well — the first step is to admit you have a pattern. Knowing your behavioral default is the critical starting point, because you can't interrupt a pattern you can't see.
Scott: Good. The second move: write observations about data before you go into the meeting. Not conclusions. Not recommendations. Observations. When I look at X, I notice Y. If you practice converting conclusions into observations before you're in the room, you start to build that muscle. When the stakes are low, it's easier to do it — and it becomes available when the stakes are high.
Jackson: Yeah. I probably have a reputation for getting analytically to the thing behind the thing at a pretty high clip. And one of my challenges has been: I get there and the rest of the room is still somewhere else — which makes it very hard to influence. But the more you practice the questions, the more precise and insightful they become. And now it's just naturally what I do. "Hey, I'm noticing this. Have you thought about the other implications there? I'm curious what you might uncover." You're basically telling the person they didn't think it all the way through — but you're doing it in a way that lets them get to that conclusion themselves. And then you can reinforce it and move on.
Here's the third move: use bridge phrases. And if I could ask you to write down one thing from this episode, it would be: build these into your active vocabulary. Phrases like:
- Help me understand…
- How have we evaluated…
- I'm curious as to what we would see if…
- What would it mean if the data showed…
Pick the one that works best for you. These phrases signal inquiry without signaling uncertainty. Write them down, practice them — and when they become automatic, that's when you know you've gotten there. It's a choice. You can do this. It's not easy, but it is a practice skill.
Scott: Write them down and practice them — but make sure they're in your authentic voice, because they have to come out like a genuine question you're really listening for the answer to. Not one you're using as a setup.
Here's the fourth move: debrief one challenge conversation per week. After a meeting where you challenged something, take five minutes. Write down what you said. Write down what happened next. Write down what you'd do differently. Writing it down is important — it's a commitment. You're not going to invent it and replay a filtered version in your head. This is the feedback loop that a lot of leaders skip. The CHRO who systematically learns from their own challenge conversations will compound faster than anybody around them.
Jackson: And here's the fifth: model the move in your next meeting — for a leader on your team. When one of your direct reports makes a statement that feels incomplete, and your natural inclination would be to correct it, ask the question instead. Do it visibly. Let others on the team watch you choose curiosity over conclusion. Especially if you have a history of doing the opposite — that's the fastest way to shift the behavior in the meeting. And it will have a huge implication for the culture in your function. You cannot, in my view, install a skill that you don't personally demonstrate.
Scott: And the cool thing about that is the stakes feel lower in those conversations — so it becomes easier to practice. Which becomes muscle memory for when the stakes are higher. Can I throw in a sixth?
Jackson: Sure. There's a lot of help here this week.
Scott: The sixth move: identify the one conversation you've been avoiding. We all have them. The conversation where you know something's off and you've been calculating whether to raise it. That conversation. Write down the data observation — not the conclusion. Practice the question. Then have the conversation. The silence is already costing you. The question costs you less than you think.
Jackson: Yeah, that one's probably the hardest for most HROs. I don't exactly know why, but sometimes the silence feels more protective — and it's not. All you're doing is delaying. The risk doesn't go away. In fact, it compounds.
Okay. We are at the part of the podcast, senior leaders, where this is in fact your Talent Sherpa Summary. Or, as Scott always says: the louder you say it, the more people will agree with you — even when you're completely wrong.
Scott: I think I've lived that one. All right, let me do the summary.
Number one: challenging with curiosity is not soft — it is precision. It's how you surface the thing underneath the thing without triggering the defensive response that closes the room.
Number two: silence and force are both exits. Silence removes you from influence. Force removes you from access. The third path is inquiry delivered with genuine intent to discover.
Number three: the skill is learnable — and specifically learnable by CHROs, because CHROs sit at the incredible intersection of people dynamics, business risk, and decision-making authority. And that intersection is exactly where challenging with curiosity matters most.
Number four: your credibility in the room is not built from being right — it's built from being useful. The CHRO who makes the room better earns a different kind of access and a different kind of respect than the one who makes the room feel challenged.
Jackson: Yeah. The big takeaway for me is this: the skill that keeps CHROs in the room is not analysis, not being right, not credentials. In my first CHRO job, that's what I thought it was. But it's not. It's the ability to raise a hard thing in a way that opens the conversation rather than closes it. That is the behavioral edge. And it compounds. Every room you navigate well increases your access to the next one.
So learn to challenge well, and the influence will follow.
That's it for this week. I want to thank everyone for tuning into the Talent Sherpa Podcast — this is where senior leaders come to rethink how human capital really works. And it is so much fun to do this with all of you.
I wanted to give a quick shout-out to one of our favorite listeners — hi, Drake from Baton Rouge. By the way, Drake is a CFO listening to the show. Thank you for being part of the Talent Sherpa community. And we want to thank everyone for listening, whether it's in Salt Lake City, Utah, or Pretoria, South Africa. Yes, we've hit our fifth continent. We now have listeners on five of the seven continents. Antarctica is probably not in our future — but South America should be. So if you have a friend down in South America, please send them a note and ask them to start listening. Scott actually speaks both Portuguese and Spanish, allegedly. And he's promised that if we get someone to listen, he'll do part of a segment in Spanish.
Scott: I speak Portuguese to correct your Portuguese — but I do speak Spanish. If you liked today's episode, hit the like button — or better yet, subscribe and leave us a review on your favorite platform, whether that's Apple Podcasts, Spotify, or YouTube. It's free, it's really helpful to us, and it might be helpful to somebody else.
Jackson: And look — if you're a CHRO wondering where to start your AI journey, or a CFO wondering where to start the AI journey for human capital, don't forget to check out Propulsion AI at getpropulsion.ai. They're building a team of AI teammates that help human capital leaders focus on what matters most to the business. Scott, remind us — what is it you're helping people with these days?
Scott: Yeah, we use artificial intelligence to coach managers — to do the heavy lifting and turn value creation plans into actual results in the field. And don't forget — if you're an early-stage CHRO, Jackson has helped a lot of people just like you — and honestly, just like me — through personal coaching, through the CHRO Ascent Academy, and through his best-selling Substack. You can find access to all three at mytalentsherpa.com.
Jackson: Thank you, Scott, and thanks to everyone who's listening. And until next time — keep raising the bar. Keep asking the question that opens the room. And keep on climbing.
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