You Already Know It's the Wrong Job

The CHRO role is one of the most context-dependent jobs in the executive suite. Same title. Completely different work. And most leaders stepping into it for the first time skip the evaluation that actually matters — "am I right for this context, this CEO, this investment thesis, at this moment?" 

That gap between those two questions is where careers get derailed.

This episode is a masterclass in CHRO self-evaluation. Jackson is joined by Scott Morris and Scott Bontempo — 20-year PE veteran and former CHRO at Frito-Lay — to unpack three evaluation lenses every senior HR leader needs to use before saying yes: skills with evidence, the actual work (not the job description), and the real conditions for success. 

Scott Bontempo: https://www.bontempoadvisory.com

What You'll Learn

• Why only ~25% of CEOs who say they want a "strategic partner" actually mean it — and how to diagnose which bucket you're walking into before you accept the offer
• How to evaluate your skills with real evidence, not practiced resume recitations — including the mirror-up technique that exposes actual gaps
• What the investment thesis reveals about the work — and why a public company playbook will get you fired in a PE portfolio company
• Why you need to define your walkaway criteria before you're in the process, not during it — and what that list should actually contain

Sources for Statistics Cited

• 53% of new CHRO appointments in 2024 were first-time CHROs — Russell Reynolds Global CHRO Turnover Index
• CHRO turnover hit 15.5% in the Fortune 200, up 36% year-over-year — Talent Strategy Group CHRO Trends 2024
• 52% of CHROs turn over within 12 months of a CEO transition — Talent Strategy Group CHRO Trends 2024
• ~1 in 7 (15%) of 2024 CHRO appointments came from outside HR entirely — Russell Reynolds: The CHRO of the Future
• 66% of HR leaders confident identifying skills for growth; 48% know how to acquire them — Korn Ferry
• EBITDA margin expansion as primary PE value driver, replacing financial engineering — Bain Global Private Equity Report 2024

Keywords: CHRO career evaluation, CHRO job search, CHRO and CEO alignment, human capital strategy, CHRO skills assessment, private equity CHRO, first-time CHRO, CHRO tenure, executive career decisions, talent strategy.

Transcript

[COLD OPEN — Scott Bontempo]

And I think about that in the context of a checklist — building that ahead of time. I'm contemplating this role, I'm contemplating how my skill sets align. If they tell you what success looks like and can articulate that very clearly to you, you have another data point that says, "Hmm, what they think success looks like plays to my strengths" or "identifies more weaknesses than strengths." So I think that's also a helpful tool inside of a checklist-building exercise.

[INTRO]

Jackson: Well, 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 am joined by my co-host Scott Morris — a former CHRO with the scar tissue to prove it, a genuine believer in the best of people, and the founder of Propulsion AI.

So, Scott, we're going to tackle something today that every CHRO thinks about but they rarely talk about honestly, and that's the notion of evaluation. And I'm not talking about evaluating other people, but I'm talking about evaluating yourself, the work itself, and whether the opportunity in front of you is worth taking. It's like being a mountain climber who's never actually assessed whether they are ready for the summit, whether the route makes sense, or whether the weather is in fact going to kill them.

And one of the reasons I'm excited about this episode is I've made all of these mistakes myself. Early in my career, I took a role because the title sounded great — it was a public company CHRO, it was where I wanted to live, it was all the good things. And it turns out the CEO wanted a traditional people person, not a human capital strategist. And that mismatch cost me two years and then one more unnecessary move from my family.

[CHRO TURNOVER AND CONTEXT RISK]

Scott Morris: I know exactly what you mean on this one, because I've made the exact same mistake. And I think it probably resulted in the greatest career failure I've ever had, even though I was at the top of my game on what I could do.

Before we dive into this, Jackson, let me ask everyone — please subscribe to the podcast. Just take a moment and click the button, or leave us a comment if you're able to do that. Drop us a quick review on your preferred platform. It's how we grow the pod, and it's how we keep the content sharp for other senior leaders.

Jackson: So, Scott, diving into this. Every CHRO has heard the conventional wisdom. You gotta know your worth. You need to network more. You need to figure out a way to get on the short list. And the Executive Search Industrial Complex has kind of turned career advancement into a series of platitudes — "position yourself," "build the brand." And most of that is... well, I can't say it. It's a family show. But here's what we're going to talk about today: no two CHRO positions are alike. And that's not a cliché — that is a capital allocation problem hiding in plain sight.

Scott Morris: You are 100% right. And the data backs it up too, Jackson. Russell Reynolds found that 53% of new CHRO appointments in 2024 were first-time CHROs — more than half of the people taking the top HR role had never sat in it before. And CHRO turnover hit 15.5% in the Fortune 200 last year, up 36% from just a year ago, according to the Talent Strategy Group. So there are a lot of people figuring this role out on the fly.

Jackson: And look, Morris, this is the thing behind the thing. It depends on which data you're looking at, but somewhere between 52 and 66% of brand new CEOs come in and they replace their CHRO within the year. That has a material impact on what a CHRO does when they're looking at opportunity — it means you're not evaluating just the job. You're also evaluating the stability of the team, your peers, the investment thesis, the board dynamics. The work itself is different in every context.

Scott Morris: You and I talk about this one privately a lot. Think about the range that the role has, right? At one end, you've got a CHRO for a Fortune 50 company with 200,000 employees and a $15 billion HR budget. That's just a fundamentally different job than the CHRO at a PE portfolio company that has 2,000 — or even fewer — employees and 18 months to prove value before exit. Same title, but completely different work.

Jackson: And if you look at the most recent Bain private equity study, they're talking about this in even more detail — because of the importance of EBITDA margin expansion as the primary creator of value, versus the more financial engineering that we've been relying on over the last decade. And public company boards are starting to catch up on this thing too.

Scott Morris: So let's make this one painfully obvious. The evaluation that you and I are going to talk about today is not, "Am I ready to be a CHRO?" The evaluation is, "Am I ready to be this CHRO, in this context, with this CEO, for this business challenge?" And most people skip that analysis entirely.

Jackson: And you and I couldn't do this ourselves — we're not smart enough to handle this alone — which is why we have brought in someone who has done this very evaluation work hundreds of times. His name is Scott Bontempo. He has spent 20 years in private equity, first as a CHRO and then a decade leading human capital initiatives for two major PE firms. And now he is in his 10th year running Bontempo Advisory Services — a catchy title.

He's developed and evaluated more top-tier talent than anyone I know. He built the foundation at Kraft Foods, then moved over to Frito-Lay, where he led HR for North America operations — over 20,000 employees, billions of dollars in products, and 80-plus HR professionals. Plus, speaking personally, he was the best HR boss I ever worked for, with all due apologies to Sandy Carmen and Jeff Becker. I want to say he hired me for my very first job at Frito. We became friends almost immediately, and he's been a mentor of mine for the last 27 years. So it's a joy to have you. Scott, welcome to the pod.

Scott Bontempo: Thanks, Jackson, for those kind words. And Scott, good to be with you as well.

Jackson: Now, we're going to start off here — and I guarantee I'm going to screw up the names at some point as we go through this, so hopefully you guys know who I'm going to be calling on when I say "Scott." But I want to begin by talking about some of the faulty assumptions that get leaders stuck when we talk about this evaluation work. So Bontempo, let's lead off with you. One of the things I hear from people is, "I've done the work before, so I can do it anywhere." The underlying assumption behind that is that CHRO competencies are portable and context is independent. What say you?

Scott Bontempo: Some of the basic competencies are portable. You will hear people say, "Well, you know, it's like finance or it's like IT — there are a lot of common things that move place to place." But I think that's a major fallacy for individual people looking at opportunities, because they are vastly different. What plays to your strengths? What's the company got to get done in the window that you might be there? And what are the challenges you're going to face between the opportunities that are out there for you?

You alluded to it in your introduction — what are the missteps that people can try to avoid? You're only going to get so many turns at this in a career. And picking the right ones is really important. Picking the right first one is particularly important, because it — like everything else in your career — builds the basis for the next thing. So very different solutions for very different problems. And I look forward to talking with both of you today about how an individual might parse their way through those choices.

[DO CEOs REALLY WANT STRATEGY?]

Jackson: Earlier this week, I was talking with a senior leader at one of the big search houses, and we were talking about the second assumption I want to challenge. The assumption is that the CEO says they want a strategic partner and that what they say in interviews reflects what they actually want. What my friend was finding — and it matches my experience — is that that's not always true. What say you?

Scott Bontempo: I think you hit on a really key point here. I would back up a little bit and say half the CEOs out there will say, "I want somebody to make sure the trains run on time, I'm compliant, you keep me out of the ditch." And the other half will say, "I want a strategic partner." The problem — and where the big pothole is for candidates — is that of that 50%, half of them don't really want that. They say they want it and they don't.

So if you step back, 25% of CEOs really want a strategic business partner and mean it — because they know what it is, for whatever reason. They've experienced it before, they want it again, they know that's the right thing. It's when the person says, "Oh yeah, I want a strategic partner," and then you take the job, you show up on the first day, and they forget to invite you to the staff meeting — that's when the light bulb goes off. "Whoops. Wish I'd have known that ahead of time."

I think part of avoiding that problem is: what questions are you asking? If you're at the stage where you're sitting in front of the CEO, candidates should think about, "I'm interviewing the CEO. They're not interviewing me." You've already proven yourself to get there — you went through a search firm probably, got vetted a bunch of times, they probably did reference checks on you already. This is about: can I work with this person? Are their words lining up with their actions? Attacking it that way is pretty critical to getting to the right conclusion for you.

Scott Morris: There's a muscle memory to that. A discipline. You have to learn how to actually do that, because it does feel a little odd — when you're there trying to get a job — to put yourself in the frame of mind that you're doing part of the interviewing. But I think this is the subject to do it on.

And Scott, I'm curious about your experience with CEOs especially, because the first tier you've got to probe through is: do they say they want a strategic partner and do they mean it? But I think the second tier is arguably more important — do they even understand what "strategic" means? The three of us have a pretty shared view of what strategic human capital looks like. But does the CEO, in your experience, how many have really internalized what it means to have that strategic HR partner?

Scott Bontempo: Not enough. Not too many and not enough. It probably falls into that 25 to 35 percent range.

One of the things I'm always curious about — or would suggest people ask in that interview — is understanding who they've worked with before. "Describe to me your relationship with prior CHROs. If you were a division head somewhere else and this is your first CEO gig, what was that relationship? How was it done? What were your interactions? Was that person important to you? Were they on the team? Where did they sit relative to you?" Because if they've got you parked three stories down in the building, it tells you something.

What you're really trying to assess is: have they worked with a really good-to-great HR person before? Because if they have, they know what that looks like, and if they want to replicate it, they're probably looking for a strategic partner. If they've worked with that before and said, "I didn't like that — that was too much stuff, I just need someone to run the trains," they'll tell you that too, just by the examples they give you.

"What was important to you?" "Well, making sure our compliance stuff was spot on and our performance management ran perfectly every year and we hit the budget down to the right-hand side of the decimal point." Yes — but for great HR people, that's just table stakes. If your CEO does not see you as a business person first with an HR skill set, then they're not looking for a strategic partner.

Jackson: Here's the question I've asked that I think can ferret it out pretty quickly. And candidly, this question has probably caused me to turn down opportunities and caused them to turn me down for opportunities too — so it's not risk-free. The question is: "Walk me through the last three decisions you had to make without me in the room that you would have wanted me to be a part of." If those are business problems, you learn one thing. If those are administrative functional problems, then you know you're walking into it with a low-altitude mandate.

Which then leads me, I guess, to the next assumption I hear quite a bit: "If I'm not sure if this is the right role, I should probably just take it and figure it out." The assumption is the downside of a wrong decision is limited and recoverable. I think that used to probably be true. I'm not sure it is anymore. What do you guys think?

Scott Bontempo: I think that's a bad way to choose your next career spot. I always like to ask people: "Am I running to something or am I running from something?" Am I going to take this job because I hate the one I'm in, or hate the city, or hate the industry? Or is this a really great opportunity that fits what I do well, where I feel confident I can succeed, and in the interview I liked the CEO because I think they value what I bring?

Taking any old job — I don't think it's a good idea. You could luck into it and be successful and lever that into the next opportunity. But it's really more important to find the right thing versus a thing, every time. It's easy to say in hindsight. The first time you're going through it, you feel really good because someone wants you to do a CHRO job you've never done before, and you think, "I better grab it because I don't know when the next one's coming." But if you're good enough for them to hire you, somebody else is going to see an even better match. You've got to be self-aware enough to figure out what you're good at and line that up against the challenges of the business and the role.

Scott Morris: And there's more to it too than just "do I have the skills to do the job." The how that CEO wants you to do the job also matters. I'll tell you from my own biggest career failure story — I was coming from a CEO I liked very much, a very strong partner, who was very aggressive about how he wanted to go after the business. I came into a new environment and tried to apply that how as I was doing the what, and it didn't work. In fact, it was countercultural, and it led to a huge failure.

But I wanted that how. What I missed was that environment was not the right place for the how I wanted to bring. That was the piece I missed in my own evaluation. So you've got to pay attention beyond just skills and "do I want to work on these problems?" It's: how do you want to work on the problems? And does that environment want that how?

[THE SKILLS LENS — WITH EVIDENCE]

Jackson: I think that's a great insight, Morris. And it's funny, because when I stubbed my toe in my first big CHRO job, one of the things I missed was looking at the work itself. I said, "The company's problems are something I do really well, and I have an opportunity to come in and show them." And that's an assumption many of us make — that there's a fundamental structural or cultural problem you can overcome through personal excellence. I found firsthand that that's not always true.

I talked with John Boudreau during that season of my career and said, "John, how do I not do this again?" He said, "The way you figure out whether you are going to be doing progressive HR work is: go to a company that says we're doing progressive HR work." Not the problems, not your personal evidence, not even what your CEO has seen before — although if they've been in one of those good progressive HR communities, you have a better shot, provided they have the organizational gravitas to go do stuff.

So maybe what I'm hearing from this conversation is there are three lenses to look through. One is individual skills. One is the actual work itself. And the third is the opportunity writ large. So I think it'd be interesting to dive into that and talk about how we reframe the way we look at these opportunities. Scott, how do we move from "am I qualified for the job" to "is this the right match at the right time?" Walk us through how you actually evaluate candidates and opportunities.

Scott Bontempo: As I evaluate them — and as I'd ask people to self-evaluate — if you're looking for a strategic business partner, some of the key dimensions that people have to have are:

Do you understand the business that you're in today? Can they articulate the business, whatever level they're at? How it works, how it makes money, what are the key levers, the key functions? It tells me if you're a business person or an HR wonk.

Second: can they get stuff done? While all of us early in our careers might naively think the CHRO sits in the corner and points at things, the reality is most of these jobs — Fortune 50 excepted — are dirty-hands jobs. You're working down half a level from the title. So can you take a project all the way to completion? The world is littered with people who can take it to the two-yard line and can't punch it in. You've got to be able to get all the way in and move on to the next one, versus having five things stuck at 98% done.

And then — like it or not — people who have worked in really strong HR organizations sometime in their career have a much higher chance of succeeding in future roles, because they've been around what great looks like. You know what "A work" is. You know what the organization can't handle. That cuts both ways — you know what good looks like, but you also know when you're giving them what you'd consider "B work" that will be a step-function difference for them and will change things monumentally.

Being self-aware about those things is really important. And I would just tell people: be honest with yourself about your own self-assessment. If not those things, what am I good at? And where does that lead? That starts to lead you toward matching what a company might be calling you about.

Jackson: As we're looking through that first skills lens — "what am I really good at?" — when you're sitting down with a CHRO candidate, what's the question you ask that separates the people who really know what their strengths are from the people who've practiced reciting their resume?

Scott Bontempo: I tend to ask the question in the format of: "Okay, if we hang up the phone here and I pick up the phone and call your current CEO — with the right permissions and timing — and ask what are the two or three best things that Jackson did while he worked for you, what are you going to tell me? What do you think the CEO is going to say?"

Because they're not going to lie about that. They may soften the blow, they may add some sugar on top, but they'll bring the topic up. And then you can probe. Well, tell me more about that. Why did that fail? You can start to parse whether it's a skill issue, or they just weren't capable, or there were other factors.

Not everybody can be great at everything. And by asking those questions, you can find blind spots — at least in terms of what they've been doing.

Scott Morris: Scott, the weakness side is arguably harder to get out of people than the strength side. People are generally happy to talk about their strengths. But a lot of us have been conditioned to try to express weaknesses as strengths. It just comes across as so much BS a lot of the time. How do you get the real truth out of people about their weakness — from a technique standpoint?

Scott Bontempo: I try to impart upon them that I'm going to ask this question of your CEO. People are much more likely to tell you the truth versus, "Tell me about a time you had a failure," which they spin just like you described. Instead it's, "What will your CEO say about something that didn't go well or was a miss?" They're not going to lie about that. And from there you can probe further.

Scott Morris: What are you listening for in the answers when somebody's talking about their weaknesses? Is it just, can they be honest? Or is it the type of failure? Or a combination?

Scott Bontempo: If they're avoiding the question — and this is the pretty obvious one — they will talk in broad brushstrokes. On the positive side, "I was really good at communicating with this person or that person." And on the negative side, "Well, it didn't go so well because we had a timing issue and this third-party vendor..." They won't take ownership.

Good leaders will own it. There's not an excuse about this person or that thing. So if they're not owning the success humbly — or flat out owning the failures — they're probably telling you something less than the whole truth somewhere else along the way too. And then you can just trigger to that in your follow-ups.

[CONDITIONS FOR SUCCESS AND STAKEHOLDERS]

Jackson: And Scott, just to piggyback on that — Russell Reynolds found that about one out of seven brand new CHROs in 2024 came from roles outside of HR entirely. That means they were very honest about what they brought — but probably also honest about the stuff around them.

So wrapping up the first lens: you've got to look at what your skills are, what you're bringing to the table, and be candid about it. You want to be able to express your successes in a way that provides evidence. And you want to be very direct about owning your gaps — experience or otherwise. You can't BS your way through it, because that opens up a Pandora's box of, "What else are they making up?" Do I have that basically right?

Scott Bontempo: I would add: if you've gotten to the place where you're being considered for a C-suite job, chances are you've gotten feedback throughout your career about what you're good at and what you're not. If it's become repeatable, believe it. If somebody told you you have this gap in style or content or exposure, and you continue not to have it — you already know where your holes are.

That gets us into the self-awareness thing, which starts to line up with what the prospective company might want you to do. If I've been getting this feedback and I'm not a star at this thing — and this next role might need that — I ought to be honest with myself about whether that's an opportunity I should pursue further.

Scott Morris: Jackson, I know we need to keep pushing to explore all three lenses, but Scott — I'm curious. I've certainly made this self-evaluation where I found a role where I thought, "I like this, but I'm weak in a couple of areas." My next move has been to look at the team that's in place and ask: are the skills of the chief lieutenants going to be enough to compensate for my gap? And will I trust them? That's also hard to get to when you're interviewing. Do you think I'm getting that right?

Scott Bontempo: I do think being mindful of the team you're inheriting is important, because they're widely varied. We've all inherited teams that are really good — and we've heard stories about ones that are not, where you end up doing a lot more of the work yourself.

As a candidate, it's very fair to say, "I'd like to talk to some of the people who are going to be working for me" — assuming the job is open, not filling around a sitting person. I'd want to talk to the majority of my potential direct reports to get a sense of their skills.

[THE WORK LENS AND INVESTMENT THESIS]

Scott Morris: Let's push on into that next lens Jackson articulated — the work. What does the company actually need done? A lot of the job description is marketing copy, regrettably. How do you help a candidate figure out what actually needs to happen in the first 18 months?

Scott Bontempo: If you're looking at a private equity environment — what's the investment thesis? What are you guys trying to get done in the next three to four years? And where am I joining in this process? Just happened — I'm at the beginning? Or am I in the middle of it, maybe because my predecessor couldn't get there from here?

Ask to see the CIM or plan. It lays out the next three to four years and why they're investing. Is this growth trajectory reasonable, or is it a hockey-stick thing at the end where everything becomes perfect in year four? Sign an NDA — big deal. If they're really serious about you, they'll let you see it.

Important to understand for a couple of reasons: one is the work, but also your own personal financial stake in what's going forward. Is that a realistic expectation that everybody set?

Here's the thing though — many times a PE firm won't be able to perfectly articulate what the people challenges are for that business. They may say, "We're going to grow 25%," and a sub-bullet says, "We've got to hire 50 salespeople to do that." But that's probably the limit of where it ends up in the big picture. So you look at those things and say: am I good at that? Do I have the support of the firm? More importantly, does the executive team get it? Does the CEO get it? Does the CFO — hopefully my partner — get it?

Scott Morris: And it's not just, "Am I good at hiring?" Because you know what? I'm really good at hiring. But I'm not good at hiring fast. And if the thesis is "we're going to grow X percent a year," building that talent pipeline and system for recruiting fast — you'd better be really good at that. It's important to be really specific with yourself about not just the top line, but deep into the detail.

Scott Bontempo: Exactly. Just saying "I've checked this box, I've got these sub-skills built in" — they are not necessarily a match. You might be able to talk the language, but understanding what hyper growth means and being able to execute against it — big difference.

A narrow example: healthcare has had great difficulty hiring for certain jobs. People who figured it out said, "How do I let someone apply on their phone via text and automatically have them come in tomorrow at noon to meet two people who are going to make a decision — with a go/no-go within 24 to 36 hours?" Somebody who has worked through that can make it happen again. Very different from the traditional approach.

Jackson: There's also a difference between the work inside a private equity company versus a public company. In private equity, everything you do has to have value creation actions inside that hold period — presuming a full transaction on the other side. Anything that is not within that hold period tends not to get budget, because you might be doing work that the future owners will benefit from but they're not going to pay for today. You have the cost, and the benefit accrues somewhere else. It doesn't work.

So you have all these public company folks — usually large number-twos from good companies — who move into a PE gig and take the 10-year-horizon public company playbook and find themselves really at odds with the rest of the organization. Understanding that time horizon becomes super important. The urgency, the risk tolerance, the investment appetite for human capital — the work itself is just different.

So maybe with that we can move to the third lens: the conditions for success and whether they're real. Scott, do you want to hit that one?

Scott Morris: Scott, you could be the right person with the right skills for the right work and you can still fail. What are the conditions you evaluate to determine if success is actually possible?

Scott Bontempo: You've got to evaluate the culture and thought process of the firm. Are they buying distressed assets? Tech companies? Where do they buy in the industry curve — buying good companies and trying to make them great, or buying poorly run companies and trying to make them average? All of those are viable, all of those exist today. And understanding which one you're getting into really matters.

If you're really good at training and put a lot of emphasis on learning and development, a distressed asset business you're trying to make average is probably not your place.

Scott Morris: Does board involvement matter? Does board sophistication matter?

Scott Bontempo: It's a nice-to-have, but it's hard to understand the level of sophistication and interplay from the outside. Some firms have all owners and financial sponsors on the board. Others have outside industry experts who are friends of the firm.

I think the key thing is: who are the lead one or two people on the deal? Whose deal is this? Having the opportunity to speak with those people is a reasonable ask — even if the CEO says, "I'm going to fill this job any way I want." That's fine. I still want to talk to those people, because I'm going to have to interact with them moving forward. I want to know what they think is important. If it doesn't matter to them that HR work is important, that should give you pause. You could be the best person ever. You will not change their mind on that topic if they don't have it coming in.

Scott Morris: Jackson and I do this all the time. And the CEO — almost table stakes. But there's the rest of the C-suite too, that you need to be thinking about before you take that CHRO job.

Scott Bontempo: Agreed. And for the same reason, you want to talk to those folks. I would not take a job without talking to the CFO. That person could be your best friend or your worst enemy, and you want the former. Then probably the key line-of-business leader — if it's a sales and marketing company, I want to talk to the sales and marketing leader. Because those four people — you, the CFO, the CEO, and that person — are the ones who should be running the company. Those are the relationships that matter most.

Scott Morris: One of the biggest failures I've had: I was actually leading the search for the CFO. We put that person in place, and that person became my absolute nemesis with money. I got it 100% wrong. But that dynamic is totally right.

We like to break the conversation down into real practical steps that people can take starting Monday morning. Jackson, you want to lead us off on the playbook?

[A PRACTICAL CHECKLIST AND WALKAWAYS]

Jackson: Yeah. The first thing I'd recommend: build that skills inventory — with evidence. And for those of you who have not read AI-Driven Leader, you can use AI as a thought partner. I did this not so long ago as I was thinking about what I want to do next — have your AI agent interview you about your skills and the evidence, then build all of that out so you understand what you're good at and what you're not.

Korn Ferry found that 66% of HR leaders are confident in identifying the skills for growth. That's actually a really low number. And even lower is 48% of them know how to go out and acquire the skills they're missing. So understanding the playing field — creating the taxonomy of what skills you have and what you're good at and not as good at, so you can apply them to the other two lenses — I think is really helpful.

Scott Morris: Scott, what's another step that a person can take starting Monday?

Scott Bontempo: Building on Jackson's thought about AI agents — I've gotten great value personally by talking to people I used to work for and with and asking for their honest input. "Hey, I think I'm good at this, but let's have a real conversation, because this role I'm considering has these skills involved. Where do I really stack up?" Get somebody you trust to tell you the real truth.

Most people have that person. If you're any good in your career, you've got a couple of people you're willing to ask those hard questions of — or who will give you honest feedback. Because once somebody forces me to say it out loud, I realize — "Just because I went to Europe on vacation doesn't make me an international HR person." Somebody holding the mirror up is super helpful.

Scott Morris: Here's another one I would add: make a checklist. But the checklist is the conditions for success. Don't do it when you're in the midst of looking at a particular opportunity. Do it well in advance. Write down the conditions that have to exist for you to feel like you're going to succeed. There are two disciplines: one, get the checklist created. Two, stick to it as you start evaluating opportunities. Do the checklist now.

Scott Bontempo: Along the lines of a checklist — I often try to ask myself, and I really want to ask CEOs and board members: "When I look up a year from now, what does success look like for me in this role?" If they tell you what success looks like and can articulate it very clearly, you have another data point. What they think success looks like — does it play to my strengths or identify more weaknesses than strengths? That's a helpful tool inside of a checklist-building exercise.

Jackson: Good. And let me build on that for the last thing I'd recommend: figure out your walkaway criteria in advance. Once you've invested time, gotten to know some of the people, maybe fallen in love with the title and the comp package — and by the way, the longer you're between opportunities, the more your confidence can drop and you end up chasing things you should be walking past.

So how do you avoid that? Write down the conditions that would make you say no. Write them down for any opportunity, not inside of a particular one. And then hold yourself to it as you look at skills versus work versus opportunity versus peers. You've got to have the discipline. And I think that's harder than it sounds — which for me is usually a sign that's exactly what I need to do. Because if I do all my thinking without the emotions, I will make better decisions than when I say, "I can make this work."

Scott Bontempo: I think you're 100% right. Those things can be as simple as: "I'm not going to look at opportunities in a given geography because in the end I'm not moving to XYZ part of the country." The same for industries. I know there are certain sectors that don't play to my strengths — I won't entertain them. Geography, sector, type of business, hyper growth — people should absolutely have those things in mind going in. Very healthy.

[KEY TAKEAWAYS AND NEXT STEPS]

Jackson: We've talked on the pod in the past about a talent philosophy — the key is to write down and align on how you're going to handle situations as you move forward, and that allows you to just point to it and say, "This is what we've all agreed to." The same theory applies to these checklists. Really helpful and really important.

But we've reached the point of the pod that I know everyone looks forward to — it is the Talent Sherpa Summary. And as Scott always says, "A CHRO who does not evaluate the opportunity is like a Sherpa who does not check the weather report."

Scott Morris: I've never said it — but since I want to climb Everest one day, I think I'm going to start saying it. Alright, here's the summary.

So, Jackson, I'm going back to the three things we started with: skills, work, and opportunity.

One — you've got to evaluate your skills honestly by documenting with specific evidence your distinctive capabilities, not just general competencies.

Two — you've got to evaluate the work by mapping what actually needs to happen, not what the job description says. Then assess the overlap between that work and your own strengths.

Three — you've got to evaluate the opportunity rigorously by looking at the conditions that actually exist: CEO commitment, capital availability, how fast or slow the business has to move, C-suite collaboration opportunities and where the heads are on that — especially the CFO.

And I'll add a fourth: be willing to walk away. There is discipline to writing the list, defining the criteria, understanding what success looks like, and then sticking to it. The discipline to say no to wrong opportunities protects your career more than saying yes to every opportunity. That's my summary. Scott Bontempo, what have I missed?

Scott Bontempo: I don't know that you missed anything, Scott. That's a good summary. I think people just need to be self-aware of what they're really good at — and be honest about where their strengths lie — and then layer that against the opportunity. Know this walkaway piece.

Because as I said earlier: if you're good enough to be in this interview process and this isn't the one, there'll be another one. So be picky. Be just as picky picking these jobs as you would be about picking candidates you would hire. Think about it in the same manner, and I think you'll make good choices for your next career opportunity.

Jackson: The takeaway for me — stealing a little bit of what you just said, Scott — is that the best CHROs treat their own career decisions with the same rigor they would bring to any other capital allocation decision. Because that's what you're doing. So stop asking, "Am I ready?" Start asking: "Is this the right investment of my human capital at this moment in time?" That's the evaluation that ultimately matters more than anything else.

So I want to say thank you so much for tuning into the Talent Sherpa Podcast — this is where senior leaders come to rethink how human capital really works. I speak for both Scotts in saying this was so much fun. Bontempo, thank you again for joining us and for sharing your decades of wisdom on this topic. If folks want to follow you — how can they find you?

Scott Bontempo: Probably the best way to find me is my website — BontempoAdvisoryServices.com — all run together. It gives a good outline of the work that we do for our clients. Again, guys, thanks for having me. It's been a great honor and a pleasure to be on with you.

Jackson: And we'll have that in the show notes for anyone looking for that work.

I want to give a quick shout out to one of our favorite listeners — hello, Julie in Austin. Thank you for being a part of the Talent Sherpa community. And we want to thank everyone for listening, whether you're in Accra in Ghana or in Dayton, Kentucky. It's so great to have you with us.

Scott Morris: Scott Bontempo, I just want to add my own thanks. It's been great to get to know you, and it's been great — honestly, as the three of us have prepped — to learn from you as well. Thank you for taking the time to come on.

Scott Bontempo: You guys are doing a great job. I really appreciate watching the podcast as well as reading the writings coming out from the Talent Sherpa. Continued success.

Scott Morris: And if you enjoyed the podcast today, do us a favor right now — hit the like button. Or even better, subscribe to the podcast so that you have episodes delivered to you each and every week. You can leave us a review on your favorite platform, whether that's Apple Podcasts, Spotify, or YouTube — we're across all of those. It benefits the community. Just leave a review. It's how the algorithm activates and helps us spread the pod to others.

Jackson: And if you're a CHRO wondering where the heck to start your AI journey — don't forget to check out Propulsion AI at www.getpropulsion.ai. They're building a team of AI teammates to help human capital leaders focus on what matters most to the business. And Scott, why should people reach out to you?

Scott Morris: We help organizations build clarity into their roles, and we help private equity operating partners translate value creation plans into actual EBITDA.

Don't forget — as you're listening to this episode — I've watched Jackson do all of the things we talked about today. So if you're a new CHRO, or new into the CHRO role, Jackson has helped people just like you through personal coaching, through the CHRO Ascent Academy, and through his best-selling Substack. You can find all three at mytalentsherpa.com.

Jackson: We've announced recently that we have a new CHRO Ascent Academy starting May 1st. We're about halfway filled up already, so if you're interested, reach out — you have to get interviewed before we let you in. But the first cohort gave outstanding responses and we'd love to have you there as well.

Thank you, Scott. And Scott — once again, thank you so much. Everyone knows now why I've included Mr. Bontempo as a mentor of mine over the last 27 years, which doesn't feel like we met at the Frito-Lay plant that long ago. But it's true.

Thanks to everyone else who's listening. Until next time: keep raising the bar, keep doing the honest evaluation work, and keep on climbing.