Send us a text

Every organization running a transformation has people who see exactly what's going to fail. Most of them stay silent. Not because they lack courage, but because they lack permission.

In this episode, Jackson breaks down the red team pre-mortem: a structured way to surface uncomfortable truths before they become expensive failures.

He shares a real example from his time at Nestlé Dryer's, explains why most pre-mortems produce nothing useful, and walks through five plays that actually work.

What You'll Learn:

• What a red team pre-mortem actually is and why it matters now more than ever
• The five reasons most pre-mortems fail before they start
• Why "staffing with believers" guarantees you'll miss the real risks
• The difference between a leader explaining intent and defending a decision
• How to use the People, Process, Technology frame to structure the conversation
• Why your incentive structure might be rewarding the wrong behavior
• Five actionable plays to build a red team that captures real intelligence

Key Moments:

[[02:15] Why most organizations never get the benefits

[04:30] The Nestlé Dryer's story: "Is this going to go perfect?"

[07:45] The five reasons pre-mortems fail

[12:30] Psychological safety defined: belonging after dissent

[15:00] The People, Process, Technology frame

[17:20] Five plays to make your red team work

[22:00] The flaw-finder problem: who gets celebrated?

[24:30] Four takeaways to put into practice

Quotable Moments:

• "You're asking people to find the fatal flaws before they become fatal. That's the genius of this."
• "The person who catches a problem before launch gets a polite thank you. The person who heroically fixes it afterward gets celebrated."
• "One defensive reaction teaches everybody what's actually welcome."
• "Psychological safety means you can put an uncomfortable truth on the table, argue about it, maybe even be wrong, and still belong to the team."
• "You already have the diversity. The question is whether you've built a structure that lets it speak."

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

The company hires a new CHRO. The CEO introduces them like they've found the missing gear in the leadership machine. The board nods in relief. The executive team exhales.

And then, month by month, the narrative starts to shift.

Around month nine, the CEO starts offering compliments that land a little oddly. Around month 12, the tone tightens. And by month 15, the question isn't coded anymore: Are we getting the strategic partnership that we need?

This is part one of a two-part series naming the quiet pattern that ends CHRO tenures without a headline, without a blowup, and without a clean post-mortem. Today is the diagnosis. We unpack why this pattern exists and why it catches even experienced CHROs off guard.

The data is stark: 31% of first-time CHROs are fired in their first 18 months. 52% are fired within a year of a new CEO being appointed. The CHRO thinks they're doing a good job. The system is grading them against a job description that was never spoken.

What You'll Learn

The enterprise context that's changed:

• Strategy windows are shorter, margin pressure is higher
• Execution speed has become a competitive advantage
• Boards have less tolerance for slow-motion operating models
• What CEOs need from CHROs has changed, even when the language hasn't

Why the strategy gap exists:

• CFO and COO roles are standardized, CHRO expectations are all over the map
• "Strategic" means a dozen different things to different CEOs
• CHROs get hired into undefined versions and gravity takes over
• The CEO says strategic, the CHRO hears make HR better, but the CEO means see the business in systems

The boardroom diagnostic:

• The CEO opens with narrative, CFO sharpens with margin and cash, operators layer in execution risk
• If the CHRO talks about engagement trends and time to fill, they're running a parallel narrative
• Parallel narratives get trimmed first when the clock runs out

Four faulty assumptions that keep this pattern alive:

1. Delivering results automatically creates strategic credibility (early wins set the altitude of the role, you build credibility as an operator and get evaluated as an architect)
2. Strategic is a shared word that will align over time (ambiguity never stays neutral, it becomes muscle memory)
3. Experience protects you (it doesn't, prior success isn't portable unless you renegotiate the value equation)
4. The CHRO role has the same enterprise ceiling as the CFO (it doesn't, CHRO expectations depend entirely on the CEO)

Four diagnostic questions:

1. Is our business strategy inside the business model or sitting next to it? (Being in the room isn't being inside the model)
2. Are we rewarding operational reliability over strategic

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

Most CHROs lose credibility not because they fail, but because they succeed at the wrong things. They deliver what was asked, show up prepared, complete the work. And still, when critical conversations happen, the CEO routes elsewhere. This isn't a relationship problem. This is a forecast problem.

Jackson Lynch breaks down three ways CHROs train CEOs to discount their judgment—and five plays that create predictable accuracy.

What You'll Learn

The forecast problem: CEO deciding whether to move CFO out? They talk to board chair, not CHRO. Product org missing dates? They pull in COO. CHRO gets sanitized version two weeks later. Why? CEO cannot predict what CHRO will see.

Three ways CHROs lose credibility:

1. Overpromising timelines (say 4 weeks, deliver in 6)
2. Delaying hard truths (waiting to name underperformance)
3. Confusing activity with impact (updates disconnected from decisions)

What builds credibility: Being predictably accurate about what you can deliver, what you see as risk, what connects to business outcomes.

Five Plays to Create Predictable Accuracy

1. Optimize timelines for reliability, not speed Ask "how long when two people are on vacation?" not "how fast could this go?"

2. Name risk before you're asked "I'm seeing a pattern. Decisions are delayed, team escalates around them. That's creating drag in three areas..."

3. Connect every update to a CEO decision Ask "what decision does this inform?" If none, don't bring it.

4. Build a talent risk dashboard CEO actually looks at Answer: Do I have talent to execute strategy? Capability gaps? Succession risk in pivotal roles? Decision velocity by function?

5. Create standing "watching" agenda item Reserve 5 minutes weekly: "Three things I'm watching that might become decisions." Patterns forming, not problems yet.

Key Quotes

"Credibility is built on whether the CEO can predict your forecast. When they can, they pull you in earlier. When they can't, they route around you."

"Every time you miss a deadline, you're teaching the CEO your estimate is unreliable on everything else."

"The goal is to make it impossible for the CEO to make a critical decision without first asking what you see that they don't."

"Precision beats speed. Conservative timelines you hit build more trust than aggressive timelines you don't."

Four Takeaways

1. Credibility is built on whether CEO can predict your forecast
2. Most CHROs lose credibility by succeeding at wrong things
3. Goal is to make it impossible for CEO to decide without you
4. Precision beats speed—conservative timelines build trust

Until next time: Keep raising the bar, keep building predictable accuracy, and keep climbing.

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

Most companies say trust matters, but when they run interviews, they only evaluate skills and polish. They focus on what candidates have rather than how they operate. And when you hire that way, you get predictably unpredictable results.

Lou Adler has spent over 50 years studying the difference between people who elevate an organization and the people leaders end up managing around. He's examined thousands of hires across roles, industries, and eras, and he keeps seeing the same 12 behavioral traits in every top performer. Those traits might also be the strongest predictors of trust on a team.

This is episode 100, and we're giving you a practical roadmap for hiring people who make the company better the moment they walk in the door.

What You'll Learn

Why recruiting feels broken:

• AI didn't break recruiting, it exposed it
• The system is optimizing funnels while ignoring clarity
• We're recruiting for static experience in a dynamic environment
• The best candidates aren't in funnels at all

The fundamental shift in how to hire:

• Why a job description listing skills is stupid
• How to define work as performance objectives, not person requirements
• The difference between screening for credentials vs. outcomes
• Why doing the wrong thing faster is still stupid

Lou's performance-based hiring method:

• Start with what a person needs to do, not who they need to be
• Define 4-5 key performance objectives (KPOs) for every role
• Test for excitement about the work, not excitement about getting the job
• Solve for motivation (the N factor) alongside ability

The 12 universal traits of top performers:

• Being proactive, seeing the big picture, understanding and influencing people
• Why ownership beyond boundaries predicts success
• How to assess traits that matter more than technical skills
• The importance of volunteering for things over your head

The hiring formula for success:

• Ability to do the work + Fit factors = Success
• Fit drives motivation (raised to the power of N)
• How to dig 5-6 layers deep into accomplishments
• Why you need evidence, not opinions, before making an offer

Key Quotes

"A job is stuff that people do. What you've defined is a person doing a job. Let's forget the person and let's define the work."

"Doing the wrong thing faster is stupid. If you're producing bad widgets, stop producing bad widgets. But in HR, we say, do you have any more bad candidates I can interview?"

"HR should throw away the existing hiring process and build it from scratch. They wouldn't do anything they're doing now."

"The ability to do the work is actually the easiest part to measure. Understanding perfo

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

You cannot bolt a "serve first" identity onto someone who has spent 20 years operating on achievement, control, and self-preservation.

No seminar is going to rewrite that. Pretending otherwise is how companies end up with inspirational quotes and mediocre execution.

Jackson Lynch breaks down why servant leadership, as it's popularly sold, is one of the biggest myths in leadership—and what actually works: engineering leadership context instead of trying to reprogram personality.

What You'll Learn

Why servant leadership collapses: Instinct always wins under pressure. Leaders rose through systems that rewarded execution and personal drive. You can't fake a serve-first orientation when stress hits.

Two flawed assumptions: (1) Leaders can be reprogrammed—they can't, their operating system is built from 20 years of reinforcement. (2) Servant leadership is universally ideal—it's not, many avoid conflict or hesitate in high-pressure decisions.

The real solution: Engineer leadership context, not personality. Build expectations, operating rhythms, decision rights, and measurement systems that drive consistent behavior.

Four Plays CHROs Can Run This Week

1. Define the leadership instinct your strategy requires - Speed requires different instincts than precision. Match leaders to strategy.
2. Engineer the environment - Build clarity tools, decision rights, accountability loops that shape behavior.
3. Hire for instinct, not aspiration - If your culture demands speed, hire people wired for that.
4. Coach behavior, not personality - You can coach clarity and accountability. You can't rewire someone.

Key Quotes

"Managers leave these sessions inspired for about seven minutes. Then reality enters the chat."

"The goal is not to manufacture servant leaders. The goal is to engineer leadership context."

"Hire people whose instincts align with your strategy, then create conditions where those instincts compound."

Connect

Subscribe, leave a five-star rating, tag @TalentSherpa

Until next time: Keep raising the bar, keep driving clarity, and keep climbing.

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

Ready for the sting that actually helps?

We pull back the curtain on why AI fails in organizations that can’t define outcomes and introduce the clarity ratio, a simple metric that exposes whether your team is truly ready to scale AI or just good at shipping slide decks.

If your top workflows can’t be expressed in one sentence—Do X so that Y—you’re at risk of scaling confusion instead of value.

We start with the 2026 reality: CEOs want adoption, boards want ROI, and employees want straight answers about what changes and why. Then we surface the three traps that quietly derail execution—assuming shared definitions of success, mistaking tools for clarity, and confusing activity expertise with outcome ownership.

From there, we break down the clarity ratio, why 0.7 is a line you can’t ignore, and how this number reveals leadership alignment, investment priorities, and which workflows should be rebuilt or retired before any AI pilot.

You’ll get six focused plays to raise clarity fast: replace task lists with outcome statements, assign a single accountable owner, measure latency, throughput, and right first time, pilot AI only where outcomes are crisp, add the clarity ratio to the operating rhythm, and train every leader to use the one-sentence formula.

Along the way, we share a real win from a listener who cut meeting time in half by enforcing Do X so that Y in staff meetings. Expect practical guidance grounded in leadership, operations, and AI readiness—not buzzwords.

If you’re serious about making AI an accelerator rather than a mirror for chaos, start with outcomes, not tools.

Subscribe, share with a colleague who owns a messy workflow, and leave a review telling us your clarity ratio and what you’ll pilot next.

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

In the final episode of the year, Jackson Lynch revisits ten workforce predictions made at the start of 2025 and scores them against what actually happened.

Using real data and observable outcomes, the conversation walks through headcount reductions, early-career hiring collapse, AI adoption, merit-based systems, board oversight, and the widening divide in the labor market.

The episode matters because it separates narrative from reality. Growth masked inefficiency for years, but constraint forced leaders to reveal what they truly believe about performance, accountability, and talent value.

Senior leaders and CHROs will leave with a clearer understanding of how economic pressure reshapes behavior, why many talent strategies failed under stress, and where to focus next if clarity, execution, and outcomes actually matter.

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa

Send us a text

If your CEO has ever said, “Let us get back to nuts and bolts HR,” you are not hearing clarity. You are hearing a leadership alarm bell. That phrase sounds responsible, but it is really code for something far less strategic. It means the CEO wants relief, not growth. It means they want HR to remove complexity instead of building capability. And it means the organization is about to drift backward.

In this episode, Jackson breaks down why strong CHROs get trapped when CEOs revert to administrative HR. The episode digs into the core tension. You cannot run a modern talent system inside a leadership environment designed for administrative work. When the CEO retreats, the whole system collapses.

A must listen for CHROs who want to stay strategic in organizations that prefer comfort over capability.

You can subscribe to this podcast on your platform of choice. Just go to https://talentsherpapodcast.buzzsprout.com.

If you are a CHRO looking to start your AI transformation, please check out ⁠www.Getpropulsion.ai⁠. Scott and his team are creating a team of agentic teammates to enable your human capital leaders to focus on leading the business forward.

And don’t forget to visit ⁠www.mytalentsherpa.com⁠ where we have tools and coaching for CHROs to make an impact on day one, including the brand new CHRO Chronicles and the CHRO Ascent Academy. Also, if you want a Sherpa to guide your ascent, check out the work with me section.

Skyrocket your LinkedIn sales with Dripify! Automate outreach, personalize with AI, and contact hundreds of leads daily. Boost ROI by 40%, Try it now at https://try.dripify.com/talentsherpa