They Knew. They Didn't Tell You.

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."

Transcript

A red team is a pre-design stress test.

Before you launch a major initiative, you gather a group of people and ask them to assume the initiative has already failed. Their job is to point to what went wrong. You are asking people to find the fatal flaws before they become fatal.

That is the genius of this.

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 am your host and your talent Sherpa, Jackson Lynch.

Today we are talking about something I have realized many leaders have never actually used. It is called a red team pre-mortem.

Back in September, I was at the 2025 SHRM Visionaries Summit, and Johnny Taylor and I were talking on stage. We got into a conversation about how organizations stress test their biggest decisions before launch. I used the term red team.

What struck me was how few people in the room had ever even heard of the concept, let alone run one. The idea was somewhat familiar, but the practice was almost non-existent.

As we kept talking, the reason became clear.

Every organization is running some sort of transformation right now. Technology. Operating model. Workforce design. The stakes are high, and the margin for error is thin.

The people closest to the work often see the problems that never make it to the decision table. They see all of them.

Today I want to walk you through what a red team actually is, why most of them produce nothing useful, and how to build one that actually captures the intelligence your organization already has and is dying to tell you.

Before we get started, a quick word about coaching.

If you are a first-time CHRO or preparing to step into that role, I would love to work with you. The transition to enterprise altitude is real. The learning curve is steep. You do not have to climb alone.

I offer one-on-one coaching for senior HR leaders who want to accelerate their impact and avoid the traps that quietly cap influence and sometimes cost careers. You can find everything you need at mytalentsherpa.com.

All right, let’s get into it.

Let me start by naming what a pre-mortem is and what a red team is. I am going to use the terms interchangeably.

You have heard of postmortems. This is the same idea, moved up front.

You give people the opportunity to fix things before they break, by assuming they will break.

A red team is a pre-design stress test.

Before you launch a major initiative, you gather a group of people and ask them to assume the initiative has already failed. Their job is to point to what went wrong.

You are asking people to find the fatal flaws before they become fatal.

When it works, three things happen.

First, you get a list of structural vulnerabilities while you still have time, and often flexibility, to address them.

Second, your change leaders get to voice concerns in a productive and welcomed way. That is far better than letting those concerns leak out in team meetings.

There is something therapeutic about being asked what you are worried about and why you think something might not work. It gets it out of their system, and it is healthy.

Third, your execution plan improves because it now includes perspectives that would otherwise have stayed silent.

Most organizations never get these benefits.

Some do not even run postmortems. When they do run a pre-mortem, it often produces the same risks everyone already knew. The same concerns already listed on the project plan.

No surprises. No real stress test.

Then six months later something breaks, and someone saw it coming, but did not have a way to say it.

That is what this addresses.

The first time I used a pre-mortem was at Nestlé Dreyer’s.

We had Dreyer’s Grand Ice Cream with Häagen-Dazs. That was a pretty cool job. We had just bought Kraft Pizza, also pretty cool. We were integrating both and pulling them into Nestlé USA.

The challenge was that we had three different human capital systems, and for several reasons we could not parallel test. We were going to do a hard cutover.

In a final planning meeting, the head of Nestlé USA and the head of Nestlé Americas asked, “Is this going to go perfect?”

Much to the chagrin of the team, I said, “Absolutely not. There is no way this can go perfect. There are too many things that can go wrong.”

That got everyone concerned.

Then I added, “But we ran a series of red teams and pre-mortems. We assumed it would break. We identified the top twenty things that could go wrong, and we have recovery plans for each.”

“So the question should not be whether this will go perfect. Of course it will not. This is a major transformation.”

“The real question is whether we know what is likely to break, and whether we have a plan for that.”

The answer was yes.

That experience clarified something important.

The value of the red team is the permission structure.

You create a moment where people can tell their leaders that their ideas have flaws, in a way that improves outcomes.

Something did go wrong in that implementation. It was on our list. We fixed it within twelve hours.

That is how it is supposed to work.

Most people do not volunteer that kind of feedback. You have to ask for it. You have to make it safe.

We talk a lot about psychological safety. Here is my definition.

You can put an uncomfortable truth on the table, argue about it, maybe even be wrong, and still feel like you belong.

The red team is one of the most practical ways to do that.

So why do they fail?

First, they get staffed with believers.

If the people who designed the initiative are asked to critique it, it does not work. Their identity is tied to the success of the idea. Seeing flaws feels like self-criticism.

You need people who did not build the thing.

Second, they run it too late.

If budgets are locked and commitments are public, people sense the real decisions are already made. They will share concerns that are easy to absorb, but not the ones that require rethinking.

You have to do this early.

Third, the leader defends.

The leader can be in the room to explain intent and design, but not to defend. The moment a leader pushes back, the room learns that dissent has a cost.

One defensive reaction teaches everyone what is truly welcome.

Fourth, vague concerns are tolerated.

Someone says, “I am worried about adoption,” and everyone nods. It gets noted. Nothing happens.

A useful red team requires specificity.

What exactly breaks? Which assumption is wrong? What happens downstream?

Fifth, organizations fail to recognize the people who catch flaws early.

The person who fixes a problem after launch gets celebrated. The person who finds it before launch gets a quiet thank you.

That incentive structure points the wrong way.

If you want problems surfaced early, you have to reward problem finding.

Here is the shift to consider.

A red team is a formalized permission structure.

That is it.

You create a moment where uncomfortable truths can be put on the table without anyone losing standing.

I use a simple frame to structure the conversation.

People. Process. Technology.

Those are the three places transformations break.

When you run the red team, you say: assume the initiative failed. It broke in people, process, or technology. Tell us where and why.

That structure keeps the conversation focused and useful.

Diversity in the room matters.

Operations sees risks strategy misses. IT sees dependencies HR assumes will work. Someone two levels down sees how this lands with frontline managers.

You already have this intelligence. The question is whether you let it speak.

Five plays to make this work.

First, staff for vantage point. Different functions, altitudes, and relationships to the outcome.

Second, run it before commitments are locked.

Third, leaders listen. Explain, clarify, do not argue.

Fourth, require specificity. Turn worry into action.

Fifth, recognize the flaw finders publicly.

Over time, this shifts the culture.

Unstructured conversations do not surface uncomfortable truths. Permission does.

When you get this right, you capture intelligence your organization already has and usually wastes.

Four takeaways.

One, a red team is a pre-design stress test.

Two, most fail because of staffing, timing, defensiveness, vagueness, or incentives.

Three, the real value is the permission structure.

Four, use people, process, and technology as the frame.

Thank you for spending time with us today, whether you are in Madrid or Chicago.

If you want to start your AI journey, begin with role clarity. That is the first step.

If you are a first-time CHRO or preparing for the role, I would love to work with you. You can find everything at mytalentsherpa.com.

Until next time, keep raising the bar. Keep building permission structures that let your people tell you the truth. And keep climbing.