Red Teaming and Peak OS: Why Strong Plans Get Challenged Up, Down, and Across the Organization

A leadership team can spend two days building an excellent strategic plan and still be wrong.

Not because the people in the room lack experience.

Not because they did not think deeply enough.

And not necessarily because the strategy itself is flawed.

The problem is simpler: the people who built the plan can only see the organization from the perspectives available in the room.

The U.S. military has spent significant time thinking about this problem.

The U.S. Army's Red Team Handbook begins with a scenario that would feel surprisingly familiar to many CEOs. Senior leaders and planners gather to develop a plan. They share similar experiences, operate inside the same hierarchy, and quickly reach agreement about what leadership wants and what everyone assumes to be true. The plan is accepted—and fails. The handbook explores why: assumptions were not challenged, alternatives were overlooked, ambiguity was discounted, and people with contrary information may not have felt comfortable challenging more senior voices.

That is the problem Red Teaming is designed to address.

The Army's publicly available Red Team Handbook describes Red Teaming as a flexible approach to thinking and planning that uses structured techniques to identify hidden dangers, reveal unseen possibilities, and develop alternatives that improve decision-making. Importantly, the handbook states that it is not itself official doctrine, although its practices support Joint and Army doctrine.

The Marine Corps has applied a similar philosophy. Its published Red Team policy described Red Teaming as a way to introduce independent critical thought and alternative perspectives into problem-solving and decision-making. The goal was to reduce risk, expand opportunity, and expose plans and concepts to rigorous examination so organizations could adapt more effectively.

Peak OS does not have a formal military-style Red Team, and Peak was not developed from Red Teaming.

But there is a compelling parallel in how Peak approaches organizational planning:

The leadership planning session is not the moment the organization should stop thinking about the plan. It is the point at which the plan becomes clear enough to expose to the rest of the organizational system.

Before planning, information moves up.

Leadership creates an initial organizational plan.

After planning, that direction moves down, up, and across.

Teams test what it means in reality.

Dependencies emerge.

Assumptions are challenged.

Boards and other up-teams contribute another perspective.

Feedback comes back.

The plan gets stronger.

That process matters because a plan should not only reflect the intelligence of the leadership team.

It should benefit from the collective intelligence of the organization.

Red Teaming Begins With a Recognition That Smart Groups Still Have Blind Spots

One of the most useful ideas in military Red Teaming is that intelligence and experience do not eliminate bias.

Sometimes they increase confidence in assumptions.

The Army handbook describes several ways planning groups can get into trouble. People may assume they understand a situation because they have encountered something similar before. They can fall back on familiar approaches, ignore ambiguity, accept what the group already believes, or hesitate to contradict senior people and subject-matter experts. In groups, these normal human tendencies can become amplified.

This is highly relevant to executive teams.

Imagine an experienced leadership team building its One-Year Plan.

The CEO has spent months with investors and the board.

The Head of Sales has direct customer information.

The CTO understands the technical architecture.

The CFO understands runway and capital requirements.

The Head of Product understands the roadmap.

The Head of People understands organizational capacity.

Everyone is smart.

Everyone is informed.

But everyone still sees only part of the system.

The CTO may understand what is technically possible but not know that three key hires are likely to take six months.

The Head of Sales may understand what customers are demanding without fully appreciating the engineering dependencies behind delivering it.

Finance may understand the company's capital capacity while missing an operational constraint occurring deeper in Manufacturing.

The CEO may have the broadest organizational view but be furthest from some of the operational realities underneath the plan.

The board may understand financing, market conditions, executive experience, and strategic risk from a perspective no internal function possesses.

No individual perspective is complete.

That is why strong planning cannot simply be about putting the smartest people in one room.

It needs a mechanism for challenging the picture those people create together.

Peak Planning Starts Before the Leadership Session

One of the important ways Peak addresses this is through the work that happens before leadership planning.

Functional leaders do not have to arrive at an Annual, Quarterly, or Semiannual Session relying only on their personal interpretation of the company.

They gather input from their teams.

In Peak Teams, the Three-Year Vision planning process explicitly calls for functional leaders to bring input from their own teams into planning. The book describes bottoms-up involvement as important to both buy-in and planning quality. Functional leaders then bring proposed objectives into the leadership conversation, where the entire leadership team discusses and iterates them together.

That distinction matters.

The Head of Engineering represents Engineering in the leadership room.

But the Head of Engineering does not personally contain all the knowledge inside Engineering.

People closer to execution often know things senior leadership does not.

They know where technical debt is accumulating.

Where a process is breaking.

Where a deadline is unrealistic.

Where another team is creating an unseen dependency.

Where capacity is stretched.

Where a customer request is more complicated than it appears.

Where an assumption made three months ago is no longer true.

Good planning allows that information to move upward before the organization commits to a path.

The same principle can operate above the leadership team.

The CEO also has an up-team.

For many growth companies, that includes the board, investors, or other significant stakeholders.

They may see the organization from a different vantage point.

The board may understand financing conditions, market cycles, governance risks, executive patterns, strategic alternatives, or comparable companies that management cannot see from inside the business.

That does not mean the board should build the operating plan.

It means leadership planning improves when the organization is willing to gather information from outside the leadership team's immediate field of view.

Then the Leadership Team Has to Synthesize the Whole

Bottoms-up input alone does not create a plan.

Someone has to integrate it.

That is the responsibility of the leadership team.

Peak's Three-Year Vision and One-Year Plan bring functional perspectives into a common organizational conversation.

Each functional leader contributes objectives.

But those objectives are not simply compiled into a document.

The leadership team examines how they relate.

Peak Teams describes this cross-functional alignment explicitly. Marketing objectives have to connect with Sales. Product plans have to make sense alongside Engineering. Finance and runway have to support hiring plans. Each functional leader presents objectives, and the group discusses and changes them as needed so the pieces fit together.

This is important because planning can easily deteriorate into functional negotiation.

Sales wants five things.

Product wants six.

Engineering wants four.

Finance wants three.

People wants five.

Everyone defends their priorities.

Leadership eventually produces a document containing some of everyone's requests.

That is not an organizational plan.

It is a negotiated collection of functional plans.

Peak asks a harder question:

What does the company need to accomplish as a system?

The leadership team has to synthesize the different perspectives into one picture.

That synthesis creates the initial organizational direction.

But it should not create organizational certainty.

Leadership Planning Produces a Plan Worth Testing

This is where the Red Teaming parallel becomes especially interesting.

A weak planning culture tends to view challenge as something that should happen before the decision.

Once leadership has decided, everyone else is expected to execute.

There are situations where that is absolutely necessary.

Organizations need decisions.

Endless debate creates its own form of dysfunction.

But there is an important difference between continually relitigating a decision and testing whether the organizational assumptions underneath the decision are sound.

The Marine Corps Red Team policy described Red Teams as exposing plans and concepts to rigorous examination and providing alternative perspectives and independent critical thinking during planning and special projects.

Peak creates an analogous organizational function without establishing a formal Red Team.

Once leadership has created organizational direction, that direction goes back into the organization.

Now the people closest to execution can examine it.

Can we actually do this?

What would have to be true?

What are we assuming?

What does this mean for our team?

Who else do we depend on?

Do we have the capabilities?

Is the timing possible?

Where does this conflict with another commitment?

What did leadership overlook because the people in that room were not close enough to the problem?

This is not resistance to the plan.

It is part of making the plan executable.

Down-Team Review Tests the Plan Against Operational Reality

Consider a leadership team that decides the company should launch a new product platform by the end of Q3.

At the leadership level, the objective makes sense.

Market demand supports it.

Sales believes customers want it.

Product supports it.

Engineering leadership believes it is achievable.

Finance can fund it.

The objective goes into the plan.

Then the plan moves downward.

A software team identifies an integration dependency that is not yet scoped.

A hardware team realizes a component has a nine-month lead time.

Quality points out that the validation process will require a test capability that has not yet been built.

Manufacturing recognizes that the proposed design changes tooling requirements.

Customer Success identifies migration concerns for existing customers.

People realizes the company needs a specialized engineer who historically takes five months to recruit.

None of those teams is necessarily saying:

"The plan is wrong."

They are contributing information the leadership room did not possess.

That information changes the organization's understanding of the plan.

Maybe the Q3 date is still right.

Maybe scope changes.

Maybe the company needs to make a supplier decision immediately.

Maybe the hiring plan changes.

Maybe another objective has to be deprioritized.

Maybe the organization discovers that what looked like one Product objective is actually a company-wide capability-building initiative.

This is why Peak's team-to-team planning matters.

The leadership plan becomes more accurate when it is exposed to the teams that will have to make it real.

Up-Team Review Tests Different Assumptions

The same principle works in the opposite direction.

After a leadership planning session, the CEO may review the direction with the board or other relevant up-team stakeholders.

Their questions can challenge a completely different class of assumptions.

Is the capital plan consistent with the growth plan?

Does the hiring strategy assume financing the company has not yet secured?

Is the organization taking on too much execution risk at one time?

Has leadership underestimated how a market shift may affect the plan?

Does a board member have experience from another company that reveals a pattern the team has not considered?

Is management optimizing for this year's outcome in a way that creates a longer-term problem?

Does the plan reflect what investors and the board believe the company must prove during the coming year?

Again, the board should not become management.

The leadership team's responsibility is to operate the company.

But good governance creates another source of perspective.

The board is far enough away from day-to-day execution to see some things differently.

The people inside functional teams are close enough to execution to see other things differently.

Leadership sits between those perspectives.

That can create a powerful planning architecture:

Up-team perspective.

Leadership synthesis.

Down-team operational reality.

Each sees something the others cannot.

The Plan Also Has to Move Across

Vertical feedback is only part of the challenge.

Many of the most consequential planning problems are horizontal.

One team creates a plan that looks perfectly reasonable inside its function.

The problem only appears when another team sees it.

Sales wants to enter a new market.

Product understands the required features.

Engineering can build them.

Then Legal or Regulatory identifies a requirement that changes the sequence.

Engineering plans a release.

Manufacturing realizes the change creates a supplier dependency.

Marketing plans a launch.

Product moves the release date.

Finance builds a hiring model.

Engineering changes the talent requirements.

The individual plans are not necessarily bad.

The interfaces between them are where the problem lives.

Peak explicitly treats these cross-functional relationships as part of planning. The Peak Teams process calls for everyone on the leadership team to participate in discussion of functional objectives because one area's work frequently affects another. It also expects teams to refine functional objectives after seeing the company-level OKRs and then bring those objectives back for discussion.

That creates the third dimension of challenge:

Across-team review.

Not:

Does Engineering like its plan?

But:

Does Engineering's plan work with Product's plan?

Does Product's plan work with Sales commitments?

Does the Sales plan work with Customer Success capacity?

Does the hiring plan support all of them?

Does Finance understand the combined resource requirement?

Does the organization's full set of commitments fit together?

That is how planning becomes organizational rather than functional.

Up, Down, and Across Creates a Stronger Planning Loop

Viewed together, Peak creates a planning pattern that is much richer than traditional top-down cascading.

Before the leadership session, information moves up from teams and can incorporate perspective from the CEO's up-team.

During the session, leadership synthesizes the organizational direction.

After the session, the plan moves down so teams can understand and test what execution actually requires.

It moves across so dependencies and contradictions between teams become visible.

Material feedback then moves back up.

Leadership can incorporate what the system has learned.

The plan becomes clearer.

Then teams move into execution with a stronger shared understanding.

The sequence looks something like:

Gather → Synthesize → Share → Challenge → Reconcile → Refine → Execute

The important point is not the sequence itself.

It is that planning benefits from perspectives distributed throughout the organization.

The leadership team does not abdicate responsibility.

It uses the organization to improve the quality of that responsibility.

Red Teaming Is About Better Decisions, Not Creating Opposition

The word "Red Team" can create the wrong mental image in a company.

It can sound like one group exists to attack another group's work.

That misses the deeper principle.

The Army handbook describes Red Teaming as a flexible cognitive approach designed to help organizations identify hidden dangers, uncover unseen possibilities, generate alternatives, mitigate groupthink, and ultimately make better decisions.

The Marine Corps policy similarly described the objective as bringing independent thought and alternative perspectives into decision-making, reducing risk and expanding opportunity.

The objective is not opposition.

It is perspective.

That distinction matters in Peak as well.

A down-team should not receive the leadership plan with the instruction:

"Tell us why this won't work."

That can create defensiveness.

The better question is:

"From where you sit, what do we need to understand to make this work?"

An up-team should not be invited to replace the plan.

It should help leadership see risks, opportunities, assumptions, and perspectives management may have missed.

Cross-functional leaders should not protect their own objectives.

They should make the organization's entire plan stronger.

The goal is not criticism.

It is better organizational thinking.

Challenge and Commitment Have to Coexist

There is a second danger.

Organizations can become so committed to inclusion and feedback that they never actually finish planning.

Every person has another perspective.

Every team wants another iteration.

Every stakeholder has another concern.

Eventually the organization stops improving the plan and starts delaying execution.

Peak's emphasis on Communication and Alignment provides an important counterbalance.

In Peak Teams, high-quality communication does not mean everyone always agrees. People need the opportunity to speak and be heard, but strong teams are also able to disagree and still commit to the direction the team decides to take.

That principle is essential to this planning model.

Challenge before and during refinement.

Commit during execution.

Then use the operating rhythm to learn from reality.

The purpose of exposing a plan to up-teams, down-teams, and cross-functional teams is not to achieve unanimous agreement.

It is to make sure the decision has been informed by enough of the system that leadership can make it with greater confidence.

Once the decision is clear, the organization moves.

The People Closest to the Work Often See the First Weak Signals

There is another important reason to involve down-teams in planning.

Weak signals often appear far from the executive team.

A manufacturing engineer sees the supplier problem before the CFO sees its financial impact.

A frontline Customer Success leader sees customer friction before churn appears in the KPI.

An engineer sees increasing technical debt before the roadmap begins slipping.

A recruiter sees a talent constraint before leadership realizes the hiring plan is unrealistic.

A salesperson hears a shift in customer buying behavior before it appears in the forecast.

When those people only receive the plan, leadership loses intelligence.

When they are given a structured opportunity to engage with the plan, their information becomes part of organizational understanding.

This is a strong connection between Peak planning and Organizational Intelligence.

Organizational Intelligence does not mean leadership knows everything.

It means the organization has mechanisms for relevant information to move to the places where it can influence understanding and decisions.

Planning is one of those mechanisms.

Operating rhythm is another.

Strong Leaders Have to Be Willing to Have Their Assumptions Challenged

This planning architecture depends on leadership behavior.

A CEO can ask for feedback while making it obvious that disagreement is unwelcome.

A leadership team can ask functional teams to review the plan while treating every challenge as resistance.

An executive can gather bottoms-up input and then ignore all of it.

In those environments, information quickly stops moving.

People learn what the Army Red Team Handbook warns about: the safest path is to agree with what senior people already appear to believe.

That creates a dangerous illusion.

Leadership hears agreement.

Therefore leadership assumes alignment.

But silence is not alignment.

Agreement is not necessarily understanding.

And a lack of challenge is not evidence that a plan is strong.

This is particularly important for founder-led companies.

Founders often possess extraordinary conviction.

That conviction helped create the company.

It is a competitive advantage.

But as the organization becomes larger and more specialized, leadership needs a system that allows conviction to interact with distributed expertise.

The CEO still owns the direction.

The organization helps make the direction more executable.

Frontier-Tech Companies Have More Perspectives That Need to Be Integrated

This becomes especially important in frontier technology because the knowledge necessary to create a good plan is unusually distributed.

Consider an aerospace, defense, robotics, autonomous-systems, or advanced-manufacturing company.

A leadership plan may touch:

systems engineering,

software,

hardware,

manufacturing,

quality,

supply chain,

program management,

field operations,

security,

regulatory requirements,

government customers,

commercial customers,

finance,

capital,

talent,

and external partners.

No single meeting room contains every relevant detail.

And the consequences of hidden dependencies can be significant.

A decision made today may affect a hardware build months from now.

A component assumption may eventually affect certification.

A hiring constraint may change a program timeline.

A customer commitment may create technical consequences several functions away.

A capital decision may alter the organization's ability to deliver a program.

That is why a strong planning system needs more than executive intelligence.

It needs organizational intelligence.

People throughout the organization need a way to contribute what they know while leadership still maintains a clear decision structure.

For military and former-military leaders entering frontier tech, that principle can feel familiar because Red Teaming begins with a similar recognition:

plans become stronger when they are deliberately exposed to perspectives that the original planners do not possess.

The Peak Parallel Is Not a Formal Red Team

It is important not to overstate the comparison.

Peak does not require a Red Team.

A functional team reviewing the company plan is not performing formal military Red Teaming.

A board is not a Red Team.

Cross-functional discussion is not automatically Red Teaming.

The parallel is in the organizational purpose.

Military Red Teaming exists to introduce alternative perspectives, challenge assumptions, reveal risks and opportunities, mitigate groupthink, and improve decisions.

Peak's planning architecture can produce some of those same benefits by deliberately exposing the plan to different organizational perspectives.

The up-team sees one reality.

Leadership sees another.

Down-teams see another.

Adjacent functions see another.

The strongest organizational understanding emerges when those perspectives can be integrated without losing clarity of ownership or decision authority.

That distinction makes the comparison more meaningful, not less.

The lesson is not:

Companies should create military Red Teams.

The lesson is:

Leadership teams should be suspicious of any important plan that has only been evaluated by the people who created it.

Planning Quality Comes From the Organization, Not Just the Planning Session

This may be the most important distinction.

Companies often evaluate planning quality by looking at the planning session.

Was the agenda good?

Did the team have the right discussion?

Did they create clear objectives?

Did everyone leave aligned?

Those things matter.

But they are only part of the answer.

A strong plan is the product of an organizational process.

Did leaders arrive with real input from their teams?

Did the leadership group reconcile functional dependencies?

Did the CEO bring relevant context from the board and other up-team relationships?

Did the plan go back to the people responsible for executing it?

Did those teams identify hidden assumptions or constraints?

Did adjacent teams reconcile their dependencies?

Did material feedback make its way back to leadership?

Did the organization refine the plan where new information warranted it?

Those questions reveal something much more meaningful than whether the offsite went well.

They reveal whether the organization can think together.

Organizational Challenge Is Part of Organizational Execution

Peak OS emerged from more than two decades of work with hundreds of CEOs, founders, investors, and leadership teams. One recurring lesson from that work is that organizational execution does not improve simply because leadership creates a better plan. The organization has to understand the plan, connect to it, coordinate around it, execute it, learn from it, and continuously maintain alignment as reality changes.

Red Teaming offers an important external parallel to one part of that system.

The Army's Red Team Handbook describes human groups as vulnerable to familiar assumptions, deference to hierarchy, unchallenged beliefs, and overlooked alternatives. Its Red Teaming approach is designed to create better decisions by exposing those weaknesses and widening perspective.

The Marine Corps similarly described Red Teaming as bringing independent critical thought and alternative perspectives into planning while subjecting plans and concepts to rigorous examination.

Peak arrives at the challenge from a different direction.

The organization itself contains different vantage points.

The board sees something.

The CEO sees something.

Leadership sees something.

Functional teams see something.

People closest to the work see something.

Adjacent teams see the dependencies between them.

A strong planning process creates a way for those perspectives to interact.

That produces an important principle for any complex organization:

Do not ask the leadership team to know everything. Build an organization capable of improving what the leadership team knows.

A Strong Plan Has Been Exposed to the Organization

The best leadership teams need conviction.

They need to make decisions.

They need to establish direction.

They cannot outsource leadership to a committee.

But conviction becomes more powerful when it has survived serious examination.

The strongest plan is not necessarily the one leadership created most confidently.

It is the one that has been exposed to the realities above it, below it, and beside it—and has become clearer because of what the organization learned.

That is the deeper parallel between Red Teaming and Peak OS.

Listen up.

Plan together.

Test down.

Challenge across.

Bring the learning back.

Refine where necessary.

Then execute with commitment.

For military and former-military leaders building complex frontier-tech organizations, that pattern may feel familiar.

Not because Peak OS is a military planning system.

But because both systems recognize something fundamental about execution:

the first version of a plan reflects what the planners know. A stronger version reflects what the organization knows.

Related Insights

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What Is a Business Operating System?

What Is Operating Rhythm?