By Kelly Shambaugh
We’ve all been there: You’ve spent months designing a major learning rollout or change initiative. You’ve aligned with leaders, planned communications, built content, and prepped managers. Then the program goes live, and things don’t go quite as planned. Engagement is lower than expected, adoption lags, or unexpected resistance surfaces from corners you hadn’t considered. Sometimes, team members struggle because of insufficient training, unclear processes, or competing priorities that weren’t visible during planning.
What if you could uncover those blind spots before your initiative went live?
Enter red teaming, a strategic process borrowed from the military and intelligence fields that helps teams pressure-test their plans, challenge assumptions, and strengthen their approach. While it’s a familiar concept in cybersecurity and strategic planning, it’s still largely untapped in learning and development (L&D) and change management, two fields that would benefit tremendously from its mindset.
I’ve used red teaming on several large-scale projects, and the outcomes have been consistently powerful: better stakeholder alignment, smarter implementation strategies, and stronger confidence from both leaders and team members. Red teaming didn’t just make the plans better; it made the teams better.
What is red teaming?
At its core, red teaming is about thinking like an adversary—not to defeat your own plan, but to improve it.
The approach originated in military strategy, where “red teams” simulate enemy tactics to expose weaknesses in operations or decision-making. Over time, industries such as cybersecurity, finance, and business strategy adopted it to test resilience before launching critical initiatives.
In a red teaming exercise, a designated group called the red team challenges the assumptions, strategies, and blind spots of the main project team, often called the blue team. The goal isn’t to criticize, but to illuminate—to uncover what the core team might have missed because of overconfidence, groupthink, or simply being too close to the work.
Applied to learning and change management, red teaming becomes a powerful tool for anticipating resistance, improving clarity, and building adaptability into your plans before going live.
Why red teaming matters in learning & change
Learning and change professionals are already in the business of influence. We design experiences that shift mindsets, behaviors, and culture. But even the best-planned initiatives can fail when they collide with the messy reality of organizational life.
Here are a few common challenges where red teaming makes a difference:
- Assumptions about readiness: We assume team members are motivated, leaders are aligned, or technology will work smoothly until we discover otherwise.
- Hidden resistance: Some team members may quietly question the “why” behind a change, but their concerns never reach the project team.
- Communication gaps: Messages that sound clear to us may not resonate across levels, regions, or roles.
- Blind spots in culture: A plan that fits the organizational chart might not fit the organizational climate.
Red teaming helps expose these realities before they derail your initiative. It gives voice to the skeptics, the quiet resistors, and the “what if” thinkers. When you build this challenge process into your project cycle, you’re not inviting conflict, you’re building resilience.
One of my most successful projects involved introducing red teaming during a compliance rollout. The initiative aimed to correct long-misinterpreted system issues that had caused team members to collect inaccurate data for years. Because the change would significantly impact how both sales and operations teams worked, we formed a red team of 20 people—16 team members from sales and operations, and 4 leaders from those same functions.
Their diverse perspectives were invaluable. The red team surfaced issues we hadn’t fully considered: communication gaps between field and corporate teams, training content that didn’t reflect real-world workflows, and dependencies that could have delayed adoption. They also helped refine the messaging so it resonated more effectively with frontline teams.
By addressing those insights before going live, we achieved faster adoption, higher accuracy in data collection, and stronger confidence among leaders and team members. The process didn’t just improve the plan—it deepened ownership across the organization.
How to apply red teaming in your work
Red teaming doesn’t have to be complicated or formal. You can adapt it to fit any project, from a new learning curriculum to a multi-phase change initiative. Here’s a simple five-step framework you can start using right away:
1. Frame the challenge
Define what you want to test. It could be your change communication plan, training design, or implementation roadmap. The key question: “What do we most need to get right, and what could go wrong?”
Example: We want to ensure our rollout plan for new performance tools will be understood, adopted, and supported by managers.
2. Assemble a red team
Select a small, diverse group of people who can think critically and aren’t afraid to ask tough questions. They might include internal skeptics, frontline team members, or even external partners. Diversity of perspective is what makes the red team valuable.
Tip: Choose members who represent the people most affected by your initiative, not just senior voices.
3. Set the ground rules
Psychological safety is essential. The red team must understand that their role is to challenge ideas, not individuals. Clarify that this process is about learning, not judgment.
Sample ground rule: Assume positive intent. Our goal is to make the plan stronger, not to win an argument.
4. Run the simulation
Give the red team access to your plan, then ask them to stress test it. Encourage them to look for gaps, unrealistic assumptions, or unintended consequences.
This can take many forms:
- Scenario testing: What happens if adoption is 30% lower than projected?
- Role-playing resistant stakeholders
- Reviewing communications for clarity and tone
- Identifying risks or dependencies that might derail timelines
5. Debrief & integrate insights
After the red team exercise, capture key findings and discuss how to adjust your approach. Often, the most valuable outcome isn’t just the fixes, it’s the conversation that happens when people see their plan through a different lens.
Be sure to share what you learned with stakeholders and document how the red team’s input strengthened your plan. This builds credibility and shows that your process values critical thinking.
The benefits go beyond the plan
When you integrate red teaming into learning and change work, the value extends far beyond problem detection. You also cultivate:
- Stronger stakeholder buy-in, because your plan has already been tested from multiple perspectives.
- Higher team confidence, because you’ve proactively explored potential risks.
- Greater agility, because red teaming teaches teams to pivot faster when real challenges arise.
- A learning culture, because you model curiosity, humility, and openness to feedback.
In one organization I worked with, leaders initially viewed red teaming as an unnecessary step until they saw how it exposed critical misalignment between the change narrative and team-member sentiment. Adjusting those narratives early saved time, money, and credibility later.
Making red teaming a habit
Red teaming works best when it becomes part of your regular project rhythm, not a one-time event. Consider building it into:
- Major initiative checkpoints, such as before going live
- Learning design reviews for large programs
- Change readiness assessments
- Stakeholder communication planning
Even a short, two-hour red team session can yield insights that reshape your approach. Over time, your teams become more comfortable inviting challenge, and that’s when innovation really thrives.
Final thoughts
Red teaming doesn’t replace traditional project reviews or stakeholder feedback, it enhances them. It injects a level of rigor, curiosity, and humility that helps learning and change professionals avoid blind spots and make smarter decisions.
At its heart, red teaming is about practicing what we preach: continuous learning, perspective-taking, and growth through constructive challenge.
So, the next time you’re preparing to take a major learning or change initiative live, pause and ask yourself: Who’s testing our plan before the world does?
Because when you think like an adversary, you become your project’s best ally.
Dig deeper
Explore the trends and challenges that the new year will bring to L&D in our 2026 Strategies & Trends online conference, December 3‒4, 2025. Learn to ‘Red Team’ your training with Kelly Shambaugh! You’ll also:
- Uncover strategies for elevating your virtual training
- Gain insights into why and how to transform your organization to a skills focus
- Learn the value of critical thinking and curiosity
- Dig into agentic AI
- Highlight the benefits of moving at the ‘speed of business’
- And learn from a panel of dynamic leaders what else to expect in 2026!
Image credit: z_wei
