Before your plan meets reality, let it meet resistance.

If you’ve ever led a major initiative, you know the high-stakes energy that comes with a new launch: bold goals, tight timelines, and a room full of nodding heads. In fast-moving environments, the pressure to align can eclipse the need to ask hard questions. That’s when strategic planning starts to slide into wishful thinking.

High-performing teams don’t just align, they challenge.

To avoid blind spots, groupthink, and costly missteps, high performing teams use tools like pre-mortems and red teaming to stress-test ideas before execution. These techniques build psychological safety, unlock creative risk management, and lead to stronger decision-making.

What’s a Pre-Mortem?

Unlike a traditional post-mortem, where we reflect on what went wrong after a failure, a pre-mortem asks the team to imagine that the project has already failed. The task is simple: explain why.

It’s a simple, powerful psychological shift. The project lead might say: “Let’s assume it’s six months from now. The project didn’t work. What happened?”

Now, instead of asking for criticism in a way that feels personal or obstructive, you’ve invited imaginative problem solving. The team’s job isn’t to attack the current plan, it’s to channel foresight and curiosity, to look around corners and name potential pitfalls before they happen.

A Real-World Example

One healthcare technology company I worked with used this approach ahead of a high-stakes product release. They were preparing to roll out a new platform feature designed to support mental health access at scale, a critical initiative with implications for clinical outcomes, enterprise clients, and user trust. Before development began in earnest, the product sponsor gathered the cross-functional team and said: “It’s six months from now. The release failed. Why?”

Each person took two minutes to jot down potential failure points. Then, one by one, they shared what they saw. No blame. No ego. Just insight. The leader went first, modeling honesty and vulnerability to set the tone.

By the end of the session, they had surfaced risks related to:

Integration complexity
Data privacy concerns
Uneven stakeholder alignment
User adoption barriers

Surfacing these early didn’t stall the project, it strengthened it. That willingness to imagine failure gave the team a sharper path to success.

Here’s the kicker: the team left the room more confident. The plan wasn’t perfect, but they had kicked the tires, stress-tested assumptions, and built psychological safety into the process. Everyone agreed on the most likely risks, and that led to a far stronger, smarter plan.

Why This Works

Pre-mortems tap into a few key human truths:

People are more willing to speak up when failure is hypothetical. The social cost of saying “this might not work” is much lower when everyone’s in a mindset of collective imagination.
The brain is wired for storytelling. By framing failure as a story that already happened, people naturally engage their creativity, and often name risks that would stay hidden in a standard risk log.
It builds a culture of candor. When leadership makes it safe (and even admired) to name weaknesses, it sends a signal: truth matters more than politeness.

Beyond Pre-Mortems: Red Teaming

If you want to take it a step further, consider red teaming, a practice borrowed from military strategy and cybersecurity. In red teaming, a designated group or individual’s job is to poke holes in a strategy, stress-test assumptions, and think like an adversary or skeptic.

It’s not personal. It’s part of the process.

Red teaming works best when:

Stakes are high.
The group is too close to the problem.
There’s a risk of groupthink.
A “green team” (the planning team) needs an honest, outside view.

In corporate settings, red teams often come from other parts of the business, or are composed of people trained in strategic dissent. Their goal? Help the planning team uncover blind spots before reality does.

Red Team Your Metrics, Too

Red teaming isn’t just for strategic plans, it’s just as powerful when applied to metrics and incentives. If you’re using KPIs to drive behavior, it’s worth asking: what happens when this measure becomes the target?

One of my clients, an engineering leader, wanted to encourage engineers on call not just to fight fires, but to improve the systems that generate those alerts in the first place. We explored ways to track impact, things like “hours saved” or “alerts avoided” to make process improvement more visible.

We also red teamed those metrics before rollout. Could “hours saved” be inflated? Might teams chase easy optimizations rather than meaningful ones? By pressure-testing the metric before implementation, my client preserved the spirit of the goal, better systems, without letting the metrics distort the mission.

The takeaway: metrics are strategies in disguise. Red team them with the same rigor.

How to Start

Pre-Mortem Lite (30 min):

Brief the team on the plan.
Ask: “It’s six months from now. The project failed. What happened?”
Everyone writes for 2–3 minutes.
Go around, share one item each. Capture everything.
Group the risks into themes and discuss how to mitigate them.

Red Team Preview:

Identify one person or small group not involved in the project.
Brief them quickly.
Ask them to spend 30 minutes trying to find flaws, risks, or overlooked assumptions.

Debrief with the team. No defensiveness, only learning.

Final Thought

The best leaders I know don’t just rally support for their ideas. They design ways to challenge them.

They know that foresight is a muscle, and when you build it into your team culture, your projects get smarter. Your people do too.

See article here as well https://www.linkedin.com/in/kathrynmfulton/