Tips for high performance leadership and teamwork: Red Teaming and Pre-Mortems – stress-testing your plan

RAF Harrier G77A on board a RN aircraft carrier just about to launch

“No plan survives first contact with the enemy.”

This old military adage rings as true in the boardroom as it does on the battlefield. Whether you’re launching a new product, entering a new market, or implementing an ambitious transformation, your strategy will collide with reality. And when it comes to the final outcome, reality gets a vote.

So how do high-performance teams prepare? They don’t just hope for the best. They stress-test their plans before execution with two powerful tools: Red Teaming and Pre-Mortems.

A story from the flightline

Within the military fighter community, a key part of the planning process is finding holes in the plan. The crews gather and try to answer a blunt question: “How could this mission go wrong?”

The plan is gone through step by step, imagining what the adversary might do, where technology might fail, and where human error could creep in. The aim of this is to find the cracks before someone else does.

We'll discover vulnerabilities we hadn’t considered, exposed overconfidence, flawed assumptions and so refine the plan until it can withstand the unexpected.

This same approach has application to business. Your competitors, the market, and even your own assumptions are your “enemy” in many ways. If you don’t challenge your plan internally, someone else will and potentially at a much higher cost.

What is Red Teaming?

Red Teaming originated in the military and intelligence communities as a structured way to challenge assumptions and test strategies from an adversarial perspective. In practice, it means creating an independent team – or assigning people internally – to play the role of a challenger. Their mission is to identify flaws, blind spots, and unintended consequences in your strategy.

Key principles of Red Teaming:

Independence – The Red Team shouldn’t be emotionally attached to the plan.

Constructive Dissent – Their job is to challenge ideas, not people.

Permission to Speak Freely – This only works if leadership welcomes candor.

It’s uncomfortable. That’s the point. Discomfort in the planning room is far more preferable to disaster in execution.

The power of the Pre-Mortem for High Performance

If Red Teaming feels like the heavyweight option, the Pre-Mortem is its nimble cousin – and it’s just as effective in many scenarios. Coined by psychologist Gary Klein, a Pre-Mortem flips traditional planning on its head. Instead of asking “What could go wrong?” you assume the project has already failed spectacularly. Then you ask: “Why did it fail?” This simple mental shift unlocks deeper insights. People feel safer admitting risks when speaking about a hypothetical failure than when challenging a live plan. Suddenly, cognitive biases like optimism and groupthink loosen their grip.

Pre-Mortems work because they:

• Normalise discussing failure without the associated stigma.

• Surface hidden concerns from the quieter voices in the room.

• Trigger creative thinking to prevent mistakes that would otherwise have lain dormant.

It’s a quick, high-impact exercise you can run in less than an hour – no special tools required.

Why Stress-Test your plans?

You might be thinking: “We already do risk assessments – why bother with something new?”

The problem is that traditional risk assessments are usually relatively generic in their approach and often can actually be used/made/shown to validate the plan. Red Teaming and Pre-Mortems are designed to break this mindset. We all suffer from confirmation bias, overconfidence, and groupthink – especially when under pressure. These biases trick us into seeing the plan as stronger than it is. Stress-testing your specific plan is much more likely than relying an extant risk assessment to expose those blind spots before they cost you time, money, and credibility.

From the cockpit to boardroom: Making it practical

How do you bring these techniques into your team without turning meetings into war games? Here’s a simple approach:

1. Run a Pre-Mortem at the start

Before finalising your plan, gather the team and say:"Imagine it’s six months from now. The project failed completely. What happened?" Write down every possible cause. Then turn that list into mitigation strategies.

2. Assign a Red Team role

For critical projects, designate someone to actively challenge assumptions. Rotate the role so it doesn’t feel personal. Give them permission to be blunt. Their objective is to punch holes in the plan now so reality can’t later.

3. Create Psychological Safety

This whole thing only works if people feel safe to speak up. Leaders must model openness by acknowledging their own blind spots. This vulnerability isn’t weakness – it sets the foundations for real learning. Read our blog here on the power of vulnerability.

4. Capture and act on insights

Don’t let these sessions become academic. Document what you find, adjust the plan, and communicate changes clearly. Take the learning forward for future plans!

The cultural payoff for High Performance Leadership and Teamwork

Beyond better plans, these tools build something deeper: a culture where challenge is healthy. When teams see that dissent is welcomed – not punished – they engage more fully, think more critically, and collaborate more effectively. Be aware, this isn’t just for big strategic moves. You can use Red Teaming and Pre-Mortems on sales pitches, marketing campaigns, product launches and even hiring decisions. High-performance teams don’t retreat from scrutiny. They walk towards it.

On Target Tip

Don’t wait for failure to teach you what success requires. Build time into your planning cycle for deliberate challenge. Whether it’s a quick Pre-Mortem or a full Red Team exercise, stress-test your plan before reality does it for you.

In the boardroom, just like in the cockpit, the cost of being wrong is always higher than the cost of being ready.

Final thoughts

The best teams plan twice: once to execute, and then to break the plan before reality does. Red Teaming and Pre-Mortems aren’t about pessimism. While they may feel negative at first, they’re about resilience.

So next time you’re ready to launch, ask yourself: “Have we really tried to kill this plan?” If the answer is no, you’re not done with your planning.

Call to Action: If you found this useful, check out our previous blog on building a feedback rich culture – and start building a team that embraces challenge as a strength.

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Mike Mason and Sam Gladman – Co-founders of On Target

Mike Mason and Sam Gladman are the co-founders of On Target, a leadership and team development company that brings elite fighter pilot expertise into the corporate world. With decades of combined experience in high-performance aviation, they specialise in translating critical skills such as communication, decision-making, and teamwork into practical tools for business. Through immersive training and cutting-edge simulation, Mike and Sam help teams build trust, improve performance, and thrive under pressure—just like the best flight crews in the world.

If you'd like to learn more about how On Target can help your team, contact Mike and Sam at info@ontargetteaming.com