The pre-mortem mindset: Why smart leaders imagine failure before it happens

Introduction

Projects rarely fail dramatically at the start. In fact, the most dangerous phase of any initiative is often the period when everything appears to be going well. Plans are approved, teams are enthusiastic, early progress looks promising, and confidence builds quickly.

Yet many experienced managers can recall projects that looked perfectly healthy at the outset but eventually stalled, delivered disappointing outcomes, or quietly disappeared from organisational memory.

When leaders reflect afterwards, the warning signs often seem obvious in hindsight. Assumptions were never fully tested. Risks were recognised but not discussed openly. Concerns were quietly dismissed in the momentum of progress.

One useful discipline that helps organisations avoid these traps is the pre-mortem.

Rather than analysing failure after the event, the pre-mortem asks a simple but powerful question at the start:

By deliberately imagining failure before it occurs, leaders can uncover risks that would otherwise remain hidden beneath optimism and momentum. In an age increasingly shaped by artificial intelligence, this discipline may be more important than ever.

Why intelligent teams still overlook obvious risks

It is tempting to assume that experienced managers and skilled teams naturally anticipate problems. In reality, human decision making is influenced by a number of well-documented psychological biases.

One of the most common is confirmation bias - the tendency to favour information that supports our existing beliefs while overlooking information that contradicts them.

Another is groupthink, where teams unconsciously prioritise harmony and consensus over critical questioning. When a project gathers momentum, raising doubts can feel uncomfortable or even disloyal.

There is also the phenomenon sometimes referred to as success momentum. When early progress appears positive, teams may interpret that progress as validation of their assumptions rather than an early stage of learning.

In these situations, the real risks often remain invisible until it is too late to correct course. The pre-mortem disrupts this pattern by making it legitimate, and expected, for people to voice concerns early.

The shift in perspective can reveal issues that conventional planning discussions often miss.

What a pre mortem actually involves

The concept of the pre-mortem was developed by psychologist Gary Klein as a structured way to improve decision quality.

The technique itself is straightforward. Before a project begins, the team imagines that the initiative has already failed. Participants are asked to write down the possible reasons for that failure.

Once the risks are identified, the team can adjust the strategy, strengthen safeguards, test assumptions more rigorously, and clarify responsibilities and decision points.

Importantly, the goal of the exercise is not pessimism. It is disciplined foresight.

Good leaders remain optimistic about outcomes. But they also recognise that optimism without scrutiny can be dangerous. A pre-mortem ensures that the enthusiasm of launching a new initiative is balanced by thoughtful examination of its vulnerabilities.

Why this matters even more in the age of AI

Artificial intelligence is transforming the way many organisations analyse information, generate ideas, and plan initiatives.

AI systems can produce reports, strategic frameworks, and recommendations at remarkable speed. Tasks that once took days or weeks can now be completed in minutes.

While this capability offers enormous benefits, it also introduces a subtle managerial challenge.

AI systems tend to produce outputs that are fluent, structured and persuasive. Even when the underlying assumptions are weak, the presentation can appear highly convincing.

This can unintentionally amplify existing biases within organisations. A strategic proposal generated with AI assistance may appear impressively comprehensive. A market analysis may look detailed and authoritative. A project plan may feel well structured and complete.

Yet the apparent sophistication of the output does not guarantee that the underlying judgement is sound.

Managers therefore face a new form of risk: the illusion of certainty created by well presented information.

In this environment, the pre-mortem becomes a particularly valuable leadership tool. It forces teams to step back from the apparent confidence of the plan and ask harder questions about its foundations.

In simple terms, as execution becomes faster, reflection must become deeper.

A simple framework for leaders

Managers do not need elaborate workshops to apply pre-mortem thinking. A short, structured conversation before launching an initiative can significantly improve decision quality.

Leaders might begin by asking five straightforward questions:

Even a brief discussion around these questions can significantly improve the robustness of a plan.

Turning pre-mortems into a leadership habit

The most effective organisations treat pre-mortems not as occasional exercises but as part of their decision culture.

Leaders who consistently encourage this type of thinking send an important signal: questioning assumptions is not negativity; it is responsible management.

This approach improves the quality of strategic decisions by surfacing risks earlier, encourages psychological safety within teams, and reduces hindsight regret when reviewing outcomes.

In many cases, the greatest value of the pre-mortem lies not in predicting specific failures but in fostering a culture of thoughtful challenge.

Leadership in a faster world

Modern organisations operate in an environment of accelerating change. Digital tools, artificial intelligence, and global connectivity allow ideas to move from concept to implementation at unprecedented speed.

Speed can be a competitive advantage. But it also increases the cost of mistakes.

In such an environment, leadership requires more than enthusiasm and momentum. It requires disciplined reflection.

Imagining failure before it happens may feel uncomfortable. Yet it is often the mark of mature leadership.

The most dangerous moment in any project is rarely when things begin to go wrong. It is when everything appears to be going perfectly right.

Sometimes the simplest question can be the most valuable:

“If this project fails, what will we wish we had thought about today?”

Author Bio | Keith Grinsted MBA FRSA

 

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Keith Grinsted is a business author, strategist, and AI adoption advocate based in Essex, UK.

He works at the intersection of leadership, resilience, and intelligent technology - helping organisations move from viewing AI as a technical tool to recognising it as a practical business partner.

Keith is currently writing AI as a Business Partner, exploring how AI can support everyday decision-making, productivity, governance, and strategic clarity across private, public, and third-sector organisations. His work focuses on pragmatic implementation rather than theory - helping leaders integrate AI into daily workflows in ways that enhance judgement rather than replace it.

With experience spanning startups, retail, corporate environments, local and national government, and charity boards, Keith brings a cross-sector lens to organisational transformation. He has been described as a modern-day Sir John Harvey-Jones for his ability to identify overlooked opportunities and unlock underused capability within teams and systems.

He is Founder of Pathway Collective, a platform integrating AI literacy, executive coaching, charity-sector insight, and second-act career development. Through this work he supports senior leaders, trustees, entrepreneurs, and professionals navigating change in an AI-enabled economy.

Keith is also the author of previous business titles with Business Expert Press (New York) and has written for national publications including Huffington Post UK. His commentary has appeared on BBC television and radio.

Alongside his work in technology and leadership, Keith has led national conversations around loneliness, workplace wellbeing, and career reinvention. His LAUNCHPAD programme supports individuals facing redundancy or career transition, and he is a qualified Mental Health First Aider.

Awards include:

• Open University Business School Alumni Award for Outstanding Contribution to Society
• Investors in People Exceptional People Award for Community Engagement

Keith believes the future of work lies not in choosing between humanity and technology - but in learning how to align them.

April 2026