Why a pre-mortem? (and how to run one)

One of the best predictors of human behaviour, and project performance, is past behaviour. Most of the risks your next digital project will face aren't mysterious - they're patterns you've seen before, just in a slightly different form. The value is in recognising them early enough to plan around them.

A pre-mortem, where teams imagine a project has already failed and work backwards to identify why, can be an effective way to surface risks that optimism, power dynamics, or hierarchy might hide or leave unspoken.

For cultural organisations working with (and around) constrained resources, multiple stakeholders, and complex technical setups, it can be a structured way to have honest conversations before problems derail a project. While the exercise itself is low-stakes (it's about imagining failure, not experiencing it), the conversations it surfaces may not be - and that's the point!

As Gary Klein wrote in Harvard Business Review, the strength of the pre-mortem is in its 'prospective hindsight' (i.e. imagining failure has already happened and working back) which makes it safer to voice doubts and makes it easier to see risks that optimism might obscure e.g. it's psychologically easier for people to say "this would fail if..." than "this will fail because...".

If your organisation always struggles with sign-off, or consistently under-resources content, or habitually delays technical decisions - those patterns are unlikely to magically disappear just because this next project really matters. Pre-mortems let you name these patterns explicitly and plan around them, rather than hoping this time will be different.

Closing the reflection gap

My report on digital failure, Beyond the Promise identified the same themes again and again. Teams reported cycles of delivery without any reflection and a persistent fear of failure, both of which means that issues often surface late - which is when fixes are most expensive and complicated.

Pre-mortems can help to legitimise “productive pessimism” in a structured way, which can in turn support turning unspoken or vague worries into specific, fixable problems while there’s still time to change course.

Getting this off the ground

Running a pre-mortem isn't just about following the steps, it's about creating permission to do it in the first place.

In cultural organisations, where talking openly about failure can feel unsafe or at odds with mission-driven optimism, you might need to do some groundwork first.

If you're a digital manager seeking buy-in:

Position this as protecting what matters, not undermining confidence. Try framing it as: "Before we commit and get underway, I'd like us to spend 30 minutes stress-testing this plan so we are sure we can deliver what our audiences need" or "It'll help us spot issues while we can still do something about them".

If you're asking upwards (to a senior sponsor or board member), connect it to their concerns which will probably encompass things like risk management, due diligence, and responsible use of funds.

If you're asking 'sideways' (to colleagues in other departments), emphasise that you need their expertise and perspective to help spot risks you might miss. If people are stretched (as is likely), emphasise that 30 minutes now will genuinely save time later and that you specifically need their perspective, not just any warm body in the room to make up the numbers.

Plan for this as part of project setup in your initial thinking, not as an optional extra you're asking for later.

If you're a leader being asked to sponsor this:

Your main job in the session is to listen, not to defend or solve. If the exercise surfaces uncomfortable truths about organisational patterns, that discomfort is often a sign it's working.

The best thing you can do is signal that honest feedback won't be punished and that you're there because you want to hear it, perhaps start by sharing one thing you’ve seen go wrong in past projects - it will set the tone that candour is welcome.

If you're nervous about what might come up, that's reasonable. But maybe ask yourself would you rather find out about problems in a 30-minute workshop, or six months into delivery when it's expensive and difficult to fix?

If digital isn't your background:

You don't need to be technically confident to run or participate in a pre-mortem. The exercise works precisely because it brings different perspectives together. Your role is to spot the non-technical risks (resourcing, stakeholder management, organisational patterns) that technical specialists might miss.

When hierarchy itself is the problem:

If power dynamics are particularly fraught, or if the risks most likely to surface are about leadership or governance, you almost certainly need an impartial external facilitator. Someone from outside the organisation can:

• Ask harder questions without political consequences
• Give people permission to be more candid than they'd be if a colleague wa running the session
• Notice and call out patterns that internal staff have become used to and have normalised
• Hold senior people accountable for listening rather than defending

Signs you need external facilitation:

• Previous attempts to discuss risks have been shut down
• The project sponsor is part of the problem
• There's a history of people being penalised for raising concerns
• You're concerned that honest feedback will damage relationships

It isn't a weakness to bring someone external in, it's a mature way to meaningfully approach risk management. If you can't create safety internally, then bringing in a facilitator can help to temporarily create it via an external input.

How to run a simple 30-minute pre-mortem

A note on timings:

Thirty minutes is enough to surface meaningful risks and start important conversations. It's short enough that people will actually agree to do it, which matters more than a theoretical perfect workshop they'll never run.

However, be realistic about what 30 minutes can achieve.

• For straightforward projects with psychologically safe teams, 30 minutes can work well
• For complex projects, larger groups, or organisations with difficult power dynamics you may want to plan for 60-90 minutes (or multiple sessions).
• For teams doing this for the first time allow extra time for the idea and approach to land
• If Step 2.5 reveals significant organisational issues, or if the discussion in Step 3 uncovers more than you can properly address in one session, then that's a signal you need to organise a follow-up session.

This exercise is meant to open conversations, not close them. Thirty minutes surfaces what needs your attention but acting on it will take longer. The timings below are guidelines for a basic session. Adjust based on your context, and don't let perfect be the enemy of good enough.

Setup:

• Works best with a small group (e.g. 4-8) of people who know the project. If you have more than 8 people consider running parallel sessions with different sub-teams (tech, content, leadership), then comparing what they think. Where groups have identified different risks, that often reveals organisational silos.
• Can be done in person (on paper or with sticky notes), or remotely (using a collaborative digital tool like Miro or a Google Doc).
• Frame it as a creative exercise, not a risk register (it may lead to additions to a risk register but it is a more open/discursive task than that).