Anticipating Challenges

Choose this exercise

Purpose: Identify potential project failure modes in advance to create actionable preventive safeguards.

Use it when: Use before launching a new project, policy, or campaign to stress test plans and uncover overlooked vulnerabilities.

Skip it when: Skip when a project is already midway through a live crisis or when the basic plan scope is still undefined.

Group arrangement: Small teams of 4 to 6 people, with total working teams capped at 4 so every group has full presentation time. For headcounts not divisible by 4, balance across 1 to 4 groups (for example: 7 people form groups of 3 and 4; 13 people form groups of 4, 4, and 5; 17 people form groups of 4, 4, 4, and 5; 23 people form three groups of 6 and one of 5; 24 people form four groups of 6).

Timing: Source specifies 30 to 45 minutes; structured here as a complete 45-minute session to ensure thorough debriefing

Materials and tools

• 1 flip chart pad or large poster sheet per team
• 1 pad of sticky notes per team
• 1 marker per participant
• Wall space or tabletop for each team to display posters

Before participants arrive

1. Confirm the target project, milestone, or initiative is clearly named and understood by participants.
2. Arrange seating into small group clusters of 4 to 6 people (maximum 4 teams total).
3. Place 1 poster sheet, 1 pad of sticky notes, and markers at each table cluster.

Say this to open

We are going to conduct a structured pre-mortem. Fast-forward to the scheduled end of our project: imagine it has failed completely. The outcome was an undeniable disaster. Working individually first, take two minutes to write down every specific operational reason why we failed. Do not hold back.

How to run it

1. Set the failure scenario 4 minutes

   State the initiative being examined. Deliver the opening script. Instruct everyone to assume catastrophic failure has occurred. Emphasize that the goal is not pessimism, but discovering hidden operational risks before launch.

2. Brainstorm causes of failure 10 minutes

   Participants spend 2 minutes silently writing failure causes on sticky notes, one cause per note. An example of a useful cause is 'budget approval delayed by six weeks due to missing sign-offs,' rather than a vague statement like 'bad communication.' For the remaining 8 minutes, members post notes on their poster, cluster duplicates, and organize ideas without debating validity.

3. Prioritize critical vulnerabilities 6 minutes

   Each team reviews their clustered notes and selects their top 2 or 3 failure causes based on highest likelihood or most severe operational impact. They circle or place these top issues at the head of their poster.

4. Draft preventive actions 10 minutes

   For each prioritized cause, the team writes at least one concrete preventive action directly beside it. Actions must state an observable task, tool, or check that can be integrated immediately into current plans.

5. Share team findings 7 minutes

   Each of the teams (maximum 4 teams) gives a 90-second report naming their top identified failure risk and the primary preventive action they designed.

6. Facilitate whole-room debrief 8 minutes

   Lead a plenary debrief using the prepared questions. Collect 3 to 4 observations across groups on common systemic risks and establish operational ownership for updating the live plan.

Debrief questions

• Which identified failure risks were expected, and which surprised the room?
• What common patterns or shared vulnerabilities appeared across multiple teams?
• Who will take ownership of updating the project plan with these preventive steps?

Finished output: A prioritized poster per team listing top failure risks alongside concrete, assignable preventive actions.

Remote

Form breakout rooms of 4 to 6 people (up to 4 rooms). Provide a shared digital whiteboard with a pre-labeled workspace for each team. Participants post digital sticky notes during the silent writing phase, cluster them, and type preventive actions beside their top 2 or 3 items before returning to the plenary room.

Hybrid

Organize in-person participants into room table groups and remote participants into dedicated online breakouts. Have all groups record their sticky notes on a single shared digital whiteboard displayed on the main room screen so everyone can read and reference findings during readouts and debrief.

Access and participation choices

• Participants may contribute ideas in writing on sticky notes or verbally to a designated team scribe.
• Any participant may opt out of presenting during the team readouts without explanation.
• Participants may choose whether to write multiple failure causes or focus on a single detailed risk area.

If the session gets stuck

Participants debate whether an imagined failure is realistic instead of listing it during brainstorming.

Remind the room that Step 2 accepts all hypothetical failure causes without critique; evaluation and selection happen strictly in Step 3.

Teams write vague preventive solutions such as 'improve communication.'

Prompt the team to specify the concrete cadence, owner, or checklist item needed, such as 'institute a weekly 15-minute cross-team standup.'

Terms used here

• Pre-mortem: A planning technique where a team assumes a project has already failed before implementation starts, working backward to identify and mitigate root causes.