Nothing Fails Like Success

Choose this exercise

Purpose: Identify unexamined assumptions and formulate alternative problem definitions for an established, successful initiative.

Use it when: Use during strategic reviews, project retrospectives, or problem-framing sessions when a team has experienced steady success and risks complacency.

Skip it when: Skip during early-stage ideation or when a project is in active operational crisis needing immediate tactical containment.

Group arrangement: Small groups of 3 to 5 participants, plus whole-room debrief. A group of 5 works as a single team or splits if more people arrive.

Timing: Adapted from the 30 to 60 minute range in Relationship Makers Handbook to fit a focused 35-minute workshop block.

Materials and tools

• One printed worksheet per small group (or digital equivalent)
• Pens for each participant
• Flip chart pad or digital whiteboard for whole-room capture

Before participants arrive

1. Print worksheets or copy the prompts onto your shared virtual board.
2. Arrange seating or breakout spaces for small groups of 3 to 5 participants.

Say this to open

Past success can blind us to shifting conditions. Ian Mitroff observed that serious management errors stem from solving the wrong problem precisely. Today we will examine one of our successful efforts, challenge its baseline assumptions, and frame it through two distinct lenses.

How to run it

1. Introduce framing and prompts 5 minutes

   Read the opening script. Direct participants into small groups of 3 to 5. Hand out the worksheet with the problem-framing prompts. Provide a concrete neutral example: if the success is 'our onboarding portal cut support tickets by 40%,' an unexamined assumption is that users found what they needed, while an opposing view is that users simply gave up seeking help.

2. Challenge assumptions and find opposition 10 minutes

   Each group selects one shared success or established program. In their groups, members identify at least one baseline assumption taken for granted regarding users, clients, or staff. They also identify at least two parties who could oppose, push back on, or be disadvantaged by this approach. Groups record their answers on the worksheet.

3. Formulate alternative problem statements 10 minutes

   Groups produce two distinct, alternative formulations of the core challenge this initiative addresses. One formulation must focus on technical and operational factors. The other must focus on human and social factors. Groups write both statements on their worksheet. Groups finish when both statements are complete.

4. Share insights and debrief 10 minutes

   Reconvene the full room. Invite two groups to share one challenged assumption and their sharpest alternative problem statement (one minute per group). Then pose two debrief questions to the room, taking two quick responses per question. Wrap up on time.

Debrief questions

• Which core assumption felt hardest to challenge, and why?
• How did framing the problem through human variables shift what looks like a priority?

Finished output: Completed worksheets containing at least one challenged assumption, two opposing perspectives, and two alternative problem statements per subgroup.

Remote

Create breakout rooms for groups of 3 to 5. Provide a shared slide or digital canvas per room pre-populated with the worksheet prompts. Keep the main room open for questions, and pull all participants back for the final 10-minute debrief.

Hybrid

Form distinct remote-only breakout rooms and in-person clusters to avoid audio feedback. Use a shared digital document for all worksheets so in-person and remote participants can view each other's alternative problem statements during the debrief.

Access and participation choices

• Participants may contribute via spoken discussion, written notes on the shared canvas, or silent review.
• Any participant may pass on speaking during the whole-room debrief without explanation.

If the session gets stuck

A group defends past success and insists their assumptions are established facts.

Ask: 'If an aggressive competitor wanted to undermine this program, what hidden vulnerability would they target first?'

Problem statements remain purely technical without human variables.

Direct the group to write one problem statement that mentions only how people feel, coordinate, or communicate.

Terms used here

• Problem formulation: The specific boundary, angle, and language chosen to define an issue before generating solutions.