Leadership Challenge

Choose this exercise

Purpose: Compare observable behaviors used during difficult leadership moments and identify alternative responses.

Use it when: At the start of a leadership workshop to examine how people react under operational friction, disagreement, or unexpected obstacles.

Skip it when: When acute, unresolved workplace friction makes sharing past controversies unsafe, or when participants lack practical experience directing or influencing work.

Group arrangement: Subgroups of 3 to 4 participants; groups of 5 are allowed when room totals do not divide evenly

Timing: UWT suggested 25 minutes to allow sufficient time for small-group reflection and a realistic whole-room debrief; source records list the activity as an energizer without exact minutes.

Materials and tools

• 1 display slide or poster showing the quote by Martin Luther King Jr.
• 1 sheet of flipchart paper per subgroup of 3 to 4
• 1 marker per subgroup of 3 to 4
• Scratch paper and pens for individual notes

Before participants arrive

1. Write the quote on a flipchart or display slide: 'The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.' Martin Luther King Jr.
2. Distribute flipchart paper and markers to each subgroup table.

Say this to open

Take a look at the quote on the screen: 'The ultimate measure of a man is not where he stands in moments of comfort and convenience, but where he stands at times of challenge and controversy.' Consider what this means for your daily work. We will reflect on how we actually lead when projects hit difficulty, controversy, or stress.

How to run it

1. Introduce quote and initial reflection 3 minutes

   Display the quote and read it aloud using the opening script. Ask participants to write one sentence of personal interpretation on scratch paper. Invite two brief comments from volunteers to read or summarize their written interpretation for the room.

2. Share adversity stories in small groups 8 minutes

   Form groups according to the stated group format. Prompt participants: 'You may pass on sharing, or share an observed workplace scenario instead of a personal one.' Each person takes up to 2 minutes to describe a specific challenge faced, the direct action they took, and the outcome.

3. Catalog behaviors 4 minutes

   Subgroups review their stories and record a bulleted list of concrete leadership behaviors that surfaced during those moments. For example: calling an unscheduled check-in, delaying a decision to collect data, taking sole ownership, or asking for peer help. Stop after 4 minutes.

4. Debrief whole-room findings 10 minutes

   Spend 3 minutes collecting one behavior per subgroup on a central board, keeping each share under 30 seconds. Spend the remaining 7 minutes debriefing. Choose any two questions from the debrief list based on group interest. Take exactly two volunteer responses per chosen question, limited to 1 minute each, leaving time for quick concluding remarks.

Debrief questions

• Looking at the behaviors on the board, which ones were habitual reactions versus deliberate choices?
• How might handling one of these situations differently have altered the outcome?
• When does a leader need to shift their default style instead of staying consistent?

Finished output: Subgroup flipcharts and a consolidated central list of observable leadership actions taken during challenging work moments.

Remote

Display the quote on a shared slide. Place participants into breakout rooms of 3 to 4 people for 12 minutes to share situations and list behaviors on a shared digital document. In the main room, each team pastes one behavior into the meeting chat. The facilitator pastes each debrief question into chat and invites verbal or chat comments from volunteers.

Hybrid

Seat in-person participants with table partners and assign remote participants to virtual breakout rooms. In-person tables write on flipchart paper; remote rooms write on a shared document. During report-out, alternate between in-person spokespersons and remote participants who paste their behavior into the room chat. For the debrief, remote participants may unmute to speak or type responses in chat, which the facilitator reads aloud alongside in-person comments.

Access and participation choices

• Participants may describe an anonymized or observed situation rather than disclosing a personal mistake or vulnerable memory.
• Participants may contribute to their subgroup list silently in writing or chat without speaking aloud to the full room.

If the session gets stuck

Participants turn the story-sharing phase into a venting session about unfair policies or difficult colleagues.

Intervene and redirect the room to focus strictly on their own observable actions, decisions, and words, not the shortcomings of external parties.

A participant says they have never experienced a significant leadership challenge or controversy.

Invite them to describe a tight project deadline, an unexpected scope change, or a time they had to deliver inconvenient news to a peer.

Terms used here

• Leadership behavior: An observable physical or verbal action taken by an individual directing or influencing work, distinct from internal emotions or private thoughts.