💰 Wall Street Wisdom

Step onto the bustling trading floor! Invest in our successes, audit our setbacks, and forecast improvements as we review our sprint like Wall Street pros. Let’s balance our project portfolio and generate high returns!
45–60 min
4-10 people
Based on: Glad, Sad, Mad
💰 Wall Street Wisdom
Template Columns
📈 Bull Market Wins

Share the profitable gains and smart investments from our sprint.

Base column: Glad
📉 Bear Market Losses

Reflect on downturns or financial setbacks that discouraged us.

Base column: Sad
🧾 Red Tape Frustrations

Discuss operational blockers, regulatory woes, or anything that made you want to short the system.

Base column: Mad
About this template

The Wall Street Wisdom retrospective uses a market metaphor to review a sprint, helping teams analyze their wins, losses, and operational frustrations to maximize learning and future gains.

When to use this template

Use this format when your team needs a fresh, energetic approach that emphasizes continuous improvement and candid discussion about both successes and pain points.

How to facilitate
1

Begin with a brief introduction, setting the Wall Street theme and encouraging people to think like investors reviewing a portfolio

2

Explain each column: Bull Market Wins for successes, Bear Market Losses for disappointments, and Red Tape Frustrations for blockers or process issues

3

Invite team members to brainstorm and add their notes to each column individually (5–7 minutes)

4

Once everyone has contributed, review each column together, clustering similar items and clarifying where needed

5

Facilitate a discussion focusing first on wins (what contributed, how can you double down), then losses (patterns, prevention), and finally operational frustrations (processes to streamline or remove)

6

Prioritize the most impactful discussion points, and together forecast actionable improvements for the next sprint

7

End with a quick round where everyone shares one 'investment tip'—something they personally plan to do to help the team succeed

Pro Tips

Set an energetic tone with Wall Street music or visuals to get everyone engaged

Encourage honest reflection by reminding the team that losses and frustrations are valuable learning investments

Ask: if this were real money, where would we invest more? This prompts deeper thinking about priorities and impact

Invite quieter voices to 'pitch' one item from their notes for inclusive participation

Timebox each section so momentum stays high, just like a busy trading floor

FAQ
How do I encourage honest discussion about setbacks?

Remind the team that even the best investors learn from losses. Normalize setbacks as part of improvement, and lead by sharing your own.

What if some people dominate the discussion?

Actively invite input from quieter team members by giving everyone dedicated time to share their thoughts.

How do I move from venting frustrations to actionable improvements?

Guide the team to identify patterns or root causes in frustrations and steer the conversation toward proposing specific changes.

At a glance
  • Duration

    45–60 min

  • Team Size

    4-10 people

  • Columns

    3 columns

  • Base Format

    Glad, Sad, Mad

Tags
reflection
team health
continuous improvement
fun
action-oriented
root cause analysis
Ready to get started?

Use this template to run your next retrospective