Running a Retrospective Where Everyone Only Shares Positives

RetrospectivesMid5–10 min

Introduction: What You’ll Learn

Sometimes retros feel too positive. While it's great when morale is high, avoiding hard topics can limit growth. This simulation helps you practice drawing out deeper insights without dampening team spirit.

You’ll practice:

  • Encouraging balanced feedback in a positive team environment
  • Asking deeper questions without sounding critical
  • Creating safety for raising concerns without forcing it
  • Turning praise into process insights

Step-by-Step Simulation

(The board fills quickly with "great teamwork," "good sprint," "nice collaboration." You notice there’s no feedback under Stop or Start — a sign the team might be hesitant to bring up anything critical, even small stuff.)

Scene 1: All Positives, No Depth

Facilitator: "Thanks for sharing all the positives — sounds like this sprint felt really smooth for many of us."

Facilitator: "Just out of curiosity — was there anything that almost went off track but didn’t? Or anything that felt ‘just okay’ instead of great?"

(Silence. Priya eventually speaks.)

Priya: "I guess the release timing was a little tight — but it worked out."

Facilitator: "That’s a great catch. What helped it work out? Anything we’d want to tweak next time?"

(Team slowly starts reflecting more thoughtfully.)


Scene 2: Surfacing Opportunities Gently

Facilitator: "There’s a lot of praise around teamwork. That’s awesome. What specifically made it great this time — was it pairing, async handoffs, better clarity?"

Leo: "I think we were clearer about task ownership this time. Less bouncing between people."

Facilitator: "Good to know — is that something we’d want to keep doing as a team norm? What else might make it even smoother next sprint?"

(Alex mentions clearer stories helped. Sara notes design was ready early.)

Facilitator: "Interesting — sounds like prep and clarity played a big part. Let’s think about how to preserve and build on that."


Scene 3: Wrapping Up

Facilitator: "Appreciate all the positive energy today — and thanks for digging in a bit deeper. Even small friction points help us stay sharp."

  • Keep clear task ownership — team norm going forward
  • Aim for earlier design readiness — flag dependencies in planning
  • Capture near-misses or close calls in future retros

Facilitator: "Anyone want to lead a reminder or follow-up for one of these?"

(Leo volunteers to remind about task ownership. Sara will check design timelines next sprint. Alex offers to keep a running list of ‘almost issues.’)

Facilitator: "Awesome — I’ll share this in Slack. Thanks for showing that positive doesn’t mean passive."


Mini Roleplay Challenges

Challenge 1: Someone says, “Everything went great.”

  • Best Response: “Love hearing that — what made it great? Anything that almost didn’t go well?”

Challenge 2: You ask for improvement areas and no one answers.

  • Best Response: “Think back to a small friction point or moment of stress — anything stand out?”

Challenge 3: The team resists going deeper.

  • Best Response: “Let’s pick one win and reverse-engineer it — what made it happen, and can we repeat it?”

Optional Curveball Mode

  • A manager is attending and team seems overly positive
  • One teammate keeps saying “we’re all good” and shrugs
  • Everyone adds to Continue, but nothing to Start or Stop

Reflection Checklist

Facilitation

  • Did I balance praise with gentle probing?
  • Did I help the team extract useful patterns from what went well?

Team Learning

  • Did we turn positives into repeatable practices?
  • Did we uncover even small improvement areas?

Psychological Safety

  • Did I model openness without pressure?
  • Did the team feel safe naming slight concerns?

Common Mistakes to Avoid

  • Dismissing positives as unimportant
  • Forcing criticism when none is offered
  • Letting praise stay vague or unactionable
  • Assuming nothing needs improving just because no one speaks up