Goal

What are we working toward?

Launch our new product feature by end of Q2
Reduce customer support response time to under 4 hours
Achieve 98% test coverage across all core modules
Wind

What is pushing us forward?

Our daily standups are efficient and informative
Great collaboration between development and design teams
New automation tools are saving us lots of time
Anchor

What is holding us back?

Outdated documentation is causing confusion
Too many meetings interrupting focus time
Slow approval process for new tools
Rocks

What risks do we face?

Potential system downtime during migration
Key team member leaving soon
Competing project might affect our deadline
Sun

What is making us feel good?

Our recent product launch gave everyone confidence
Great feedback from customers on latest features
Team lunch last week was really fun

What is the Sailboat Retrospective?

The Sailboat Retrospective asks your team to picture itself as a boat heading for a destination. It's a simple metaphor, and it gets people talking about forces they'd struggle to name in a plain "what went well" list. The board has five areas. The goal is where you're heading. Wind is whatever pushes the team forward, anchors are what slow it down, and rocks are the risks ahead that could sink you if nobody steers around them. The sun covers the things that keep morale up. Because one board covers both what's behind you and what's ahead, the sailboat retrospective works well when your team has drifted from its goals or is tired of the usual formats. It lets you talk about risks before they land, as well as the problems you've already hit.

Sailboat Retrospective Format

Goal

What are we working toward?

The goal represents the team's destination. Encourage participants to think about both short-term and long-term objectives. Help the team align their vision and ensure everyone understands where they're heading.

Wind

What is pushing us forward?

Wind represents positive forces helping the team move forward. Guide the discussion to identify enabling factors, resources, and practices that are working well. This helps reinforce successful behaviors and processes.

Anchor

What is holding us back?

Anchors represent impediments slowing the team down. Encourage honest discussion about obstacles while maintaining a constructive tone. Focus on identifying actionable solutions rather than just listing problems.

Rocks

What risks do we face?

Rocks represent potential future risks and challenges. Help the team think proactively about what could go wrong and develop mitigation strategies. Focus on both technical and non-technical risks.

Sun

What is making us feel good?

The sun represents positive elements boosting team morale. Encourage sharing of achievements, recognition, and positive experiences. This helps build team spirit and identifies what should be maintained or expanded.

When to use this retrospective

  • When your team has retrospective fatigue and needs a visual format to get people talking again
  • At project milestones or quarterly reviews, to check progress and plan the next stretch
  • When you want to discuss the risks ahead as well as the problems you've already hit
  • For teams new to retrospectives, who benefit from a clear metaphor to guide the discussion

Suggested icebreaker questions

  • If your current project was a type of boat, what would it be and why?
  • What's your favorite memory of being near water (ocean, lake, river)?

Want a warm-up your team plays, not just answers out loud? Browse free icebreakers →

Ideas and tips for your retrospective meeting

  • Explain the metaphor before anyone writes a note, so everyone knows what each part of the boat stands for
  • Keep the picture visible all session so people place each note against the part of the boat it belongs to
  • Give the anchors and rocks as much time as the wind and sun, so the session doesn't turn into a list of complaints
  • Go around the room for each area so quieter team members get a turn
  • Finish by picking the actions with the most impact that the team can actually carry out
  • Split larger teams into breakout rooms so everyone gets a chance to contribute

Frequently asked questions

What is a sailboat retrospective?
It's a retrospective format that pictures your team as a sailboat heading for a goal. Wind stands for what pushes you forward, anchors for what holds you back, rocks for risks ahead and the sun for what keeps morale up.
How do you run a sailboat retrospective?
Explain the metaphor, then give everyone a few minutes to add notes privately to each area. Group similar notes, vote on the anchors and rocks that matter most, and agree on one or two actions before you close.
When should you run a sailboat retrospective?
Use it at a project milestone, at the end of a quarter, or when the team has lost sight of its goal. It also works well when your usual format has gone stale.
What's the difference between anchors and rocks?
Anchors are things slowing the team down right now, like slow approvals or outdated documentation. Rocks are risks you can see ahead that haven't hit yet, such as a key person leaving or a vendor delivery slipping.
Is the sailboat retrospective the same as the speedboat retrospective?
They're close relatives. Speed Boat, one of Luke Hohmann's Innovation Games, focuses on the anchors slowing a boat down. The sailboat version adds wind, rocks, the sun and a goal, so you also talk about what's helping and what's ahead.
Ready to run this retrospective?Try this retrospective live