The Perfect Project Retro - How to Run a Sail-Boat Workshop
With templates to get you started.
I've sat in project post-mortems where teams struggle to pinpoint what went wrong. "The brief changed." "The timeline was too tight." "The client wasn't clear."
Sound familiar?
I find these conversations can miss the bigger picture. Teams need to discuss what helped and hindered their projects in a way that fosters a culture of improvement.
Enter the sailboat exercise.
A simple (hour-long) workshop that hits the collaborative sweet spot and gives you clear actions to take forward to your next project (or Sprint).
What Is the Sailboat Exercise?
It uses a metaphor we can all understand: a boat on a journey.
Your project is the boat.
Your goals are an island on the horizon.
The winds represent forces pushing you forward.
Anchors are what's holding you back.
And rocks in the water? Those are the risks that could sink everything.
Pretty simple right?
I first encountered it when learning about Design Sprints by Jake Knapp, John Zeratsky & Braden Kowitz, from Google. Then through one of their partners AJ & Smart who are an agency in Berlin.
Side note: The book Sprint is a must-read for project managers. Check it out.
Why It Works Well for Agencies
For several reasons:
It's inherently visual
We have a lot of visual communicators – designers, copywriters, art directors etc. This approach speaks everyone's language without resorting to loads of jargon that will have people zone out.
It balances positives and negatives
Nothing runs smoothly all the time and people make mistakes - it happens. So it’s important to put those things in the past and balance with all the good stuff that keeps the project (and people) charged up.
It encourages open discussion.
Some people struggle with honest conversations and putting across their point of view.
The techniques used in this workshop will give them the voice they deserve. Watch out for the quiet ones!
Actions are clear
I literally had a meeting last week when I came out no clearer than when I went in. With the sail boat, you’ll get clear next steps with accountability from people picking up tasks.
PM’s - you’ll love this.
How to Run Your First Sailboat Exercise
Here's the step-by-step approach, but if you don’t have time right now, or are more of a visual person, then skip to the templates at the end - bookmark this article as a reference.
Step 1: Get Set Up
Book 60 minutes with your project team.
Try it a few times, and you’ll reach your agency sweet spot when it comes to timings and the people you work with.
For supplies, you'll need:
A large whiteboard and colourful sticky notes for in-person sessions
Pens
Dot stickers (for voting)
Miro, FigJam, Mural, or another virtual whiteboard for remote teams
Draw a simple sailboat – don't worry about artistic talent here!
Having a stick-figure boat can create a bit of light-hearted comedy.
Include:
A boat (your team/project)
An island (your goals)
Wind (helping forces)
Rocks (creating risk)
Anchors (hindering forces)
Choose a specific focus.
I’m talking about projects, but it will also work for a client relationship, your team's process and even your own objectives - a boat for one!.
The more specific, the better the outcome you’ll get.
Step 2: Lead the Exercise
Start with context. I usually say something like: "We're all in this boat together, heading toward that island (I just thought of the Maldives - wouldn’t that be nice).
Today we're going to identify what moved us move forward, what held us back, and what dangers we needed to navigate around."
Begin with your destination
Ask: "What specifically are we trying to achieve?"
For example, our learning from the production of our latest campaign for X client.
Next, identify your winds
Ask: "What helped us move toward our goals?"
Give everyone 5 minutes of silent sticky note writing, then have each person share their thoughts.
You'll be surprised at the positives that emerge – this is where that quiet developer suddenly finds their voice.
Watch out for rocks
Ask: "What were the project risks that we should have identified?"
Give everyone another 5 minutes of silent sticky note writing, then have each person share their thoughts again.
Then move to anchors
Ask: "What was slowing us down or made things difficult?"
Common agency anchors include approval bottlenecks, last minute brief changes, resource constraints, client IT teams late to the project, or communication gaps.
Assemble patterns
After collecting all the inputs, facilitate a discussion about patterns.
Group similar items and have the team vote (using the dots) on which have the biggest impact on your project's success.
Step 3: Turn Insights into Action
This is where most team exercises fall flat.
Don't let your sailboat exercise become just another "nice discussion" that leads nowhere.
For your biggest winds: How can you amplify these positives? If your team identified that early client involvement improves outcomes, formalise this in your process.
For your heaviest anchors: What specific steps will remove or lighten the issues next time? If feedback delays are killing momentum, create a new client feedback template with clear turnaround expectations.
For each priority item, assign a specific owner and deadline. Then create a plan for following up.
Be realistic – it's better to address three things well than to create an overwhelming list that no one has the time to implement.
Make It Part of Your Agency's Toolkit
The sailboat exercise isn't a one-and-done solution.
Here's how you can incorporate it into your agency's workflow:
Run mini-sailboat check-ins at project milestones. A quick 15-minute version can prevent small issues from becoming project-killers. Maybe in a daily stand-up.
Use it during client onboarding to set expectations and identify potential challenges early.
Schedule quarterly team sailboat sessions to spot patterns across projects. This broader view often reveals systemic issues in your agency processes.
If your agency uses OKRs (or another objective setting technique) use it to analyse how things are progressing.
Your Next Steps
There's something powerful about having a structured approach in your back pocket when you're dealing with chaos.
Remember, as a project manager, your job isn’t just about tracking tasks and making sure the right people are in meetings.
With workshops like this, you can add a lot more value to your agency (and your projects) by solving problems and creating processes that impact the bottom line.
Ready to Try It?
Why not block time this week for your first sailboat workshop?
Choose a project that could use some fresh thinking, gather your team, and see what insights emerge.
Here are some templates that will help you get things kicked off:
Bonus next level workshop
Check out AJ&Smarts ‘Lightning Decision Jam’ workshop on Miro.
This is my favourite (includes the Sailboat) and levels things up a few notches.