Have you ever felt like your team was spinning their wheels, unable to move forward on an important project? I once worked with a product development team that had spent three months going in circles on the same problems. Meetings were frustrating, morale was dropping, and they'd lost sight of their original goals. The team was completely stuck.
In contrast, I later observed a design agency facing similar roadblocks. Instead of continuing to push against the same barriers, they paused and ran a structured workshop using specific tactics designed to identify obstacles and generate solutions. Within a single afternoon, they'd regained clarity on their goals, pinpointed the root causes of their issues, and developed an actionable plan to move forward.
The difference between these teams wasn't talent or resources—it was their approach to getting unstuck. In this guide, I'll share three powerful workshop tactics from Workshop Tactics by Pip Decks that will help you and your team break through barriers and regain momentum.
ℹ️ Watch a live recorded demo of how to do the Get Unstuck recipe with Workshop Tactics.
What We'll Cover in This Guide:
- Understanding your goals with Sailboat
- Getting to the root cause with Five Whys
- Finding solutions to problems with Reverse Brainstorm
Let's explore these tactics with a real example: Pip's Engineering Firm, which needs to address team demotivation by identifying issues and developing a plan to improve morale.
1. Understanding Your Goals with Sailboat
Before you can solve a problem, you need to clearly understand what you're trying to achieve and what's holding you back. That's exactly what the Sailboat tactic helps you do.
👥 Who is needed? Yourself and your team (optional: just you)
⏱️ How long is needed? 1 hour
🧠 What's the goal? Get the team's imagination flowing and set an aspirational vision to work towards.
👀 Why this matters: This tactic helps you find out what your goals really are, the reasons behind them, and what's stopping you from achieving them. It brings together teams and stakeholders to gain a shared understanding of their goals, drivers and barriers. You can discover what is slowing you down, or if the purpose or goals themselves aren't quite right.
💡 Tip: Make sure to talk about what a S.M.A.R.T. goal is: Specific, Measurable, Achievable, Relevant, and Time-Bound.
How to Use Sailboat:
- Since this is the start of your overall workshop, begin with an icebreaker to warm everyone up.
- Draw a boat to represent the team/project and an anchor to represent the barriers. (3 minutes)
- Draw an island to represent the goal. Ask each participant to write down the team/project goals on sticky notes. (7 minutes)
- Share and Theme Sort them near the island. (10 minutes)
- Ask the group to write down the drivers towards the goal on sticky notes. (5 minutes)
- Share and Theme Sort them near the sailboat. (10 minutes)
- Write down the barriers (problems) to achieving the goals on sticky notes. (5 minutes)
- Share and Theme Sort them near the anchor. (10 minutes)
- Secret Vote the goals to find out what the group believes are the most important goals. (5 minutes)
- Finally, Secret Vote the barriers to understand what the most important problem to solve is. (5 minutes)
Example from Pip's Engineering Firm:
Pip's Engineering Firm used the Sailboat tactic to identify their goals (increased team collaboration, delivering projects on time, maintaining technical excellence) and the barriers holding them back (siloed communication, lack of shared understanding about priorities, outdated technology). After voting, they discovered that the most important barrier to address was the lack of shared understanding about priorities.
2. Getting to the Root Cause with Five Whys
Once you've identified your main barrier, you need to understand why it exists. The Five Whys tactic is a simple but powerful tool for digging deeper and uncovering the root cause of a problem.
👥 Who is needed? Yourself and your team (optional: just you)
⏱️ How long is needed? 30 minutes – 1 hour
🧠 What's the goal? Find out what is driving your team, and what may stop you achieving your vision.
👀 Why this matters: This tactic helps you get to the root cause of a problem affecting your project. It channels your inner inquisitive toddler and asks "why?" five times to get to the heart of the issue. By identifying the root cause, you don't waste time solving superficial problems.
💡 Tip: Use your barriers from the previous step with Sailboat.
How to Use Five Whys:
- Invite key stakeholders to the workshop (use Stakeholder Map beforehand to help you invite the right people).
- Select a meeting leader to lead the discussion. (decide before the meeting)
- For each barrier in turn, ask "why?" five times. Include the previous answer in the question to keep a narrow focus on the problem. (20 minutes)
- Use Who, What, When to assign responsibility for putting solutions into action. (10 minutes)
Example from Pip's Engineering Firm:
The team started with their main barrier: "We don't have a shared understanding of priorities."
- Why #1: Why don't we have a shared understanding of priorities? "Because different teams have different priority lists."
- Why #2: Why do different teams have different priority lists? "Because each department manager creates their own list without consulting others."
- Why #3: Why does each manager create their own list without consulting others? "Because we don't have a structured process for setting company-wide priorities."
- Why #4: Why don't we have a structured process for setting company-wide priorities? "Because we've grown quickly and never established one."
- Why #5: Why have we never established one despite growing quickly? "Because we've been too focused on delivering projects to pause and set up proper internal processes."
Root cause identified: The team lacks internal processes because they've prioritised immediate delivery over organisational health.
3. Finding Solutions with Reverse Brainstorm
Now that you understand the root cause of your problem, it's time to generate solutions. Reverse Brainstorm is a creative technique that approaches problem-solving from an unexpected angle to generate fresh ideas.
👥 Who is needed? Yourself and your team (optional: just you)
⏱️ How long is needed? 45 minutes
🧠 What's the goal? Understand what skills each team member has so you can work better together.
👀 Why this matters: This tactic allows you to come up with solutions to the worst, most despicable things that could derail your project. This exercise leads to absurd suggestions, which can give you ground-breaking solutions when reversed.
💡 Tip: Try asking people for things that would get you all fired if you really want their most despicable ideas.
How to Use Reverse Brainstorm:
- Identify and write down your problem (this can be a "How Might We…" question) on a large surface so it's clear for everyone to see. (3 minutes)
- Reverse the problem. (2 minutes)
- Run Idea Eight to generate ideas for the anti-problem. (20 minutes)
- After sharing the ideas, collect them and randomly distribute the anti-ideas back amongst the group. (2 minutes)
- Ask the group to reverse the ideas they've been given. These will now become real solutions for the actual problem. (5 minutes)
- Do it again to gather even more ideas. (15 minutes)
Example from Pip's Engineering Firm:
Starting with their problem: "How might we create a structured process for setting company-wide priorities?"
The team reversed it to: "How might we ensure we NEVER have a structured process for setting priorities?"
Some of their anti-ideas included:
- Never document any decisions
- Change priorities daily without telling anyone
- Intentionally give contradicting priorities to different teams
- Have all managers set priorities secretly
When reversed, these became potential solutions:
- Document all priority decisions in a central location
- Set a regular cadence for reviewing priorities (monthly or quarterly)
- Create a unified priority list visible to all teams
- Hold regular cross-functional priority-setting meetings with all managers
What if We Don't Have Time for All This?
Some teams resist structured workshops, believing they take too much time. But consider this: the average stalled project wastes 3-4 weeks of team time in frustration and false starts. A well-facilitated "Getting Unstuck" workshop using these tactics takes just 2-3 hours.
Think of it as an investment. You're spending a few hours to potentially save weeks of lost productivity. Teams that skip these exercises often find themselves still stuck months later, having wasted far more time than the workshop would have taken.
As one team leader told me: "I used to think we didn't have time for workshops. Now I realise we don't have time NOT to use them when we're stuck."
Ways to Use These Tactics
- Over multiple days: three to five short sessions.
- On one day: two two-hour sessions with a longer break in the middle.
What You Need Before You Start
In person
- Preparation (book room, invite people, write and share agenda)
- Materials (whiteboard, sticky notes, pens)
- Tech check (charger, adapter, screen projector)
- Room setup (refreshments, temperature, chairs, wall space)
Hybrid
- Preparation (book room, send call link, invite people, write and share agenda)
- Materials (whiteboard, sticky notes, pens, Miro board)
- Tech check (charger, adapter, screen projector)
- Room setup (refreshments, temperature, chairs, wall space)
Online
- Preparation (invite people, write and share agenda, create and send call invite)
- Materials (Miro board)
- Tech check (charger, adapter, microphone/headphones)
Real-World Success: From Deadlock to Breakthrough
A marketing agency I consulted with had been stuck for weeks on a major rebranding project. The client kept changing direction, internal teams had conflicting visions, and deadlines were being missed. Frustration was high, and they were considering abandoning the project.
We ran a half-day workshop using these three tactics. The Sailboat exercise revealed that different team members had drastically different understandings of the project goals. Five Whys uncovered that the root cause was poor initial client briefing. And Reverse Brainstorm generated several practical solutions for getting back on track.
The most remarkable result wasn't just that they salvaged the project—they actually delivered it ahead of the revised schedule. As their creative director said, "We wasted weeks going in circles before the workshop. If we'd done this at the first sign of trouble, we would have saved ourselves so much pain."
Common Mistakes to Avoid
Even with these powerful tactics, there are pitfalls to watch for:
- Rushing through the exercises: Give each tactic the time it deserves. Hurrying through them will likely result in superficial insights.
- Avoiding uncomfortable truths: Teams often avoid discussing the real issues. Create a psychologically safe environment where honesty is encouraged.
- Failing to follow through: These tactics generate insights and solutions, but they're useless without action. Assign clear ownership and deadlines for next steps.
- Inviting the wrong people: Ensure you have the right stakeholders in the room who can speak to the problems and implement solutions.
Putting It All Together
These three workshop tactics from Pip Decks' Workshop Tactics form a powerful sequence for getting unstuck:
- Sailboat helps you understand your goals and the barriers in your way
- Five Whys uncovers the root causes of those barriers
- Reverse Brainstorm generates creative solutions to overcome them
Together, they transform confusion into clarity and inaction into momentum. They replace frustrated discussions with structured conversations. And most importantly, they help your team get unstuck and moving forward again.
Remember the team I mentioned at the beginning? The one that had spent three months going in circles? They eventually used these tactics and discovered that their main barrier was a fundamental misunderstanding about the project's constraints. Once they clarified this, they completed the project in just six weeks.
Your team deserves the same clarity and momentum. Whether you're stuck on a design challenge, a business strategy, or team dynamics, these tactics will help you break through and move forward with confidence.
Ready to Get Your Team Unstuck?
Start implementing these tactics in your next stuck situation and experience the difference they make in your team's ability to overcome barriers and regain momentum.
These three Workshop Tactics are just a small sample of the powerful facilitation tools available in the full Workshop Tactics deck by Pip Decks. With 54 carefully designed workshop recipe cards, you'll confidently lead teams through any collaborative challenge.
Workshop Tactics helps you:
- Run effective workshops that produce real outcomes
- Put an end to pointless, unproductive meetings
- Give your team clarity on complex problems
- Uncover hidden skills within your organisation
- Generate truly innovative, out-of-the-box ideas
As one workshop participant put it: "We accomplished more in a three-hour workshop than we had in three weeks of regular meetings."
Based on the Get Unstuck recipe from Workshop Tactics
"I designed this recipe to help teams break through barriers and regain momentum when they feel stuck."
– Charles Burdett, Founder of Pip Decks
One of the few newsletters I look forward to.
— Dave Cunningham, Head of DesignOps @ NHS
