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How to run a ‘lessons learned’ session in 5 steps

PostsProject management
Georgina Guthrie

Georgina Guthrie

December 13, 2024

They say failure paves the way to success, but that’s only true on one condition: that you learn from your mistakes. 

Reflection should be an important part of both our personal and professional lives. When we review how we behaved or performed with honesty, then true growth takes place. But it’s not all about failure — reflection should encompass successes, too. 

Armed with a clear-sighted view of how things went, you can ramp up what works and kill what doesn’t. It’s like a shortcut to performing your very best. And best of all? In the workplace, it’s actually very easy to do, thanks to some simple techniques. 

Today, we’re going to talk about lessons learned, a framework that encompasses all forms of professional reflection — whether it’s looking back over project results, fine-tuning workflows, or looking forward to your own workplace development. So let’s get into it! 

What are lessons learned in project management?

It’s all too easy to jump to the next task once you’ve finished a project. But this skips an important step: learning. Every project has successes and mistakes. Lessons learned capture this experience and turn it into useful knowledge.

For example, maybe the team found a new tool that saved time. Or maybe they faced delays because tasks weren’t planned well. Writing these things down means the team can repeat good practices and avoid problems later.

These lessons are not just for one team. They can help the whole organization. When you share your findings, you create a library of knowledge everyone can use. It’s like passing the torch to make sure no one has to “reinvent the wheel.”

TL;DR version

Lessons learned are exactly what they sound like: the insights you get once a project is done and dusted. They show what went well and what you can do better next time. 

Why are lessons learned important?

Lessons learned help teams improve. Every project has things that worked and things that didn’t. Learning from both makes future projects better.

Here’s why they matter:

  • Stop future mistakes: Mistakes happen. But repeating them is expensive. By learning from past errors, teams can fix problems before they happen again. For example, if you miss a deadline because you didn’t have freelance backup when a team member was off sick, you can boost your network of support staff the next time around. 
  • Boost success: Successes are just as valuable to study as failures. Knowing what worked well gives the team a playbook for the future. For instance, if a communication tool kept everyone on track, it should be used in the next project too.
  • Save time and money: When teams know what works, they can focus on those methods. This reduces wasted effort and avoids delays. Smarter processes mean smoother projects — and that saves money too.
  • Encourage growth: Reflecting on lessons helps team members build their skills. They learn how to handle challenges, work better together, and solve problems faster. It’s a way to grow stronger as a group.
  • Build a knowledge base: When lessons are shared, they don’t just help one team — they help the whole company. Other teams can learn from these insights, creating a culture of constant improvement.

The different types of lessons learned approaches 

Lessons learned take various shapes, depending on the team and project at hand. The one thing they all have in common, though, is the mission to reflect and improve. 

One popular method is The Five Whys. This approach digs deep into the root cause of problems by asking “Why?” five times until you reach the bottom of the issue.

For example, if the team misses a deadline, they ask, “Why did this happen?” Each answer leads to another “Why” until the core issue is clear. This method is simple but powerful, helping teams uncover deeper lessons.

The Retrospective Method is another approach that’s common in Agile projects. Teams reflect on three key questions:

  1. What went well?
  2. What didn’t go well?
  3. What can we do better next time?
    This approach is straightforward and encourages open, honest discussions.

For particularly knotty issues, teams can also use the Fishbone Diagram, also known as a cause-and-effect diagram. 

This visual tool organizes possible causes of a problem into categories like people, process, tools, or environment. It’s especially useful for spotting patterns in recurring issues.

Fishbone Diagram created in Cacoo

Created in Cacoo

Each methodology offers a unique lens to reflect on a project. Teams may choose one or combine several to suit their needs. What’s important is using a consistent approach so every lesson is clear and actionable. 

5 steps to running a lessons learned session

Capturing lessons learned is simple if you follow a clear process. Here are five steps to guide you through it.

Step 1: Plan the lessons learned process

Start early. Don’t wait until the project is over to think about lessons learned. Plan at the beginning of the project, and decide when and how you’ll gather feedback. Will you do it after each phase, or only at the end?

Create a schedule and set a time for reflection. If everyone knows this step is coming, they will be ready to share their ideas. Also, choose tools to help you, like surveys, meeting templates, or discussion boards.

Step 2: Gather input from the team

Make sure everyone has a chance to share their thoughts. You can collect feedback via surveys, group meetings, or one-on-one chats. Ask clear, simple questions to guide the discussion.

For example:

  • What worked well during this project?
  • What didn’t go as planned?
  • How can we improve next time?

Be sure to create a safe space. Team members should feel comfortable speaking honestly without fear of blame.

Step 3: Analyze the feedback

Once you have all the input, take time to review it. Look for patterns. Did several people mention the same issues or successes? Group similar feedback together to make it easier to spot key themes.

Dig deeper into the problems using tools like The Five Whys or a Fishbone Diagram. These can help uncover the root cause of issues. Remember, it’s not just about fixing what went wrong — it’s also about repeating what went right.

Step 4: Take a note of the lessons learned

Write everything down in a clear, organized way. Use simple words so anyone can understand them. Focus on making the lessons specific and actionable.

For example:

  • Vague: “Improve time management.”
  • Specific: “Use a shared calendar to track deadlines and set weekly reminders.”

Include both positive and negative lessons. Highlight your successes so the team knows what to do again, but also explain what needs fixing.

Step 5: Share and apply the lessons

Once you’ve written everything down, don’t just forget about it. Share your lessons learned with the team and others in the organization, and store it somewhere accessible. Maybe your company Wiki, or a project management tool.  

Most importantly, make sure you apply what you’ve learned. Review your lessons at the start of every project to build on what went well, and avoid repeating past mistakes. This step turns lessons into action.

A lessons learned questionnaire template you can steal

Why reinvent the wheel? Here’s a template for when you need to collect feedback from the team. Just copy, paste, and send! 

Project name:
[Enter project name here]

Your role in the project:
[Enter your role here]

Date:
[Enter date here]

Section 1: What went well?

  1. What parts of the project do you think were most successful?
    Example: “The kickoff meeting helped everyone understand their roles.”
    [Your answer]
  2. Which tools, methods, or processes worked best?
    Example: “Using Backlog for project updates kept things organized.”
    [Your answer]

Section 2: What didn’t go as planned?

  1. What challenges or problems did you face during the project?
    Example: “We often missed updates because not everyone used the task tracker feature.”
    [Your answer]
  2. Were there any risks or issues that weren’t spotted early enough? If yes, what were they?
    [Your answer]

Section 3: What could be improved?

  1. If you were doing this project again, what would you change or improve?
    Example: “I would add daily standups to track progress better.”
    [Your answer]
  2. Were there any tools, resources, or training you needed but didn’t have?
    [Your answer]

Section 4: Final thoughts

  1. What lessons did you learn personally from this project?
    [Your answer]
  2. Do you have any other feedback or suggestions for the team?
    [Your answer]

How diagramming tools can help

Diagramming tools help make complex problems clear by visually mapping out causes and solutions. And if you use a cloud-based solution like Cacoo, everyone can view and edit the doc, add comments, and share it with the wider team. 

Cacoo, our own tool, comes with a big bank of templates. Whether you’re creating a fishbone diagram or mapping out the Five Whys, the simple drag-and-drop interface makes it easy to organize data and dig deeper into issues by showing the root causes. The team can also simultaneously log in and add comments, making the process that little bit more collaborative. 

These tools not only clarify where things went wrong, but also make it easier to spot patterns and fix problems quickly. They bring much-needed clarity to project management, making lessons easier to understand and apply, so the next project is even better than the last. Reay to take Cacoo for a spin? Try it for free today! 

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