Project Toolkit

Lessons Learned

Lessons Learned

Lessons Learned

Capturing and applying lessons from project experience.

Lessons Learned

Lessons learned capture project experience to improve future performance.

Purpose

Lessons learned ensure:

  • Knowledge is captured before it’s lost
  • Mistakes aren’t repeated
  • Good practices are shared
  • Continuous improvement occurs
  • Organisational capability grows

When to Capture Lessons

Timing Purpose
Stage end Review before moving on
Project end Comprehensive review
After issues Learn from problems
After successes Understand what worked
Continuously Capture insights as they occur

Lesson Categories

Category Focus Areas
Planning Estimation, scheduling, scoping
Execution Delivery, quality, testing
People Team, stakeholders, communication
Process Methods, tools, governance
Technical Architecture, design, technology
Vendor Suppliers, contracts, relationships

Lessons Learned Process

flowchart LR A[Identify] --> B[Analyse] B --> C[Document] C --> D[Share] D --> E[Apply] classDef blue fill:#108BB9,stroke:none,color:#fff class A,B,C,D,E blue
Step Activities
Identify Gather experiences from team
Analyse Understand root causes
Document Record in structured format
Share Communicate to stakeholders
Apply Implement improvements

Facilitation Techniques

Appreciative Inquiry

Focus on what went well:

  • Discover - What worked?
  • Dream - What could be?
  • Design - What should be?
  • Deliver - How do we implement?

Start/Stop/Continue

  • Start - What should we begin doing?
  • Stop - What should we stop doing?
  • Continue - What should we keep doing?

Timeline Review

Walk through the project chronologically, identifying key moments and lessons at each stage.

Mad/Sad/Glad

Emotional reflection on the project:

  • Mad - What frustrated you?
  • Sad - What disappointed you?
  • Glad - What made you happy?

4Ls Retrospective

  • Liked - What did you enjoy?
  • Learned - What did you learn?
  • Lacked - What was missing?
  • Longed for - What did you wish for?

Sailboat Retrospective

flowchart TD A[Wind
What helped us?] --> B[Boat
The Project] C[Anchor
What slowed us?] --> B D[Rocks
What risks?] --> B B --> E[Island
Our Goals] classDef blue fill:#108BB9,stroke:none,color:#fff class A,B,C,D,E blue
Element Question
Wind What pushed us forward?
Anchor What held us back?
Rocks What risks did we navigate?
Island Did we reach our destination?

Five Whys

Drill down to root causes:

  1. Why did this happen? → Answer 1
  2. Why did that happen? → Answer 2
  3. Why? → Answer 3
  4. Why? → Answer 4
  5. Why? → Root cause identified

Workshop Facilitation Guide

Workshop Planning

Element Consideration
Timing 2-4 hours depending on project size
Location Neutral, comfortable space
Attendees All team members, key stakeholders
Facilitation Neutral party, not the PM
Materials Sticky notes, markers, flip charts
Pre-work Optional survey to gather initial thoughts

Choosing the Right Facilitator

Option Pros Cons
External facilitator Neutral, experienced Cost, availability
PMO colleague Knows methodology May lack independence
Peer PM Understands context May be too close
Team lead Knows details May inhibit openness
Best Practice: The Project Manager should not facilitate their own lessons learned session. They should participate as a contributor, allowing others to share openly.

Sample Workshop Agenda

2-Hour Session (Small/Medium Projects)

Time Activity Duration
0:00 Welcome and ground rules 10 min
0:10 Project timeline overview 10 min
0:20 Individual reflection (silent) 10 min
0:30 What went well? (group discussion) 25 min
0:55 Break 5 min
1:00 What could be improved? (group) 25 min
1:25 Prioritise lessons 15 min
1:40 Action planning 15 min
1:55 Close and next steps 5 min

4-Hour Session (Large/Complex Projects)

Time Activity Duration
0:00 Welcome, introductions, ground rules 15 min
0:15 Project timeline walkthrough 20 min
0:35 Individual reflection and note-taking 15 min
0:50 Phase 1 review (small groups) 30 min
1:20 Phase 2 review (small groups) 30 min
1:50 Break 15 min
2:05 What went well? (plenary) 30 min
2:35 What could be improved? (plenary) 30 min
3:05 Break 10 min
3:15 Root cause analysis (selected items) 20 min
3:35 Prioritise and vote 15 min
3:50 Action planning and owners 20 min
4:10 Summary and close 10 min

Setting Ground Rules

Establish these at the start of every session:

Rule Purpose
Vegas rule What’s said here stays here
No blame Focus on improvement, not fault
All perspectives valid Everyone’s experience matters
One voice No interrupting, let people finish
Phones away Full attention on discussion
Specific examples Concrete, not vague generalisations
Action focus Turn insights into improvements

Facilitator Script

Opening:

“Thank you for joining this lessons learned session. Our goal is to capture what we’ve learned from [Project Name] so we can improve future projects. This is not about blame or finding fault - it’s about honest reflection and continuous improvement. What’s shared here stays within this group unless we agree to share it more widely.”

Transition to challenges:

“We’ve had a great discussion about what went well. Now let’s shift to areas for improvement. Remember, this isn’t about criticising individuals - it’s about identifying how we can do better as an organisation. What would you do differently if starting this project again?”

Closing:

“Thank you for your honest contributions today. We’ve identified [X] key lessons and [Y] actions. [Name] will circulate the lessons report within [timeframe]. These insights will be added to our knowledge base and shared with [relevant teams].”

Facilitation Question Prompts

Planning Phase

Category Questions
Scope Was the scope clear from the start? What would have helped?
Estimation Were estimates accurate? What was underestimated?
Requirements Were requirements well defined? What was missing?
Planning Was the plan realistic? What constraints weren’t considered?
Resources Did we have the right skills? Was capacity adequate?

Execution Phase

Category Questions
Delivery What enabled delivery? What blocked progress?
Quality Did we meet quality standards? What affected quality?
Testing Was testing adequate? What would you change?
Change How did we handle changes? Was change control effective?
Dependencies How did we manage external dependencies?

People & Communication

Category Questions
Team How did the team work together? What would improve collaboration?
Stakeholders Were stakeholders effectively engaged? What would you change?
Communication Was communication effective? What fell through cracks?
Decision-making Were decisions made quickly enough? By the right people?
Support Did you have the support you needed? What was missing?

Process & Tools

Category Questions
Methodology Did the approach work? What would you change?
Tools Were the tools fit for purpose? What would help?
Governance Was governance appropriate? Too much? Too little?
Reporting Were reports useful? What was missing?
Documentation Was documentation adequate? What would help?

Handling Difficult Situations

Situation Response
Blame game Redirect: “Let’s focus on what we can change for next time”
One person dominates “Thank you. Let’s hear from others. [Name], what’s your perspective?”
Nobody talks Use round-robin: “Let’s go around the room. [Name], start us off”
Gets too detailed “Let’s capture that specific example and continue with broader themes”
Becomes emotional Acknowledge: “This clearly matters. Let’s take a brief pause”
Conflict emerges “Both perspectives are valid. Let’s note both and move on”
Strays off topic “Interesting point. Let’s park that and stay focused on our lessons”

Managing Sensitive Topics

flowchart TD A[Sensitive Topic
Raised] --> B{Relevant to
Improvement?} B -->|Yes| C[Acknowledge &
Capture Neutrally] B -->|No| D[Park for
Separate Discussion] C --> E[Focus on
Action] D --> F[Follow Up
Offline] classDef blue fill:#108BB9,stroke:none,color:#fff class A,B,C,D,E,F blue

Tips for sensitive discussions:

  • Don’t dismiss genuine concerns
  • Avoid naming individuals in documented lessons
  • Focus on systemic issues, not personal failures
  • Offer to discuss privately if needed
  • Ensure psychological safety

Virtual Facilitation

Running lessons learned sessions remotely:

Tools and Setup

Tool Purpose
Video conferencing Primary discussion (Zoom, Teams, Meet)
Digital whiteboard Collaborative capture (Miro, Mural, Jamboard)
Polling Anonymous input, prioritisation (Mentimeter, Slido)
Document Real-time notes (shared Google Doc, OneNote)

Virtual Session Adaptations

In-Person Virtual Equivalent
Sticky notes on wall Virtual sticky notes
Dot voting Poll or reaction buttons
Breakout discussions Breakout rooms
Reading body language Camera-on policy, check-ins
Energy management Shorter sessions, more breaks

Virtual Facilitation Tips

  • Shorter sessions - 90 minutes max, then break
  • Camera on - Encourage visibility for engagement
  • Active facilitation - Call on people by name
  • Use chat - Alternative for quieter participants
  • Anonymous input - Polls for sensitive topics
  • Record with consent - For those who can’t attend
  • Clear instructions - Step-by-step for tools

Pre-Workshop Survey

Gather input before the session to maximise workshop time:

Sample Survey Questions

1. What were the project's biggest successes?
   [Open text]

2. What were the main challenges you faced?
   [Open text]

3. If you could change one thing, what would it be?
   [Open text]

4. Rate the following (1-5):
   - Clarity of requirements
   - Effectiveness of communication
   - Quality of planning
   - Team collaboration
   - Stakeholder engagement
   - Adequacy of resources

5. What topic should we prioritise in the workshop?
   [Open text]

Lesson Template

For each lesson captured:

Field Content
Title Brief description
Category Type of lesson
Context What was the situation?
Event What happened?
Impact What was the effect?
Root cause Why did it happen?
Recommendation What should be done differently?
Owner Who will action this?

Common Lessons Topics

Area Common Lessons
Estimation Tasks took longer than expected
Requirements Scope wasn’t clear enough
Stakeholders Engagement should have started earlier
Testing More time needed for UAT
Communication Status updates could be clearer
Risk Risks weren’t escalated soon enough

Making Lessons Stick

Lessons are only valuable if they’re applied:

Action How
Embed in templates Update standard documents
Update processes Revise procedures
Training Include in onboarding
Checklists Add to quality gates
Knowledge base Store in searchable repository

Sample Lessons

Well-Written Lesson Example

LESSON: Requirements sign-off process

Category: Planning

Context: The project had multiple stakeholder groups
with different requirements priorities.

Event: Requirements were gathered but not formally
signed off before development began. Two weeks into
development, a key stakeholder raised significant
changes.

Impact: 3-week delay and £15,000 rework costs.
Team frustration and credibility impact.

Root Cause: No formal sign-off gate existed.
Assumed verbal agreement was sufficient.

Recommendation: Implement mandatory requirements
sign-off gate with documented approval from all
stakeholder groups before development commences.
Use a RACI matrix to define approval authorities.

Owner: PMO to update project template
Due Date: End of month

Poorly-Written Lesson (Anti-Pattern)

BAD: "Communication could have been better"

Why it's poor:
- Too vague - what aspect of communication?
- No context or specific example
- No root cause analysis
- No actionable recommendation
- No owner assigned

BETTER: "Daily stand-ups missed key stakeholders.
Add business representative to daily stand-ups
for projects with significant business change."

Common Anti-Patterns

Process Anti-Patterns

Anti-Pattern Problem Solution
Skipping lessons learned “No time” - miss learning opportunity Schedule in project plan from day 1
Only at project end Wait too long, details forgotten Conduct at each stage/milestone
Only capturing negatives Demoralising, miss what works Balance positives and improvements
PM facilitates own session Team won’t share openly Use neutral facilitator
No pre-work Workshop time wasted on recall Send survey beforehand

Documentation Anti-Patterns

Anti-Pattern Problem Solution
Naming individuals Blame culture, legal risk Focus on process, not people
Vague lessons Can’t be acted upon Require specific examples
No root cause Treats symptoms Use Five Whys technique
No owner/action Nothing changes Assign accountability
Filed and forgotten No improvement happens Active follow-up process

Facilitation Anti-Patterns

Anti-Pattern Problem Solution
Senior person dominates Others won’t contradict Anonymous input, silent brainstorm first
Jumping to solutions Premature closure Separate identify → analyse → solve
Too ambitious Try to fix everything Prioritise top 5 lessons
No psychological safety Surface issues only Establish ground rules, model vulnerability
All talk, no action Cynicism for next time Assign owners, track to completion

Lessons Follow-Up

Capturing lessons is only half the job. Follow-up ensures they’re applied.

Follow-Up Process

flowchart LR A[Document
Lessons] --> B[Assign
Owners] B --> C[Track
Actions] C --> D[Embed in
Standards] D --> E[Verify
Application] classDef blue fill:#108BB9,stroke:none,color:#fff class A,B,C,D,E blue

Action Tracking Table

Lesson Action Owner Due Date Status
Requirements sign-off needed Add gate to template PMO 31 Jan In Progress
Testing time underestimated Update estimation guide QA Lead 15 Feb Not Started
Stakeholder mapping valuable Include in initiation checklist PM 1 Feb Complete

Embedding in the Organisation

Embed In How
Templates Update standard documents with new sections
Checklists Add items to quality gates
Training Include in PM onboarding
Knowledge base Add to searchable repository
Stage gates Include review questions
Estimation Update effort guidelines

Lessons Learned Checklist

  • Workshop scheduled?
  • All team members invited?
  • Facilitation approach chosen?
  • Documentation template ready?
  • Lessons captured and categorised?
  • Recommendations identified?
  • Owners assigned?
  • Report distributed?
  • Actions tracked?
Last updated: 13 January 2026
Themes

Knowledge Management

Governance