Welcome to On a Back of an Envelope – an alternative view on Project Management. Here you will find a mix of humour, commentary and project management information that will both inform and entertain.
The Highlight Report is our section of commentaries on current project management practice and projects in the news.
Hall of Fame is where we honour individuals both real and fictional who have added to our understanding of Project Management or have offered an insight into the way the project world works.
Humour contains the lighter side of project management.
OBOE – On a Back Of an Envelope our glossary of project management terms.
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Project management has its serious side — but we all need a laugh. Our Humour section collects cartoons, anecdotes, and tongue-in-cheek observations that highlight the lighter moments of project life.
The Highlight Report is where we take a closer look at what’s happening in project management today — from major programmes in the news to lessons from real-world delivery. Expect concise, opinion-led pieces that explore what worked, what didn’t, and why it matters for practitioners.
Uncertainty is not new in project management, but in today’s world, the scale and frequency of disruptions demand a different mindset. Financial crises, global pandemics, political upheavals like Brexit and Trump-era shifts, and ongoing conflicts such as the wars in Ukraine and the Middle East create volatile environments where traditional linear planning often fails. Project managers need to adapt, lead with resilience, and keep delivery moving forward in the face of unpredictability.
Why Uncertainty Matters
Projects don’t happen in a vacuum. Economic shocks affect budgets, pandemics disrupt supply chains and teams, political instability alters regulations, and wars create humanitarian and operational challenges. These uncertainties can derail even the best-laid plans — unless project leaders anticipate and adapt.
The Nature of Uncertainty
Former U.S. Defense Secretary Donald Rumsfeld famously framed uncertainty in terms of “known knowns, known unknowns, and unknown unknowns.” The first are the things we understand, the second are the gaps we can identify, and the third are the most dangerous — the surprises we cannot even anticipate. This taxonomy, when combined with Luft and Harrington’s Johari Window, resonates strongly with project management and strategic decision-making, reminding us that uncertainty is layered rather than singular.
Lessons from Recent Crises
Financial Crisis (2008): Projects stalled as funding dried up, highlighting the importance of strong business cases and flexible resourcing.
COVID-19: Remote working, disrupted supply chains, and rapid reprioritisation showed the value of digital tools and agile ways of working.
Brexit: Uncertainty around regulations, tariffs, and workforce mobility required scenario planning and stakeholder communication at scale.
Trump-era shifts: Changing trade policies and executive orders reminded project leaders to account for political volatility.
Wars in Ukraine and the Middle East: Energy prices, supply disruptions, and security concerns stress-tested global projects and highlighted the human cost of instability.
The rise of home and remote working in a post COVID world
Strategic Uncertainty
The Duke of Wellington once remarked that “the whole art of war consists in guessing what is on the other side of the hill.” His observation underscores that uncertainty is not new; it has always been central to decision-making with incomplete information. Leaders and project managers must act even without perfect visibility, making judgments under conditions of incomplete knowledge about competitors, environments, or future conditions.
The Challenge of Prediction
As the physicist Niels Bohr quipped, “Prediction is difficult, especially when it involves the future.” This paradox highlights why uncertainty cannot be eliminated — only managed. We can model scenarios, but the future resists neat forecasting. What matters is building resilience, adaptability, and awareness rather than expecting certainty.
How to Manage Projects in Uncertain Environments
Build resilience into planning: Use scenario planning and rolling-wave planning rather than rigid long-term schedules.
Strengthen risk management: Distinguish between risks you can mitigate and uncertainties you must monitor.
Prioritise communication: Sponsors, teams, and stakeholders need clarity when the environment is unstable.
Embrace agility: Iterative approaches allow adaptation as conditions evolve.
Focus on people: Psychological safety and wellbeing are critical in times of external stress.
Keep sight of purpose: A clear vision and set of objectives anchor teams when external events create noise and distraction.
Leading Through Uncertainty
In uncertain times, project managers are no longer just planners — they are navigators. Their role is to provide clarity when information is incomplete, confidence when conditions are volatile, and purpose when teams face disruption. Uncertainty is not an obstacle to be feared but a reality to be embraced. The most effective leaders turn volatility into an opportunity: they build resilient teams, adapt plans without losing sight of objectives, and guide delivery forward when the path is anything but straight.
Key Takeaways for Project Managers
Accept that uncertainty is inevitable — focus on resilience, not elimination.
Use frameworks (Rumsfeld, Johari) to map what is known and unknown.
Remember Wellington: anticipate the “other side of the hill” with scenario planning.
Every project starts with a purpose, but not every project has a vision. A vision statement is more than a sentence on a project charter — it’s the north star that aligns the team, stakeholders, and sponsors around what success truly looks like. Without one, projects risk becoming a collection of tasks rather than a mission that inspires and unites.
A strong vision statement answers three essential questions:
• What are we trying to achieve?
• Why does it matter?
• By when?
When defined well, the vision doesn’t just communicate what is to be delivered, it fuels motivation and decision-making throughout the project lifecycle. It also helps prevent scope creep: when new requests or objectives appear, the team can test them against the vision. If they don’t align, they may dilute focus rather than strengthen it.
A Classic Example: JFK’s Moonshot
A classic project vision statement came not from a corporate boardroom, but from a US President. In 1961, John F. Kennedy set out the vision for the Apollo program:
This nation should commit itself to achieving the goal, before this decade is out, of landing a man on the Moon and returning him safely to the Earth.
Why does this remain a gold standard of vision statements?
• Bold and inspiring – it captured imagination and rallied an entire nation.
• Clear and concrete – not vague aspiration, but a tangible outcome.
• Timebound – “before this decade is out” gave urgency and focus.
This single sentence aligned everyone from the humblest worker to the engineers, scientists, contractors, and leaders under one banner. Crucially, it gave decision-makers a test: does this move us closer to the goal of landing on the Moon within the decade?
That is the power of vision: it creates clarity, unity, and momentum, even when the path is uncertain.
Vision Statements vs. Project Objectives
It’s important to distinguish between vision and objectives:
• Vision Statement: A big-picture expression of what success looks like, why it matters, and the impact it will have.
• Objectives: Specific, measurable steps to get there.
For example:
• Vision: “Deliver a safe, efficient rail link that transforms regional connectivity and reduces travel time between cities.”
• Objective: “Complete track installation for Phase One by Q4 2026 within the allocated budget.”
Both are essential, but the vision provides the why that energises people beyond the task list. Objectives may flex as conditions change, but the vision endures as the guiding principle.
Why Project Sponsors and Leaders Should Care
Vision statements aren’t just for the delivery team — they’re critical for leaders and sponsors. Why?
• Decision filter – When trade-offs arise, leaders can check alignment with the vision.
• Stakeholder alignment – A strong vision makes it easier to rally support across diverse groups.
• Sustained motivation – Projects often run for years; vision keeps energy alive when milestones feel far away.
• Clarity in communication – Leaders must repeatedly tell the project’s story; the vision gives them the narrative hook.
• Guardrail against scope creep – Sponsors can push back on unfocused additions by asking, “Does this serve the vision?”
How to Craft a Strong Vision Statement
When drafting your own, aim for the following qualities:
• Inspiring – motivates people at every level.
• Concise – one or two sentences, not a paragraph.
• Concrete – avoid buzzwords; be clear on the outcome.
• Timebound – where possible, include a timeframe.
When Projects Struggle Without Vision
Common signs of a missing or weak vision include:
• Team confusion about priorities.
• Decisions made in isolation, without a clear strategic anchor.
• Stakeholders pulling in different directions.
• Deliverables produced, but lacking lasting impact.
In short: projects without vision may deliver outputs, but they rarely deliver meaningful outcomes.
Takeaway
A strong vision statement is the foundation of project success. It sets direction, aligns people, and inspires action.
As JFK’s Moonshot showed, when a vision is bold, clear, and timebound, it can galvanise entire organisations — even nations — to achieve what once seemed impossible. A strong vision not only inspires — it protects. It keeps projects pointed at meaningful outcomes and shields them from distractions along the way.
Team having a Retrospective standup in front of a Kanban board
In traditional Waterfall project management methods like PRINCE2, the “Lessons Learned” session has been the formal mechanism for capturing insights. These are usually held at stage boundaries or project closure — often too late to benefit the current project. Agile flips this model on its head. Instead of waiting until the end, teams run retrospectives at the end of every sprint. This rhythm transforms reflection from a one-off report into a continuous improvement engine.
So why do retrospectives deliver real change, when Lessons Learned often become shelfware?
Retrospectives vs. Lessons Learned
Timing
Retrospectives: Held frequently — usually every sprint (two to four weeks). Insights can be applied immediately.
Lessons Learned: Typically come at the end of a project stage or only at project closure. By then, the learning is too late, and team members may have already moved on.
Focus
Retrospectives: Practical and actionable. The team agrees on one or two concrete changes to test in the next sprint.
Lessons Learned: Often descriptive — documenting what happened rather than focusing on what to change now.
Follow-through
Retrospectives: By design, agreed actions flow straight into the backlog, making follow-up unavoidable.
Lessons Learned: Too often captured in a report that is archived, skimmed, or forgotten. Many organisations have libraries of “lessons” that were never implemented.
👉 The cautionary truth: Lessons Learned are only valuable if they drive behaviour. Retrospectives succeed because they embed action into the delivery rhythm.
Why Retrospectives Matter
Psychological safety: They provide a regular, structured forum where team members can raise issues without fear of blame.
Continuous feedback: Problems are spotted and addressed early, rather than waiting for a post-mortem.
Team ownership: Improvements are chosen by the team, not imposed from above, which drives buy-in and accountability.
Adaptability: They make teams more resilient by institutionalising reflection and adjustment — a critical trait in complex, uncertain projects.
Making Retrospectives Work
Keep them short and focused — 45–60 minutes is plenty for a two-week sprint.
Vary the format — don’t just repeat “what went well / what didn’t.” Use creative prompts such as:
Start / Stop / Continue (simple, clear actions).
Mad / Sad / Glad (focus on emotional drivers).
Sailboat (a visual metaphor):
Project = the sailboat heading for an island (the goal).
Wind in sails = forces propelling progress.
Anchors = what’s holding the team back.
Rocks = risks lurking beneath the surface.
Sun = positive factors such as morale or culture.
Keep it focused — aim for one or two concrete improvements, not a laundry list.
Review last time’s actions — close the loop so improvements stick.
Make it safe — create an environment where people can speak openly without blame. Facilitators should model openness, listen actively, and frame issues as team challenges, not personal failures.
Why Sponsors and Leaders Should Care
Fewer repeated mistakes: Problems are corrected mid-flight, not documented after the fact.
Quicker course correction: Sponsors see earlier signals of risks and blockers.
Greater predictability: Teams that continually improve reduce delays and firefighting.
Higher morale: A team that feels heard and empowered is more engaged and productive.
In short, retrospectives improve delivery outcomes and reduce escalation headaches for leadership.
When Retrospectives Don’t Add Value
Too infrequent — they lose impact if held rarely or only when things go wrong.
Unstructured — without a clear facilitator or format, they risk becoming a venting session.
No follow-up — if actions don’t translate into visible change, teams disengage quickly.
Retrospectives as Modern Lessons Learned
For organisations steeped in PRINCE2, the retrospective can be seen as an evolution of Lessons Learned: same intent (capture and apply insight), but with a faster rhythm, tighter feedback loop, and stronger emphasis on implementation.
Where Lessons Learned risk becoming static documents, retrospectives are dynamic and cumulative — each one builds on the last, creating a living culture of continuous improvement.
Takeaway
Retrospectives aren’t just a “nice to have.” They’re a discipline that ensures every sprint contributes not only to the product, but to the team itself. While traditional Lessons Learned remind us to reflect, retrospectives remind us to act.
For project managers moving between Waterfall and Agile contexts, the principle is the same: learning without implementation is wasted. Retrospectives make sure the learning sticks.
