One of my previous bosses had a rule: “If a project manager claims they delivered every project on time, within scope, and under budget—I won’t interview them.”
He wasn’t being cynical. He was being realistic.
In the real world, even high-performing teams struggle to deliver according to plan. Roadmaps slip. Milestones move. That QBR deck that was due last week is still “in progress.” The product launch gets pushed. Strategic initiatives lose steam midway.
Why does this keep happening - even when the teams are smart, aligned, and motivated?
It’s not a process problem. It’s not about effort.
It’s about the gap between how we think work will unfold and how it actually does - a gap rooted in how human brains evolved, and how mismatched they are to modern workflows.
Until we build systems that account for this mismatch, our best-laid plans will continue to unravel.
The planning fallacy is a universal trap - teams consistently underestimate how long tasks will take and overestimate their ability to stay on track. Whether it's a new feature rollout, a hiring push, or a strategic pivot, people default to ideal scenarios and underestimate the messiness ahead.
Why? Because of optimism bias - the belief that this time will be different. That cross-functional dependencies will align. That no one will get pulled into firefighting. That feedback will be quick. That things will go according to plan.
It’s the same psychological force that made people say during the pandemic, “I won’t catch COVID—I’m careful.” (Remember the Covidiots?)
That confidence helped us survive in earlier times - but in today’s complex, interdependent systems, it sets us up for overcommitment, resourcing gaps, and timeline slippage.
Planning offers structure. Execution rarely plays along.
On a Gantt chart, everything lines up. Dependencies are mapped. Timelines are clean. But once the work begins, it gets chaotic. Priorities compete. People shift focus. Stakeholders revise expectations. Delays compound.
Why does this feel so destabilizing?
Because our brains evolved for clarity, simplicity, and immediate feedback. Our ancestors dealt with tangible goals - hunt, build, gather, rest. Decisions were short-term, visible, and mostly under their control.
Contrast that with today’s work:
We’re running modern projects with Stone Age instincts. And that mismatch creates the friction we keep mislabeling as inefficiency.
Why do people check emails instead of preparing a client deck?
Or fix a small UI bug instead of pushing on the quarterly strategy?
Or tidy up slides rather than tackle stakeholder alignment?
Because cognitive bias favors immediate rewards
Quick wins feel good. They’re concrete, measurable, and give us the sense of momentum. Strategic work, on the other hand, is long, murky, and often thankless in the short term.
This wiring made sense when the goal was to find food or avoid predators. It doesn't help when your team is trying to launch a multi-phase product with seven interdependent deliverables and five stakeholders in different time zones.
Plans that look robust in a kickoff deck can turn into minefields during execution.
Too many subtasks. Too many interdependencies. Too many meetings. Too many tools.
When plans get too complex, people freeze. Decision-making slows. Ownership gets fuzzy. The team gets pulled toward what’s urgent or familiar — not what’s important.
Complexity without clarity leads to drift.
Execution becomes about managing chaos, not moving forward.
Planning fallacy isn’t an individual glitch - it’s an organizational pattern:
Add group dynamics like diffusion of responsibility, and things get worse. Everyone assumes someone else is tracking that critical piece. Nobody sounds the alarm until it’s too late.
Without clear visibility, ownership blurs - and blurred ownership is a breeding ground for delays.
Delays in professional settings aren’t always caused by distraction—they’re often the result of risk aversion.
People hesitate to present early-stage thinking.
They wait for data to validate intuition.
They sit on decisions to avoid pushback.
Decks get stuck in rounds of revisions — not to polish, but to shield against critique.
This isn’t about perfectionism. It’s about preserving stakeholder trust.
In tribal life, social rejection meant isolation. Today, the same fear manifests as over-refinement and slow cycles—because not getting it “right” the first time can feel reputationally risky.
We don’t need more slogans about “ownership” or “better communication.” We need systems and workflows that account for the way humans actually behave — under pressure, in teams, and with imperfect information.
Here’s how:
Modern work is dynamic. Your plans should be too.
Create structures for frequent recalibration: weekly check-ins, short planning cycles, real-time visibility. Don’t treat the initial plan as sacred—treat it as a living document.
The best plans aren’t perfect. They’re responsive.
Long review cycles, unclear next steps, and too many approvals drain momentum.
Empower teams to move faster with pre-decided boundaries:
Fewer open loops mean more forward motion.
Too much in flight? Break it down.
Instead of assigning “Prepare Q2 strategy,” say: “Draft first 3 slides for Q2 strategy deck by Friday.” The smaller and more defined the task, the easier it is to act on.
Progress isn’t about velocity—it’s about clarity.
People show up differently when they know their work is seen.
Use dashboards, asynchronous updates, or even simple Slack rituals to make momentum visible. Public wins build energy. Public blockers invite collaboration.
Private drift, on the other hand, goes unnoticed—until it’s too late.
Organizations reward thought leadership, alignment, and strategy—but don’t always reward follow-through with the same energy.
Flip that.
Celebrate teams that ship. Highlight results, not just intentions. Build a culture where completion is as valued as vision.
Even with the best systems, drift happens.
Instead of treating it like failure, normalize structured resets:
Momentum isn’t about staying on course 100% of the time. It’s about recovering early and resetting well.
Projects don’t derail because people are lazy.
They derail because most work systems ask humans to act like machines—with perfect memory, consistent motivation, and frictionless decision-making.
The solution isn’t tighter controls or more layers of process. It’s systems that are built for the way people actually operate — flawed, brilliant, distracted, ambitious humans trying to move complex work forward in an uncertain world.
Because in the end, every plan is a guess.
And execution? That’s where the real work begins.
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