Obsession with timelines costs time and money

Anyone who has spent some time in the corporate world must have realized the obsession with timelines. Especially when dealing with multiple stakeholders, like multiple companies, every project needs step-by-step planning, and more importantly, setting a timeline for each step. Even if the task in question involves too many unknown variables, “we’ll complete this as fast as possible” is never an acceptable plan.

As far as I see, there are a couple of somewhat understandable reasons for this.

1- Large organizations need to coordinate multiple teams and stakeholders. When a project involves multiple teams, each team needs to know when they’ll be needed. Without clear timelines, teams can’t plan their resources effectively. A vague “as soon as possible” leaves everyone in limbo.

2- Corporate budgeting requires predictable timelines. Projects need to be mapped to fiscal quarters and annual budgets. Unpredictable timelines make it difficult to allocate and justify resources.

3- Performance evaluation in large organizations often depends on delivering projects “on time.” This creates a culture where meeting arbitrary deadlines becomes more important than optimal execution. Especially when some of the stakeholders don’t really understand the ins and outs of the task, they require success criteria that they can easily measure.

Let’s be honest, though. Estimating how long a task will take accurately is almost an impossible task in itself. Any project that’s complicated enough to require planning will also include many unknown variables and surprises along the way that make estimating impossible. Take Microsoft’s Windows Vista for example - it was originally planned for a 2003 release as “Longhorn”, but after numerous delays and feature cuts, it wasn’t released until 2007. The project became so complex and ambitious that even Microsoft, with all its resources and planning capabilities, couldn’t accurately predict the timeline. Or consider Berlin’s Brandenburg Airport - what was supposed to be a showcase infrastructure project planned to open in 2011 faced nearly a decade of delays due to construction issues, fire safety problems, and poor planning, finally opening in 2020 at more than triple the original budget.

This emphasis on predictable timelines naturally encourages padding estimates with buffers. Teams learn to overestimate timelines to account for unexpected delays and protect themselves from missing deadlines. A task that might take 2 weeks in optimal conditions gets estimated at 4-6 weeks to account for potential roadblocks, stakeholder reviews, and general organizational friction. While this makes timelines more predictable, it also means that projects move slower than they theoretically could. The practice becomes self-reinforcing - as buffers get built into every estimate, they become the new normal, and the cycle continues.

This obsession with timelines creates an interesting opportunity for startups or indie hackers. While large organizations optimize for predictability, startups can optimize for speed. When a startup sees an opportunity, they can pursue it immediately without waiting for the next planning cycle or getting multiple stakeholders to align their calendars.