---
title: 'Take the Outside View: A solution to the planning fallacy'
teaser: "Optimism is our kryptonite but history is our saviour. \n"
tags: planning,estimation,product management
author: Jared Turner
published_on: 2023-06-30
---

> Hofstadter's Law: It always takes longer than you expect, even when you take
  into account Hofstadter's Law.

Humans are bad at estimating. Really bad.

We are cursed with optimism and blind to points of failure. We plan assuming
nothing will go wrong, we believe that the problem is clearly understood and
the solution is well scoped.

There won't be any interruptions or distractions, no blockers or delays. Things
will flow gently down the stream, along the yellow brick road, like daisies on
a gentle breeze.

Then reality hits. Like a brick wall to the face in a nuclear winter. The
6-week dream turns to 10-12-16-24!

This is the [planning][planning] [fallacy][fallacy]: We suffer from an optimism
bias and always underestimate how long a task (or project) will take. This
occurs even when we are asked to consider _as much detail as possible_ about
the work.

## But this time I'll be realistic

[Study][study1] [after][study2] [study][study3] has shown that we are eternal
optimists when estimating our own work. So much so that when asked for
predictions based on:

- realistic "best guess" scenarios; vs
- hoped-for "best case" scenarios

we give [the same answers]!

Thankfully there is a way to temper that pesky optimism.

## Take the Outside View

Forget about trying to break down a project into tasks, hours, days and then
adding up the times. Instead, identify some roughly similar projects that
you've previously completed and use their durations. That's it.

<aside class="info">
  <p>
    Not sure how to start? Grab a list of your previous projects and start
    grouping them loosely by size (how long did they take?). Don't be afraid
    to reshuffle if things aren't fitting. Then you can apply some labels like
    <a href="https://asana.com/resources/t-shirt-sizing">T-shirt sizes</a>.
  </p>
</aside>

Previous projects use real historical data. They are unbiased by optimism and
take in the cold hard truth of delays and unknown unknowns.

> "But past projects can't know about the specifics of _this_ project! What
  about this particular complexity? We need to consider it!"

But that's precisely the point. Taking the "inside view" and trying to consider
the granular specifics of a project will never account for the unexpected.
Sadly, this is true even when we are asked to consider the worst case scenario.

## Phone a friend

The alternative to thinking of your own past projects is to ask an expert. An
outsider who isn't aware of the details of a project but has plenty of
experience to draw from will be more realistic (pessimistic!) and likely more
accurate.

## In the wild

We see the outside view applied to some common software development workflows: 

[Story point estimation]. Teams assign a level of effort (not time!) relative
to _past tasks of similar effort_. A good pointing process will periodically
review past estimations and recalibrate as needed.

Even better, Kanban advocates for measuring Cycle Time: the time it takes for
tasks to move from In Progress to Done. What's important to note is that
nowhere do you ask anyone to estimate _anything_. You simply take the
historical data which allows you to forecast a _rough_ backlog completion.

## Step outside

A bias of optimism can often be a good thing. But when planning it is our
downfall. Don't sweat the small stuff, take the outside view; then baulk at
your seemingly outrageous yet accurate estimates!

[planning]: https://en.wikipedia.org/wiki/Planning_fallacy
[fallacy]: https://www.lesswrong.com/posts/CPm5LTwHrvBJCa9h5/planning-fallacy
[study1]: https://web.archive.org/web/20130908065829/http://www.dtic.mil/dtic/tr/fulltext/u2/a047747.pdf
[study2]: https://www.researchgate.net/publication/233153892_It's_About_Time_Optimistic_Predictions_in_Work_and_Love
[study3]: https://www.researchgate.net/publication/232604065_Inside_the_Planning_Fallacy_The_Causes_and_Consequences_of_Optimistic_Time_Predictions
[the same answers]: https://www.researchgate.net/publication/12309770_People_focus_on_optimistic_scenarios_and_disregard_pessimistic_scenarios_when_predicting_task_completion_times
[Story point estimation]: https://www.atlassian.com/agile/project-management/estimation
