Stop asking "How long is this going to take?"

There's a much more powerful alternative to the most common question that always comes up in any kind of project meeting.

It's from the book "Shape Up: Stop Running in Circles and Ship Work that Matters" by Ryan Singer, Head of Product Strategy at Basecamp. It's been one of the most useful ideas that I've come across in the last year.

The Basecamp team have always been very open about sharing ideas about their culture and how they work. They're a refreshing antidote to pedalling the hamster wheel faster and faster hustle approach.

They're a great example of Derek Sivers' idea that "When you make a company, you make a utopia. It’s where you design your perfect world."

But back to Shape Up. If you're in a meeting talking about creating a website or developing a new product, someone is always going to ask "how long is this going to take?"

The problems with "How long is this going to take?"

We're all really bad at estimating how long something is going to take. This problem gets worse if this isn't something that you do often. Usually we don't allow enough time for fixing unexpected problems either. (Daniel Kahneman talked about this in "Thinking Fast and Slow".)
You're always going to come up with new features to add or ways to improve something. Then you end up shipping much later than you first thought or even never at all.
If you're prone to perfectionism like I was for many years it makes the problem even worse.

Projects that roll on way past their intended ship date end up being monsters that suck all the energy and enthusiasm out of everyone working on them. What started as a great idea becomes a millstone around your neck that you can't wait to get rid of.

So here's the alternative. Instead of asking "How long is this going to take?" ask "How long do we want to spend on this?"

How long do we want to spend on this?

There's a few advantages to asking the question this way:

It forces you to concentrate on the elements of the project that are going to make the most difference. (There's always going to be another feature you can add or something else to tweak but usually that can wait for the next iteration.)
At some point soon you're going to have something tangible. It reduces the risk that you ship late or don't ship anything at all.
It can help you stop or at least cut down on overcommitting, saying yes to too many things.
You're not going to work on something forever and a day without taking a step back and reviewing where you've got to. At Basecamp they work in six-week cycles so they never go any further than that without checking where they're at.

Avoiding the Sunk Cost Fallacy

Asking "how long do we want to spend on this?" is one way to mitigate the damage of the sunk cost fallacy. That's when you've invested a lot into a project so you keep going to get something back for all the time, effort and money you put it. If you've ever had a car that kept needing repairs to keep it on the road you know what I'm talking about.

You don't need to be working on a team or company-wide project to use this idea, it works just as well if you're working on your own.

The same goes for things that you know you should be working on regularly but don't like the classic "working on not in your business" stuff. How long do you want to spend on that this week?

You can use this with things outside work too. If you've got a busy week but you still want to make sure you get time to exercise you can ask "how long do I want to work out for today?" If you usually spend 30 minutes on the treadmill you might only go for 20.

My clients know that I've never been a big fan of using what I call artificial due dates as a lever. It's so easy to get overwhelmed and lose sight of the real deadlines. At the same time having projects that rumble on and on isn't helpful either.

So "how long do I want to spend on this " is a really versatile idea. If you read the Ideas blog you might know that I'm a big fan of this sort of forcing function question and this has been a great addition to my toolbox.

I'm finding it a much more useful question to ask than "how long is this going to take?" and I think you will too.