People who know me know that I like to have a plan, but I’m the first one to stray from it. This may seem like a strange contradiction or worse hypocrisy, but here’s my justification: if everything goes according to plan, the best outcome is limited to your initial imagination.

I’m not willing to settle for our “initial” imagination because routinely our best ideas come mid-stream during the project. If you are doing work where creativity counts and innovation is part of the formula, you might find that giving that creativity more room to breathe in your plan makes good sense. A great way to do this is with ranged estimation. We usually talk about a ranged estimate (e.g. 5 days – 20 days) as a way to capture uncertainty but it is also a great way to give room to possibilities in your schedule as well. Once you’re willing to admit that you can’t figure it all out up front, this gets easy, just ask your team to make the ranges a bit wider for things they have lingering and nagging thoughts about. You can always narrow it when you get closer but now you’ve left a bit of room.

With all this room in the schedule, why plan? Planning keeps us from getting lost and helps us stay focused on delivering business value. In our team’s case, that value is not always what we set out to do; sometimes it’s better because we didn’t follow the plan.

Of course because LP is flexible and eats changes for breakfast, our plan was smart enough to follow us.

Without further ado…

If you build software for a living, you surely have eaten these words at least once. My last major utterance was about two years ago when I said to Jason and Bruce, “How hard can it be to build a project management tool that doesn’t suck?”.

I said it about the time we had just finished sending the top 80 people in Expedia’s technology group through estimation training at Construx. The training was based on work by Steve McConnell and later published in his book, Software Estimation: Demystifying the Black Art. If you are a software professional, this book is required reading. Go buy it now, then come back here.

What we discovered is that almost any team, from buttoned-down waterfallers to die hard Scrum fans, can improve their game significantly by doing just one thing: they need to stop using single point estimates (eg. 10 days) and start using ranged estimates (eg. 5-15 days).

Ranged estimates rock because they acknowledge and capture the uncertainty that exists in our projects. If you don’t capture uncertainty, it will lurk like a silent killer in your projects; as we like to say around here, you can’t manage what you can’t see.

This idea of estimating in ranges caught on quickly at Expedia, and you can probably guess what happened next. Teams ran to Excel, because “how hard could it be to build a task list that uses ranged estimates?” It unfolded the way building project management tools in a spreadsheet always goes - a happy start that turns into a slow agonizing death as some poor soul gets stuck trying to maintain a beast of a spreadsheet for the whole organization. You get a tool that does not scale, is hard to use, and nobody trusts. It also turns out that you need something a wee bit more powerful than Excel to do probabilistic scheduling in real time.

So, how hard can it be to build a radically new scheduling engine and drop it into a breakthrough interface that treats project management as a social application? Uhmm… pretty hard. It took us 14 months from concept to V1.

Please enjoy LiquidPlanner for free during our public beta and let us know what you think. We love feedback and if you happen to find a problem, we’d be happy to fix it in 5-10 days (give or take).

Charles.

p.s. My deepest and sincere thanks go to the LP team for making V1 happen: Adam, Asha, Barney, Bill, Brett, Bruce, Bryan, Christa, David, Jake, Krishnaveni, Liz, Marisa, Melinda, Murat, Rob, the team at Cypress Consulting, and of course my co-founder Jason.