Estimate, Estimate, Estimate

So often in project management, we get an estimate for a project at the beginning of the project (when we know the least) and then never revisit the estimate during the course of the project (when we know more than we did at the beginning). Worse, we never compare our original estimate with actual results to hone our future skills.

In our practice at my organization, we estimate once a week on every project. Even for those tasks we have previously estimated, but haven't worked on yet, we estimate again. Why do we do this? There are several reasons:

1. We get better at estimating the more we do it.

2. Sometimes we now know more and that helps our estimating.

3. Sometimes we learn we didn't know as much as we thought we did, and that helps our estimating.

4. Often when a new technology is involved, early estimates have “fear” built in, and as we learn more about the new technology, the fear-based component lessens.

5. Estimating is a great “conversation” in our world, since we estimate as a group activity.

Finally, the best way to get better as estimating is to make sure you also keep track of actuals so that the team gets feedback on how well they did in estimating. My only warning: you can't use this information to punish the team! True accountability around estimating doesn't involve getting people to hit their estimate, but rather to have them warn you as soon as they think they are going to miss.

Here is a simple game you can play to drive home the power of estimating and feedback. Get three different empty jars of increasing size and fill them with jelly beans. Record how many jelly beans it takes to fill up every jar.

Get together a group you are trying teach about estimating and ask them to estimate the number of jelly beans in the smallest jar. When I teach this, I have people work in pairs.

Give them only a short time to come up with an estimate and then have them WRITE IT DOWN. Collect the estimates by having each pair read their estimates aloud. Write them down on a whiteboard or flipchart. Do the same for the second and third jars of jelly beans.

Finally, tell them that this is a good way to do estimating, thank them for their input, and ask if there are any questions before you move on. It never fails. Someone will ask how many jelly beans there actually are in each jar. THEY WANT TO KNOW! Let them dangle a while and then tell them how silly they are. After all, it's just a jar of jelly beans.

Now you have them right where you want them. Ask them how many times they've had the data to give feedback to their team on FAR MORE IMPORTANT topics and they scoffed and dismissed it as unimportant. Overlooking feedback to their teams will not happen again.