Gantt ChartEstimating and delivering a product on-time is a tricky thing. When you’re looking at a piece of work that is nebulous and will require an estimated delivery date, it’s always best to err on the side of safety and over-communicate any changes that come up. I bring this up not only because I’ve run into the wrong end of this with a couple of vendors lately, but because my record isn't entirely spotless either. It’s good to share a reminder about the potential domino effects of over-promising and under-delivering. When you tell someone that you'll have X done by a certain date, you have to fulfill that promise. If you can’t, you need to communicate the delay as soon as possible. Doing so quickly accomplishes a couple of things. First, it preserves your integrity. Even if your estimate is off, or unanticipated events cause a delay, people generally give you the benefit of the doubt if you’re honest and prompt in delivering the bad news. Just don’t make a habit of getting into delays or you'll be branded "the boy who cries estimation/wolf." Second, prompt communication aids all of the people working on dependent tasks, so they can give similar updates to the people they've made promises to. Especially if you’re just starting out, it helps to keep a personal track record. It can be a spreadsheet, a text doc or a physical piece of paper. Write down your estimate, then follow up with the actual delivery date once the project's done. Over time, you’ll be able to see how far off you typically are. You may need to start padding a little more, or shortening up.  Eventually, you’ll be fairly predictable. One parting tip: Never buy into the "herculean effort" myth and sit on delay information. If you get behind, don’t convince yourself that you can pull some long days, or work a weekend to make up, with no one being the wiser. You might be able to pull it off--but have you learned nothing about unanticipated events? What if something gets in the way so you can't put in the extra hours? Then you’re in real trouble. It’s best to let everyone depending on you know that something has come up that will result in a delay. Then if you want to kill yourself with extra hours to get it done by your original commitment, great, you’re a hero. Got any of your own tips to share with our fellow Dicers? Let's hear from you in the comments below.