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27 March 2006

Ignoring your own deadlines

It's not just that I don't feel like I do a good job of estimating projects. When I'm estimating projects, I don't feel like I'm doing my job.

Every weekday around 5:30 I get a call from Laura letting me know she’s ready to go. We work across the street from each other, so we carpool. I’m her ride.

Before she gets off the phone with me she invariably asks me, “how long?”. Anybody who knows me well knows I’m terrible at estimating how long it will take me to do anything or get anywhere, or really anything to do with time or numbers or quantities at all. She knows too. That’s why she’s asking.

If I say five minutes, I’ll be ten. If I say ten minutes I’ll be twenty. And I hate being late. So instead I tell her what I’m doing, and what I need to do before I can pick her up.

I’m just finishing up this email, then I need to put my stuff in my bag, put on my coat and get the car from the lot.”

What I’m really saying is, “I have no idea. Your guess is as good as mine.”

She usually cooperates. “Ok, 10 minutes?”

Her estimate, not mine. But now I have a deadline, something to shoot for.

At this point usually one of two things happen. Either she overestimates and I get there first, or she underestimates or I get sidetracked on the way and I’m late. I’ll let you guess which one works out better for me in the long run. Either way (except on those serendipitous afternoons when we’re both turning the corner at the same time and she hops in at a stoplight), one of us usually waits a while.

This is not unlike what happens when I’m estimating a project for a client. When I get to the part about the timeline, I end up doing the same thing. I put a lot of stuff in the proposal about what I need to do, and I do everything I can to avoid being too concrete about how long it will actually take. I use ranges (2–3 weeks) or sometimes I leave the dates out altogether. And I always overestimate timelines. I hate being late.

What I’m really saying is, “I have no idea. Your guess is as good as mine.”

What usually comes out of this is one of two things. I don’t get the work because my timeline is too long, or the client magically comes back with a hard deadline. Invariably, I’ve asked them for this before. Now they tell me. They need it done by their investor meeting in 2 months, or they want to launch the new site before their old hosting contract runs out. Now I have something to shoot for.

Obviously it’s not helpful of me to be wishy-washy with clients about timelines and it doesn’t do me any good to lose work because I’m always overestimating for fear of coming in late. It’s not just that I don’t feel like I do a good job of estimating projects. When I’m estimating projects, I don’t feel like I’m doing my job.

What I’m starting to do with new projects is spend less time estimating and more time working with the client to nail down two things: budget and the final deadline. Usually these two things are fixed in the client’s mind, whether they know it yet or not. They may not have the information they need to be confident about how feasible it is, but usually they have a number in mind and some idea of when they want it done. It’s my job to give them the information they need to give me the information I need, not to throw up arbitrary hoops that I can jump through to make them feel like progress is being made.

I learned from Jim Coudal that out of schedule, features and budget, you can pick two to be fixed and the other one will have to slide. I’ve never worked on a project in my life where every feature that was requested made it into the final product, so that leaves the other two. How much is it worth to you and when do you need it done?

Once I’ve got those answers, my decisions are much clearer. If I think I can do what they want in that time for that money, I’ll take the project. If I don’t, I’ll try to talk them out of a few features to make it more manageable. If that doesn’t work, I’ll recommend they talk to somebody else.

If I’m wrong either way, it’s my fault and it’s up to me to make it up. But at least I only have one thing to be wrong about: either I get it done or I don’t.

And if I keep getting sidetracked on my way to the parking lot after work, I’m going to get really good at apologizing.


  1. 4 April 2006


    I like you a lot. :-) Your writing makes me smile, and I think it’s usually pretty spot-on :)

  2. 10 April 2006


    I once worked with a print production manager who would to say to clients….”cheap, good or fast—which 2 out of the 3 do you want?”

  3. 30 April 2006


    That’s why the only deadline for many people with their projects is “when it’s done”.