Enough with the heroics

My boss keeps telling me that the great thing about startups is that everyone wants to do everything. And the worst thing about startups is that everyone tries to do everything.

I should have listened more closely. Heroic efforts are good sometimes. But you can’t base realist plans on that. If you do, it’ll bite you in the ass. That’s what happened to me.

Turning a weakness into…less of a weakness

I’ve never been great at creating plans. And that’s due to one key problem: I estimate time based on an optimistic view of my best effort. Which means that when someone asks me how long it will take to complete a task, I pull out a number based on how long it would take if I had nothing else to do, complete focus, and if the information was easy to acquire.

And if I didn’t need to eat, sleep, and could maintain 100% efficiency during months of work. Even then, the numbers I come up with are stupidly low: I tend to come up with lower numbers because I think it will make my bosses happier.

Any rational estimate is the number I come up with, doubled. Then doubled again. Sometimes even that isn’t enough.

Considering the other factors

When you’re planning a task, you can’t just estimate your own time. There are always additional factors to consider that significantly increase the amount of time, and decrease the accuracy of your prediction.

  • Who else is involved? What percentage of their time can they make available to you? And consider a worst-case scenario for that.
  • Do you have backup subject matter experts (SMEs)? Will they be available?
  • You’ve got your SMEs lined up: How quickly do they respond? Are they offsite? Is there a communication lag that you need to build in to your schedule?
  • How many other tasks do you have piled up for the same time period? How many tasks are added every week? Every day?

And that’s just off the top of my head.

Even more considerations

There are more questions that you might not need to include in your project plan, but which you need to answer for yourself:

For example, how much time can you devote to the task you’re planning for? Is this thing even feasible? Or is it time to turn this into a request for more resources (contract, fulltime, or pulled from other departments)?

How important is this task to you, your organization, and the company? Do any executives share this view, or do you need to do some internal persuasion and education?

How likely is it that this project will get pushed aside by a more important task? Or a critical, Must Be Done Now project?

These last questions come down to this: Is this project feasible? Someone needs to answer that, and be ready to explain it up and down the hierarchy.

How I screwed up

I had a lot of those answers in place, and I had a good estimate of the amount of time required (appropriately doubled and re-doubled to become realistic numbers).

But I assumed that I would be working on this project, when I had clearly stated that I wouldn’t be able to. I very clearly stated that I would need more resources for this project. The people involved accepted this.

But I still have it in my head that of course I can do this myself, given enough time and a bit of help from other people. Because I can totally do it all myself, right?

But because I didn’t get past that blind spot (and arrogance, and unwarranted faith in my ability) I didn’t include the amount of time required to hire that person and get them up to speed on the project.

That adds 6-8 weeks to the project, and that might be overly optimistic. I handed my boss a time estimate that was at least two months too low, and two months has a significant impact on the decision of how to pursue this project.

What I’m doing now

My career goal is to manage a support, training, and docs team. And then I go and completely screw up my first major proposal. I’ve been scrambling to undo this well-intentioned but stupid mistake. (Or possibly just selfish and stupid.) I’ve gone over the time estimates again and I’m working to describe the assumptions that I’m working with (more than “Assumption: I assume that everyone is thinking what I’m thinking”).

More importantly, I’ve been going over what I did wrong, picking it apart to make sure I don’t do this again.

And I hope it finally sinks in this time.


2 thoughts on “Enough with the heroics

  1. Ah. So you’re the guy at the bar, wearing a cape and telling anyone who’ll listen: “My superpower is absurd optimism when estimating projects.”

    No, wait. I think that was me.

    Since you’re taking the time to learn — really learn — from your mistake, I’d say that you’re still on course to reaching your career goal. Don’t let one failure deter you. And here’s a tip: When this project is complete, you’ll have some data on how long it really took to do the work — and you can use that as a base for preparing your next estimate.

    1. Thanks, Larry.

      This is something that I’ve been able to get away with for a while: Maybe my numbers were off, but then I just had to put in extra hours to finish the project somewhere close to the predicted schedule. We all have skill gaps, and that’s fine. The lesson to take from this is to admit when you’re out of your depth, and not let it get to the point where you’re drowning (or dragging down other people with you).

      And I worry that I should know all of these things, because everyone else seems so confident!

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