The power of continuous reestimation

Not long ago a software developer I work with suggested that building software could not, and so should not, be managed to a delivery date. “You can’t know everything you’re going to encounter while you build it,” he said, “and so it just takes the time it takes to get it done.”

I said that I agreed: you don’t know what you don’t know, and the work takes the time it takes. But I couldn’t agree that projects should be open-ended, finishing when they finish.

Capitalism interferes. Pesky, pesky capitalism. Most of us make software that achieves some corporate goal about making piles of money. Because the company has plans for that money, it needs to know when it will start rolling in. The money can’t start rolling in until you ship.

Or maybe you’re making a prototype that will be demoed at a trade show in hopes of attracting investors, or you’re fixing a batch of bugs that have angered a key customer who is threatening to walk, or you have to deliver some fixes to comply with some new regulation that’s about to go into effect. Point is, your company has good reasons to ask when you’ll ship.

So you need to set expectations about the size and duration of your work. But fortunately, these guesses don’t have to lock you in and enslave you to your keyboard. That’s because every day you can check your progress, adjust for the things you’ve learned, and see if you need to set new expectations.

You’re driving to a destination

Getting your work done is a lot like taking a road trip. I love road trips! You never know what you’re going to encounter. Road construction, bad weather, mechanical failure, and even fun roadside attractions can all slow you down. You have to steer your way through all of these things.

The road to MadisonWhen you’re on the road, it’s pretty easy to know at any time about when you’ll get where you’re going. It involves answering these three questions:

  • How will you know when you get where you’re going? On the road, you just recognize your destination. But I’m going to fit this metaphor to your work, where it isn’t always as clear what it means to arrive.
  • How far do you have left to go? Watch the signs; they’ll tell you.
  • How fast are you going? Just check your speedometer.

Every time you see a sign, divide the number of miles to go by your average speed, and you have the best case for how long it will take to arrive. You can’t control what might go wrong on the road ahead, of course. But after something on the road does slow you down, you can just recalculate and get a new arrival time.

You can manage your own work in much the same way. But it means you have to build some skill at estimating.

“Uh, two weeks”

Here’s how not to estimate. My first post-college job was as a technical writer in a software company. My first assignment was to convert a thick product manual from an old publishing platform to a new one. It was hardly a mission-critical project, but I was green.

When the boss asked when I’d be done, I had no idea, so I shrugged and said, “Uh, two weeks.” Then the task turned out to be enormous and tedious. I had to put in a ton of extra time to finish in two weeks.

When my boss asked “how long” on my next assignment, I guessed a number – and then doubled it to account for the unknown. Success! I worked no extra time and finished my project before the deadline.

Except that I hadn’t learned anything of value. My “guess” estimating technique became “guess and pad like crazy.” And I still had the problem that if I didn’t pad enough, my only recourse was to work tons of extra hours. I had no way of knowing on any given day whether I was on track to finish when I said I would. I just had to work hard and hope.

It’s okay that you don’t know what you don’t know

If I could tell my 21-year-old self something, it would be this: Ask the boss if you can get back to him in two days. Then use your two days to do this:

  • Think about what done looks like. What must you do to finish the work? How will you know when you’ve gotten through it all? In this case, I had about the easiest possible situation: “Done” meant running out of pages to convert. You may have a number of requirements to code, or a batch of test charters to execute, or a set of stories to complete – there are any number of ways to chunk the work.
  • Do some of the work. Pay attention to how many chunks you complete in your two days. Then note how many chunks you have left. There’s your speedometer and your miles-to-go sign. Divide to get your rate: chunks per hour or chunks per day.
  • Calculate how long the rest of the work will take. Divide your rate into the number of remaining chunks. Lay that number out on a calendar to find your finish date. Tell that to the boss.

And then as you work, recalculate every day based on how much you got done that day. If you need to put in a few extra hours to stay on track, just do it. But when the amount of extra effort needed to stay on track starts to edge toward heroic, it’s time to negotiate.

That’s right, negotiate. You are the master of your own work, after all; nobody knows the reality of it better than you. Your estimate is what you believe it takes to reach Done, and you need to stand up for it. This is true, by the way, even when your boss has given you a due date.

So go to the boss and ask which is more important: the due date or this body of work? In other words, can you change what it means to be done, removing enough work to hit the date? Or can you move the date out to get all the work done? Or can you do a little of both?

Sometimes the answer to this question doesn’t go far enough to make the remaining work match the due date. So ask yourself if you can give some of the work to someone else, enough to hit the due date. If so, ask for people to help you.

What you’re doing is giving the boss and all of your project’s stakeholders as much runway as possible to understand the probability that you’ll deliver the originally defined Done on time. Should that probability drop, your negotiations give them the opportunity to change course, change expectations, or both.

Sometimes, you’ll get no answers to all of these questions. Sometimes, you’ll get yes answers to some or all of them and it still won’t be enough. But asking these questions is your best chance of avoiding working heroic hours.

An estimate should not be a commitment

If no is always the answer, or your bosses just expect you to rise heroically to every occasion, or your initial estimate is interpreted as a contract or an iron-clad promise, you just might be an in environment with dysfunctional beliefs about accountability. Consider finding another place to work.

Your estimate is only your best (and, hopefully, educated) view into when you will finish. It assumes that you don’t know what you don’t know. When you learn more, your estimate is obviously going to change. You’re better off working someplace that has at least an elementary understanding of this.

And now you understand it. Estimate based on what you do know. Go ahead and pad a little (a little!) for the unknown.

But then steer your work to successful completion.

I thank my brother, Rick Grey, who tests software for his supper, for contributing several key concepts to this post.

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2 thoughts on “The power of continuous reestimation

  1. Words to live by! Those are some excellent ideas. I would add a few ideas from different perspectives:

    1. Communicate, communicate, communicate. Especially if there’s deadline pressure and there are inevitable problems, keep the boss and all other stakeholders informed.

    2. Know your own blind spots. If you ask me how long something will take, I know exactly how my subconscious mind calculates the answer: “Let’s see. If everything I need is available, and there are no unexpected problems, and I’m at my best every day, and no other projects demand an unexpected amount of my time, then this task will require X days / hours.” Those conditions are rarely met, but that’s still my default calculation. As long as I’m aware of that, I can remind myself to double the default answer and then add a fudge factor, which gives me an answer that’s reasonably safe.

    3. When possible, under-promise and over-deliver.

    4. As Voltaire said, “the perfect is the enemy of the good.” You can spend 20 percent of your time getting a project to 95 percent perfect, and then spend 80 percent of your time struggling to get it to 100 percent, most likely ending up around 97 percent. There’s good, there’s perfect, and there’s good enough. In real life, “good enough” is what we want instead of the unattainable “perfect.”

    5. “Good enough” is defined primarily by what the customer needs, with honorable mention going to what the customer wants, what the customer likes, and what the customer has been promised. Everything else is dispensable.

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