Breaking Down a Project: How Much Detail?

The Undocumented Features blog is exactly right that we should be aiming at a detail of tasks that are around 1 day in duration when beginning development. But there is a cost associated with having a person crank out those estimates. Often a project will need to “get the go-ahead” from the project sponsor before you can spend development team resources doing detailed estimates.

Those high level estimates are what often are so wrong. I think that one of the biggest reasons is that as project team members we’re giving estimates like “2 weeks”. “2 weeks” isn’t really an estimate, it’s a guess, a prediction.

An estimate is something like “1-4 weeks” or “3-5 days”. It really should be a range. One big downside of single-point guesses is that the guess is likely to be treated like a promise. On the other hand, giving a ranged estimate opens the discussion of what could happen (risks) that would push the effort towards the worst case end of the estimate or bring it in towards the best case end.

One of the primary problems is that project managers need a single number to plug into MS Project (or any number of similar tools). That coupled with the observation that these single-point guesses (especially at the high-level) are treated as promises pretty much make a person want to give up on high-level estimation altogether.

If you always give all of your estimates in ranges (e.g. 4-6 person weeks, 1-3 days, 6-9 staff months, etc) it is quite clear that it is an estimate, not a prediction or a promise. Giving a range opens the discussion of what could happen (risks) that would push the effort towards the worst case end of the estimate or bring it in towards the best case end.

Another nice thing about ranged estimates is that when you are asked to estimate something with poorly defined requirements you can give wide ranges to communicate the uncertainty. Well defined, believable requirements get estimates like 5-7 weeks whereas poorly defined, nebulous requirements get estimates like 4-20 weeks. This is especially true when giving high-level estimates.

There’s pretty much no way to get around doing high-level estimates. Your business needs some idea of the investment required to complete a project in order to make trade-offs. Hopefully this happens before your development team spends a bunch of time doing detailed estimates. Also folks in other departments (e.g. marketing, operations, manufacturing,…) need some idea of when they are likely to take delivery of the software. A team that can accurately (not precisely) give high-level estimates for these things gives their company a real competitive advantage.

So while it is frustrating, there are ways to do it and retain your sanity.

Multi-Tasking is Killing Your Business

I read a couple of articles recently and can now distill the vague feeling that I've always had that multi-tasking is not a good thing down to a simple statement that it is certainly a very bad thing.

And I can prove it.

Watch, nothing up my sleeve...

We all know there's thrash when switching, but let's assume that you've got some kind of dream team that can switch tasks perfectly. I do this because I don't want to get into a long discussion of "how good I am at multi-tasking".

Suppose we have 4 projects of 6 months duration each. Let's have the team multi-task and do all those things in parallel. They work one month on Project 1 , then move on to Project 2, and so on. Since there's no thrash it shouldn't hurt much right?


The average time to complete the projects is 22.5 months or just short of two years.

Now let's have our same team concentrate on one project at a time and see what happens.


This time the average time to complete is 15 months. That's 2/3 of the average for the multi-tasking schedule. But wait... it gets worse. What if those four projects are not of equal value.

We know that all projects are not created equal. Some are more valuable to your business than others. It is quite possible that your highest value project is a factor of ten more valuable than your least valuable project (or more). Let's model this by saying that each project on our stack-ranked list is twice as valuable as the one below it. Remember, I'm talking value not effort here.

Let's look 30 months out and see what each method has delivered in value to the business. Here's what the plots look like when the vertical scale is business value per month. The light green shaded area is the total value the projects have generated 30 months after project initiation.


So the multi-tasking project management method has delivered 124 units of value (8*9 + 4*8 + 2*7 + 1*6 = 124). But the single-tasking project... whoa... look out!


That's a whopping 294 units of value (8*24 + 4*18 + 2*12 + 1*6). More than DOUBLE.

In other words, if I worked for Single-Tasking Enterprises and you worked for Multi-Tasking Incorporated we'd be kicking your ass. (And no, you wouldn't be an acquisition target since we don't want your crappy multi-tasking IP.)

Okay, so multi-tasking sucks. What can you do about it?

I think the most important thing is to work off of a single prioritized list. You need one single list stacked top to bottom by priority for your people to use. The list must be public within your company. That way everyone is on the same page as to which project gets worked on first.

But I can hear you saying, "Hey, we work on many things at once because we're so busy and need to get all this stuff done yesterday!"

Yeah, and you can keep doing that. And as I've shown it will keep killing your business.

As leaders (and I mean anyone who has people under them) we must set hard priorities and stick to them. Constant switching of a person's "top priority" is a sure sign of weakness as a leader. If you are doing this STOP.

But what if you made a mistake in the priority order?

Look, even if we reverse the business value order and deliver the lowest value projects first we still come out ahead single-tasking. We get 156 units of value at the 30 month mark (1*24 + 2*18 + 4*12 + 8*6). That's still 25% more than the multi-tasking result with the "proper order".


The lesson is that it is less important that you pick exactly the optimal order in which to do projects. It is critically important that you build teams that focus on delivering one project at a time. Your teams must be empowered to protect their time and their schedule by telling all distractions to "piss directly off". Your leads must understand this and be rewarded for protecting their folks from distractions.

I find this stuff fascinating. How could I have run projects for all these years and never noticed how bad this is before?

Statistical Frustration

Okay... I must be getting old.

Anytime you find yourself saying things like, "Friggen kids these days know nothing about statistics", you pretty much know that oldness has happened. It's just driving me crazy that people don't understand what the hell "expected value" is or what the difference between the mean and the median is. Golly, people have a hard time with standard deviation, how the heck am I supposed to explain confidence in an estimate to them?

At the heart of this is the problem that most people don't get what is meant by probability or what is probable. Suppose for a minute that the VP of Customer Placation comes into your office and asks, "How long will it take to add frammerstammers to the hoopydo?"

Now, because you're not a n00b at estimation you hand him back a range.

"That'll take 5-20 days", you say. And you add, "I'm about 90% confident."

This is where about an hour and a half of useless discussion about "what the heck you mean" is going to go on because Mr. (or Mrs., Ms., Miss) VP just doesn't really want to know what is going on here. They just want a date that you promise that the hoopydo will have frammerstammers.

While willful ignorance is pathetic and deplorable (like spam) it is just a fact of life (like spam). Lecturing on probability and what it means to be confident will do you no good. They want a social contract not a lesson in Stat101.

So what to do?

Well, I think you need to know more about statistics than they do and be able to abstract away the math and crap like that from the discussion so that they come away with a good english language understanding of what you have promised them.

You need to explain that you don't know how long it is going to take. "Whadda I look like? The amazing Randy?" Then you can go on to explain that

You need to explain to them that if they make you promise to give them frammerstammers for the hoopydo on a specific date that the date will need to be out past the end of your range and that no, you can't just take the average and call it the promise. Be wary, be very wary, of giving a single number at this point. They will want to start using one. Don't fall for it.

Because the minute that you use a single number it becomes the default promise date. 3 months from now nobody but you will remember that you said 5-10 weeks. They'll only remember the 7 week number that everyone kept saying in the meeting. "Seven is in the middle, right?"

Yeah... uh... right.

If people could just grasp a couple of simple concepts from statistics this would all be so much simpler. We'd have a shared vocabulary to use when talking about estimates.

At its heart a good estimate is a range of values that you think the actual value will fall inside of. The narrower the range, the less likely you are to be right. Let me give an example. I'm going to give several estimates of the number of teeth you have.

32 is a bad estimate. It's a perfectly good guess. But a bad estimate. Because it is only correct if you have the normal number of teeth for an adult human and have not had your wisdom teeth removed.

0-50 is a better (though nearly useless estimate) since I'm almost certain that the actual number of teeth you have falls somewhere inside that range (100% confidence). Knowing nothing else I'd estimate the number of teeth you have at 25-32 and 80% confidence.

With more information my estimates get better. If you tell me that you are a 90 year old ex-hockey player I would estimate that you have 0-20 teeth. For a 16 year old bookworm I'll estimate 27-32 teeth. Again, 80% confidence.

The confidence part there is important. It helps tell you how statistically likely I think the actual value is to fall within my range. Once you start viewing these things as statements of probabilities a whole world of possibilities opens up. I'll explain some of the fantastic things that simply fall out of using probabilities in 2-5 future posts.