A few weeks ago I was in the midst of reading Steve McConnell’s Software Estimation: Demystifying the Black Art when I had the conversation with my friend Marc that I have written about previously. Marc, as I mentioned before, is the founder of and Chief Product Officer at a small startup called Wesabe. When I told him what I was reading, he asked, “Do you believe it?”

“Sure,” I said. By which I meant nothing in the book had struck me as patently bogus. A lot of it is good sense about the limits of estimation, the relation of estimation to planning, and why estimation is so hard. Parts II and III of the book present specific estimation techniques that, assuming one had the relevant inputs and historical data, seem likely to be capable of producing fairly accurate estimates. Now, the descriptions of some of these techniques made me think — wow, if that’s what it takes to produce good estimates, no wonder we all muck along with crappy ones. But it did for the most part seem like the kind of thing we Serious Software Professionals™ should be doing.

Marc — it turns out — is far more skeptical about the whole enterprise of software estimation. He tells me that at Wesabe they never make schedule estimates. He manages his developers, as he has explained in a blog entry, by trying to get them excited enough about the features he thinks should be added to Wesabe that they decide to go ahead and add them. Or they may get excited about their own ideas and add them instead. Marc retains final authority over what gets added to the product and a Wesabe developer who consistently gets excited about developing things that Marc refuses to allow into the product should probably make sure their resume is up to date. But he never asks them for estimates. He does encourage his developers to spend most of their time working on things that they can finish quickly and get into the product, but that seems to be as much about what he thinks most likely to keep his developers happy as anything else. When they need to, Wesabe developers will tackle bigger projects, still without estimating how long they will take. Marc’s point of view, I take it, is that the only reason to do these big projects is because you have to, and if you have to, it doesn’t really matter how long it’s going to take.

Now, Marc’s a smart guy and he’s been managing software developers for as long as I’ve known him (more than a decade) and I know he thinks a lot about how he does what he does. On the other hand, Steve McConnell’s also a smart guy whose books I’ve been a big fan of for about as long. So, how to reconcile these two points of view? Is Marc’s approach only tenable in a startup? Or maybe McConnell’s approach to estimation is only worthwhile in big organizations, that are doing more or less the same thing over and over again.

So I returned to reading Software Estimation with a new question in mind: Why estimate? The nearest McConnell comes to an answer is in section 1.7 “Estimation’s Real Purpose”, where he gives this definition of a good estimate:

A good estimate is an estimate that provides a clear enough view of the project reality to allow the project leadership to make good decisions about how to control the project to hit its targets.

I think the key word in McConnell’s definition is “targets”. The reason Marc can get away with not estimating is because he’s found a way to manage without setting targets. So the question “Why estimate?” is better expressed as “Why set targets?”

Sometimes we set targets in order to convince others, or ourselves, that something can be done. We may set targets to inspire ourselves to do more, though it’s not clear that’s a winning move, and even less so when managers set a target to “inspire” the folks who work for them. (See DeMarco and Lister’s Peopleware, chapter 3 and the discussion of Spanish Theory managers.) We may also set targets to give ourselves a feeling of control over the future, illusory though that feeling may be. After the fact, a target hit or missed can tell us whether or not we did what we set out to do. However if we missed a target, we can’t know whether that’s because the target was unrealistic or because we didn’t perform as well as we should have. Setting and hitting targets does make it look like we know what we’re doing but we need to keep in mind that targets rarely encompass all the things we care about — it’s much easier to set a target date for delivering software than a target for how much users will love it.

If the goal is simply to develop as much software as we can per unit time, estimates (and thus targets), may be a bad idea. In chapter 4 of Peopleware, DeMarco and Lister discuss a study done in 1985 by researchers at the University of New South Wales. According to Peopleware the study analyzed 103 actual industrial programming projects and assigned each project a value on a “weighted metric of productivity”. They then compared the average productivity scores of projects grouped by how the projects’ estimates were arrived at. They found that, as folks had long suspected, that programmers are more productive when working against their own estimates as opposed to estimates created by their boss or even estimates created jointly with their boss, averaging 8.0 on the productivity metric for programmer-estimated projects vs 6.6 and 7.8 for boss-estimated and jointly-estimated. The study also found that on projects where estimates were made by third-party system analysts the average productivity was even higher, 9.5. This last result was a bit of a surprise, ruling out the theory that programmers are more productive when trying to meet their own own estimates because they have more vested in them. But the real surprise was that the highest average productivity, with a score of 12.0, was on those projects that didn’t estimate at all.

There is, however, one other reason to estimate: to coordinate our work with others. The marketing department would like the developers to estimate what features will be included in the next release so they can get to work writing promotional materials. Or one developer wants to know when a feature another developer is working on will be ready so he can plan his own work that depends on it. Note however, that in cases like this, estimates are really just a tool for communication. Marketing needs to know what’s going to end up in the release and the developers, by virtue of being the ones building it, have the information and somehow that information has to be communicated from the developers to the marketers. But there are lots of ways that could happen. In a small company it might happen for free — everyone knows what everyone else is working on so the marketers will have as good an idea as anyone what’s actually going to be ready for the release. If water-cooler conversations are insufficient, then marketing and development could meet to talk about it on a regular basis. Or the developers could maintain an internal wiki about what’s going on in development. Some of these methods may work better than others but it’s not a given that using estimates is always the best way.

To decide whether estimates are a good way to communicate, we need a way to compare different methods of communication. I’d argue that all methods of communication can be modeled, for our present purposes, with the following five parameters:

Preparation time required

Communication time required

Rate at which information is conveyed

Rate at which misinformation is conveyed

Other benefits and costs

The idea is that communication happens in this pattern: one or more people spend some amount of time preparing to communicate. This would include activities such as thinking, writing, estimating, etc. Then the communication proper happens, which takes some time. This may require time from both the sender and the receiver (conversations, meetings, presentations, etc.) or only the receiver (reading an email, looking at a web site).

After the communication is complete, some amount of information has been conveyed and also, sadly, some amount of misinformation. The misinformation may arise from faulty preparation, from misstatements by the sender, or from misunderstandings by the receiver. Obviously different methods of communication will be able to convey more or less information in a given amount of time and will be more or less prone to miscommunication.

Finally, different methods of communication can have benefits beyond the information conveyed and costs other than the time spent and the misinformation conveyed. For instance, chatting around the water-cooler may build team cohesion while highly contentious meetings may have the opposite effect. Another important kind of benefit is that the preparation and communication phases may itself improve the communicators’ understanding of what they are communicating about. For example, writing clearly on any topic invariably forces the writer to clarify their own thoughts and the give and take in a well-run meeting can help bring out and refine what were previously only amorphous notions.

Now we can look at estimation as a communication tool according to this model. The preparation time for good estimates is fairly high. This is why so many developers try to avoid estimating or give it short shrift. The communication time is low — since an estimate distills things to the essence of “these features by this date” or “this much effort for that much functionality” it can be quickly conveyed. However, exactly because estimates do distill things, they are a low bandwidth form of communication. Without a lot of other communication about what exactly the features are going to look like, a list of features and the dates when they will be done, leaves out a lot. Worse yet, estimates are notoriously prone to conveying misinformation, either because the estimate is inaccurate or because an accurate estimate is misunderstood. McConnell devotes a whole chapter, “Estimate Presentation Styles”, to discussing how to present estimates so they will be less likely to be misunderstood, but no presentation style can help the poor estimator who’s giving an estimate to an audience that hears “2 to 4 weeks” as “2 weeks”.

When it comes to other costs and benefits, it’s hard to say. If we assume for the sake of argument that it is possible to make good estimates, does the very act of preparing the estimate have its own benefits? Certainly, making a good estimate requires identifying all the work to be done, so a team that has gone through the exercise of estimating may identify all the work that actually needs to be done sooner than a team that hasn’t, which may allow the work to be done more efficiently. Another potential consideration is that in a company where non-developers expect developers to be able to provide reliable estimates, then meeting those expectations has the social benefit of giving the rest of the company confidence in their development team.

On the other hand, there’s no guarantee of obtaining those benefits. Estimating badly certainly has bad ancillary costs. Leaving aside the consequences in terms of the misinformation it generates, it’s just no fun to estimate when you know your estimates are bad. Either you feel guilty because you believe it’s possible to do well and that you should be better at it or you think it’s actually impossible and therefore whoever is asking you for the estimate is wasting your time. And if good estimates can increase the company’s confidence in their developers, bad estimating can destroy it. Or, worse yet, developers can be unfairly deemed unreliable because the rest of the company expects more precision in estimation than is actually possible. According to McConnell, at the beginning of a project even the best estimators can be up to 4x off in either direction. Which means unless folks can accept an initial estimate of “from three months to four years” and a promise to refine it over time, developers are bound to disappoint.

So we have: High preparation cost. Low communication costs. Low bandwidth with high potential for misinformation. Ambiguous ancillary costs and benefits. Clearly, if you’re going to estimate, you’d better do it well and accept the costs that entails. But if you doubt it’s possible to do well, either in principle, or in your particular situation, then it can be useful to think about other ways to make sure the necessary communication happens.

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