Halloweening is that process that happens near the beginning of a non-trivial project or initiative when you know you will be doing work and have the elevator pitch for what the work is, but the details are either vague or in flux. For me, this collection of general starting points kicks off a period where I go door-to-door with stakeholders and colleagues, ring the doorbell and say “trick-or-treat.” One person gives me a spreadsheet, another gives me a collection of Visios or some emails and so on.
After I finish going door-to-door, I take my proverbial bag of goodies back to my desk and start sifting through it all, looking for the good bits. Slowly but surely, a picture of the project goals and probable implementation paths starts to coalesce, which enables me to go out and start filling in the blanks. “What about this feature?” “How would we accomplish that?” “What about the legacy system?” “How does this tie into other things we are trying to do?”, etc. There are always blanks, but knowing where the dragons are let’s us fill them in.
I have always found myself doing a bit of halloweening to start a project. No requirements document, email or diagram has ever completely obviated the need to ask around and there are almost always multiple tales to hear and many viewpoints to reconcile. I must say that there is a degree to which I enjoy it. It is like solving a murder mystery where we are finding something to be created rather than something that has been destroyed.
What are the keys to good halloweening? How do we go about getting the good stuff? I’ve usually found the first step is to know which houses to go to. Sadly, there is a degree to which this is mostly a matter of having enough knowledge of the organization, enough of a mental rolodex to know who to speak to. When in a situation where few contacts are known, the whole thing becomes a matter of discovery. I usually start with what I know and see where asking questions leads me.
The most important thing along the way is critical listening. If treated as a passive exchange of information, halloweening will end abruptly. Without the “critical” part in critical listening, questions cannot be asked and huge segments of canvasable territory will be missed.
The one warning to add is that it is important to be careful how much solutioning or decision making goes on. I try to treat the process as information gathering and I continue until my efforts are redirected to some other bit of work or until I stop hearing new information or getting new contacts.
There is a time and place for lobbying, of course, but without a solid working knowledge of what is being asked and the context into which the solution must be placed (and there is always a context), we really do not have a good notion as to what it is for which we should lobby. Ultimately, that is what halloweening is all about - putting oneself into a good position to create proposals, designs or presentations for future work.