Goal of this stage: get out of hand-waving, crisis-of-the-day land and clearly identify what needs to be done. Develop a strategic vision that’s independent of resource constraints

Size: between N person weeks and 6*N person weeks Scope: with enough of a description that most people would know what it is and what it isn’t Extent: it’s ok if the project requires other teams to execute

Of all these things, getting the size right can be the most challenging. It’s too early in the process to have even good educated guesses about how “big” these things are in calendar terms. Nonetheless, it’s also critically important that you’re dealing with projects are are all “roughly the same size” and “big enough to be strategic while small enough be digestible”. I’ve tried, oh how I’ve tried, to get people to resist the urge to think in terms of calendar time to define a size of a project and to instead work with the guidance of “roughly the same size and big enough to be strategic while small enough to be digestible”. And I’ve failed. People simply aren’t programmed to think that way.

So, instead, it’s best that you surrender and offer up the false precision of “please size the projects somewhere between N person weeks and 6*N person weeks” where N is the size of your average sprint. So, if you have 2-week sprints, then say “please size the projects somewhere between 2 person weeks and 12 person weeks”. “But, Tim, how do I know how many weeks a project is if I haven’t even really defined it yet?” you might ask. Well, you don’t. That’s what I meant by “offer up false precision”. The best you can do is let the asker decide for themselves what a “2-person-week project” is just based on their gut and move on. Will they be wrong sometimes? You bet your ass they will. Will any two given people have wildy different ideas of what can be done in 2 weeks? Also yes. This will all be ironed out later, so just deal with it for now. Try not to get stuck here. It’s an unresolvable tarpit.

If they’ve got a bunch of small stuff that’s less than the lower threshold, then encourage people to bundle those things with other small things and make a block of stuff, ideally with a coherent theme (see here). At the absolute worst case, you can always create one or more time-boxed blocks called “tactical queue block #N” see (here) for what a “tactical queue” is. Alternatively, you can designate sticky resources that just work down the tactical queue off to the side and aren’t counted as resource in this strategic process. Either works equally well and has various tradeoffs.