How have you trained your customers to NOT expect estimates? What's your model for billing and managing budget, strictly Time and Materials, or do you valuate the Planned Deliverables?
Many thanks for a thought-provoking, and wonderfully complete, post.
A PM can often estimate delivery timetables by analyzing historical lead time. For example, if it normally takes 10 days for a 2-star card to move from Next Up to LaunchPad, then you can guess when it will get shipped. Pad it a little, and make sure you give yourself time to get it IN to the next up column, and you're good.
I was wondering if you had some compelling (magical?) communication that shifted your clients attitudes, but you're basically guesstimating based on past performance.
I didn't see where a star rating equated to effort. I'll look again.
How have you trained your customers to NOT expect estimates?
If you try this sort of thing yourself what you'll often find is that you can get the cycle time of stories (the time from the story going on the board, to the time it gets deployed) to be fairly constant. It can take some work to get top this point, but it's possible and useful in almost all circumstances.
Once you get to this point you can pretty confidently predict that stories are 1week/1month/2months away from getting deployed - and you can use this as the basis you base customer estimates on.
Arlo Belshee coined this style and called it "Disney Line" planning (y'know - like the one-hour wait from this point thing). Arlo has a great video on this sort of approach to planning http://www.youtube.com/watch?v=6t4bZtnnQJA that might be worth a watch.
Just to expand on what Rich said: we try to build products that solve people's problems. We're very focused on making sure additional features solve a lot of people's problems (our feedback forum helps us figure this out: feedback.uservoice.com/forums/1-general-feedback), not just single clients (even if they have a lot of money). It's a lesson we've learned (painfully) several times. So we tend to make our own schedule and try to delight customers with the things we add, rather than rush to keep up with things potential customers have on their shopping list.
We're a SaaS business so I don't think there's much we need to do here. We launch/promote something only when it's ready. The only deadlines we operate on are internal (ex: we need feature X in time for event B).
Many thanks for a thought-provoking, and wonderfully complete, post.