Every once in a while Ill work with old fashionsd project managers, in data/software projects, who pair deliverables with deadlines, instead of working iteratively in an “agile” way. But I realize that as much as PI Planning is a kind of rebranded waterfall plan , it is likely a good answer to the real world where “old fashioned " is still just “how the world works”.

What happens

Per my observations so far, on this planet, every and any project will always be renegotiated w.r.t. the iron triangle, that is, with more time , less scope, lower quality or more resources. (Unless of course you already built the solution and no time required for updates).

Why does this happen. The agile manifesto was a response to this. Many people have written about this over the last two plus decades and No Estimates describes this reasonably. Projects will always have unknowns and gotchas that cannot be predicted in advance. Unknown requirements and unknown dependencies. Simply put, the devil is in the details. And actually doing the project is the time you would need to produce an air tight estimate.

So if the cheapest bid always wins , then what is “the optimal strategy “?

So which is better : (A) spend a long time to precisely lay out Level of Effort and Statement of Work and eat anything you missed and hold customer accountable to anything they missed .

Or (B) guesstimate the Level of Effort , and a loose Statement of Work , but double or triple it simply. So you will probably win way fewer contracts but you’ll waste less time on pointless estimation.

Well, option A, will have a lot of estimation overhead and your old hat PM will fight tooth and nail to claim updates were part of the original spec.

And trying option B in a company, might not work if the PM asks you to justify your multiplier, so you may be stuck itemizing after all.

And that’s why PI Planning can look good here, because it gives both sides something to work with.

It is still not purely iterative like an agile shop, but in PI Planning, you offer timelines which PMs can write down in their notebooks but you also write out a sort of loose statement of work paired with assumptions and risks, that might help you when you have to ultimately renegotiate your position multiple times during the project lifetime .

And as is emphasized in No Estimates, renegotiating , cutting down, the scope, is likely going to be the best tool at your disposal along the way.

So then timelines become your friend, if both parties can wink nod and agree to play the renegotiation dance along the way.

Why is “the real world” unwilling to live with unknowns?

This is simple: you cant see unknowns and acknowledging them would put a PM at odds with their liege.

The customer needs someone fully on their side in spirit.

And we have various biases that blind us from uncertainties, which allow us to –evolutionarily?– function in an otherwise chaotic world.