[codingdave]

I don't take care of timelines. That isn't part of either "what" or "how". It is a whole different question of "when". I push back hard on even asking that question.

What I do instead is focus on priority. If the leadership thinks they need a date, I ask why. Often it ties to KPIs they need to hit, or promises they made up the chain, or sometimes even something real like: "We're out of funding in 4 months.". But once I know "why", I can tailor the "what" to focus tightly on that "why", and deliver. If they push for hard dates, then we're back into micromanagement to get the scope to hit the date, and we are wasting time again. So I don't measure effort... at all. I just let the team know what is most important, and we do the work.

The trick is to get leadership to trust that this works. Most of them are used to timelines, scrum cadences, 6 month roadmaps, etc. And if that works for them, great. But it isn't what I recommend for building an effective team who can deliver quickly while enjoying the work.

Edit: I always think of one more thing after I type up a comment... I can succeed in this scenario because I used to be an engineer. I know if something takes an hour vs. a day/week/month and can break things out accordingly. If a product person really does not have that sense, they'll need to ask about effort... but it can be at that high level of hour/week/day/month.