Jira and MS Project are execution tools wearing a planning hat

Genuine question for other PMs and delivery managers here: how many of you have opened Jira or MS Project to build a proposal, and felt like you were forcing a square peg into a round hole?

Here's the mismatch I keep running into. Jira is built to track work that's already been broken down and assigned. MS Project is built to schedule work that's already been scoped. Both assume the hard part - figuring out what the work even is and how confident you are in your numbers - already happened somewhere else.

But the initiation phase is exactly where that hard part lives. You're sitting with a client who hasn't signed anything yet. You don't have a backlog. You don't have a confirmed scope. What you have is a rough idea of tasks, a gut feeling about risk, and a need to produce a number you can defend.

Neither tool gives you that. Jira will let you create epics and stories, but it has no concept of "this task could take 40 hours or it could take 90, and here's how confident I am." MS Project will let you build a Gantt chart, but the moment a client asks "what if we cut this feature," you're not adjusting a live model - you're rebuilding a schedule and hoping the dependencies don't break.

The real cost isn't the rebuild. It's what happens during the meeting while you're not answering. You say "let me get back to you," the moment passes, and you've burned one of a limited number of shots you get with that client.

That gap - no probability modeling, no live recalculation - is what got me building something of my own for this specific phase. Still think Jira and MS Project are the right tools once a project is signed and scoped. This is just about the part before that, where you're trying to win the work in the first place.

Curious how others have hacked around this. Spreadsheets? A separate estimation tool? Just eating the pain and rebuilding offline each time?