Clarify why your request matters / purpose: What's In It For Them?
Who are you influencing specifically? What is their role in the problem? What authority do they have? What is the perspective from their seat? Be prepared to construct and monotonously repeat a tagline pitch with this structure (taken from our Project Management practice):
My issue, when resolved will (Increase Revenue -or- Avoid Cost) for our organization (replace with your words) by doing something very important.
In other words: Sell. The. Dream. People want to be helped with important and engaging work. Help them explicitly connect the dots.
Clarify roles and accountability
Be mindful that there is a big difference between the perspective of a Project Sponsor, Project Manager and critical Stakeholders similar to what Barry Oshry wrote about with Tops, Bottoms, Middles and Customers. Adapt your approach. Who has the ability to approve timelines, budgets, dates and who does not? Which people are required for networking to get to the decision makers? Build a strategy to move to the right person for the right decision. Understand how decision making and governance really works in the organization.
Clarify what you need specifically
We often start meetings without clarifying what we expect of the people we have invited. My friend, Jeff Clancy (retired CIO), shared this model that he used to start meetings to clarify what his meeting expectations were. Supporter means he is holding the meeting to inform, not to change anything. Clarifying questions are fine, but the decision has been made and feedback is not useful. Evaluater, on the other side of the spectrum, means that he is in prototyping mode and wants all the feedback he can get. No decision has been made. Meetings are usually somewhere between these two extremes and by drawing this on the board at the start, you can clarify what you want:
Tell the truth about constraints and risk
If you don't know, find out by behaviors (not words) how you would prioritize and whether you are limited by money, time or quality. If your highest leader were to prioritize these, what order would they be in? Again, everyone wants all of these, but choices show what's really the most critical. In addition, if you know there are risks that are very likely to occur, share these authentically. Here's a table to help you figure out your messaging around risk (taken from our Project Charter template) :