This is the best opportunity for the designer to set the tone for the project. This meeting should include explaining the Design Process, determining the best communication style that will be most effective with stakeholders, setting expectations, determining goals, and nailing down the scope of a project.
Overview
Often, stakeholders are unaware of how much thorough research is involved in the design process. Additionally there is a larger picture to consider when designing an interdepartmental application. Transparency about what stakeholders and users can expect from the design process earns the designer an appropriate amount of professional respect, and sets a collaborative tone moving forward.
Hopes and Dreams
Similar to the start of the Double Diamond approach to design, opening up the discussion and asking stakeholders what their hopes and dreams are gives them a chance to spell out all of their goals, desires, and even vent about their frustrations. Listening and observing during this phase gives designers a good feel for the communication style that might be most effective moving forward. The stakeholder will often talk themselves out of off-the-wall requests that would be costly to build with minimal payoff, simply after seeing the design process laid out ahead of them. This helps narrow focus to the issues that need design work the most.
Automation / Manual Work
Most employees at Heritage have too much on their plates, and spend time working on repetitive, analog tasks that often take place on sticky notes or in spreadsheets. Identifying and automating these processes minimizes human error, records more meaningful data, and gives employees more time to focus on the more important tasks on their plate.
Milestones
Depending on the scale of the project, a threaded design approach may help. If it is possible to implement smaller parts of a bigger solution, setting smaller milestones will get incremental improvements out for users faster, and will make for easier testing and adoption.
Scope
In my experience at Heritage Auctions, the demand for design work is very high, and our team is very small. By reassuring stakeholders that the solution will be a living organism, and this is "just phase one", the designer ensures nobody will walk away from the kickoff meeting feeling they need to rush and squeeze in all of their requests at once. It is important not to dismiss the ideas that won't be included in the scope of the project. Instead, it helps to suggest the project manager involved should follow up with the stakeholder after the meeting and help set up Jira tickets to go on the Design Queue. Since Jira sorts by business value and ROI, these projects will wind up in the correct place on the queue, and will receive attention when they are towards the top.
Once the stakeholders are satisfied with the agreement that there will be tickets for additional features down the road, the project scope can be defined.
Metrics
In order to present a project's success to C-level managers, a designer should be prepared to discuss metrics. When stakeholders define their goals, it becomes clearer what should be measured.
Goals
Having stakeholders define their goals helps to determine what metrics would be the most useful, and helps prevent future scope creep. While not all goals need to be numeric, it is invaluable for designers to be able to translate the goals and successes of a project to dollars and cents so they can effectively communicate in the proper language to C-level executives, managers, and employees alike.