The Jibility style of roadmap is designed to show a dot to represent an outcome. This is similar to seeing only the milestones on a Gantt chart. We do not show the duration of an initiative on our roadmaps, but there are some options to address this.
Suppose you have an initiative called "Operating Model Delivered" that is completed in Q3, but it is started in Q2. So, you have three options:
Explain to your stakeholders that this style of roadmap is simply to agree on the scope and sequence of delivery, not the duration because we don't know the resource allocation and it is not possible to work out the duration. Therefore, you have an initiative called "Operating Model Delivered" represented in Q3. Once the roadmap is agreed upon, then you can start on an implementation plan, in which case this could be a Gantt chart that shows the duration of the initiative.
Break up your initiative into multiple steps. For example, "Operating Model Delivered" is comprised of "Operating Model Design" completed in Q2 and "Governance Operating Model Implementation" completed in Q3.
Place "Operating Model Delivered" in Q3 and while in the Roadmap step, drag/drop a new initiative directly into Q2, and call this "Operating Model Start". The "Operating Model Start" is just a placeholder and you don't prioritize this initiative or define any actions for it.
The above options are illustrated below:
Note, you can distribute the initiative's estimated cost and benefits over multiple stages. So, you can define that a portion of the Operating Model Delivered initiative's cost is incurred in Q2 and the benefits are realized starting from Q2 as well. Refer to the Distributing cost over multiple stages and Distributing benefits over multiple stages articles for more details.