In a recent LinkedIn post, Janna Bastow tackles a common executive request: roadmap dates. Bastow, CEO of ProdPad, argues that when a CEO asks for specific dates on a product roadmap, they are often seeking something much deeper than a simple timeline. The underlying need, she suggests, is confidence – confidence in the team’s direction, the strategic allocation of resources, and the assurance of progress, especially when direct oversight isn’t possible.
Bastow highlights the disconnect between the CEO’s request and their true underlying needs:
When your CEO asks for dates on the roadmap, they’re not really asking for dates.
This initial statement sets the stage for her analysis, proposing that ‘dates’ are merely a proxy for a more fundamental requirement. As Bastow elaborates, the request for dates is a tangible, albeit often misguided, way for leadership to gauge the health and trajectory of product development.
The True Meaning Behind the Date Request
Bastow delves into the core of what leadership is truly seeking when they press for a roadmap schedule. It’s not about the precision of a calendar entry, but rather about assurance and visibility into the product development process. She explains:
They’re asking for confidence. Confidence that the team has a direction, that money is being spent wisely, and that progress is happening even when they can’t see it.
This perspective frames the CEO’s inquiry not as a demand for rigid deadlines, but as a quest for reassurance. In Bastow’s view, leaders need to feel secure that the significant investments in product development are yielding tangible results and are aligned with the company’s strategic objectives. Without a clear understanding of progress, dates can become the most accessible, albeit imperfect, metric to request.
Beyond Dates: Fostering True Confidence
The crux of Bastow’s argument is that while dates might feel like the definitive answer to a CEO’s query, they are often a superficial solution to a deeper problem. She suggests that focusing solely on dates can lead to a misallocation of effort and a potentially misleading picture of progress. Instead, Bastow advocates for a more nuanced approach to communication and reporting.
According to Janna Bastow, the key lies in understanding and addressing the underlying need for confidence. This involves demonstrating strategic alignment, responsible resource management, and consistent, visible progress. The challenge for product leaders, as highlighted by Bastow, is to find ways to communicate these elements effectively, moving beyond the simple delivery of dates to foster genuine trust and understanding with executive leadership.
Bastow’s insights, shared via her SimplyProduct platform, encourage a re-evaluation of how product teams communicate value and progress to the C-suite, emphasizing that true confidence is built on more than just a schedule.
📝 About This Content
This article is based on insights shared by Janna Bastow on LinkedIn.
📅 Originally posted on February 18, 2026 | View original post on LinkedIn →