In a recent LinkedIn post, Janna Bastow draws a striking parallel between how businesses communicate with Artificial Intelligence and how they communicate with their own teams, arguing that a critical context gap often hinders effective collaboration within organizations.
Bastow highlights a common practice where extensive context is provided to AI tools before expecting complex outputs, contrasting this with the often insufficient information given to human teams, particularly in strategic discussions like roadmap reviews.
“Most of us have learned to write context files, background docs, and one-pagers before asking AI to do anything important. Then we walk into a roadmap review with three columns and expect the execs to fill in the gaps correctly. They will fill in the gaps. Just not correctly.”
This observation, sparked by a conversation with Tami from Miami Reiss, points to a fundamental issue in organizational communication. Bastow suggests that the detailed, layered approach we instinctively use with AI is precisely what human teams often lack, leading to misunderstandings and misaligned expectations.
The AI Context Advantage
Janna Bastow’s core argument centers on the disparity in how information is prepared for AI versus human colleagues. When engaging with AI, professionals meticulously craft prompts, provide background documents, and define parameters to ensure the AI understands the task at hand. This investment in context is seen as essential for achieving accurate and relevant results from AI.
As Bastow notes, this is a learned behavior: “Most of us have learned to write context files, background docs, and one-pagers before asking AI to do anything important.” This meticulous preparation is a testament to our understanding that AI, while powerful, requires explicit guidance to perform optimally.
Applying AI’s Context Lessons to Team Collaboration
The crux of Bastow’s message is that the same rigor applied to AI communication should be extended to internal team dynamics. She points out the fallacy of expecting human executives or team members to interpret sparse information accurately during critical meetings like roadmap reviews.
According to Bastow, the expectation that a simple three-column format is sufficient for complex strategic discussions is misguided. She warns that while gaps will be filled, the interpretations made by team members without adequate context are unlikely to align with the intended strategic direction.
The ‘On the Radar’ Layer
Bastow, referencing Tami from Miami Reiss, proposes a practical solution: incorporating an “on the radar” layer into strategic planning frameworks. This layer complements traditional “Now-Next-Later” roadmaps by making visible the ideas and initiatives that are not yet committed but are being considered.
This approach, Bastow argues, ensures that nascent ideas and potential future directions are not lost but are instead part of a broader, more transparent strategic conversation. It acknowledges that strategic planning involves more than just the immediate or near-term actionable items; it also requires visibility into the exploratory and tentative stages.
“keep an “on the radar” layer alongside your Now-Next-Later, so the not-yet-committed stuff is visible too.”
By making these less defined elements visible, organizations can foster a more informed discussion, allowing for better strategic foresight and alignment across teams. Janna Bastow’s insights suggest that bridging this context gap is crucial for unlocking the full potential of human collaboration, mirroring the careful approach often taken with AI.
This method, Bastow implies, can help prevent the misinterpretations that arise when information is incomplete, ensuring that all stakeholders have a clearer, shared understanding of the strategic landscape.
📝 About This Content
This article is based on insights shared by Janna Bastow on LinkedIn.
📅 Originally posted on July 22, 2026 | View original post on LinkedIn →