The one-on-ones uncover information that doesn’t exist in any document. A VP mentions that the last cross-functional initiative ended badly and two of the leaders in the room still carry the fallout. A director reveals that their function was excluded from prior planning and the team is skeptical about being included this time. A chief of staff explains that the executive sponsor and one of the workstream leads have unresolved scope disagreements that neither has raised publicly. This information shapes behavior: it determines whether stakeholders engage openly in collaborative sessions or protect their positions, whether the room builds together or fractures along historical lines. It never appears in a charter, a RACI chart, or an intake document. The Organizational Landmines section of the Stakeholder Map is where it gets documented.
What Organizational Landmines Are (and Are Not)
Organizational landmines are specific historical events, political dynamics, and invisible constraints that will influence how stakeholders behave during collaborative planning sessions. They’re not interpersonal preferences or management style differences. Two categories cover most of what the interviews reveal: Prior failures and political sensitivities. An initiative that was canceled, a launch that went poorly, a reorganization that created winners and losers. The specific event matters less than the residue it left: which leaders were associated with the failure, which teams felt blamed, and how those dynamics will play out when the same people are in the room for a new initiative. Contested territory between functions, competing visions between leaders that were never resolved, and pending organizational changes that haven’t been announced also fall here. These sensitivities create zones where certain topics will trigger defensive or avoidant behavior; we need to know where those zones are before designing sessions that might enter them. Invisible constraints. Commitments, relationships, or dependencies that aren’t documented but constrain what’s possible. Dependency Discovery during one-on-ones is the mechanism that pulls these into the open. A handshake agreement between two VPs about resource sharing. A relationship with an external partner that limits how a function can change its processes. A board-level commitment that constrains the program’s timeline but hasn’t been communicated to the working team. The common thread: all of these contain information that’s known to some people in the organization but not documented anywhere the planning team can find it. The one-on-ones are the mechanism that uncovers it.
How to Document Landmines So They’re Actionable
The quality bar for the Organizational Landmines section is specificity. A vague entry doesn’t help us navigate the dynamic; a specific entry does. For each landmine, the section captures:
- The specific event or dynamic. Not “tension between teams” but “the Q2 platform migration was delayed four months; Product attributes the delay to Engineering’s capacity constraints while Engineering attributes it to scope changes initiated by Product. Both teams’ leaders will be in the architecture session.”
- Who is affected. Which stakeholders carry the history and how it shapes their current stance. “The VP of Engineering is cautious about committing to timelines after the Q2 experience. The VP of Product is focused on locking scope early to prevent the same pattern.”
- The behavioral implication. What we should expect in collaborative settings and how to design around it. “Avoid pairing these two leaders on scope and timeline discussions in the same breakout. Address scope stability in the session design before asking for timeline commitments.”
The behavioral implication is what makes the section actionable. Without it, the landmine list is historical context. With it, the list becomes a session design input. We use the implications to structure exercises, assign breakout groups, sequence topics, and anticipate moments where the room might stall. Making the invisible visible starts with acknowledging what the organization carries into the room. The Organizational Landmines section doesn’t resolve the history; it ensures we’re not surprised by it.
Traps That Undermine Landmine Documentation
Two traps cause teams to produce landmine sections that look thorough but aren’t useful. The harmony trap. We avoid asking uncomfortable questions during the one-on-ones because we don’t want to uncover conflict before the group convenes. We ask about priorities and concerns but steer away from questions about organizational history, prior failures, or political dynamics. The resulting landmine section is empty or superficial because the conversations that would have populated it never happened. The antidote is to ask directly: “What has been tried before, and how did it go?” “Are there any historical dynamics between the people in this room that I should know about?” “Is there anything about this initiative that concerns you that you wouldn’t raise in a group setting?” These questions, asked with explicit confidentiality, produce the material the section needs. Stakeholders expect to be asked; teams that don’t ask are the ones who get surprised. The gossip trap. We collect political observations from multiple conversations and record them without assessment. The section becomes a catalog of interpersonal dynamics rather than a curated list of dynamics that will affect the planning engagement. A landmine list with twenty entries is a gossip log. A landmine list with five to seven entries, each with specific behavioral implications, is a planning tool. Our judgment determines which dynamics are relevant to the engagement. The section should contain the dynamics that, if unmanaged, would derail collaborative work or produce plans that look agreed-upon but aren’t.
How Landmines Connect to Session Design
The Organizational Landmines section feeds directly into how we design collaborative sessions. Two design decisions depend on it most. Topic sequencing and group composition. If two leaders have contested history around scope, the session should establish scope boundaries using a structured exercise before asking the room to build on them. If scope is introduced casually, the contested history appears as an argument rather than a structured discussion. Similarly, if a function feels historically marginalized (i.e., excluded from prior planning, overlooked in decision-making), the session design should give them a visible and substantive role early, signaling that the dynamic has changed. If the function is assigned to a breakout group where they’re outnumbered by the teams that marginalized them, the historical dynamic repeats. Facilitation approach. If the room carries a prior failure, we should acknowledge it early in the session rather than pretending it doesn’t exist. “The last initiative had a difficult outcome. This engagement is designed differently in specific ways.” Naming the history creates permission to move past it. Ignoring it allows it to operate as an undercurrent. Most planning processes don’t document what the organization carries into the room. The history gets discovered live, when the room stalls or escalates and nobody understands why.
Go Deeper: The Stakeholder Map
This article covers one dimension of the Stakeholder Map, the second of nine artifacts in the Planning & Roadmapping method. The Stakeholder Map answers the board question: “Who sees what?” Explore the full Stakeholder Map → Want us to build this with you? Book a consultation →
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