Beyond the Org Chart (Part I): Critical Questions Leaders Must Ask During Onboarding
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The early days of an executive’s tenure are filled with promise and pressure—it’s a time of introductions, immersion, and inevitable information overload. While most onboarding processes focus on organizational charts, strategic priorities, and compliance, the most successful leaders know that the real work lies beyond what's written down. They understand that every organization—no matter how structured on paper—has its own ecosystem of relationships, histories, and unspoken truths. This article outlines two critical questions new leaders must ask to decode the visible and invisible dynamics that shape organizations—and to lead with clarity, integrity, and inclusion.
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When new leaders step into an organization, much of their attention is understandably drawn to what’s visible: structure, metrics, role descriptions, and strategic plans. But beneath that surface lies a deeper, more influential layer—one that includes informal power structures, cultural expectations, and shared (but unspoken) histories. Too often, onboarding processes neglect this terrain, leaving new leaders to navigate the invisible by trial and error. Yet what is not immediately visible is often what shapes how decisions get made, which ideas gain traction, and why change efforts succeed or stall.
In this first instalment of a two-part series, we explore the questions leaders must ask—not to fill a checklist, but to build clarity and credibility. We begin with two foundational inquiries: Who really holds influence here—and how is it exercised? and What are people afraid to say out loud? Together, they form the groundwork for understanding not only how an organization functions, but how it feels.
These are not one-time questions—they are postures. And leaders who adopt them from the start are far more likely to create the kind of relationships and insight that drive sustainable, human-centred leadership.
1 Who really holds influence here—and how is it exercised?
On paper, the lines of authority are clear. But formal authority is only one piece of the puzzle. Informal power—the ability to influence decisions, shape culture, or serve as a trusted voice—often resides elsewhere.
Michael Watkins, in The First 90 Days, underscores the importance of mapping not only the organizational structure but also its power dynamics. Without understanding where influence truly lives, leaders may misread stakeholder expectations or inadvertently bypass key voices, weakening their credibility early on (Watkins, 2013, pp. 10-15).
Understanding influence involves identifying culture carriers, trusted advisors, and informal brokers who quietly shape consensus. These individuals may not hold senior titles, but their roles in guiding sentiment and operational decisions are pivotal. To uncover these players, leaders must approach their first days with structured curiosity:
Conduct stakeholder mapping: During early one-on-ones, ask, “Whose perspective should I hear before making decisions?” Watch for names that surface repeatedly across departments.
Use influence mapping tools: Consider tools like OrgMapper or simply draw informal relationship maps to visualize who talks to whom—and who holds sway.
Observe meeting dynamics: Who do people look to for nonverbal cues? Who interrupts without pushback? Who influences the outcome, even without speaking much?
Ask trusted staff: Executive assistants, project coordinators, and long-tenured team members often know where power really lies. A well-placed, “Who helps things really move around here?” can unlock a world of insight.
Another practical move: schedule informal “discovery coffees” across levels and departments—not just with your direct reports. Position these as learning conversations, not performance assessments. These chats often reveal not only who has influence, but how that influence is earned, how it’s perceived, and how it can help (or hinder) your early efforts. Influence is visible—if you’re watching for it. But more than that, it’s discoverable when you ask sincerely, listen generously, and look beyond the chart on the wall.
2 What are people afraid to say out loud?
Every organization has its ‘undiscussables’—topics or truths that stir discomfort, evoke defensiveness, or have been historically dismissed. These unspoken realities often exist in the spaces between formal policies and lived experience. And while silence may offer short-term stability, it erodes long-term trust. These are the places where resistance festers, risk hides, and innovation stalls.
In her book The Fearless Organization, Amy Edmondson reminds us that psychological safety isn’t about comfort—it’s about candour. High-performing teams are those where members feel safe to speak up, offer dissenting views, and challenge assumptions without fear of retribution (Edmondson, 2018, p. 5). Yet candour rarely emerges on its own. It must be invited—and it must be protected.
Leaders set the tone. If team members sense defensiveness or detachment, they will stay silent. But when leaders model vulnerability and openness, they create a culture where speaking the truth becomes not just safe but expected. New leaders can begin building this trust with intentionality:
Ask permission to learn aloud: Phrases like, ‘I know I’m still learning—what am I not seeing?’ or ‘What would a courageous conversation sound like here?’ invite honesty while signalling humility.
Host skip-level conversations: Speaking directly with people a few levels removed from your own role often reveals operational friction points, cultural inconsistencies, and hidden frustrations that aren’t visible from the top.
Use structured listening tools: Try anonymous Q&A platforms (e.g., Slido, ThoughtExchange) in town halls or team meetings to surface issues that people might hesitate to voice out loud.
Create ‘red flag rituals’: Some leaders make it routine to ask in team huddles: ‘What’s one thing we’re avoiding that we shouldn’t?’ Over time, this repetition normalizes the naming of uncomfortable truths.
Make it safe to challenge you: Offer explicit permission by saying, ‘If I miss something important or move too fast, I want you to call me on it. That’s how we’ll do our best work.’
Most importantly, don’t punish honesty—even subtly. If someone takes a risk to name a tension or disagree, respond with curiosity, not correction. Thank them. Dig deeper. Revisit the issue later, even if the answer isn’t immediate. Listening with openness—and without rushing to fix or defend—is not just an act of empathy. It is a strategic move that allows critical truths to surface before they become crises. The leaders who hear what others fear to say are the ones who earn long-term trust—and create workplaces where everyone can thrive.
Conclusions
Leadership starts with listening—and the questions you ask shape the answers you’ll receive. In Part I, we explored the importance of discovering where influence truly lives and creating the safety for truth to surface. These actions aren’t just helpful—they’re foundational. By observing power dynamics and cultivating psychological safety, new leaders lay the groundwork for trust, connection, and credible decision-making. They begin to show—not just say—that they are here to learn, not just to lead.
In Part II, we’ll continue this journey by exploring what success really looks like, how to navigate inherited legacies, and how to expand the circle of inclusion in meaningful, measurable ways. Until then, let the questions guide you. Because leadership that listens first is leadership that lasts.
Bibliography
Edmondson, A. C. (2018). The Fearless Organization: Creating Psychological Safety in the Workplace for Learning, Innovation, and Growth. New York: Wiley.
Watkins, M. D. (2013). The First 90 Days, Updated and Expanded: Proven Strategies for Getting Up to Speed Faster and Smarter. Cambridge, MA: Harvard Business Review Press.
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