Beyond the Org Chart (Part II): Critical Questions Leaders Must Ask During Onboarding
Industry Trends
Effective leadership begins with questions, not answers. In Part I, we explored how new leaders can build trust and uncover hidden dynamics by asking who truly holds influence and what people are afraid to say. In Part II, we turn to questions that help leaders align with the organization’s true definition of success, understand the legacies they inherit, and lead with intention. These questions are essential for building credibility, advancing inclusion, and laying the foundation for sustainable leadership.
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Bata Shoe Museum, Canadian Council for the Arts, CEE Centre for Young Black Professionals, City of Toronto, David Suzuki Foundation, Fasken, Genome Canada, George Brown College, GTAA, Humber, IMCO, Kids Help Phone, Luminato, McMaster University, MLSE, OICR, Ontario Presents, ROM, Sankofa Square, Sick Kids, TD Bank, TTC, UHN Foundation, United Way Greater Toronto, University of Toronto, University of Waterloo, University Pension Plan Ontario, York University
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If Part I of this series was about uncovering the invisible dynamics that shape organizational life, Part II is about aligning action with meaning. When new leaders step into an organization, they often feel pressure to perform quickly. But lasting impact depends less on speed and more on intention. What does success really mean here? What came before me, and how should I honour or evolve it? Who hasn’t had a seat at this table—and how can I make room? In this article, we explore two more critical questions that help leaders deepen their insight, define their leadership identity, and move from listening to meaningful action.
1 What does success look like here, and how is it actually measured?
For a new leader, success is often a moving target. Rarely is it defined by metrics alone. In reality, the earliest indicators of effectiveness are relational, cultural, and contextual—often tied more to perception than to immediate results. Especially in the first year, ‘success’ tends to hinge on whether the right relationships are built, the right people are in the right roles, and the tone of leadership signals both clarity and adaptability.
According to Ty Wiggins and Rebecca Davies in their 2024 Harvard Business Review article Inside the First Year as a CEO, the top priority for newly appointed CEOs is building and assessing their senior leadership teams. Of the 35 CEOs interviewed, most made their first change within 2.8 months, but on average, it took 9.2 months to have the ‘right’ team in place (Wiggins & Davies, 2024). Many were still working to get their teams performing optimally a full year into the role.
What does this mean for a leader stepping in? It means that success isn’t measured by how fast you implement change—it’s about how thoughtfully you assess the human systems that drive performance. It also means context is everything. What constitutes success in one organization may not apply in another. Some boards prioritize stability; others want rapid innovation. Some teams value collaboration and morale above all; others reward technical precision or speed. Without this contextual clarity, a new leader may pursue results that go unnoticed—or worse, cause friction. To understand and align on what success actually means, leaders should consider the following practical steps:
Ask multiple people to define a ‘win’: Don’t rely on a single point of view. Ask your board chair, direct reports, and frontline employees: ‘What does a win look like here in the first six months?’ Note where the definitions align—and where they diverge.
Track not only KPIs but trusted indicators: What’s on the dashboard may not reflect what’s truly monitored. Ask, ‘Which outcomes matter most in our team discussions and performance reviews?’ or ‘What signals tell you things are going well—or not?’
Make success a shared conversation: Early on, establish a cadence of check-ins with key stakeholders: ‘Here’s what I’m aiming for—does that match your expectations?’ Adjust if needed. Clarity up front reduces course corrections down the line.
Balance outcomes with impact: Leaders should assess not only what they achieve, but how they achieve it. Were people brought along? Were changes sustainable? Did new practices build trust—or simply impose order?
The Wiggins & Davies research also revealed that many CEOs were caught off guard by the state of the culture, the health of the business, and the emotional weight of the role. This reinforces the idea that success is never just technical—it’s emotional and social, too. New leaders should therefore ask themselves:
Am I being evaluated on what I deliver—or how I deliver it?
How aligned is my own definition of success with that of those around me?
What early outcomes will build trust and create momentum without overextending my team?
These aren’t one-time questions. They’re part of a reflective practice that shapes leadership identity over time. In the end, success is not something to be declared—it’s something to be discovered, co-created, and continuously recalibrated.
2 What legacy am I stepping into?
Leadership transitions are rarely neutral. They ripple through an organization—stirring anticipation, anxiety, and often, unresolved emotion. According to a McKinsey & Company study, transitions rank among the most stressful professional events leaders face, on par with bereavement and divorce (Keller & Meaney, 2018). The stakes are high: nearly half of all executive transitions are viewed as failures or disappointments within two years, and the consequences cascade quickly. When transitions falter, the performance of direct reports drops by 15%, and attrition increases by 20%. One of the most overlooked factors in these outcomes?—Organizational legacy.
The McKinsey study research shows that 68% of failed transitions stem from misalignment with culture, politics, and people—not from strategic missteps or lack of technical skill. New leaders often assume they are being hired to bring change. But meaningful change cannot happen without understanding the deeper currents that shaped the organization before they arrived. To navigate a legacy successfully, leaders must recognize that they are entering a story already in progress. That story includes prior decisions, lingering disappointments, sacred conventions, and institutional memory. Pretending the past doesn’t exist—or rushing to replace it—undermines credibility. Effective leaders begin by listening to the past with respect, not resistance. Practical ways to do this include:
Conduct a ‘narrative audit’: Ask a range of employees—new hires, long-timers, managers, and frontline staff—'How did we get here?’ and ‘What’s the story people tell themselves about the last few years?’ This will reveal how history is interpreted and internalized at different levels.
Look for unfinished business: What initiatives were launched but never fully implemented? What ideas were shelved but not forgotten? Revisiting them can uncover buried potential—or unresolved tension.
Surface unspoken contracts: Promises, whether formal or implied, shape employee expectations. Ask, ‘What commitments were made by previous leaders—and do people believe they were fulfilled?’
Engage your predecessor’s allies thoughtfully: They often hold valuable insight—and influence. Ignoring them risks alienation. Including them, even informally, can ease the transition and build goodwill.
It’s also critical to name what will not continue. As Keller and Meanley highlight, successful leaders are 1.8 times more likely to communicate what they are stopping, not just what they are starting; to this point, they highlight Alan Lafley’s transformation of Procter & Gamble as a well-documented example. His early effectiveness came not just from bold strategies, but from halting nearly $200 million in distractions that diluted focus. A ‘stop-doing list’ helps create strategic clarity—and organizational relief.
Finally, resist the pressure to conform to arbitrary timelines. The often-touted ‘first 100 days’ playbook may offer useful structure, but it can also create false urgency. Most CEOs take more than six months to make a real impact—and stakeholders are generally more patient than they appear, as long as they feel engaged. Legacy work isn’t about nostalgia. It’s about integration: discerning what must be honoured, what can be released, and what is ready to be reshaped. Leaders who begin with this clarity don’t just lead forward—they carry the best of what came before into the future.
Conclusions
The best leaders don’t impose vision. They shape it with others. They understand that legacy, success, and inclusion are not just concepts to manage but relationships to tend. When a leader takes the time to ask what success really means, they align their efforts with the values that matter most. When they honour legacy, they lead with humility. And when they make room for previously excluded voices, they build cultures where everyone thrives.
Part II closes this series, but in truth, these questions never end. They evolve. And the leaders who continue asking them—at every stage of their journey—are the ones who leave organizations better than they found them.
Bibliography
Keller, S., & Meaney, M. (2018). Successfully Transitioning to New Leadership Roles. Retrieved from https://www.mckinsey.com/~/media/mckinsey/business%20functions/people%20and%20organizational%20performance/our%20insights/successfully%20transitioning%20to%20new%20leadership%20roles/successfully-transitioning-to-new-leadership-roles-web-final.pdf
Wiggins, T., & Davies, R. (2024). Inside the First Year as a CEO. Retrieved from https://hbr.org/2024/08/inside-the-first-year-as-a-ceo
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