How To Start a New Role - Part 2

Insights from CxO Leaders on Navigating Your First Days

A few weeks ago, I shared insights on how to approach a new job, focusing particularly on those critical first few days in an executive role. Since then, the article has sparked a lively conversation with a network of seasoned C-level executives I regularly collaborate with, leaders who have successfully navigated transitions multiple times across a range of industries and organizational cultures. What unfolded was an exchange of experiences, each offering fresh perspectives on the onboarding process and surfacing key lessons learned from both successes and failures.

What became apparent is that stepping into a new role goes far beyond those initial instincts of making a strong impression. It’s a nuanced process that requires a balance of learning, observing, and leading. After reflecting on the valuable insights shared during these discussions, I realized that this collective wisdom should reach a broader audience. There’s no playbook for starting a new role that works universally, but when you hear directly from those who have lived through the challenges, made mistakes, and thrived, it provides a powerful framework to guide others.

In this article, I’m bringing together a diverse set of strategies and hard-won lessons from these executives, what worked, what didn’t, and how they balanced learning, leading, and delivering value in those first pivotal months. Whether you’re about to step into a new leadership position or refining your approach, I think you’ll find these insights invaluable for shaping your transition.

Listening with Intent: The "Day in the Life" Approach

When you step into a new executive role, the natural inclination might be to make your presence known as soon as possible. You’ve been hired to drive change or lead a team, and it can feel as though immediate action is necessary to establish credibility. However, one of the most frequent points echoed by the executives I spoke with was the importance of intentional listening before jumping into decisions or making changes.

The idea of a "listening tour" is common advice, but to truly understand the pulse of an organization, you need to go beyond formal meetings and surface-level conversations. Several leaders recommended adopting what they called the "Day in the Life" approach. This involves spending meaningful time with different teams and departments, immersing yourself in the daily realities of their work. It’s not enough to sit in conference rooms and listen to reports, leaders who have done this successfully shared how they rolled up their sleeves and participated in frontline activities. For example, sitting with the customer service team to experience how they handle inquiries or joining a client call alongside the sales team.

This hands-on immersion provides insights that you won’t find in dashboards or high-level presentations. You get a firsthand sense of the underlying challenges and opportunities that are influencing the business. More importantly, you start to understand the human dynamics at play, how different teams work together, where friction exists, and where there’s potential for improvement.

Listening with intent means listening for the unspoken truths as much as for what is being directly communicated. Ask questions that dig deeper, such as: “What do you think is the most significant challenge that’s not being discussed openly?” or “Why do we do things this way?” By doing so, you uncover the historical and cultural context that underpins the current state of the organization. Understanding these layers helps you make more informed decisions later, avoiding impulsive changes that might backfire due to unseen complexities.

And, perhaps most importantly, listening builds trust. The team you are inheriting is watching to see what kind of leader you’ll be. Will you listen to their ideas? Will you try to understand before you act? In the first few weeks, listening is a powerful signal that you value their experience and perspectives. By investing time to understand the people behind the processes, you foster an environment of trust and collaboration, which is the foundation for future success.

The 90/10 Rule: Listen More, Speak with Purpose

One of the most critical lessons any new executive can learn is the power of restraint in communication, particularly in the early days. This is where the 90/10 rule comes into play: spend 90% of your time listening and only 10% speaking. This may sound counterintuitive, especially in high-pressure environments where demonstrating leadership quickly can feel like a necessity. However, the executives I spoke with stressed how crucial it is to resist the temptation to over-communicate before you’ve gathered enough context.

When you enter a new organization, you are under a microscope. Your team, peers, and superiors are assessing who you are, what you stand for, and how you’ll approach leadership. The instinct to immediately prove your value through frequent or authoritative input can backfire, creating the impression that you’re not interested in learning the lay of the land. The 90/10 rule flips this approach, ensuring you gather the insights needed to make informed, meaningful contributions when it counts.

But the 10% of time that you do spend speaking is just as critical. When you do speak, make sure it’s with intent and purpose. Summarize what you’ve learned so far, ask thoughtful questions, or share early reflections that demonstrate you’re synthesizing information. For example, instead of jumping in with a solution, you might say, “From what I’ve gathered so far, it seems that our biggest challenge is X. Is that consistent with your experience?” This doesn’t just show that you’re listening, it also invites further dialogue and input from others, which encourages collaboration and deeper problem-solving.

In addition, this rule is not about being silent for the sake of it. Rather, it’s about ensuring that when you do contribute, your words are thoughtful and drive the conversation forward. Your team will appreciate that you’re not there to talk just for the sake of talking but that you’re offering valuable insights based on what you’ve learned. It also positions you as a leader who understands the balance between action and reflection, which in turn helps build your credibility.

Another effective application of the 90/10 rule comes when you’re engaging with people across the organization. In those first interactions, frame the conversation around them, what they see as opportunities, what they’re excited about, and what challenges they face. You’re there to listen first, not to dictate. And when you do speak, use it as an opportunity to validate what you’ve heard, offer appreciation, or share a considered perspective. This approach establishes respect and shows you’re committed to leading with understanding, not just authority.

Navigating Stakeholder Expectations: Balancing Urgency with Understanding

One of the most difficult parts of stepping into a new leadership role is balancing the expectations of various stakeholders, especially when they don’t align with the pace at which you want or need to proceed. While some organizations allow new leaders a grace period for observation and learning, this isn’t always the case. Often, there’s pressure, from the board, peers, or even your team, to deliver quick results.

The challenge, of course, is that while you may feel the pressure to take immediate action, acting too soon without a full understanding of the business can lead to costly mistakes. One of the best ways to navigate this is by clearly communicating your process. If your board or CEO is expecting fast results, offer them a phased approach. For instance, you could propose providing an initial assessment within 30 or 60 days, highlighting key observations and outlining a timeline for deeper, more strategic decisions.

Transparency is key here. By sharing what you’re learning along the way, you keep stakeholders informed without being forced into premature commitments. This also buys you the time needed to dig deeper into the organization and gather the context that will make your decisions more impactful and sustainable.

Another important aspect is distinguishing between urgency and importance. Stakeholders may push for quick wins, but not all urgent requests are truly important in the long term. For example, an early budget request might seem pressing, but if you don’t have enough context to make an informed decision, it’s critical to communicate the risks of moving forward too soon. Balancing short-term pressure with long-term thinking ensures that your actions are aligned with the organization’s bigger goals and avoids rushed decisions that could undermine future success.

At the same time, your team will look to you for direction, especially if there has been a leadership gap before your arrival. While listening is essential, offering small, confidence-building actions, such as providing feedback on a current project or approving a small initiative, can demonstrate that you’re ready to lead without making sweeping changes. These early actions help establish your presence while giving you more time to gather information before making larger decisions.

Stopping vs. Starting: Prioritizing Impact Over Action

When stepping into a new role, there’s often a temptation to launch new projects or initiatives to show immediate value. However, one of the most effective strategies shared by the executives I spoke with was focusing first on what to stop rather than what to start. This approach helps create clarity and focus while also demonstrating that you’re willing to tackle difficult decisions head-on.

Stopping an initiative that’s no longer delivering value or addressing a misaligned project can have an immediate positive effect, freeing up resources for more impactful work. It also signals that you’re focused on prioritizing what matters most to the organization rather than simply adding more to an already crowded agenda.

Before you make any changes, though, it’s important to take the time to understand why existing projects or processes are in place. As the Chesterton’s Fence parable states, “Don’t tear down a fence until you know why it was built.” Make sure you have the full context before eliminating anything. This ensures that when you do stop something, it’s an informed decision that won’t lead to unintended consequences.

On the flip side, achieving early wins can build momentum and establish credibility with your team and stakeholders. These wins don’t have to be massive initiatives; they can be small, impactful changes that address immediate pain points or areas that have been overlooked. These early wins serve as a proof of concept for your leadership style, showing that you're capable of driving positive change, even in a short time frame. By focusing on resolving existing bottlenecks or improving processes that directly impact the team's day-to-day work, you demonstrate a commitment to making practical, meaningful improvements. This not only boosts morale but also builds confidence among stakeholders, as they see immediate value in your actions. Such early successes lay the groundwork for deeper, more strategic initiatives down the road, creating a strong foundation for long-term impact.

Incorporating Leadership Expectations

One highly effective strategy for fostering alignment and mutual accountability within a leadership team is to extend the concept of setting "working norms and expectations" to include the team's expectations of their leader. Rather than simply outlining what is expected from the team, leaders can dedicate time during an offsite or planning session for the team to collectively define what they expect from their leader.

This collaborative approach encourages transparency, allowing the team to voice their needs and expectations openly. By bringing everyone together to create a shared list of expectations for the leader, this process prevents assumptions or misinterpretations that can arise from fragmented feedback gathered in one-on-one settings. It ensures that the leader is attuned to the collective needs of the team, fostering a sense of shared ownership and alignment from the very beginning.

This method not only helps a leader better understand how to provide support but also creates an environment of trust and open communication. When expectations are clear and mutually agreed upon, both the leader and the team can work more effectively toward shared goals. It’s an approach that helps eliminate ambiguity, builds stronger connections, and creates a foundation of accountability, all of which are crucial for long-term success.

Incorporating a session where the team defines their expectations of leadership is a powerful way to ensure alignment, encourage collaboration, and set the tone for a productive and trusting working relationship.

Conclusion

Starting a new executive role is one of the most challenging yet rewarding experiences in leadership. It’s an opportunity to not only make an impact but to shape the direction of a team, department, or even an entire organization. However, as the experiences of seasoned CxOs illustrate, the first few months should be spent building a deep understanding of the business, its people, and its culture, rather than rushing into action.

Intentional listening, thoughtful communication, and carefully balancing the pressures from stakeholders are key to a successful transition. These strategies, listening more than speaking, seeking understanding before acting, and focusing on what to stop as much as what to start, form the foundation of informed leadership. By taking the time to immerse yourself in the organization’s operations and aligning early actions with long-term goals, you not only build trust but also set the stage for sustained, impactful leadership.

In the end, leadership is as much about when to act as it is about what action to take. Those who excel in new roles are the ones who recognize the value of patience, strategic decision-making, and leading with purpose. By embracing these principles, you position yourself not just to succeed in the immediate term but to build a lasting legacy of effective leadership and meaningful change.