- by Jane Halford and ChatGPT

The first months of a new CEO’s tenure is both exciting and uncertain. The whirlwind of introductions and orientation starts to settle down, and the real work of leadership begins. For board members, this is a pivotal moment to provide support without overwhelming the new leader.

So, what should you focus on when meeting a CEO in the first month into the job? Here are some practical ways to frame the conversation and set them up for long-term success.

Start With Their Impressions

One of the most valuable questions at this stage is simple: “What has surprised you so far?”

Early impressions often reveal blind spots or misalignments that could become stumbling blocks later. Asking about surprises, challenges, and early wins helps you understand how the CEO is interpreting the organization and where they may need support. The new CEOs perspective can also reveal critical organizational insights that were not previously known by the board.

Follow up by asking about priorities: “What feels most critical in the next 90 days?” Their answer will give you a sense of whether they’re focused on the right things and aligned with the board’s expectations and the organization's top priorities.

Encourage Relationship Building

No CEO succeeds alone. Strong relationships with board members, senior leaders, and all team members are lifelines.

Remind the new CEO that taking time to listen and connect is not a distraction from “real work”—it is the work of leadership.

Encourage them to use this early period to build trust and rapport in conversations and to understand history and context. By having the new CEO ask others, “What’s working well?” or "What’s one thing you’d change?”, they can speed up their learning curve by identifying common themes and opportunities to build momentum.

These questions signal genuine curiosity and help surface the organization’s realities.

Handle Sensitive Feedback Thoughtfully

You may hold information the CEO hasn’t yet discovered, like feedback from mid-level leaders or operational recommendations that were raised during the CEO search process. The question is: when do you share it?

The key is timing and framing. Instead of delivering a list of problems, position feedback as an opportunity.

You might say:

“During the search process, some leaders shared specific ideas about operations. Would it be helpful if I shared those now, or would you prefer to revisit them later?”

This approach respects the CEO’s autonomy while signaling your support. This delicate balance allows space for the new CEO to make their own discoveries from an unbiased perspective. However, please consider the consequences of having the new CEO be blindsided by more substantive issues.

Address Leadership Gaps Directly—but Constructively

Some organizations may be coming from a recent history of leadership churn or an interim CEO. In those cases, the senior team may be craving stability and direction. A new CEO stepping into this environment has a unique opportunity to reset.

Frame your observations in a constructive way:

“This team is ready for strong, consistent leadership. They’re looking for someone to empower and support them. You have a real chance to set that tone.”

Encourage the CEO to ask the senior team directly: “What do you need from me as your leader?” It’s a powerful way to build trust and show commitment.

Shape a Personal and Professional Brand

When a CEO comes from another region or has been away from the community, there’s a chance to be intentional about their personal brand. Encourage them to reflect on three things:

1. What makes you unique? (global perspective, past experiences, passions)
2. How do you want to be known? (collaborator, visionary, problem-solver)
3. How does this align with the organization’s identity?

Then, help them translate that into action: sharing their story, being visible with stakeholders, and ensuring their authenticity shines through.

In the early months, a new CEO doesn’t need to have all the answers. What they need is support, perspective, and encouragement to lead with intention. As a board member, you role is not to hand them solutions but to create the space for them to listen, reflect, and grow into the leader their organization needs.

If your board or leadership team is preparing for a new CEO, explore our free CEO Transition Resource Kit. It’s designed to help leaders and boards navigate this pivotal moment with confidence. 

Further Reading:

What New CEOs Should Ask Themselves in Their First 100 Days, Harvard Business Review

The Right Way to Bring a New CEO On Board, Harvard Business Review

How to Onboard Your New Boss, Harvard Business Review

Beyond the Hire: Maximizing The Impact Of Your New CEO, Forbes

Have questions about leadership transition, governance, or family business? Try our free AI tool: Ask Jane