One of the first things I did when I stepped into my new CEO role was schedule conversations. Not orientation sessions. Not briefings. Conversations.

Michael Watkins makes the case for this in The First 90 Days. The idea is simple: before you can lead well, you have to listen well. I took that to heart and built a structured listening tour into my first weeks.

With my direct reports, I run three separate conversations, roughly one per week across the first month.

The first is about their work. What does their functional area cover, what is working, and where do they anticipate needing support. I want to understand how they see their own responsibilities before I layer any of my assumptions on top.

The second conversation draws on a set of diagnostic questions adapted from a SWOT framework. I ask about the biggest challenges facing the organization and why those challenges exist. I ask about unexploited opportunities and what would have to be true to act on them. I ask about sensitivities, the things that do not always make it into meeting agendas or written reports. And I always close with the same question: who else should I be talking to? This helps me understand where the hidden power structures are and who is an up-and-coming thinker.

The third conversation shifts from the organization to the person. I focus on professional development, personal goals, and what they need to do their best work. By the time we get here, enough trust has usually been built that the conversation can be open and honest.

In parallel, I am running the same SWOT questions with board members and key volunteers. The questions are identical. What I am learning is not just about the substance of what people say but about the degree of alignment across the board. When people who share governance responsibility give very different answers to the same questions, that is very revealing.

Typically, I get more knowledgeable as I do more of the conversations. After I have a few under my belt, I can start to probe more deeply into the reasons behind the group’s thinking, and this helps me understand the culture of the organization as well as the strategic issues.

I am still in the middle of these conversations. The external listening tour comes next, and that will be its own post.

For now, the structured approach is doing what Watkins said it would. It is building relationships at the same time it is building knowledge. In the early months of a CEO’s tenure, those two things do not have to happen separately.