As a CEO or ED, you need a strong leadership team around you. That work starts on day one. You are building trust and assessing fit at the same time. If you do it informally, you will miss patterns and rely on gut instinct. A short series of structured conversations gives you a better signal, faster.

Conversation 1: Establish your relationship and build trust

Start by building a strong relationship and trust. Your leadership team knows more about their work than you do, and they definitely know more about the organization. Here are questions that tap into and respect that expertise.

• What do you want me to understand about you as a leader and as a person?
• What motivates you about this job?
• What should I know about your work style so I do not misread you?
• What do you need from a CEO to do your best work?
• Where do you feel the most pride in the team you lead?

Conversation 2: Understand their strengths and areas of growth

Approach this conversation from a strengths-based approach. You are learning how this person thinks, leads, and responds under pressure. That is what will help you support them and evaluate fit. Before this conversation, you may want to review the individual’s goals and prior feedback.

• When you have felt most effective here, what conditions made that possible?
• When you are under pressure, what patterns show up in how you lead?
• What feedback have you received that you think is accurate?
• What would your team say is the best and hardest part of working for you?
• What are your professional development goals, both near-term and longer-term?

Conversation 3: Gather intel on their portfolio

In parallel to the work with the staff, you are assessing the organization’s portfolio. Your direct reports are the experts in their portfolio what is really happening on the ground.

• What are the initiatives you are accountable for, and which one matters most right now?
• If you could change one thing about how your area is resourced, what would it be and why?
• What risks keep you up at night in your portfolio, including people, money, systems, or reputation?
• What work looks “green” on paper but is actually shaky?
• Where are the handoffs failing between your area and others?
• What decisions are coming in the next 60–120 days that I need to be ready for?

Conversation 4: Establish your working relationship

Finally, establish the best way for the two of you to work together. I like to have this last so it is not just theoretical but can be built on prior conversations and work. If you are the type of person who likes to set ground rules early, then by all means move this earlier in the process.

• What are the best ways for us to communicate day to day and in a crisis?
• What decisions do you want to own fully, and where do you want me involved?
• What does “support” look like from me when you hit blockers such as resistance from peers or stakeholders?
• How do you want me to handle disagreement with you in real time?
• What expectations do you have of me in my first 90 days that will help you be successful?

If you have ways of working that you want to share, do it here.

Reflection

Once you have had some or all of these conversations with your team, take time for reflection. Here are some prompts to help you think through what these conversations imply.

1. Are my team and I aligned on near-term priorities?
2. Do my direct reports have the right balance of workload and responsibilities?
3. What is the level of trust and collaboration between team members?
4. Where am I seeing role confusion or decision overlap?

Ultimately, you want to figure out if your leadership team has the right structure with the right job descriptions/responsibilities filled by the right individuals.