I am often asking in mentoring sessions how best to structure key one to one conversations.
In particular:
- CEO 1:1s with their leadership team
- CEO check-ins with their Board Chair
- Skip level conversations across the organisation
They serve different purposes, but together they form an important part of how leaders stay aligned, hear early signals, and make better decisions.
Below are a few reflections from what I have learnt along the way.
1. CEO 1:1s with your leadership team
These are often treated as operational updates. In practice, they are far more valuable when used as strategic alignment and judgement conversations.
Some lessons that have worked well for me:
Frequency should reflect the role. Some leaders benefit from weekly check-ins, particularly when time zones or operational complexity make informal conversations harder. Others work better with bi-weekly or monthly rhythms.
New joiners often benefit from weekly conversations in their first few months. It gives space to surface questions, observations, and early concerns while they are still forming their understanding of the organisation.
The leader should own the agenda. Useful topics usually include priorities and progress, decisions they need from you, emerging risks, leadership or team dynamics, and forward-looking thinking.
The most valuable conversations are often about judgement calls rather than updates. Talking through options, risks and trade-offs helps strengthen leadership capability and prevents bottlenecks.
And one final point that matters more than it sounds. Do not cancel them. You can postpone if necessary, but consistency builds trust.
2. Check-ins with your Board Chair
When someone first becomes a CEO, the relationship with the Board Chair can feel unclear.
The Chair is not your boss, but they are often your closest governance partner. Managing that relationship well makes board meetings far more productive.
It helps to establish a predictable rhythm. Many CEOs find weekly or bi-weekly short check-ins useful, along with time before and after board meetings and ad hoc discussions when needed.
Think of these conversations as a strategic sounding board rather than reporting. Typical topics might include strategic questions on your radar, emerging risks, external developments, leadership team dynamics, and how upcoming board discussions should be framed.
One lesson I learnt over time is to share early signals rather than finished thinking. It is much easier to discuss issues before they become formal board agenda items.
These conversations are also useful for board management. Discussing what belongs with management versus the board, how sensitive topics should be framed, and which board members may need additional context can make board meetings more focused and constructive.
Clear boundaries matter too. The Chair supports the CEO and leads the board, but operational direction remains with management.
3. Skip level conversations
The risk for senior leaders is that information becomes filtered as it moves up the organisation.
Reports look good. Leadership meetings sound positive. But the real signals about culture, motivation and friction often sit deeper in the organisation.
Skip level conversations create space to hear directly from people across teams.
Sometimes these are small group discussions to understand how the organisation is functioning. Sometimes they are one to one conversations with high potential leaders to understand their experience and ambitions.
In some cases these discussions can also become stay interviews. A structured conversation designed to understand why people stay, what motivates them, and what might cause them to leave.
Typical questions might include what energises them in their role, what obstacles make it harder to do their best work, which talents are underused, and how they see their career developing.
The aim is simple. Understand the signals before they show up in exit interviews.
In summary
Each of these conversations serves a different leadership purpose:
CEO 1:1s help align priorities and strengthen judgement across the leadership team.
Board Chair check-ins ensure governance alignment and make board discussions more productive.
Skip level conversations allow leaders to hear early signals from across the organisation.
Together they form a rhythm that helps leaders stay connected to the organisation and ahead of emerging issues.
Warmly,
Liz
Strategic Advisor | Former CEO | Founder, Volante
Based in Kenya, available globally
