Succession
Executive succession planning: one conversation a month.
Regular conversations with leaders can keep your view of talent current and give your succession planning a useful outside perspective.
Matthew Guss
Founder & CEO, Next Horizon Leadership · September 15, 2026 · 3 min read
Updated September 23, 2026
Imagine a senior leader tells you they are leaving. Alongside your internal succession plan, you have recent conversations to draw on: people whose work you understand, questions about the role and a clearer view of the experience you may need.
A monthly conversation with a leader outside your organization can help build that knowledge. Treat it as a useful addition to formal succession planning, candidate assessment and the development of your own team.
Stay ahead of your company’s evolving leadership needs
Start with the work your business expects its leaders to do. Expansion, a new business model or a change in the team can affect the experience a role requires.
Review your succession plan against those requirements. What has changed since the last discussion? What new experience have potential successors gained? Which assumptions need to be checked?
The habit: one conversation a month
Set aside an hour to speak with a senior leader whose work you respect. Be clear that you want to learn about their experience and share perspectives, without attaching the conversation to an open role.
Ask what they are building, which decisions are taking their attention and what they have learned. Share something useful from your own work as well.
- Explain the purpose. Give the other person a clear reason for the conversation and respect what they choose to share.
- Keep useful notes. Record relevant professional experience and questions to revisit, within the confidentiality agreed for the conversation.
- Stay in touch thoughtfully. Follow up on the discussion when you have something relevant to contribute.
Bring the learning back to your team
Over time, these conversations can give you examples of how other organizations define roles and develop leaders. Use those examples to test your own assumptions.
They may also help you identify people worth considering in a future search. A conversation does not establish someone’s readiness or interest. Reconfirm both when there is a real role to discuss.
Apply the same attention internally. Discuss development with potential successors, give them opportunities to build relevant experience and revisit their readiness as the business changes.
Start with one person
Think of a leader whose experience would broaden your perspective. Invite them to a conversation and bring one question you would value their view on.
The aim is to build knowledge and trust steadily. When you next review succession, use what you have learned alongside the evidence from your team and the wider market.
A question worth asking
Who could offer a useful outside perspective on the leadership roles your business will need next?
