When No One Wants to Talk About Succession

Succession planning is one of the most important conversations a leadership team can have, especially in founder-led or family-owned businesses. But in many organizations, it’s also the conversation no one wants to start.

Why don’t we want to talk about succession?

Let’s be honest… It’s uncomfortable. This is the type of discussion that can hurt feelings, spark tension and disagreement. And, for those approaching their own transition, it can bring up the very real weight of retirement and letting go. Then, once you start the conversation, it can be uncomfortable because your organization isn’t ready – the people who would like to grow might not be ready, or the leader might not want them in that role.

Before you get to the point that a crisis takes place, there are ways to bring up succession without stating “Hey… you are retiring and we need to find your replacement”.

How to Start the Succession Conversation (Even If It’s Uncomfortable)

1. Use an External Trigger: If you reference an external event, an article, or a story that you heard where this happened to another business, it takes the pressure off it being personal. Example: I heard about a company here in Edmonton where the (role) was in an accident, and they didn’t have backup – what would we do if that happened?
   • If you are looking for a place to start, our Succession Planning: Preparedness Assessment can be a good trigger.
2. Ask a future-focused question: Especially with AI, this is a simple way to ease people into the topic. Example: What roles and skills are critical to our success over the next five years?
3. Focus on the Business Impact: Frame the discussion around leadership capacity rather than a specific person. Example: We have done a lot of work building this team – who in our team do we need to continue to grow? And how does that support us in the next 3-5 years?
4. Acknowledge it’s Awkward: If you want to be a little more straightforward, it is possible. If it’s uncomfortable, name it. Example: I know this is a sensitive topic, and it’s easy to put off. But it’s also one of the most important things we can do for the future of the organization.

Now if you get the conversation started but aren’t sure how to move it forward, or there are sensitivities that you need help navigating around, this is where bringing in a Facilitator to provide a facilitated succession conversation can be helpful.

Creating a Safe Space for a Hard Conversation

A skilled facilitator brings structure, neutrality, and emotional safety to succession discussions. For initial facilitated succession conversations, they can help you start with the basics of what you need to focus us and the questions you need to ask. With succession, it is easy to make assumptions, or not talk about the elephant in the room – so a facilitator can help you by focusing on clarifying what success looks like, and create space to talk about what legacies look like and what the future can be.

What a Facilitated Succession Conversation Might Include

At X5, we have a defined approach for our workshops on succession, which focus on:

• Clarifying leadership goals and the long-term vision for the organization
• Identifying critical roles and what the future demands of them
• Outlining development plans and transition timelines for successors
• Defining how the current leader wants to stay involved (or step back)
• Addressing concerns, assumptions, and what’s not being said

When done right, a facilitated succession conversation builds alignment, trust, and momentum. But they do start with a potentially uncomfortable conversation.

At X5 Management, we help organizations navigate the human side of succession planning. Our facilitation creates the structure and safety teams need to move from hesitation to clarity.
Whether you’re at the start of the process or stuck in the middle, we can help you move the conversation forward. Let’s talk about what your team needs to get started.

Author: Lenora Thomas
Lenora Thomas is Director of Operations & Innovation at X5 Management, with deep experience in customer success and team leadership. Read more about Lenora Thomas.