Navigating retirement conversations the right way

A client once asked me how to approach a delicate situation: they had a long-serving employee in a senior position and were wondering whether it was okay to ask if the person was planning to retire. Their question was understandable—but so was their concern about overstepping or appearing discriminatory.

We worked together to develop a lawful, respectful, and practical approach, centred around open communication and good planning—without making assumptions based on age.

Step 1: Know the Legal Boundaries

First, I guided them through the Equality Act 2010, which protects employees from age-related discrimination. We reviewed their internal retirement and succession planning policies to make sure these conversations, if they happened, would always be voluntary and employee-led.

Step 2: Shift the Conversation

Rather than focusing on retirement, we encouraged the manager to hold a broader career development conversation. This allowed space to talk about future plans, growth, and goals—offering a natural opportunity for the employee to share anything they wanted about retirement plans without feeling pushed.

The manager asked open questions like, “Where do you see yourself over the next few years?” and “Are there areas you’d like to develop or scale back?”—keeping the tone exploratory and supportive.

Step 3: Provide Practical Support

We made sure the employee had access to retirement planning resources, including financial advice, pension information, and optional HR support. Crucially, this was offered to all employees at relevant stages of their career, not just those perceived as being ‘near retirement’.

Step 4: Respect Confidentiality

When the employee later shared some tentative plans about retiring within the next couple of years, this was documented sensitively. The information was treated confidentially and only used for legitimate workforce planning purposes.

Step 5: Plan Ahead Without Singling Out

The business wanted to be proactive, so we enhanced their succession planning. We focused on identifying key roles and developing talent pipelines—without making it about specific individuals or their ages.

Step 6: Check and Balance

Finally, we agreed that if there was ever any doubt about how to approach a similar situation in the future, the manager would check in with HR first. Keeping clear records of career discussions and decisions helped ensure compliance and transparency.

This approach helped the manager feel confident, and the employee felt respected—not singled out. It’s a great example of how good intentions, combined with careful handling, can lead to conversations that are productive for both the business and the individual.