A working life contains decisions that changed a company, risks that did not pay off, people who were shaped by their mentoring, and knowledge that exists nowhere except in one person’s head. Almost none of it gets written down. Retirement is the natural moment to fix that, for the family, for the business, or for both.
Decide whose story it is
There are three different books here, and it helps to pick one. A personal career story for the family. A founder’s story of how a business was built. Or an institutional record for the company itself, capturing how things came to work the way they do. They overlap, but the shape and the audience differ.
What to ask
- What did you want to be before you knew this job existed?
- How did you actually get your first role?
- What did a normal day look like in your first decade, and how had that changed by the last?
- What is the decision you are proudest of?
- What went badly wrong, and what did it teach you?
- Who mentored you, and who did you mentor?
- What did you know that nobody wrote down?
- What was the hardest conversation you ever had at work?
- What changed in your industry over your career?
- What did the work cost you, and what did it give you?
- How did you know it was time to stop?
- What would you tell someone starting out now?
Gather the other voices
A career story gets much richer when colleagues contribute. Ask a handful of people who worked with them at different stages for one memory each, and for the thing they would say about them if the person were not in the room. Gather these yourself beforehand, because the story is told to Sage by one person, who can then bring the collected memories into the conversation. Done quietly, it also makes an excellent surprise element for a retirement presentation.
Do it before the last day, not after
People are more forthcoming while the work is still current. Once someone has retired, the detail softens surprisingly quickly, and the specifics that make the story worth reading are the first to go. A few weeks before is better than a few months after.
Writing it up
Doing it yourself
- Interview them and any colleagues, and record it.
- Transcribe and edit into a readable narrative rather than a CV.
- Chase and format the contributions from colleagues.
With Chapternity
- Sage interviews them the way a business biographer would.
- It writes the result into chapters with real narrative.
- Extra copies cost less, so the family and the team can each keep one.
Frequently asked questions
- What should you ask someone about their career before they retire?
- Ask how they actually got started, what a normal day looked like at the beginning compared with the end, the decision they are proudest of, what went wrong and what it taught them, who they mentored, and what they knew that was never written down.
- Is a career story a good retirement gift from colleagues?
- It works well, particularly when several colleagues have each offered a memory beforehand. One person tells the story to Sage, so collect the contributions first and they can be woven in as the story is told. It honours the whole arc of a working life rather than just the leaving date, and the family usually values it as much as the retiree does.
Explore more guides or read about career storys.