“Where do you see yourself in five years?”
It’s quite a question when someone is still trying to work out what they want from the next six months. Especially if the honest answer doesn’t fit neatly into the role they already have.
In my conversation with Talitha Cummins on F*ck, I’m Nearly 50!, she talked about moving from journalism into jewellery and learning the practical skills that came with it. She described studying diamond grading, working on the business and feeling frightened along the way. Confidence hadn’t arrived before she began.
There’s something useful there for a career conversation at work. You don’t always have enough information to make a big decision. Sometimes you need an experience that helps you find out.
Get specific about the curiosity
If someone says they want to move into strategy, what interests them about it? Understanding customers? Solving a problem? Having more say in what gets made? Those answers might lead to quite different next steps.
And if someone says they’re bored, I’d want to understand that before suggesting another training course. They might need to learn something. They might need more responsibility. They might be spending most of their time on work they’re perfectly capable of doing but have no interest in continuing.
Being good at something can make it surprisingly difficult to move on. Other people know they can rely on you for it. You know how to get it done. It’s worth asking whether your next development plan is taking you somewhere you actually want to go.
Choose something you can learn from
A small experiment gives you a more useful starting point than another conversation about all the possibilities.
For someone curious about presenting, that might mean taking one part of a meeting with preparation and support. Someone interested in customer research could observe an interview and help make sense of what they heard. Someone considering management could support a new starter on a defined task, with their manager available to help.
Agree what the experience is meant to tell you. Put a limit around it, make time for it and decide when you’ll talk afterwards. A stretch assignment piled on top of a full workload is a poor invitation to grow.
At the review, ask what surprised them. Which part did they enjoy? What was harder than they expected? Would they like another go with more support, or has it helped them realise they’re interested in something else?
Either answer gives you something to work with. You don’t need to turn every experiment into a permanent role change.
There’s a responsibility on the manager here, too. Be clear about what you can offer. If there isn’t a promotion or a new role available, don’t let someone build their plans around a possibility you haven’t discussed honestly.
The connection between a person’s aspirations and the business matters. It deserves more attention than an annual box on a form. A useful next conversation might begin with: “What would you like to try, and what would help you give it a proper go?”
Listen to my conversation with Talitha Cummins and find the free episode guide.
For the With Humans perspective, read Why is connection important? If you’re thinking about development conversations in your business, let’s talk.