Those are things you can discuss. Describing them gives someone a clearer picture of the role than asking them to be more independent and hoping you both mean the same thing.
Describe what self-management looks like in the role
I need people who can receive direction, go learn what they need to learn, and keep their curiosity connected to the work we are doing. I can give thoughts, ideas, and direction. I also need someone to take responsibility for making progress from there.
That describes a working relationship. Different roles need different amounts of instruction and support, and people bring different experience to them. Be specific about the relationship you need and the support you can provide.
In a hypothetical small business, an assistant is asked to find a replacement for packaging the usual supplier has discontinued. The business needs packaging that fits the product, can arrive before existing stock runs out, and stays within an agreed cost range.
The assistant can check the current specifications, review possible suppliers, and compare suitable options. Before an order is placed, the owner will review the recommendation. That gives the assistant a useful piece of work to manage and a clear point where the decision returns to the owner.
Explain the progress someone can make independently and the decisions they need to bring back to you. Include where they can find information, what a useful result looks like, and when you need it. Then ask them to describe how they understand the assignment. You may hear a question that shows where your explanation needs more detail.
Look at how the person handles an unfamiliar part
When you are considering someone for a role, ask about a piece of work they had to learn how to do. What did they check first? Where did they find help? What did they try, and how did they decide they needed another person's input?
Listen for what they actually did. A description of the sources they consulted, the question they asked, or the correction they made gives you something to explore further. Ask how the work turned out and what they would do differently now.
That conversation gives you part of the picture. As someone begins working with you, observe how they approach an agreed task after they have the information and support it requires. Their behavior in that setting gives you more to discuss than a general impression that they seem confident or hesitant.
Look for useful action within the assignment, including knowing when to ask for help. In the packaging example, the assistant might discover that two suppliers use different measurements. Asking which measurement is critical to fit could prevent an unsuitable recommendation. That is a question that helps the work move forward.
A person who has asked for clarification may be taking care of the work. Find out what they need before treating the question as evidence that they cannot manage themselves.
Keep curiosity connected to the result
The assistant could spend time researching a whole new ordering system. It might be interesting, but the packaging shortage still needs an answer. The value of the research depends on whether it helps with the responsibility they were given.
Discuss how much investigation is appropriate and when to bring back what they have found. A useful update could include the suitable options, what remains uncertain, and a recommendation with the reasons behind it. If the original requirements cannot be met, that is information the owner needs while there is still time to choose another approach.
Self-management includes keeping the purpose of the work in view while deciding what to do next. Someone can pursue an answer, recognize a limit, and return with a focused question. They can also stop pursuing an interesting possibility when it takes them away from the agreed result.
Make room for that kind of judgment in the way you respond. When someone brings a recommendation, talk through the reasoning. If a boundary was unclear, clarify it. If they needed information that was unavailable, address that gap. The conversation should help both of you understand what the next similar task will require.
Compare the role's needs with the support you can give
If the work repeatedly stalls, review a specific example together. Was the result clear? Did the person have the necessary information, access, and preparation? What did they do when they reached an unfamiliar part? What support would help them proceed?
You may find a skill to develop, an instruction to clarify, or a decision you have kept out of reach. You may also find that the role needs more direction than you are able to provide. Those possibilities deserve examination before you decide whether the working arrangement fits.
Be honest about the support a person needs and the support the role will receive. Someone may do excellent work with close instruction while a different role calls for more independent investigation. Discussing that difference helps you make a decision about the work without turning it into a judgment of the person.
For the next responsibility you hand over, explain what the person can investigate and decide, what you need them to bring back, and when help is available. Then pay attention to how the two of you work through it. That is where the meaning of “manage your own work” becomes something you can both understand.