Most 1:1s fill up with status questions — "how's the project going?", "any blockers?" — which are useful for task management but almost never open up a real conversation. If your 1:1 feels repetitive, it's probably because the questions are designed to gather information, not to start a conversation.
These five are designed for the second thing.
1. "What are you not telling me because I haven't asked the right way?" People rarely answer this the first time they hear it — it needs to be repeated across more than one 1:1 before they trust that the question is real. But when they do answer it, it's often the most valuable thing in the entire conversation.
2. "What part of your work is costing you more energy than it should?" This isn't the same as "what's difficult for you?" This question separates necessary effort from wasted effort — and there's almost always more of the latter than the person themselves had noticed.
3. "What's a recent decision of mine you didn't fully understand?" They're going to avoid answering this directly the first time. Push gently, calmly. Decisions that aren't understood don't disappear — they turn into quiet resentment or half-hearted execution.
4. "What do you need from me that you're not asking for?" Most people don't ask for what they need because they don't want to seem like they can't handle it alone. Asking directly gives them permission.
5. "What's actually working that we haven't named?" The average 1:1 is pure problem diagnosis. This question closes with something real to reinforce — and without it, the whole conversation ends up feeling like a list of what's wrong.
You don't need to use all five in every session. It's enough to pick one, ask it calmly, and leave real room for the silence that follows — because the best answer almost always comes after the uncomfortable pause, not before it.
Which of the five haven't you asked your team in months? Reach out or start with the leadership assessment.