The weekly 1:1 is one of the highest-leverage activities a manager has. Done well, it builds trust, surfaces problems early, accelerates development, and keeps high performers engaged. Done poorly — or reduced to a status report — it's 30 minutes of time neither person can get back.
The difference between a great 1:1 and a mediocre one usually comes down to the questions being asked. Here are five that consistently move conversations from transactional to meaningful.
1. "What's taking up more of your energy than it should right now?"
This is not the same as "what are your blockers?" Blockers tend to surface tactical obstacles — a decision that needs to be made, a resource that's missing. Energy drains are different. They might be interpersonal friction, unclear priorities, work that feels misaligned with someone's strengths, or a low-grade anxiety about the direction of a project.
Asking about energy opens a different kind of conversation. It gives the person permission to talk about what's weighing on them, not just what's in their way. And it often surfaces issues that would never appear in a status report.
When you hear the answer, resist the urge to immediately problem-solve. Sometimes the most useful thing you can do is acknowledge it: "That sounds genuinely draining. Tell me more about what's making it feel that way."
2. "What have you learned in the last few weeks that you didn't know before?"
High performers are learning all the time. This question makes that learning visible — and communicates that you care about their growth, not just their output.
It also works as a diagnostic. If someone struggles to answer this question week after week, it might signal that their current work isn't stretching them. That's useful information. It's an early signal of disengagement that's far easier to address in a check-in than after someone has already started looking elsewhere.
The corollary — "What do you want to learn more about?" — is equally powerful. It opens a conversation about development that feels natural and forward-looking rather than formulaic.
3. "Is there anything I'm doing — or not doing — that's making your work harder?"
This one requires the most psychological safety to answer honestly, which is exactly why it's worth asking regularly.
Most employees won't volunteer feedback upward unless there's a clear signal that it's safe to do so. Asking directly, consistently, and with genuine curiosity creates that signal. It also models the kind of openness you want from them.
When you ask this question, your response to the answer matters more than the question itself. If someone shares that your last-minute changes are making planning difficult, and you become defensive, you've closed the door. If you thank them, ask clarifying questions, and follow up on what you're going to do differently, you've built trust.
Over time, this question shifts the dynamic from "manager who evaluates" to "manager who partners."
4. "What's one thing that would make the next few weeks feel more successful?"
Forward-looking questions are often more useful than backward-looking ones. This question does several things simultaneously:
It helps people clarify what success looks like to them — which is surprisingly rare in most work environments. It surfaces priorities that might not be visible to you. And it creates a natural accountability structure: you can return to this question in the next check-in.
The phrasing "feel more successful" is intentional. It invites both objective and subjective answers — someone might say "shipping the feature on time" but they might also say "feeling less scattered" or "having a clearer sense of what matters most." Both are valid and useful.
5. "How are you doing — really?"
This sounds almost too simple to be useful. It isn't.
The key word is "really." It signals that you're not looking for a reflexive "fine, thanks" — you're genuinely asking. And the pause that often follows the question is where the real conversation begins.
People carry a lot that doesn't show up in their work, and what's happening in their lives affects their work whether either of you acknowledges it or not. This question doesn't require you to become a therapist or cross professional boundaries. It just signals that you see the whole person, not just the contributor.
Often the most honest answer to this question will tell you more about what someone needs from you — and from their work — than any other question on this list.
Putting It Into Practice
These five questions don't all need to appear in every 1:1. Think of them as a toolkit — some weeks one question opens everything up, and you spend the whole time there. Other weeks you move through several.
What matters is that you're asking questions designed to learn something, not just to check boxes. The best 1:1s feel like conversations between two people who both want the same thing: work that's meaningful, relationships that are honest, and growth that's real.
That's worth 30 minutes a week.
Waypoint Culture's check-in templates give managers a structured starting point for every 1:1 — so the conversation can be focused on what matters, not on figuring out what to say.