Most one-on-ones start the same way: "So... how's everything going?"
And most responses are equally predictable: "Fine. Busy, but fine."
Then you both sit there, trying to fill the next 25 minutes.
Why One-on-Ones Matter
One-on-ones should be the most valuable meeting on your calendar. They're where trust gets built, where problems surface before they explode, and where people actually feel heard.
But without intention, they become status updates that could've been a Slack message. Or worse, they get cancelled because "nothing urgent came up."
The difference between a great one-on-one and a forgettable one usually comes down to one thing: the questions you ask.
What Makes a Good Question
Good one-on-one questions share a few traits:
They're open-ended. "Are you doing okay?" gets a yes or no. "What's been on your mind lately?" opens a door.
They're specific enough to be useful. "How's the project?" is vague. "What's the biggest risk you see with the timeline?" gives someone something concrete to respond to.
They signal that you care. Questions like "What's something you're proud of that I might not know about?" show you're interested in more than just deliverables.
They create space for honesty. "Is there anything I could be doing differently to support you?" invites feedback that people might not volunteer otherwise.
Questions Worth Asking
For building trust:
- What's something on your mind that we haven't talked about?
- Is there anything you've been hesitant to bring up?
- How are you feeling about work lately, really?
For career growth:
- What skills do you want to develop this quarter?
- Where do you see yourself in a year? Does your current work align with that?
- What's a project or responsibility you'd love to take on?
For removing blockers:
- What's slowing you down right now?
- Is there a decision you're waiting on that I could help with?
- What's one thing that would make your day-to-day easier?
For feedback (both directions):
- What's one thing I could do differently as a manager?
- Is there feedback you've been wanting to share but haven't found the right moment?
- How do you prefer to receive feedback?
Context Changes Everything
The questions you ask depend heavily on who you're meeting with. A skip-level conversation is different from a direct report check-in. Meeting with your own manager requires a different approach than meeting with a peer.
A new team member needs questions focused on onboarding and clarity. A senior engineer might benefit more from questions about autonomy and long-term growth.
A Tool That Can Help
If you're ever stuck on what to ask, there's a free one-on-one question generator that can help. It works for engineering managers, product managers, or really any manager running 1:1s.
You select the context (direct report, your manager, skip-level, peer), choose a focus area, and it generates tailored questions using AI. You can even add additional context about your specific situation to get more focused suggestions.
Use it before your meeting to prep, or pull it up during the conversation when you want to go deeper. No signup required.
Making It a Habit
The best one-on-ones aren't about having perfect questions every time. They're about showing up consistently, being genuinely curious, and creating a space where real conversation can happen.
A few principles that help:
- Protect the time. Cancelling signals that it's not a priority.
- Let them drive. The best 1:1s are owned by the other person, not you.
- Skip the status updates. You have other channels for that.
- Follow up. If someone shares something important, remember it next time.
The Real Goal
At the end of the day, one-on-ones are about connection. They're a chance to understand what someone is dealing with, what they care about, and how you can help.
The questions are just a tool to get there.
What questions have worked well in your one-on-ones? Always looking for new ones to try – share yours in the comments.
Top comments (3)
I always have a few pre-made questions ready to go for my one on ones. I find it can make a huge difference getting to know each other. I find I always learn something new, even with the engineers I've been working with for years.
Check out Kollabes question generator, it makes it really easy to do. Even during the meeting if you forget.
I’m going to try this!