In a small business, the one-on-one is often the only time an employee gets the owner's full attention without a customer, a supplier or a crisis in the room. That makes it one of the most valuable 30 minutes in the week, and one of the easiest to waste.
The usual failure is not a lack of questions. It is asking the same one every time, "how's it going?", getting "fine" back, and spending the rest of the slot on a status update that could have been read from the task list.
This post collects the one-on-one meeting questions worth asking, grouped by what you are actually trying to find out, and a simple 1 on 1 meeting agenda that keeps the meeting about the person rather than the work.
What a one-on-one is for
A one-on-one is not a status meeting. Status belongs in the task list and the weekly team meeting. The one-on-one is for the things that do not come up anywhere else:
- How the person is actually doing, at work and around it
- What is getting in their way, including things they would not raise in front of the team
- Where they want to grow, and whether their work is taking them there
- What you could do better as their manager or employer
The simplest rule that makes this work: it is their meeting. They bring the agenda first. Your items come second.
A simple 1 on 1 meeting agenda
30 minutes, weekly or fortnightly, same slot each time.
## 1:1 — [name] — [date]
## Their items (first, and most of the time)
- [Whatever they added beforehand]
## How are things (5 minutes)
- [1 or 2 questions from the list below]
## My items (short)
- [Feedback, context, anything you need from them]
## Growth (monthly, not weekly)
- [Where they want to be, and what would help]
## Actions
- [ ] [Verb + task] — [owner] — [date]
## Carried over from last time
- [Anything not finished]
Keep the notes in the same place every week, so you can see last time's actions before you start. Nothing damages trust in one-on-ones faster than the manager forgetting what they promised.
One-on-one meeting questions
You do not need all of these. Pick 1 or 2 for the "how are things" section, and rotate so the meeting does not feel like a survey.
To find out how they are really doing
- What has been the best part of your week? The worst?
- On a scale of 1 to 10, how are you finding the work at the moment? What would make it one point higher?
- Is there anything outside work that is making things harder right now?
- What is taking more energy than it should?
To find what is in the way
- What is slowing you down that I might not know about?
- If you could remove one task from your week, which would it be?
- Is there a decision you are waiting on from me?
- Where are you spending time on something you think is a waste?
To understand the work
- What are you most proud of from the last few weeks?
- What is the part of your job you think I understand least?
- Is there anything you are doing that you are not sure is the right priority?
- What would you change about how we do [a specific process]?
To talk about growth
- What would you like to be doing more of in 6 months?
- Is there a skill you would like to build that this job could help with?
- What part of the business would you like to understand better?
- What is something I do that you would like to be able to do?
To get feedback on yourself
These are the hardest to ask and the most useful. Ask one every few weeks, and never argue with the answer.
- What is one thing I could do differently that would help you?
- Is there anything I do that makes your job harder?
- Do you get enough information from me to do your job well?
- Is there something you have wanted to tell me but have not?
How to make one-on-ones work in a small business
Never cancel, only move. If something comes up, move the slot, do not drop it. Cancelling one-on-ones tells the person that everything else is more important than them, and in a small business they will notice.
Their agenda first. Ask them to add items before the meeting. If they have nothing, that is fine, and it is a good time for a growth question.
Keep the status out. If you catch yourself asking "where are we with the Henderson order", stop. You can read that. Ask what is making the Henderson order hard instead.
Write down what you promise. Every action you take on, you track with a date. Owners are especially prone to agreeing to things in one-on-ones and forgetting them the moment a customer calls.
Growth monthly, not weekly. Asking about career goals every week gets tiring. Once a month is enough.
If you are the owner, say so. In a small business the manager is often the person who pays the wages, which makes honesty harder. Acknowledge it: "I know I'm also the one who signs your contract, and I still want to hear the bad news."
Running one-on-ones in EvyOS
A one-on-one lives in 3 places: the recurring slot, the running notes and the actions. In EvyOS those are a calendar event, a note per person and tasks.
Keep one note per person in a shared or personal folder and add each meeting to the top, so last time's actions are right there when you open it. In a shared workspace, the actions become tasks assigned to whoever owns them, including you, with the date you agreed. If you want the person to add their own items beforehand, keep the note in the workspace where both of you can edit it.
The run one-on-ones template installs this setup: a weekly slot per person, their agenda before yours, and notes that carry over. For small business owners delegating more work through these conversations, our guide to delegating tasks covers the handover.
The short version
A one-on-one is their meeting, not a status update. Let them bring the agenda first, ask 1 or 2 real questions about how they are, what is in their way and where they want to grow, and ask for feedback on yourself every few weeks. Write down every promise you make, and never cancel the slot, only move it.
Set up a workspace for your team, or see how EvyOS works for teams.