A check-in is the conversation in which a manager and an employee look at the person's work against what their role expects, agree where they stand, and decide what to work on next. Done well, it is the most useful hour either of them spends that quarter. Done badly, it is a status meeting with a form attached.
This guide covers how often to hold check-ins, how to prepare, how to structure the conversation and which questions to ask. It works for any team — support, sales, engineering, design, operations — as long as each role has written expectations to measure against. If yours does not yet, start with how to build a career ladder.
Check-ins, 1:1s and annual reviews
Three conversations tend to get mixed up:
- The regular 1:1 is about the work in front of you: priorities, blockers, how the week went. It happens weekly or every other week and rarely needs preparation.
- The career check-in steps back from the week. It asks how the person is doing against the expectations for their role, where they are strong, where the gaps are, and what they will do about them. It happens every few months and both sides prepare for it.
- The annual review is a check-in with a verdict attached — often a rating that feeds pay. In many small companies it is the only career conversation of the year, which is the problem: twelve months of work squeezed into one meeting, judged on what the manager happens to remember.
Keep the first two separate. If you fold career questions into the weekly 1:1, urgent work wins every time and the career part never happens.
In LadderKit they stay apart: a 1:1 record holds the week's notes and follow-ups, a check-in the career conversation.
How often to run them
There is no single right cadence, but there is a sensible default for companies of 20 to 200 people.
| Conversation | How often | Length | Preparation |
|---|---|---|---|
| 1:1 | Weekly or every two weeks | 20–30 min | None, or a shared list of topics |
| Career check-in | Every three to four months | 45–60 min | Self-assessment and manager review |
| Promotion | When a case is ready; standards reviewed once or twice a year | — | A written case drawing on check-ins |
Quarterly works for most teams. It is frequent enough that a gap spotted in one check-in can be visibly closed by the next, and rare enough that each one has something new to discuss. Slow-moving roles or very senior people can go to three a year; someone new in the role or recently promoted benefits from a first check-in after two or three months.
Whatever you choose, make it predictable. Put the next check-in in both calendars at the end of the current one, so it never depends on someone remembering.
Before the meeting: the self-assessment comes first
The single change that most improves a check-in is asking the employee to assess themselves before the manager does.
- The employee goes through every skill or competency their role expects and rates themselves against it — for example working towards, meeting or exceeding the level — with a sentence or two of evidence: a project, a situation, a piece of work.
- The manager then reviews, skill by skill, next to the self-rating, and writes a short summary: the main strengths, the one or two areas that matter most, and an overall view.
- The manager shares the review a day or two before the meeting. Nobody should read their manager's assessment for the first time across the table.
Going first gives the employee their own voice in the record and shows the manager how they see their role. Sharing in advance means the hour goes on the conversation rather than on reactions.
A three-point scale is enough. Five or ten points invite arguments about whether something is a 6 or a 7; three points force the question that matters: is this at the level the role expects, or not yet?
A structure for the conversation
A 45-minute check-in, in five parts:
- Open (5 min). How the person is doing generally, and what they most want to get out of the conversation. Write their answer down; come back to it at the end.
- Look back (10 min). What went well since the last check-in, what was harder than expected, and what happened to the actions agreed last time.
- The gaps (15 min). Go through the skills where the two ratings differ, or where either side rated "working towards". For each, agree what the difference really is, with an example.
- Looking ahead (10 min). What the next level asks for, which one or two skills to focus on, and what the person will actually do — written as concrete actions with dates.
- Close (5 min). What the manager will do to help, feedback for the manager, and the date of the next check-in.
Leave strengths in. A conversation that only covers gaps leaves people feeling judged; naming what someone does well, and asking how they can do more of it, is as useful for growth as fixing weaknesses.
Check-in questions to ask
Pick five or six per check-in — not all of them. Rotate them, so the same conversation does not repeat four times a year.
Looking back
- What are you most proud of since our last check-in?
- What took more effort than you expected, and why?
- Which of the actions we agreed last time did you finish? What got in the way of the others?
- What did you learn that you did not know three months ago?
Against the role
- Which skill did you find hardest to rate yourself on, and why?
- Where did you rate yourself differently from me? What did you have in mind?
- Which part of your role do you think I underestimate?
- Which expectations for your level feel unclear or out of date?
Growth and the next level
- Reading the next level's expectations, which one feels furthest away?
- What would you need to have done, a year from now, to feel ready for the next step?
- Are you more drawn to going deeper in your specialism or to leading people? Has that changed?
- Which piece of work coming up would stretch you in the right direction?
- Who in the company does something you would like to learn from?
Energy and obstacles
- What part of your work gives you the most energy at the moment? Which part drains it?
- What is slowing you down that you have not mentioned yet?
- Is there anything about how the team works that you would change?
Feedback for the manager
- What could I do differently to help you more?
- Is there anything I do that gets in your way?
- Do you get enough feedback from me between check-ins?
Closing
- What are the two things you will focus on before our next check-in?
- What do you need from me, and by when?
- Is there anything we did not talk about that we should have?
For the employee, the same list works in reverse: bring two or three of your own, especially "what would I need to show to be at the next level?" A check-in is not only the manager's meeting.
After the meeting: write it down and turn gaps into actions
Within a day, the manager completes the record: the agreed view of each skill, the summary, and what was decided. Once it is signed off, it should not change — next quarter you will want to compare against what was actually said, not against a version edited afterwards.
Then turn the gaps into growth actions: one to three concrete things the person will do, each with a due date and, where it fits, the skill it targets. "Improve stakeholder communication" is not an action; "run the monthly customer review call for the Nordics accounts, starting in November" is. The guide to writing an individual development plan covers how to word them, with examples for several roles.
If you want input from beyond the manager, ask one or two colleagues who work with the person for written feedback before the next check-in, rather than relying on the manager's impression alone.
In LadderKit, a check-in starts pre-filled with the skills the person's role requires, keeps both sides' ratings side by side and locks once completed; growth actions can be raised straight from the skills that need work.
Example: a quarterly check-in in customer support
Maria is a Support Specialist at level 2 of the customer support ladder. It is her second quarterly check-in.
Self-assessment. She rates herself meeting on issue resolution and customer communication, exceeding on product and technical knowledge — she has become the person others ask about billing configuration — and working towards on support operations.
Manager review. Her manager agrees on three of four. On product and technical knowledge he rates meeting: the billing expertise is real, but the level 3 expectation is that others can rely on it without asking her, and nothing is written down yet.
The conversation. Most of the 45 minutes goes on that one difference. Maria points out she answers four or five billing questions a day from colleagues. Her manager agrees that is exactly what level 3 looks like — and that the step from 2 to 3 is to make it scale. They agree on two actions:
- Write internal notes for the five most common billing issues by the end of next month.
- Run one 30-minute session for the team on billing configuration before the next check-in.
Next time. The next check-in starts with those two actions. If they are done and the notes are being used, product and technical knowledge moves to exceeding — and becomes evidence in a promotion case.
Common mistakes
- Skipping the self-assessment. The meeting turns into the manager reading out a verdict.
- Surprises. Anything critical in the review should have been mentioned in a 1:1 already. A check-in is a summary, not an ambush.
- Discussing every skill at equal length. Spend the time where the ratings differ or where growth matters most.
- No actions, or ten of them. Leave with one to three concrete actions with dates.
- Mixing in pay. Once money is on the table, the conversation becomes a negotiation. Keep pay decisions in their own process, separate from check-ins.
- Cancelling when things get busy. Moving it by a week is fine; dropping it tells people their growth comes last.
- Not following up. If the actions from last time are never mentioned again, people stop taking them seriously.