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The clearest sign a one on one is broken is that nobody minds when it gets cancelled. You push it for a discovery, your assistant says no problem, and three weeks later she hands you a resignation letter that lists four things you could have fixed in April. None of them were secret. You just never built a place for them to come out.
A good recurring one on one is that place. Done right, it is the cheapest retention tool a small firm has, cheaper than a raise and far cheaper than a search. Done as a weekly status recap, it is a waste of a calendar block that both of you resent. The difference is not effort. It is who the meeting is for.
It Is Their Meeting, Not Your Status Report
Most one on ones fail because they are secretly a project review wearing a friendlier name. You run down your list, ask where the factum is, confirm the filing went out, and call it a check in. That is a fine conversation to have, but it is your meeting, about your worries, and your staff can feel it. They give you the answers you want and save the real stuff for the drive home.
Flip the ownership. This is their thirty minutes to raise whatever is on their mind, and your job is mostly to listen and remove obstacles. The status of the docket lives somewhere else, in your matter list or your practice management tool, not in the one slot a week where a person gets your full attention. If you already track work in a system you trust, you do not need to spend this time reciting it back to each other.
Tip. Let the other person set the first agenda item. A simple shared note where they jot topics during the week beats any template you impose, because it is already theirs before you sit down.
The Three Questions That Open People Up
You do not need a facilitation certificate. You need three questions you actually ask, and then the discipline to be quiet afterward. These three work in almost any legal workplace.
- What is slowing you down right now? This surfaces the paper cuts: a broken template, a partner who never returns edits, a login nobody set up. Individually small, collectively the reason good people leave.
- What is something you want to be doing more of, or less of? This is where you learn the clerk wants to run files, or the receptionist is quietly drowning in intake. Growth and burnout both show up here.
- Is there anything I should know that I probably do not? The catch-all. Ask it every time and eventually people believe you mean it, and that is when the useful answers arrive.
After you ask, stop talking. Count to five in your head if you have to. The silence feels long to you and normal to them, and the thing they say to fill it is usually the point of the whole meeting.
The real issue almost never arrives in the first sentence. It arrives after the silence you were too uncomfortable to leave. A managing partner who learned this the hard way
Write It Down or It Never Happened
Here is the failure mode that quietly kills trust: your assistant raises the same thing three meetings running, you nod warmly each time, and nothing moves. From your side you had a nice chat. From hers you now know that talking to you accomplishes nothing, so she stops.
Keep a running shared document, one per person, that both of you can see. Two columns are enough: what was raised, and who owns the next step. It does not need to be fancy. It needs to be visible to the person who raised the item so they can watch it move.
| Raised | Owner | Status |
|---|---|---|
| Precedent bank is out of date | Me | Reviewing this week |
| Wants to draft simple retainers | Both | Trial run on next file |
| Overtime around trial season | Me | Discuss at comp review |
That last row is a good example of a topic you do not resolve on the spot. You are allowed to say this belongs in a proper compensation conversation, log it, and come back to it. What you are not allowed to do is let it evaporate.
Following Up Is the Whole Point
The meeting is not the deliverable. The follow through is. If you take one habit from this piece, make it this: open every one on one by walking through last time's list before you touch anything new. Thirty seconds of you moving items forward teaches more about whether these meetings matter than any speech about your open door.
Follow up cuts both ways. When your staff commits to something, note it kindly and check on it too. That is how a one on one becomes real accountability instead of a venting session, and it is why these meetings and honest two way feedback reinforce each other. It also gives you a running record of growth that makes a hard conversation, if one ever comes, fair rather than ambush.
Note. A one on one is not a substitute for onboarding structure. A new hire still needs clear first week expectations and a plan for the months after. The one on one is where you find out whether that plan is actually working.
What to Do When There Is Nothing to Talk About
Some weeks the list is short and the honest answer to your three questions is a shrug. Do not fill the space with invented problems, and do not cancel on a streak of good weeks, because cancelling is exactly what trains people that the meeting is optional. Instead, use the quiet time for the conversations you never otherwise make room for.
Ask where they want to be in two years. Ask what part of the work they would happily never do again. For an internationally trained lawyer working toward accreditation, ask how the licensing process is fitting around the job and whether the schedule is survivable. Slow weeks are when you invest in the relationship, so that in a hard week the person already trusts you enough to tell you the truth fast.
None of this requires a new app or a course. It requires a recurring block you refuse to cancel, three questions, a shared list, and the follow through to prove the list is real. Guard the time, keep the notes somewhere you both can see, and the meeting stops being one more thing on the calendar. It becomes the half hour where you find out what is actually going on in your firm, back when you can still do something about it. If you want more on the same theme, the rest of our people and hiring writing and my other posts pick up where this one leaves off.
