Monthly one on one meeting questions, and why monthly needs different ones

Weekly 1-1 questions do not survive a monthly cadence. What is on your mind this week is a fine opener when you met seven days ago. Thirty days later it gets you the last three days, because that is what the person remembers, and the three weeks before that are gone for both of you.

I have run monthly 1-1s with senior people and with reports on other continents, and the meetings only worked once I accepted that a month is long enough for something to start, go wrong, and get quietly resolved without me knowing any of it happened. The questions below are built for that gap.

The month, not the week

• Looking back over the month, what took more of your time than it should have?
• What went well that nobody asked you about?
• What did you decide on your own that you would normally have checked with me?
• What is still open from last month that you expected to be closed by now?
• If you had to describe the month in one sentence to someone outside the team, what would you say?

The third question is the important one. A month of monthly 1-1s means your report made dozens of calls without you. Most were fine. The ones that were not are the ones you want to hear about before someone else tells you.

What changed

• Is anything about the work different from how it was when we last spoke?
• Has anyone's role around you changed in a way that affects you?
• Is there something you were worried about last time that has resolved itself, or got worse?
• What have you started saying no to?

Monthly is the cadence where I lost the thread most often, because a month is exactly long enough for the thing someone mentioned to become the thing someone is upset about. Asking what changed, directly, is cheaper than reconstructing it afterwards.

Load and energy over a longer window

• Which weeks this month were too heavy, and what made them heavy?
• Did you take real time off, and did it stay off?
• What are you carrying right now that should be someone else's?
• Is the on-call or support load this month something you would sign up for again?

With weekly 1-1s you can see tiredness on someone's face. With monthly you cannot, so you have to ask about it as a pattern rather than a mood. One heavy week is a week. Three in a month is a staffing problem with your name on it.

The longer arc

• Looking at the quarter, are you doing more of the work you want or less?
• What would you like to be trusted with by this time next year?
• Is there feedback you have been waiting to give me?
• What have I promised you that I have not done?

The last one is uncomfortable and it is the one I would keep if I could keep only one. A month is plenty of time to forget a commitment, and asking it out loud gets you the list before the person decides you are not going to deliver.

Closing

• What should I know before next month that you have not said?
• What do you want to hear from me next time?
• Is monthly still the right cadence for us, or do you want more for a while?

What makes monthly work at all

Monthly 1-1s fail on memory before they fail on anything else. Four weeks of Slack, releases and other people's problems sit between two conversations, and by the second one neither of you remembers the first precisely. Two habits fix most of it.

First, write three lines after each meeting, dated: what they said, what changed, what is open. Second, keep a running note between meetings. When something about the person crosses your desk in week two, a review that got heated, a nice comment from another team, a day off at short notice, write one line in their file. By week four you have five lines you would never have remembered, and the next 1-1 starts from them instead of from how is it going.

Pick four or five questions from the groups above, not twenty, and lead with whatever your notes say is unresolved. The weekly version of this, with timings, is in the one on one meeting agenda, the full question bank by situation is in one on one meeting questions, and the free 1-1 question generator will pick a set for the situation you are walking into.