Chatting with someone senior outside a meeting can feel high stakes. It doesn’t need to be. Most managers enjoy a normal conversation, and a good relationship with them makes work far easier.
Treat them like a person
They have weekends, hobbies and kettles that won’t boil, just like you. Start with the moment, not the job.
Use the in-between moments
The elevator, the walk to a meeting room, the minute before everyone else joins a call. Short, natural gaps are the easiest places for a friendly word, with an end built in.
Keep updates short and honest
If they ask about your work, give a sentence or two, with a little humor. It’s a chat, not a status report.
Ask what they think
“What made you pick that project?” or “What was your first job here?” Most people enjoy being asked about their thinking and their story.
Remember the small things
Their trip to Lisbon, their daughter’s soccer final, the half marathon. Asking about it next week shows you listen, which matters as much to managers as to anyone.
Don’t gossip upwards
Small talk with your boss is not the place to complain about a colleague. Keep it about the moment, the work and their life. Real problems belong in a proper conversation.
Save the big asks
Promotions, pay and problems deserve a proper meeting. Bringing them up by the kettle can feel like an ambush.
Invite them in
If the team has a lunch or coffee habit, invite them. Some will say no, but many will be glad to be asked. There’s more on the wider team in How to Make Friends at Work.
On a video call
The minute before others join is small talk too: the bookshelf behind them, the weather where they are, the dog that just walked through. How to Make Small Talk on a Video Call has more.
When you run out of things to say
Ask for a recommendation: a book, a podcast, somewhere for lunch near the office. People like being asked, and it gives you an easy next conversation: “I tried that ramen place you mentioned. You were right.”
Lines to borrow
- By the kettle: “This kettle gets slower every week. Busy morning?”
- In the elevator: “Any plans for the weekend, or a quiet one?”
- After a big meeting: “I thought that went well. What did you make of the client’s last question?”
- When they ask how work is going: “Busy, but good. The launch is on track, and I’m learning a lot from it.”
- On a Monday: “Good weekend? I spent mine failing to put up one shelf.”
Practice it
The Office Kitchen practices a kettle that won’t boil with the head of your department. The Work Lunch practices getting to know a new colleague over lunch, and the At work deck in Read the Signal tests your read on managers, colleagues and clients.