Here are some questions that I use to drive the conversation:
How’s it going? (This is normally a light way to open, but importantly needs to be followed by silence on your side to allow them to speak fully. Awkward silences are great to get other people to talk — remember your job is to hold the ‘space’.) Asking “What does that mean?” as a follow up will help unpack a curt response like “fine”.
What would you like to discuss? Right off the bat give them the opportunity to drive the agenda. Hopefully they’ve brought a couple of agenda points that matter to them.
What have you learnt in the last year/quarter/month? This helps to get a perspective on what’s been important and noteworthy for them — it’s often not what you think
What do you want to learn next? Here you’re listening for where they might want to move in the org or challenges to take on to stay engaged & interested.
Do you feel challenged? Are you growing in your career / becoming more employable? For me this is the most important question. If they’re not feeling like they’re growing in your environment then you have BIG problems. Even a mediocre response here should be concerning
How do you find working with your peers? Do you get enough support? Generally, this question will raise one of the extremes, either someone not pulling their weight or someone who’s gone above and beyond. Trends from multiple people matter here more than individual comments. Be very careful not to create an expectation of culture of ‘ratting on others’ but frame it as areas where you could positively influence.
How could I/management support you better? The answer to this will almost always be positive — to your face — so even a minor negative comment you need to seriously unpack to see how you can address it.
What could we be doing better as a company? What should we change about the way we work, the office, etc? This covers business processes and culture. Here you want to try and not get caught up in the symptoms, but rather look for the underlying cause. This will often raise quick easy wins that you can do too.
What do you think is the worst part of our product? What should we focus on that we’re not? All software will have tech debt and legacy code and often talking to customers helps understand the market need — but talking to your team building it can offer structural changes and red flags that are going to cost you in the future.
Is there anything that you want to know about the company? I typically build radically transparent companies, so I’ll answer these questions as openly and directly as possible. (Salaries of others is the only no-go for various reasons — but that’s another post.) It can be anything from funding and future plans, to an office move or how we’re planning on dealing with a certain issue.
I like PPP-style for larger meetings, but from my POV 1-1s are not primarily status meetings; you can get that kind of content in an email, save your conversations for deeper stuff.
— How’s your relationship with X
— What are you stuck on
— What new things are you starting to think about
— Career conversations
The status update is seductive because it’s easy and useful (for the manager), but I think it’s not the most effective and impactful use of your time.