There's a great description of how to run a 1-on-1 in High Output Management by Andy Grove.
I like to have them every 2 weeks with a new hire, and every month thereafter. Sometimes, if something comes up midweek that feels like it needs to be addressed, I'll schedule one before that.
Structure--
Location: take a walk or go to a non-work but private space
Ask questions about their general feelings:
- How are you doing?
- How are things in the office? With co-workers?
- Are you enjoying your work? What could make it better?
Ask them for feedback:
- Is there anything that's been on your mind? Any issues either with me or other staff?
- Is there something that we could be doing better in their eyes? What would they change?
Do they have a career goal they are progressing towards?
- What position would you like to be in 1-2 years?
- What can I do to help you get there?
- How do you feel your recent projects have helped in that regard?
Only after I exhaust them and their feelings will I bring up feedback I have for them -- again, with exceptions, if the 1-on-1 was called to handle a specific issue, that will be addressed pretty fast.
I am loathe to take advice from Andy Grove, only because I feel that employment rules of engagement have changed drastically when he was a manager.
In the last 5 years, I've seen the minimum time in Silicon Valley to stay at a job drop precipitously from 2 years (the norm that I'm used to going back 20 years) down to 1 year. I see a lot of jumping around, especially at the more junior end of the spectrum, where total comp can jump by 30-50k in the first 3-5 years of experience.
And young people know this, because everyone shares their salaries and total comp openly. This is a big change from my generation. So they're aggressively leaving after the first year, moving a couple of times and earning a lot more than they would have if they simply stayed at their job for 2-4 years.
One thing young people want is to be mentored aggressively, and for them to get their careers on track immediately. I try to cater to this by meeting with them once a week, to show them that I actually do care about their career path, and also selfishly, in hopes that they don't want to leave within a year and I'm left trying to fill another headcount. If I left the 1:1 to once a month, then I would only see them less than half a dozen times before they've decided they're going to leave.
But if they know that I'm working with them to further their experience, that they're not stuck in a rut and if they stay with me, that they can trust me and they won't get screwed doing all the boring grunt work, then I have a hope they will stay 2+ years with me before they leave.
It is not clear though that the OP is from SV, or indeed what % of people reading this are from SV.
I am not, and although I have hopped a few jobs recently (not due to chasing salary) and it has been 'forgiven' by the market, the usual is still >2yr where I am based.
I like to have them every 2 weeks with a new hire, and every month thereafter. Sometimes, if something comes up midweek that feels like it needs to be addressed, I'll schedule one before that.
Structure--
Location: take a walk or go to a non-work but private space
Ask questions about their general feelings: - How are you doing? - How are things in the office? With co-workers? - Are you enjoying your work? What could make it better?
Ask them for feedback: - Is there anything that's been on your mind? Any issues either with me or other staff? - Is there something that we could be doing better in their eyes? What would they change?
Do they have a career goal they are progressing towards? - What position would you like to be in 1-2 years? - What can I do to help you get there? - How do you feel your recent projects have helped in that regard?
Only after I exhaust them and their feelings will I bring up feedback I have for them -- again, with exceptions, if the 1-on-1 was called to handle a specific issue, that will be addressed pretty fast.