As has become the tradition, a moment to clarify a definition or two:
A 1on1 is a meeting on a regular basis (whether it's weekly, bi-weekly, monthly, quarterly, etc.), and is ideally held as often as possible. I default to weekly for newer relationships and then move to twice-monthly. It is a chat either in-person or via video chat between a supervisor and their direct report.
A skiplevel is effectively a 1on1 between a supervisor and an employee who is one or more levels below them. This meeting is skipping levels of management, thus "skiplevel". It is good for all parties involved as it allows reps to know their boss' boss, it allows leadership to truly know their ICs (Individual Contributors), and keeps culture and communication flowing. If you, as a leader, have employees one or more levels removed from you, you should be conducting skiplevels on an ongoing basis and to stay ahead of them, I suggest spreading them out so that you just do a few a week.
Cross-team syncs (also, confusingly, sometimes called 1on1s) with coworkers or peers can happen with any level of person: directors with ICs, directors with directors, ICs with ICs, etc. These can happen at any time on ad-hoc bases or as regularly scheduled meetings. Again, this is helpful for regular culture and communication as well as for issue sharing.
In each of these cases I am limiting the scope and speaking only about the sorts of meetings or discussions in which one person is meeting with one other person (as opposed to standups or some other variation).
Now . . . There are so very many books, articles, thought pieces, videos, seminars, and so on that abound about the various ways in which you can or should have a 1on1 with your employees.
All of which is to say that there is no definitive right or wrong way to have one.
Actually, that's not correct. There IS a definitively wrong way to have a 1on1, that is if you don't have one at all.
I would argue that the second worst way to have a 1on1 is to make it only about the job that the representative is doing (or not doing). If you meet up with your employee and only go over their numbers, then the employee is not receiving any true benefit or coaching. This is the epitome of a meeting that could have been an email, or worse yet: a meeting that could have been a dashboard.
1on1s should be time for the EMPLOYEE. They are dedicated times for that person to spend with a member of leadership who they may not necessarily know well. To ask questions about the company, the department, their job, or even generally get advice about a tricky situation that they're facing.
It's important to remember that even though it may not feel like it sometimes, you are likely considered an expert in your field. If you are in charge of others, you have demonstrated that you have enough expertise to guide folks to success and it is very much your responsibility to do so.
So with those admonitions of what not to do, what SHOULD you do? Excellent question.
My way of doing 1on1s is actually extremely simple:
1) Set the expectations from the beginning with all direct reports/skiplevels that this is how it's going to be. If they know in advance then they'll be more likely to bring things to the table.
2) Bring any and all "concerning" issues to the person immediately throughout the day/week/month. DO NOT under any circumstances wait until that meeting. They should have confidence that their time is a "safe place" that they can look forward to without anxiety.
Pro-Tip: Ask them to do the same for you. If they have any problems, tell them to bring them to you and to not sit on them until their 1on1. It will help empower them, and you'll feel better knowing that everyone is explicitly welcome to bring problems to you any time.
3) If you do not have a dashboard for metrics already that they can proactively check themselves, review metrics with the rep in the first couple of minutes. Get it done quickly, spending no more than 30% of the meeting on it unless there has been a history of metrics-related issues, in which case your coaching should focus on the areas of concern.
4) Then turn it over to them. Whatever they want to talk about, it's their time. It can be anything work related. It can be personal (within reason). It can be in relation to their career path. Or they can vent about a customer interaction.
Pro-tip: If it DOES get too personal, let them know "Hey, I can tell this is important, but I think this is outside my wheelhouse (or outside of work appropriate or not something we should be talking about)." You can then redirect to something else OR you can ask if they'd like you to help them find someone else to talk to.
I do not personally do so, but I have worked with other leaders who ask their reps to submit a list of topics that they'd like to chat about before their 1on1 so that they can prepare as need. I can see the benefit, but I prefer to let the conversation flow.
5) The last stage is the only one that really sucks. You’ve gotta take notes. Every 1on1 and every skiplevel needs to have notes about what metrics were discussed, what topics were discussed, and how the employee responded to everything.
Pro-Tip: KEEP IT TO FACTS. This is bad: "John and I talked about the high queue. He is pissed that we haven't hired and I think he is looking for a new job." This is better: "John and I discussed the high queue. At multiple points he explicitly stated that he is upset that we have not yet hired additional representatives, and has implied that he may start looking for other employment."
"So," I hear you ask . . . "What about those syncs you were talking about?"
Good question, theoretical reader!
The thing about syncs is that they are largely similar, the only major difference being that you're not working with an employee. That difference is HUGE of course, but that's still just about it.
1) Communicate about how you like to run syncs.
2) Let them know that you'rll get in touch immediately if you have any concerns about their teams and ask them to do the same for you and your team.
3) Share your team's metrics proactively and make sure that THEY KNOW where to find them at all times. Again, if you don't have a dashboard, think about setting one up, but spend just the first few minutes discussing them on each side.
4) Spend the rest of the time discussing OTHER things. This is the opportunity for you to get an idea of what is going on throughout the company and ensure that you've got positive relationships throughout. It's how you're going to be able to get work done no matter how sideways things may go. This is politics, but it's the least part of it and sadly you're going to have to take part in it to some extent or another.
5) This one may be a bit controversial, but take some notes. Don't write ANYTHING down that you wouldn't want anyone else to read and don't keep it on official equipment/systems, but if you want to be able to keep things straight then you need to be able to remember things. However you need to record things, whether it's a system of text files in your phone or a personal notion account . . . whatever works for you. Keep track!