The more honest and frequent communication you have with your team, the better you will all handle the day-to-day struggles of work—not to mention any unpleasant surprises that come your way. Regular, private, one-on-one meetings give you the opportunity to communicate goals, concerns, and feedback in an honest and open setting. As a manager, this practice can make you and your team much more effective.
If everyone sits together on the same floor in the same building, having a one-on-one is as simple as grabbing an open conference room (or a coffee or a snack) and having a conversation. With remote coworkers, you must put in more effort.
Make the Conversation Private
Trust is essential to good one-on-ones. Trust takes time and work. Getting called in to your boss's office once in a while, out of the blue, where everyone can see you talking can be awkward. You want to avoid that situation with your team, and you need to foster that trust.
Step one is to allow the one-on-one conversation to happen in a private, honest, trustworthy place. This means that both of you need a quiet, private room where there's no eavesdropping. There's no one surprised that it's a conversation between two individuals.
It should be obvious—though it's not always so obvious in practice—that minimizing distractions is essential to good conversation. Having your partner walk behind you in your home office to do laundry while you're giving constructive (but difficult) feedback is an awkward situation. Similarly, trying to pay attention to your conversation partner over the noise of coffee shop bustle in the background can be distracting.
You'll need to put in the work to find a rhythm and pattern of location and timing where you can have a good, quiet, private, honest conversation. This could take weeks or months, but it's a foundation of a good, honest, trustworthy working relationship between the two of you and the whole team.
While regular one-on-one communication with each person who reports to you directly is essential and regular one-on-one communication with each person who reports to them (as applicable) is useful, everyone handles these conversations differently. Some people need half an hour every week. Others can get by with five minutes every once in a while, and still others need time every day. These schedules can and will change; be ready for it.
Schedule the Conversation With Care
If you're managing people remotely, you're probably depending on your shared calendar to coordinate your schedules. In that case, be sure to give your remote employees plenty of advance notice for all one-on-ones. Because you may not be in the office together at the same time (and may, in fact, be several time zones apart), you can't always predict when someone has to drop children off at school, commute to a co-working space, pick up a prescription for a family member under the weather, visit the DMV, or do anything else. When possible, set your meeting at least one working day in advance to allow for schedule changes.
The more reliable and repeatable your one-on-one times, the better—especially when your team is working on highly creative or technical tasks which benefit from big blocks of open time. Far better to set up a one-on-one every week directly after another meeting you're in together than to pick a time in the afternoon in the middle of a big block of free time. Your team will notice when you respect their schedules and will appreciate you for it.
To this end, you may have to juggle your team meetings to make things work for everyone most effectively. This requires you to understand the purpose of every meeting, whether a status report, a planning exercise, a group discussion, or dissemination of business strategy. Sometimes this informs your one-on-one schedule, such as after a quarterly business meeting.
All of these suggestions will make managing your calendar more difficult, but keep in mind that your calendar is in service of your work communicating with your team.
One final tip will help avoid interesting surprises: to the extent you can, keep the details of your calendar private to the rest of your team. By all means show when you're busy, free, out of the office, and unavailable, but hide the details of who you're meeting with and why. The default expectation—everyone has a half-hour one-on-one every week (or whatever time and frequency makes sense) should be implicit. Yet if an employee needs a 10 minute checkin every day, that's the business of no one else. If an employee needs to talk through something for an hour and puts it on your calendar that morning, that's the business of the two of you.
Invest in the Conversation
Even though you've probably used your calendar to coordinate the meeting, it doesn't dictate the conversation. Some people need a little bit of small talk to loosen up. Others get through everything they want to say in a few minutes and they're happy that way. Let the conversation happen as it happens. Nothing says you have to fill up thirty minutes of deep technical or coaching conversation every week. Keep in mind that the most important thing is to establish a healthy and honest working relationship where you communicate effectively with each other.
During the meeting, make sure to minimize distractions. If you have your email or chat program in another window, resist the temptation to read something instead of paying attention. Close it, mark yourself as away, or do whatever you need to do to invest your full attention in the other person.
When you're in the same room together, you have a lot more options to communicate through body language, posture, and active listening techniques. You probably do this to fill in the blanks of conversation automatically. In a remote setting, even with a really good bi-directional video chat system, you need to put in more work to get the same level of investment. It's worth it.
If either you or your employee are fully remote, you probably have fewer opportunities to have ad hoc hallway conversations, so you may have a list of things to talk about when you have your regularly scheduled meeting. Whatever works for you is best: a paper list, a note file for each person, a spreadsheet with tabs, all of these can work. If you have one program visible on your computer besides your chat window, it can be your electronic notes.
Keeping notes will allow you to add followup items for after the conversation. It's usually best to spend a few moments taking notes after you finish talking, but for the important items you commit to doing, feel free to note them during the conversation. (It can be helpful to say "I'm making a note of this right now", so it doesn't sound like you're sending an IM to someone else during your one-on-one.)
Technical Concerns of Remote 1:1s
The technical concerns of a good remote one-on-one are almost secondary, if you have that effective and honest conversation. Yet they're still important; they can make or break things.
As with any communication medium, the higher the bandwidth, the more you can communicate. That's why meeting face-to-face in a quiet room without distractions is still the most effective mechanism. Your second best option—and probably your best option with remote workers—is high-bandwidth video chat. Whatever program works for you is probably fine; at a minimum you should be able to hear each other clearly and see each other. It's useful to be able to share computer screens sometimes, and the better the video quality for that, the better things will be.
In general, the less setup you need, the better. If your organization uses something like Google Apps pervasively, Hangouts can be easy and free. Skype works for some groups. There's probably no need to spend a lot of money on a custom technology solution, but whatever makes your conference rooms work well with your software is a worthwhile investment.
Video is a nice feature to have. If you get video at the expense of clear audio (shared bandwidth, interference, someone's at a cabin in the hills and has a limited data connection), drop the video and stick with audio. You'll need to put more work into paying attention, in that case, but you can close your eyes and focus on the words if you must.
It may go without saying to the technically-minded, but sometimes having a reliable wired network connection is much, much better for video chatting, especially if you can count on a well-maintained network.
Do keep available a secondary mechanism of communication, such as IM or texting. It's helpful to use that alternate channel if your network freezes or you run into temporary glitches such as muting or audio artifacts. This fallback mechanism can also work if you just can't get audio or video chat to work; you can conduct a one-on-one over the phone in case of a personal or technical emergency.
Whatever works for your organization, it's your responsibility as a manager to push for an effective technical solution to remote one-on-ones. The higher the bandwidth communication, the more organizational support for frequent and recurring one-on-ones, and the more buyin from your team, the more value you will find this practice provides to your team and your organization.
The onus is on you, a manager, to provide an environment where honest, frequent, open communication can happen reliably.