Remote 1-on-1 meetings
In the last two years I've done hundreds of remote 1-on-1 meetings, both as a contributor talking to my manager(s) and as a manager talking to people in my team.
As a manager, I consider 1-on-1 meetings the most important responsibility I have: empowering other people to do their best work can greatly outmeasure any contribution I can give on my own.
What follows is some notes on what seems to work for me. It does not represent by any means a proper research on the matter, so please take it with a grain of salt.
Long term objectives
Regular 1-on-1 meetings can certainly be used to solve immediate, short-term blockers or clarify some questions, but the long term objective is building a working professional relationship where:
Both parties can safely be vulnerable and address deep issues that make day to day work more difficult. This can be anything from anxiety about the world at large, to having to homeschool kids, to difficulties in multitasking different responsibilities. Note that as a manager, you're allowed to show that you're struggling to the other person. We're human after all and that helps building transparent relationships. Needless to say, confidentiality and respect are paramount.
Trust takes time and effort. It may take months before people open up and start addressing important topics: what motivates them, problems they see in the team and in the company, their own aspirations and ultimately work on their professional growth.
Lead by example: if you ask a complex question (e.g. what do you wanna focus on this year?), answer it yourself first, so that they understand better.
Always prepare something to talk about: even if it seems artificial, it will gradually tune your perception to be on the lookout between meetings for topics to talk about and it will get easier. At the same time, if the other party doesn't provide topics over multiple meetings, make sure you address that. There's always something to talk about.
Regular 1-on-1 meetings require preparation: the easiest thing to do to ease preparation is to keep an agenda document shared between the two participants.
I can recommend a shared Google Doc, with sections titled by date and sorted in reverse chronological order (most recent first).
This way you can:
Predictably add topics to discuss between meetings (it's always at the top).
Have implicit time tracking, i.e. you know when something was discussed.
Easily collaborate in real time during the meeting to capture ideas in a form that correctly reflects the other person's thoughts.
This system is by no means perfect (especially if you end up having dozens of these documents), but it's flexible enough that you can adapt it to individual preferences. For example, I find that with some people we can use the agenda to discuss topic asynchronously in writing beforehand (and draw some conclusions in the meeting), while with other we defer discussion to the meeting itself. With other ones, we end up adding topics during the meeting as the conversation naturally goes in different directions.
In addition, it's important to prepare for the conversation, even for just 5-10 minutes before the meeting. Having such time buffer not only helps clarifying thoughts beforehand, but also gives you an opportunity to stop thinking about what you were doing before and what you're gonna be doing after the meeting.
During the meeting
Respect the agenda as much as you can, making sure that you either address all points on it or explicitly say "We'll need to address this in a separate call. Can it wait our next planned session or do you wanna schedule an earlier follow-up?".
If the conversation drifts to a completely different direction and time is running tight, make sure both parties are happy to discuss that direction at the expense of other topics. You always have the option to capture the new topic and address it at a later stage.
Be at ease in saying "I don't know, but here's how I plan to find out and here's when I'm gonna report back about it". At the end of the day, trust is built on transparency and predictability.
When the other person explains something to you and you wanna make sure you got it right, repeat it back and ask for confirmation. By doing that, you both check your understanding and implicitly ask the other person to check their own explanation. I've used this technique in all sorts of other conversations in my professional and personal life and it does absolute wonders in clarifying expectations on both sides.
If you take notes, learn how to do that quickly by using keywords, then fill in the blanks later (and ask for confirmation to the other person once done). Writing can break the flow of the conversation, so it needs to be done carefully in order to minimize its impact.
If a conversation topic implies someone taking an action, explicitly state that in the form of "I will" or "You will" or "Someone else will", with an indication of when that would happen.
If the meeting resulted in some actions, recap them at the end of the call.
Video conversations have a different pace - let people speak, listen carefully, slow down, repeat a few times if needed.
Explicitly ask the other person if they think a topic has been exhausted before moving on.
Respectfully ask the other person how they're doing, leaving them space to decide what they can comfortably share with you. Do no pry and always qualify your questions with the reason why you're asking them. For example, I've been recently asking people how they're dealing with the COVID-19 pandemic, because I noticed erratic working patterns that suggest they may be working too much (for many people, work is much simpler to deal with, so they end up using it as a safe haven - I'm not a psychologist though so this is another thing to take with a grain of salt).
Provide context: while this is important in any company, I believe it's fundamental in a remote company because people have more limited opportunities to gather context by casually taking part to unscheduled conversations. So if I'm discussing a specific project that I think it's connected to other projects, I'll share that. More often than not, the person on the other end will appreciate the additional information and will make good use of it.
After the meeting
If you have any action, just do it as early as possible. Your ability to follow up is by far the most important factor in building trust. If the other person asks you to do something, you agree to it and you don't, they will not ask you again.
If at any point you realize you didn't do something you promised to do, acknowledge your shortcoming, apologize and make up for it. It happens, and if you're transparent about it usually the other person will understand.
1-on-1 meetings are structured around the people involved: while you can definitely start from some guideline questions, they should over time develop into a unique conversation.
That said, over the course of multiple meetings you should aim at:
Unblocking specific issue related to current streams of work, e.g. "I'm undecided on how to build X, if using this or that."
Clarify responsibilities, e.g. "Yes, you need to take care of X, while Alice can take care of Y."
Provide feedback on work done, e.g. "I really liked how you did X because…" or "I'd like to speak about Y, as there's an opportunity to improve Z."
Useful things to learn about, e.g. "As you're working on X, you might enjoy learning about Y."
Connect the dots with other projects, e.g. "As you're working on X, you might be interested to speak to Alice, as she's working on Y, which is related to X as…"
Happiness, satisfaction, and future work e.g. "If we look at the roadmap, there's X, Y, Z. Do they interest you? Which one would be your initial preference to work on?"
One important aspect is balance: too often 1-on-1 meetings are focused on the day to day work and don't cover the larger picture. This is why there should be scheduled Feedback Sessions where you go through some meta-questions that allow expanding scope.
These are some examples of questions useful for those sessions:
Are you happy about the work you're doing? Is it satisfactory?
Looking at X time period, can you point out a piece of your work you're proud of?
Looking at the same time period, can you point out 3 team achievements you're proud of?
What should the team focus on in this quarter?
If you had a magic wand and could instantly change anything in the team, what would that be?
In general, Feedback Sessions are an opportunity to look at the larger picture and think about the future. For more inspiration, you can consult the Small Improvements guide to 1-on-1 meetings.
As mentioned before, this is by no means an exhaustive guide, but a collection on thoughts based on my experience. At the end of the day, if you always focus on listening to the other person and acting swiftly on their feedback, you will get good results.