If you are responsible for a team of people at work then I would recommend listening to the podcast series on One on One meetings at the Manager Tools website. You will learn how to build a good business relationship with your team. Or, maybe you are having trouble connecting with your boss. Listening to the podcast series may help you to suggest some changes to your boss that would make your relationship stronger.
There are many benefits to doing 1:1s for both parties including building a strong relationship that can withstand difficult times, helping your direct to grow professionally by really knowing their strengths, weaknesses and aspirations, and dedicating a time where your direct can tell you anything they need to that may otherwise go unsaid.
The authors emphasized that this meeting should be scheduled on your calendar and it should be weekly. Scheduling it communicates that this is important and will happen even if it is occasionally rescheduled. The dependability of this earns trust for you and as an additional benefit may actually reduce interruptions during the week for issues that could wait until your next 1:1 meeting for your direct to ask you about. The 1:1 should be weekly because you are building and maintaining a relationship and that just takes time, plus people tend to only keep the previous and next week in their mind so waiting longer means you will lose some details.
I have had the experience of a busy boss who has wanted me to track him down for the 1:1 and it was a weekly dreadful task for me instead of being something that re-energized my day. Having it on the calendar as something that can be depended on helps me prepare for it with questions to ask or topics I'd like to talk about.
I've also experienced 1:1s where the things I said were never followed-up on, which has taught me to try to follow-up on anything I need to from the 1:1 the day that it occurs if possible. Showing that as a manager you take these meetings seriously and really want to help will go a long way to building the trust you need to be able to help each of your directs.
Each direct's 1:1 should feel different
The 1:1 is about the direct, it's their chance to say whatever they want to. Some people are most comfortable sticking to business and provide a status update, others may want to talk about one specific thing they are working on, and sometimes a conversation about what someone did last weekend or is planning for vacation is what fills the time.
The authors recommend that every 1:1 has the same agenda, though. Their typical format would be 10-min for the direct, 10-min for the manager, and 10-min for talk about coaching or the future. This format can be tailored to whatever makes sense for you, though. In my experience with an agile software team, I know from the daily stand up meeting what each team member is doing and what blockages they may have. I sometimes have some organizational news to share or some advice or coaching, but I don't need 20 minutes to cover both of those.
My 1:1s generally follow a format of 15-20min for them and 10-min for me where I might ask them a question that will help me understand them better (what do you like most, e.g.), give them some advice or feedback, or share some news from a meeting they weren't present in.
After listening to the podcast series I made a change to my 1:1s. I took them out of the small conference rooms I had scheduled them in and brought them into the large breakroom with a wall of windows to give them a more open, relaxed feel. The privacy of a noisy breakroom has so far proved sufficient to be able to talk about whatever has been on our minds.
I would like there to be a podcast tailored to directs that teaches them what to expect from a 1:1 and how to prepare. I've updated my agenda to give my directs a little more information about the format and what to expect, but I think listening to a 30-min podcast about why 1:1s are important and what they can get out of them would really help them understand. I think the first episode of the Manager Tools podcast would probably suffice for this, too, but it would be nice to have it tailored to the direct instead of to the manager.
I always take notes in a notebook and then type up a few quick bullet points in One Note to help keep track of what we talked about. It would be nice if there was a 1:1 app that helped track what you discussed, things you need to follow up on, and help you to cover feedback and future goals intentionally.