What caring does mean, is doing your best to help your report be successful and fulfilled in her work. It means taking the time to learn what they care about. It means understanding that we are not separate people at work and at home sometimes the personal blends into the professional,  and that’s okay.

Even if you sit next to someone and see him every day, 1:1 let you discuss topics that may never come up otherwise- for example, what motivates him, what his long-term career aspirations are, how he’s generally feeling about his work, and more. One-on-ones should be focused on your report and what would help him be more successful, not on you and what you need. If you’re looking for a status update, use another channel. Rare one-on-one time is better spent on topics that are harder to discuss in a group or over email.
The ideal 1:1 leaves your report feeling that it was useful for them. If they think that the conversation was pleasant but largely unmemorable, then you can do better. Remember that your job is to be a multiplier for your people. If you can remove a barrier, provide a valuable new perspective, or increase their confidence, then you’re enabling them to be more successful.

How can you achieve stellar 1:1s?

The answer is preparation.
It’s rare that an amazing conversation springs forth when nobody has a plan for what to talk about. Tell your reports that you want your time together to be valuable, so you should focus on what’s most important for them. Here are some ideas to get started:

Discuss top priorities: What are the one, two, or three most critical outcomes for your report and how can you help her tackle these challenges?
Calibrate what “great” looks like: Do you have a shared vision of what you’re working toward? Are you in sync about goals or expectations?
Share feedback: What feedback can you give that will help your report, and what can your report tell you that will make you more effective as a manager?
Reflect on how things are going: Once in a while, it’s useful to zoom out and talk about your report’s general state of mind-how is he feeling on the whole? What’s making him satisfied or dissatisfied? Have any of his goals changed? What has he learned recently and what does he want to learn going forward?

It’s helpful for both the manager and the report to think through the topics they want to bring to the 1:1 conversation.
Coach’s best tool for understanding what’s going on is to ask questions. Don’t presume you know what the  problem or solution is. Too often, attempts to “help” aren’t actually helpful, even when served with the best of intentions. We all remember lectures that went in one ear and out the other because it was obvious the other party didn’t understand our real problem, or when unasked-for “help” feels indistinguishable from micromanaging or meddling.
Your job as a manager isn’t to dole out advice or “save the day”-it’s to empower your report to find the answer herself. They have more context than you on the problems they’re dealing with, so they’re in the best position to uncover the solution.

Here are some questions to get the conversation moving:

Identity: These questions focus on what really matters for your report and what topics are worth spending more time on.

  • What’s top of mind for you right now?
  • What priorities are you thinking about this week?
  • What’s the best use of our time today?

Understand: Once you’ve identified a topic to discuss, these next questions get at the root of the problem and what can be done about it.

  • What does your ideal outcome look like?
  • What’s hard for you in getting to that outcome?
  • What do you really care about?
  • What do you think is the best course of action?
  • What’s the worst-case scenario you’re worried about?

Support: These questions zero in on how you can be of the greatest service to your report.

  • How can I help you?
  • What can I do to make you more successful?
  • What was the most useful part of our conversation today?

Your report should have a clear sense at all times of what your expectations are and where they stand. If they often wondering, What does my manager think of me? then you need to dial up your level of feedback. Don’t assume they can read between the lines or that no news is good news. If you think they are the epitome of awesome, tell them. If you don’t think they are operating at the level you’d like to see, they should know that, too, and precisely why you feel that way.

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