One-on-Ones: Your List of Topics

Actions to take: Use the list of topics in this post as a launching pad for preparing your topics with employees each week.

To be a truly effective boss, the most important thing you can do is build a trusting relationship with each employee. By far the easiest way to do that is through routine one-on-one meetings. Better-boss.com recommends that those meetings are scheduled, 30 minutes, weekly, and rarely missed, with the first half of the meeting spent on whatever they want to discuss and the second half for whatever you want to discuss. All posts about one-on-ones assume this strategy.

The best boss I ever had ran truly impressive one-on-one meetings. Every week, she had a boatload of things she needed to cover. She encouraged me to think critically about my work by asking probing questions about my plans and actions. She checked in on my progress and offered support if I was in danger of missing a deadline. She celebrated successes on things that went well. She got my opinion on various initiatives that had been announced. She asked after my wife's progress in her decision to switch careers. In short, she paid attention to the things that mattered and followed up on them.

In Your Time During One-on-Ones, we talked about how to prepare your half of the meeting. This post expands that one by giving you concrete advice on what topics to cover. With the following list of topic ideas at hand, you are sure to impress your employees as much as my boss impressed me.

• Feedback: Feedback can happen any time, anywhere, provided that your comment is not easily overheard by others. However, one-on-ones are an extremely convenient place for feedback. Your employee is virtually guaranteed to be in a good mindset to hear feedback, as these meetings are largely about their work already. You will have time to compose your phrasing in advance. And, assuming you do these meetings weekly, the behavior you are commenting on will always be fairly recent.
• Follow up earlier one-on-one topics: One-on-ones build on themselves. Invariably, you will discuss topics that require further thought or action. Maybe you or your employee plan to follow up with other employees or gather more information. Perhaps the easiest way to flesh out your half of the meeting is by checking prior weeks' notes. What topics or projects accidently got side-tracked? What things did your employee continue to work on without keeping you in the loop? These things happen; we're all busy. Check in on it.
• Ask for opinion on team announcements: It is common for a manager to announce something during a team meeting, ask, "Are there any questions?" and assume everything is good to go when no one speaks up. To be blunt, this is silly. People are vastly more candid about their opinion when you ask them individually than when you ask in a group. For all important team announcements, follow up with every employee in the one-on-one. You'll be shocked how much better you understand their concerns (or excitement!) about this or that initiative. 
• Project status updates: After a few months of one-on-ones, your employees will give status updates during their time. Before they get the hang of it, make it part of your work to check in on how things are going. Deadlines get busted because managers fail to maintain their awareness of the ongoing status of the work. It is such an easy fix to spend 1 minute in this meeting touching base on progress.
• Deep dives into routine work: In an effective workplace, your employees are doing a variety of tasks that you yourself do not do on a regular basis. Occasionally, spend your half of the one-on-one by having your employee give you an in-depth understanding of one of their responsibilities (or by observing them while they do it). Done poorly, this can feel like an interrogation of the employee's abilities. If you give them a heads up the week prior, and if you make it feel like a natural, routine thing, then you will delight your employee with your genuine interest in their work.
• Check on long-term plans: The best bosses are never surprised when an employee puts in notice. That is because they routinely check in on their employee's long-term plans, goals, and desires. Once every few months, turn the discussion toward your employee's career aspirations. This conversation will naturally lead into developmental opportunities they can pursue in their current position. You will engender good will, and you will provide a natural opening for an employee to let you know when they are considering moving on. With this method, I have known up to a year in advance when an employee is likely to quit.
• Chat about personal life: One-on-ones are generally about work. That's what most people want to talk about with their bosses. That said, have a basic understanding of your employees' personal lives. You should know at least as well as the average coworker what is going on personally with your employees. When major events happen (e.g. a child's graduation, personal accomplishment, parent's health issues), it builds rapport to know about it and comment appropriately. From time to time, ask how the family is. Let the employee dictate how much they want to share.

With this list of topics in mind, it is virtually impossible for a week to pass without a half-dozen or more topics in your part of the one-on-one. Most importantly, these topics will be relevant and useful—they are things that matter to the work and to the employee. 

The average boss, if they do one-on-ones at all, underprepares. It is evident to the employee that the topics are boilerplate or filler, and they can tell the boss isn't putting time and energy into the meeting. Better bosses know that one-on-ones are about demonstrating the importance of developing a relationship with their employees. Because they prioritize those relationships, they prioritize these meetings. That means bringing meaningful, useful topics to discuss every single week.