Office Life

Three smart ways bosses and employees should talk to each other

Face-to-face meetings, whether conducted in-person or over an internet connection, are how we build relationships in the workplace. One-on-one meetings between employees and managers are especially important for strengthening ties and addressing concerns before they become problems.

But a one-on-one with a boss can easily go off the rails. One person can talk too much, another can talk too little, or someone can go off topic and never return. You want to end a one-on-one feeling like something got done, not like you’ve circled around the issue. Or one of them can feel unfairly judged and protective of his or her ego.

Here is the best way to hold a regularly-occurring, structured one-on-one so that you have a strong relationship with your boss.

Be consistent with them and don’t cancel

How often should you do them? Often enough that it becomes a habit.

The employee handbook at 18F, the U.S. government’s digital service agency, suggests half-hour weekly 1:1s. 18F says that our minds think in weekly chunks and if you’re holding your one-on-ones too infrequently, managers may miss hearing out on key details. The agency also believes that a week is longest you should go between meetings if you’re working with employees on specific issues: “If you’re only able to help someone change course once or twice a month, they’ll go a lot longer down an ineffective path before you can help.”

Of course, the cadence of your one-on-ones depends on your team’s size and goals. This could mean daily, weekly or monthly. The most important thing is to be consistent with doing them.

Make your one-on-one a repeating event on the calendar. You can reschedule of course, but don’t cancel one-on-ones. Cancelling signals that you’re not prioritizing the relationship with your colleague.

Make an agenda

The first step to making a structured meeting is to have a plan. This doesn’t mean making the whole interaction a rehearsed choreography, but a loose structure helps to focus the discussion.

Structuring the conversation means knowing what will be discussed, so people on both sides can jot down what they want to bring up. Harvard Business Review recommends giving employees a heads up if the one-on-one is around professional development, so employees have time to prepare and reflect.

18F suggests dividing the meeting into the employee’s agenda, your agenda and the future. That way, it prioritizes the discussion around what the employee wants to discuss, so if time runs over, at least that gets covered.

What to talk about

Open-ended questions help the one-on-one feel like a guided conversation and not a status report. Some people will come in with an agenda that they’re ready to discuss, while others may need some questions to get them to open up. Open-ended questions can be as broad as “How are you doing?” to as specific as “What are the challenges you’ve faced this week?”

If it’s your first one-on-one, Lara Hogan, Kickstarter’s VP of Engineering, suggests structuring it around getting to know your employee’s work rhythm. How do they like to receive feedback—publicly or privately, in Slack direct messages or in one-on-ones? Hogan said that she asks her employees, “What makes you grumpy? How will I know if you’re grumpy? How can I help you when you’re grumpy?” in their first one-on-ones.

Both sides of the one-on-one should take notes. It makes us better listeners. It reminds us of what was discussed and keeps us accountable to what action items were discussed for future one-on-ones. Doc Norton, software consultant expert, said he emails a summary with action items to his employees after one-on-ones, so that they know he is committed to their growth and that he plans to follow-up on what was discussed: “The One on One session will grow meaningless if issues are shared, but no resolve is realized.”

Above all, it’s important to be flexible with the discussion. That means knowing when to nod and listen and when to jump in with solutions.

“Sometimes, people will come to the 1:1 just needing to complain or get something off their chest. In these cases, listening, asking questions, and making sure they feel heard is all you need to do,” 18F said. “But other times, there’s a problem to be solved, and in those cases you’ll want to talk through solutions, suggest directions, and steer towards action.”