The 8 best questions to put on your next one-on-one meeting agenda

I asked almost 500 leaders from all over the world what questions they ask during a one-on-one meeting. Here’s what they said…

That one-on-one meeting is scheduled on your calendar this week. So, what should you talk about?

As a manager, executive, or business owner, this is one of the most recurring and perplexing situations you’ll face. Should you prepare an one-on-one meeting agenda ahead of time? Does it feel too stiff to do so? Should you simply have general meetings topics ready to go? What are the questions you should asking during this one-on-one?

We posed this dilemma to The Watercooler, our online leadership community with almost 500 leaders from all over the world, to see what they had to say. From that conversation, I’ve shared what these managers, business owners, and executives from The Watercooler have found to be the best questions to ask during a one-on-one meeting.

Take a look and see if you agree…

#1: How’s life?

On the surface, this doesn’t seem like a significant question to ask. After all, some managers default to asking this question as a crutch when they’re not sure how to open up a one-on-one meeting. However, this question can be actually quite powerful, if you can embrace a greater intention behind it: To build trust. When asked, most Watercooler members agreed on the importance of having trust and a strong personal rapport going into the one-on-one. The more you know about a coworker’s dreams, hobbies, pets, children’s names, etc., the greater the sense of trust is. And the greater the trust, the easier a tough conversation is. As a result, many managers from theWatercooler kick off their one-on-one with a “get-know-you” question like, “How’s life?” or “How’s [insert spouse’s name]?” or “What are you up to this weekend?”

One manager in particular emphasized the importance of talking about life outside of work way before you even have the one-on-one. That way, you build a foundation of trust to use if you need to bring up a difficult topic during your one-on-one. Prior to a one-on-one, here are some of the top 25 get-to-know you questions that can help with this.

#2: What are you worried about right now?

During a one-on-one, you want to figure if there’s anything bothering an employee, before it’s too late and they decide to leave or their performance is affected. Few questions do that an well as as this one. Recommended by a few of the Watercooler members (and a question I regularly asking during my one-on-ones), this question can help unearth the deep-seated concerns, confusion, or uncertainty an employee might be facing. A slight variation to this question that may unearth even more specific answers is: “When’s the last time you were worried about something?” This question is rooted in a specific moment of tension that can help make it more concrete for an employee when reflecting on if there’s something they might be worried about.

#3: What rumors are you hearing that you think I should know about?

Asking this question can bring to light rumors that you can dispel before they spin out of control. But on top of that, as one Watercooler member said: “What the rumor mill is saying is also often a compass pointing to places where people feel stressed.” Ask this question to uncover a deeper, disconcerting source of unease or frustration for employees. You’ll want to pay attention to that.

For one Watercooler member, asking this question had a direct effect on her entire team’s morale: She was able to nip a rumor in the bud very quickly about why an employee was fired.

#4: If you could be proud of one accomplishment between now and next year, what would it be?

To get a coworker thinking about their personal goals over the next six months, as well as their long-term careers, one manager in The Watercooler recommended asking this question. You may not get a meaningful response every single time from every employee you pose it to, as some employees may find it difficult to answer on-the-spot. However, it’s a great way to spark the initial conversation with an employee about future goals. Not to mention, it’s a more thoughtful question than simply asking, “What goals do you have for yourself?”

#5: What are your biggest time wasters?

No one likes to waste time. Few feelings are as stifling and demoralizing, especially in a work setting. As a result, asking this question during a one-on-one is imperative. Once you ask this question, be prepared to think on and follow with concrete ideas for how you think that person’s time won’t be wasted.

#6: Would you like more or less direction from me?

Feeling micromanaged is often another source of stress for an employee — and it’s one of the most common. As a manager, it can easily to unintentionally give an employee too much guidance. At the same time, employees find it equally frustrating when they’re hung out to dry with no support. When you ask this question, you can then adjust your management style and techniques. Furthermore, asking this question also signals to your coworker that you recognize the value of providing the right level of support as a manager. As a leader, this question shows you’re self-aware.

#7: Would you like more or less feedback on your work? If so, what additional feedback would you like?

Watercooler members suggest asking this question, because you’re most-likely going to get a resounding “yes.” After surveying hundreds of companies and thousands of employees through Know Your Company, we’ve found that 80% of employees say, “I want more feedback about my performance.” Your one-on-one is the perfect opportunity to figure out exactly what kind of feedback someone would like.

#8: Are there any decisions you’re hung up on?

One of the best ways to help coach an employee is to give them some support on a decision that they’re wrestling with. They could be quite distraught because they’re not sure with path to take — and you can help. Asking this question during the one-on-one is a wonderful way to alleviate the potential pain they may be feeling around a tough decision.

Whether your one-on-ones are weekly, once a month, or once a quarter, I’d highly encourage you to place one or two of these questions in your typical meeting agenda. Based on the experiences of Watercooler members who’ve asked these questions, you’re guaranteed to learn something new and create a stronger rapport with your team.

Looking for a few more resources on how to have a productive one-on-one?

P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks 😄 (And you can always say hi at @cjlew23.)