Key Questions: The Best 5 Questions to ask in 1:1's

Raymond D. White
3 min readAug 22, 2019

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Conducting one on one’s with staff is by far my favorite meeting as a leader!

It is not just because I get to see my direct reports on a regular cadence, but it is an opportunity to be intentional with connecting with them and their experience on the team.

Rather than talk about the logistical aspects for conducting successful one on one’s, including regular frequency, never cancelling, and the structure, I want to share with you some of my favorite questions to ask during these meetings and why.

The 5 Best Questions to ask in Staff 1:1's

How are you?

Alright, so I low key cheated with this one… Not many people like this because of its vagueness, but I love it!

This question is geared towards how they are personally doing, beyond their work. It could lead to asking about their weekend, checking in on a personal matter they may have shared with you in the past, or get a pulse on their hobbies.

Any question in this range builds trust and connection between one another; it shows that they are more than the work that they produce.

What are your biggest wins? What is your greatest worry?

Talk about things that are going well and areas that can be improved.

Creating space in the one on one to check in on what’s going well shifts the mindset towards something positive, especially if they are coming into the meeting with a lot of problems. Highlighting wins builds resilience and gratitude.

Then shifting to the biggest worry can provide a focal point to the conversation. Allows opportunity to tackle the biggest problem they are facing to date and you can give them coaching or a listening ear.

What else you got?

This one throws some people off guard. Some staff feel like they are overly complaining or venting too much about the issues that frustrate them. Yet, there is no better place to have concerns heard than an one on one setting.

This question shows eagerness in hearing the concerns from the team member. It allows space to validate and value their experiences. As a leader, you are assuring them that no issue is too small or too big to voice.

What do you want to accomplish by our next meeting?

This shifts the conversation from talking to action.

Too many times, we can find ourselves talking about a bunch of stuff with no follow up or next steps. It allows you both to be in agreement with something to follow up on by the next meet up.

You can explicitly hold accountability on that item and help them meet that goal.

How can I best support you?

Part of being a leader is ensuring that your team has what they need to be successful. What better way of knowing what each team member needs than asking them directly!

This gives you a specific feedback on how you can equip them, whether it’s removing barriers, giving them moral support, or helping them problem solve effectively.

Ask great questions!

One on One’s can be phenomenal if you are intentional with your time with the staff. Be sure you are asking questions that drive effectiveness and inclusiveness.

Reflective Question:

What are some of your favorite questions to ask your staff during one on one’s?

Share your response in the comments!

Raymond White loves to engage, equip, and encourage emerging leaders and their efforts to develop thriving teams. You can follow him on Instagram and Twitter!

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Raymond D. White
Raymond D. White

Written by Raymond D. White

I collaborate with leaders to integrate DEI into their people & culture strategies. Need help developing a belonging team culture? Let’s chat!

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