Get Rid of Awkward One-on-Ones Once and For All

Subscribe to The Thoughtful Leader newsletter to discover leadership insights to elevate your team's performance.

Lets face it. Meetings can get awkward, especially meetings with your boss. As the boss, or lead, what can you do to create a more comfortable, productive one-on-one meeting with your report?

Before we can talk about how to fix the awkwardness, let’s try to understand why these meetings can feel awkward. 

Potential Reasons

  1. You’re intimidating.

    It might not be you, per se, but your title. The authoritative figure. The person they’re trying to impress, and the one who has control over their work life. Although sometimes it has more to do with your position than you as an individual, your personality or actions could also play into the intimidation factor. 

  2. Unclear expectations.

    The individual may not know what the purpose of a one-on-one is. There’s confusion about this time being used for status updates on a project or another version of a performance review. 

  3. He/she doesn’t know what to talk about or what is and is not appropriate to discuss.

    When given the opportunity to discuss anything they would like, not knowing what to talk about leads to awkward silences. Even if they have an idea of what to discuss, it might be difficult for them to say what it is because it may be deemed unfitting for this meeting.

  4. He/she feels uncomfortable.

    There are countless reasons to list for their uneasiness. All the prior points are possibilities. 

Solutions

It is your responsibility as a lead to be proactive to facilitate successful one-on-ones with your reports. You might not be able to control their perceptions of you or how they feel prior to the meetings. However, you do have control over how to act in order to create a positive influence, which hopefully changes their perspective to a favorable one. Here’s what you can do:

Inform your report what to expect before the first meeting.

Clear out any misconceptions he/she might have about one-on-ones being related to project status updates, performance reviews, or any other irrelevant topics. Make sure they understand this is time you’re dedicating to:

  • Getting to know one another as individuals

  • You to act as a resource to help them achieve their professional goals

  • You to help them be successful in their role

  • Them to share feedback about what is and is not working well 

Help him/her prepare.

Feeling prepared while walking into any environment always gives a boost of confidence. Have him/her write down points they would like to address in the meeting. This article containing common questions and answers is a great place to start. 

A tip, in case they’re wondering what is and is not appropriate to bring up: tell them to write down all that comes to mind. 

Tell them not to hesitate to touch on any points they feel is important to them. During the one-on-one, if you cannot respond in relation to a point at that time, you will let them know and it can be for a later discussion. 

Create a safe space.

There are leads who have adopted walking one-on-ones, which works great for some. The point is to break away from the typical office environment to somewhere that can be considered more neutral ground and comforting. Taking a walk allows the report to focus more on the conversation and not so much on the fact that they’re “at work”. This might not work well for those who love to take notes or maybe get distracted easily. Other options include meeting at a coffee shop or over lunch.

Show compassion, be vulnerable.

Conversations will almost always become effortless, less awkward, and have deeper elements as the relationship begins to develop. It’s more difficult at the beginning due to the lack of connection and trust. Therefore, it’s important to show him/her that you are a normal human being, as they are. Be personable. Ask questions such as:

  • How do you like to spend their free time?

  • Who is an important figure in your life?

  • What do you dream about?

If your report is really struggling to open up, try to share some personal struggles. You don’t have to talk about a deep, inner struggle that you haven’t even told your best friend. Start with a skill you’ve had difficulty learning or maybe how your new-born baby is keeping you up all night, causing you to lose the ability to focus for long periods of time. 

Don’t invalidate thoughts, opinions, or emotions.

Nothing shuts down a person quicker than making them feel like they’re not being heard or they don’t matter. Here are a few examples of what you can do to make sure that doesn’t happen:

  • Nodding, eye contact, and appropriate changes in facial expressions are physical ways to show you’re listening. 

  • Avoid using the phrase “no” or “you are wrong”. 

  • When there is a disagreement, start by trying to understand their thought process. Ask them for an explanation. If you still disagree, your response should acknowledge you hear them, you understand the reasoning behind their words, then you can share your thoughts. 

Subscribe to The Thoughtful Leader newsletter to discover leadership insights to elevate your team's performance.

Previous
Previous

Skip-Level Meeting: 21 Questions to Ask Your Boss's Boss

Next
Next

4 Simple Steps to Get Started With Skip-level Meetings