Looking for Ways to Avoid Awkward Conversations?

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Awkward conversations are the worst. I remember the first time I struck up enough courage to call a girl I liked on the phone. I was in 8th grade. I’m pretty sure I said hello and then waited a solid minute for her to say something. And the truth is, sometimes leading a team or connecting with an employee in a 1-on-1 can be JUST as awkward as talking to a girl on the phone, or attending a middle school dance. We are not sure what to say, what to do, or how to respond when we step in front of the room, or when someone approaches us with expectations to be led through a challenging time. Many times, our default is to announce our presence or our agenda and let others speak up if they have something on their mind. But that’s not always helpful to the people we lead.

That’s why I get asked a lot, “How do I make conversations less awkward when leading my team?

Here are a few tips I’ve learned over the years:


Being intentional is key in your relationships in life, especially as you lead people on your team or organization. The same is true at home with your family and your people. When we lead with intentionality, we take away the awkward moments by giving purpose and meaning to the important areas of life. My context for the last 15 years has been leading in the church and I can see how being intentional has been crucial for creating amazing connecting environments and meaningful relationships. Let’s face it, with technology, people are now connected more than ever, but that doesn’t social media is always the ideal connecting environment and it doesn’t mean all of our online relationships are meaningful or have purpose. There are many ways and approaches to being intentional in the way we lead, but I believe one of the best approaches to intentionally is to lead with questions.


Remember that awkward phone call I mentioned with the girl I liked in 8th grade? If I had led with questions, I probably would have saved myself and the girl I was talking to on the phone a lot of awkward pain on the phone that day. My intention was to call and signal that I like her, but I was not intentional with asking her questions. Many leaders have given much thought to how to structure their team or organization, but haven’t given much thought on how to engage with the people who make up the team or organization. Maybe we have a list of people we connect with on a regular basis for meetings, 1-on-1’s, etc., but have we actually asked them any questions?

Questions communicate value in two ways: questions express value to the person whom we are asking the question, and questions show what we value. If we ask a teammate or colleague how they’re doing, they feel noticed and appreciated and we show that we care about them by taking the time to ask the question. Asking questions communicates that someone or something is more important than we are, especially if we listen to their answers! Here are a few other things we communicate when we ask genuine questions:

  • Questions show that you are a learner. You curious about other people and the world around you.
  • Questions help you become a better person. You ask questions because you want to learn and grow so you can make helpful changes as you lead.
  • Questions are universal. It doesn’t matter if you are leading in a non-profit or for profit, a small organization or large organization, questions guide you, help you learn about others, and deepen relationships.
  • Questions create connection. Intentionally leading with questions not only helps us shape community, but it actually creates community.

So, the bottom line to avoiding awkward conversations is to be intentional and ask questions.

If you’re nodding your head in agreement, but you’re not sure how to get started here, then these tips are for you.


Ask your team:

  • Why do we do what we do?
  • On a scale of 1-10, how healthy is our church, our team, and how healthy am I?
  • What is working well?
  • What needs attention?
  • What are the questions we need to be asking?

Ask your leaders:

  • What questions do you have or questions that you getting from others?
  • What are wins you have had recently that are worth celebrating?
  • What tensions are you feeling?
  • In what ways can I help you develop as a leader?
  • How can I support you?
  • How can I pray for you?

Ask yourself:

  • Why am I doing what I am doing?
  • What am I doing that I need to stop doing?
  • In what ways have I seen God at work?
  • What are opportunities that I see in front of me?
  • Who do I need to connect with today?
  • Why am I afraid to ask that question? 

Be Intentional:

  • Schedule consistent meetings with your team, including team days for fun and connection
  • Remember important dates like birthdays and work anniversaries
  • Check in on each member of the team personally
  • Take an interest in their interests
  • Encourage self-care and healthy sabbath rhythms
  • Celebrate their milestones and achievements

I’d love to hear from you, too! How do you avoid awkward conversations with your team?

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