When and How to Have “Awkward” Conversations with Your Team with Richard Lindner and Jeff Mask

As leaders, alignment, clarity, and trust among your team are great, but sometimes the bridge to get there is the dreaded awkward conversation.

Every leader can relate to the sense of dread that comes with knowing you need to have a difficult conversation you’ve been avoiding. How do we lead into this? How do we request an awkward conversation and then how do we handle it? In today’s episode, co-hosts Richard Lindner and Jeff Mask share some practical advice for dealing with awkward conversations and then hopefully eliminating the need for them.

Turn Awkward Conversations Into Fierce Conversations

Jeff says the most important thing you can do is practice a conversation before you have it—especially that opening sentence. The first five seconds are always the most difficult—it’s awkward, then onward. He starts conversations with “I want to talk with you about…” not “I need to talk to you about…” Replace need and to with want and with. Then fill in the space after about with a clear statement of the issue.

Rehearse that first sentence more than anything. Memorize the facial expression, tone, and pacing so you set the stage for a productive, constructive conversation.

Jeff highly recommends Susan Scott’s book, Fierce Conversations, where she gives six steps to an opening statement, then #7 is an invitation for them to respond.

  1. Name the issue
  2. Give a specific example
  3. Describe your emotion
  4. Clarify what’s at stake
  5. Own your part
  6. Indicate your wish to solve the problem
  7. Invite them to respond

Here’s an example. 1. Name the issue (how you respond to certain members of the team). 2. Give a specific example (when Stacy talks, you talk over her and don’t let her finish). 3. Describe your emotion (it’s frustrating but I don’t want to embarrass you). 4. Clarify what’s at stake (but I’m afraid if we don’t talk about it, we won’t gel as a team) 5. Own your part (I should have addressed this earlier) and 6. Indicate your wish to solve the problem (I really want to work this out.) 7. Invite them to respond.

Some Practical Advice for Before and During the Conversation

You want to start from a good place, which means getting the raw emotion out of the way and getting to logic. Share your thoughts and feelings with someone else. Write it all out in an email you’ll never send. Create a plan to move forward. Establish your desired outcome. 

When we get to that step 7 and ask for their feedback, how do we invite honest feedback and not a defensive reply? Facial expressions and body language while listening are so important. Make them feel safe. Resist the temptation to build a stronger case. Don’t get defensive. Listen. The goal is to help them feel understood—seen, heard, and valued. Don’t be on your phone. Don’t check something. Don’t lose eye contact. Not intense staring, but don’t lose focus or get distracted. Listen with your ears, eyes, and heart.

What if you mess up that feedback invitation at any point? Own it immediately. Think of a brick wall between the two of you. What you’re doing is removing brick after brick so you can see each other clearly. Immediately own up to something you did that wasn’t helpful, and ask them to continue. Don’t apologize forever.

Check your motives when you’re asking them questions. Are you truly curious and want to understand their perspective? Or do you have a judgment-type energy? 

What Is Your Body Language Actually Saying?

Richard shares a personal example of something he was doing that was sending the opposite message of the one he intended. When he’s processing, thinking, he folds his arms across his chest. It’s his default move. He does it without even thinking.

One day his business partner confronted him about it. He had shared an idea with Richard, and Richard agreed with him verbally, but his body language (crossed arms) was saying something different. Richard was pondering, considering, but his partner received it as him being defensive, closed off.

Richard has had to consciously try new ways of holding his arms/hands while processing—putting them behind his body, sitting on them, anything but crossing them over his chest. He’s had to become self-aware.

“What helps me with modeling and accountability,” he says, “is not hiding something I’m struggling with. Sometimes acknowledging the problem helps solve it. He went from unconsciously incompetent to consciously competent. He’s aware of the habit now, but it’s going to take him a while to fix it.

He took an additional accountability step and shared his struggle with his team. His assumption before was that people knew he was pondering their smart idea and considering it with his arms crossed. Now he knows that it makes people feel uneasy, bad, hurt. He and his partner came up with a funny word for him to call Richard out, and he asked the rest of the team to help him break the habit too. Now, everyone had context, and other times he had done it made sense to them. He broke the habit super quickly after that. 

Richard suggests being curious in finding out something YOU do that follows that pattern. You don’t realize you’re doing it, and it may have a negative connotation attached to it. Just the act of doing that will give you the ability to talk to an employee about this same kind of thing.

Final Pieces of Advice

One question people ask Jeff is: “How do I make sure I know the best time to have the conversation?” You know it’s too soon if your emotions are raw. You know you waited too long when you’re wondering if it’s still a big deal. Err on the side of sooner than later. When you don’t address it, you tolerate the bad behavior. That speaks loud and messes up your culture.

If you felt those butterflies in your stomach as you listened, you probably need to have an awkward conversation. Do it. Have it. Don’t let another day or week go by without having that conversation.

And then: “What do I do after I have the conversation?” The simple answer: follow up and reinforce with care.

Richard and Jeff want to hear from YOU. What other questions do you have about awkward conversations and how to handle them? What have you done that worked well? What can they do to help you lead from a powerful place? Email them here with your thoughts/questions: feedback@readytolead.com 



We're Glad You're Here

We're listening! Writing us a review not only helps us improve the show, but it helps others like you to find us. Thank you!

Get Notified About New Episodes!