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


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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....

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