"You are nothing but a great, big coward!"

The first time I watched The Wizard of Oz, it struck me how painfully direct Dorothy was to the Cowardly Lion. If you’ve ever seen the movie, you know that the Lion was all bluster — he turned tail in every tough situation. But as the story unfolds, he slowly develops the skills that help him to overcome his fears and confront the Wicked Witch of the West. Just about every one of us have been in situations where we chose to retreat from conflict or the discomfort of a courageous conversation.

A courageous conversation is one that makes both you (the ‘sender’) and the ‘receiver’ uncomfortable. You may be delivering bad news, stating unpleasant facts, or making a big request. To help you strategize before having this conversation, I’ve share a few critical questions below for you to consider. They’re based on communication theory and detail a real-life example of how a courageous conversation played out in the workplace.

If you find all of this helpful and want to hear more, I’ve planned a LinkedIn Live on Thursday, June 10 (Noon PST/3pm EST) with my colleague, Brenda Bailey-Hughes. Join us as we share more examples, some helpful ideas and take your questions. Here are questions to consider before you have a courageous conversation:

How well do you know your audience? What are their values? What do they consider a priority and how will your information help them or make their situation better or easier? In other words, what’s in it for them to listen? Consider their communication style. Are they direct or indirect? Will they quickly understand the context of your conversation or do you need to provide the back story? Finally, you need to factor in your relationship to the receiver. Do you need to show deference to their authority or are you the boss? 

Do you have a negative filter? We all are influenced by past experiences, assumptions and beliefs. When it comes to uncomfortable conversations, it’s natural to avoid them if we’ve only had negative scenarios play out. Be self-aware and check these assumptions at the door. Try to hold your position lightly and if you have a trusted friend, get their honest feedback before you act.

Is it the right time and place? Your courageous conversation may get sabotaged from the start if you haven’t thought about both time and place for it to occur. Will your receiver be able to give you their full attention, or have you chosen a bad time of the day, week, or quarter to meet? Is the meeting is scheduled in a busy work setting or in the receiver’s office or boardroom where you may have to take a more submissive position? Can you reschedule it in a more neutral setting or over coffee?

What is the right channel and are you getting any feedback? A courageous conversation is at its peak challenge state when face-to-face (even if virtual). Sending a courageous email or text doesn’t qualify as a conversation even though it’s often a good idea to forewarn your receiver that you want their time to discuss the topic. If you decide that face-to-face is the best channel, be sure to first practice with a trusted colleague or mentor to get your tone, pacing and the message right.

As you contemplate these communication strategy questions, let’s consider what happened when Rhea (a unit manager) dealt with her supervisor. The supervisor said, “You don’t know anything about the tech side of this project so it would be of no help to get you involved.” Rhea later told me this was ‘cold water in her face’ and she was upset enough to consider asking for a transfer. Below are the four steps Rhea took to strategize for addressing her boss in a courageous conversation:

Step 1 Rhea knew her supervisor well and had witnessed her being painfully direct with others in the company. She also knew she responded to direct messages and valued the straight forward approach. Rhea knew that it was important to her supervisor to shine in the eyes of the board and always hit the goals set for her team.

Step 2 The situation upset Rhea enough to consider leaving that company. She’d worked with a former boss where the same scenario played out. Rhea decided to turn this challenge into an opportunity by asking for what she needed from her supervisor.

Step 3  She looked at her boss’s calendar and determined that mid-week when they had a regular meeting would be a good time for the conversation. She confirmed that her boss would not be distracted by any last-minute deadlines or pressing issues. Their meetings usually took place in the conference room.

Step 4 Their weekly meetings were held face-to-face so Rhea had no other options. She realized that as difficult as it would be, what she had to say needed to be delivered directly. Her plan was to send a follow up email to her boss highlighting some of their discussion (if it went well).

If you’d been in the conference room, this is what you would have seen Rhea say and do. She sat tall at the end of her chair, placed her hands on the table, slightly leaned forward and said, “There’s one more thing I want to bring to your attention. Last week you said that I had no tech knowledge about the project and shouldn’t get involved. It struck me that you are right. I don’t have any tech knowledge but it doesn’t mean that I don’t want to get involved. Learning more, gaining the tech skills and providing value to the team will not only help the final project but it will help us win more contracts. I need your help. Can you get me approved for the next round of trainings? I want to be involved so I can bring results.”

Way to go, Rhea! That took courage. Courage to set your emotions aside, ask for what you want and show how you can bring value. Courageous conversations create discomfort but strategizing and practicing will make them easier. That’s the drill the Cowardly Lion followed and it worked for him. What courageous conversation will you plan for next?