9 Courageous Leadership Questions to Apply at Work


You’re too intimidated to have that overdue conversation so you utilize a form of ambiguity? You’re a manager whose style of managing is hands-off. This way you don’t have to suggest ideas that might offend, be misunderstood or be accountable.

Whether you’re a manager, human resource director or CEO, you are often required (hard-pressed) to engage in the awkward, elusive or tight rope conversations that require an element of courage. These types of “challenging” conversations test us in an uncomfortable way. Why? Because the exchange is more than just applying candor (a cousin to courage) or being brutally blunt (“Let me be honest with you…”).

Remember the old adage “Sticks and stones may break my bones, but words can never hurt me.” This timeworn saying is false. For example, “a stone is thrown” when someone says, “I don’t care how you do it, just get it done!” With the phrase “I don’t care” the receiver is most likely going to have an internal breakdown at work and then one at home. We all want to feel appreciated and valued for our contribution.

Because words are so powerful, they can hurt you, but they can also get you positive results at work, such as increased productivity, improved morale, enhanced project effectiveness, a renewed demeanor and reduced stress, to name a few. Most of the time, the best results come about when you ask a lot “you” questions. On the opposite side of the coin many times it’s one of the twelve courage obstacles such as ambiguity, intimidation, manipulation or blame that hinder courageous conversation opportunities.

If you can communicate more effectively with coworkers, you can reshape your work environment and produce the sustainable results you’re seeking. Muster the courage to try these nine simple courageous conversation questions and see if they recalibrate your approach to leadership:

1.  “How do you imagine this project progressing?” This question not only engages the person but also decreases stress because creativity and curiosity are being generated, and people are more motivated to speak up and share their ideas. Ideas are an important part of human capital and using the word imagine boosts productivity.

2.  “Is there anything else I can offer you?” and “Do you have any other requests?” Requests and offers allow people to open up and reveal the “chatter” in their head (and share what they really want), thus providing transparency in everyone’s communication and removing any awkwardness if someone ordinarily feels reluctant about speaking up.

3.  “What was your assessment about the big project we just finished for that client?”  Be cautious with your tone. This means you take responsibility for how your language affects others. Your words are a part of your daily legacy—people remember them more than the action. Will you be remembered the way you want to be remembered?

4.  “How do you envision accomplishing the task/results?” This question keeps passion alive and perpetuates retentive innovation.

5.  Because we’re human, we naturally expect the receiver to know exactly what we presume in the outcome and what we mean. Be direct and say, I have expectations that you will do this and that. Conversely, “What expectations do you have of me?” The outcome of unclear expectations: wasted time that can’t be reclaimed and unnecessary tension in the workplace.

6.  The founder of my Newfield Network coaching organization always opened our international conferences or local gatherings with “What’s cooking?” This question kicks off an understanding that it was safe to share what was internally going on with that person allowing them to display their courage. This creates the “mood” for receptivity. How do you kick off a meeting?

7.  If you are working with a prospect/business partner/project manager try, “What do you see our next step to be?” Using the word “our” in your question leads the client/customer to think of you as a partner when making a decision.

8.  First red flag warnings are everywhere. If you don’t stop and acknowledge the first one you’ve probably slid blindly into denial. Denial is saying “no” to courage. Stop and reflect, then ask this critical question: “In retrospect, were there any red flags during our project/interaction that we were blind to?”

9.  “What single task would you consider the most significant contribution in completing this project?” This reveals the individuals passion and what gives them self-fulfillment.

Comedian Lily Tomlin said, “If you can’t be direct, why be?” Think about what type of language you experience in your work environment and what you display. The words we choose can submerge us into negativity or elevate us to a different level of courage consciousness—and take our coworkers with us. That is the power of courageous questions!

Sandra Ford Walston is known as The Courage Expert and innovator of StuckThinking™. She is an organizational effectiveness consultant, speaker, trainer and courage coach. She is the internationally published author of bestseller COURAGE The Heart and Spirit of Every Woman (2001), the follow-up book STUCK 12 Steps Up the Leadership Ladder (2010) and the recently released FACE IT! 12 Obstacles that Hold You Back on the Job (2011). She is certified in the Enneagram and MBTI®. Please visit www.sandrawalston.com.

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