10 Powerful Courageous Leadership Questions You Want to Ask


“Sticks and stones may break my bones, but words can never hurt me.”

This time-worn 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, a co-worker, employee, colleague, is thwarted into a world of negativity that affects productivity and collaboration.

We all want to feel appreciated and valued for our contribution.

Would any of the following apply to you or a manager you know? You’re too intimidated to have that overdue conversation so you utilise 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 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 candour (a cousin to courage) or being brutally blunt.

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 but also decreases stress because the word ‘imagine’ generates creativity and curiosity. People are more motivated to speak up and share their ideas, a known productivity booster.

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). This provides transparency and removes any awkwardness , especially for those reluctant to speak up.

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