Courageous vs Difficult Conversations

We commonly use the terms “Difficult Conversations” and “Courageous Conversations” interchangeably; however, whilst all "Courageous" conversations are bound to be difficult, "Difficult" conversations do not blanketly warrant leadership courage, as such, especially when the justification is backed by company rules, government policies, and so on.

The point is not that we should always label conversations appropriately, the caveat is the missed opportunities if we mis-apportion our focus and energy – when these terms appear intermingled in our minds, the fallout is inevitably the time and attention we could have given to those who actually deserve it more – the high-potentials, the recent hires, the successors, etc.

Having courageously positive and growth conversations is also a litmus test for the quality of relationships between the leader and their people. Below are some sample questions designed for triggering more elaborate exchanges. However, they are not for the faint of heart. Many of these are not base-camp questions; if you find yourself on the awkward side of the fine line between anxiety and excitement, it may be an indication that you are needing to work on the basic fitness for leadership – building Trust and Relationships – before attempting these higher altitude pursuits.

More regular check-in conversations

1.      What’s been getting in the way of you having a good day?

2.      What paying-it-forward activities have you done lately?

3.      How have you been using and expanding your network lately?

4.      What’s been a persistent but undeserving item in your daily plan?

5.      What percentage of time have you been spending on the “Important but Not Urgent” stuff?

6.      Whom have you mentored in the last month?

7.      What mistakes did you make in the last fortnight and how have they helped you since?

8.      How have the corporate values influenced your decisions lately?

9.      Who or what has made you feel uncomfortable lately?

10.  What have you been doing to maintain or enhance your reputation?

Questions that require a higher level of Leadership Fitness (Trust and Relationship)

11.  What new insights have you had about yourself?

12.  Whom are you grooming as your successor?

13.  What would your legacy look like if you were fired tomorrow?

14.  How did you get to where you are today?

15.  Looking at the foreseeable future, what’s going to derail you?

16.  What conversations have we not had that you think we should?

17.  What aspects about you and your work that you really don’t want to discuss?

18.  How do your personal values jive in with our corporate ones?

19.  What would you do to ensure best outcome if I suddenly disappear tomorrow?

20.  Why are you still working for me?

Andy is an executive coach and leadership facilitator. Contact Andy: [email protected]