Asking good questions is a skill that is often neglected. Unfortunately, this means that managers often ask poor questions, ask too many questions, talk too much, do not actively listen, and shy away from being honest and direct. Good questions stimulate insight, raise awareness, provoke reflection, and lead to better answers and, often, a clearer understanding of why one answer is better than others. Take this standard coaching question, for example, “What’s the question you know you should be asking, but haven’t?”

Asking good questions can transform a conversation about careers and succession planning from a simple discourse between mentor and mentee about career choices to a strategic staff planning session. Consider the contrast between the following questions about succession planning:

• “Is he ready to be promoted?” compared with “What would help her to contribute much more where she is?” 

• “Who could fill this role in six months’ time?” compared with “Why do we need this role at all? Is it time to rethink it?” 

• “Which box does she belong in on our Org Chart?” compared with “Why would anyone that talented stay with this company?”

The change in focus is clearly evident—it shifts from technical, surface level dialogue to strategic dialogue that explores a wide range of options and has the potential to address different scenarios.

Some simple ways to become more adept at crafting good questions include:

• Notice when questions you ask have strong impact. Compare it to the criteria above. 

• Ask fewer questions. This allows you to focus on the quality of the questions you ask. 

• When you reflect upon a coaching or mentoring conversation, think about the questions you asked. Could you have asked them in a more powerful way? Consider other powerful questions you could have asked. 

• Build your own list of good questions

For more advice, check out the latest issue of TD at Work, “5 Critical Conversations to Talent Development.” In this issue, you will find seven levels of conversation that lead to deeper dialogue, case studies of conversations in practice, sample questions to promote dialogue, strategies for supporting critical conversation, and guidance for preparing for and assessing developmental conversations.