When you're faced with challenging conversations, remember that starting with the tough questions first can be a game-changer. It's a strategy that can pave the way for greater openness from your discussion partner as the conversation unfolds.

Why? Because humans have a psychological tendency to disclose more sensitive details when questions are asked in descending order of intrusiveness.

Starting with a highly sensitive or deeply probing question sets a precedent, making subsequent, less invasive questions feel comparatively less intrusive. Consequently, your conversation partner will tend to be more forthcoming as the questions become less and less intrusive.

For example, if you begin with something like, "It seems you are disengaged, no longer enjoying your work, and looking to leave. Am I reading that correctly?" you are more likely to elicit an honest and transparent response when you ask, "What isn't working for you? What needs to change for you to be able to show up and do your best work?" later in the conversation.

In this example, it's important to note that the leader is ultimately more interested in obtaining a sincere and comprehensive response to the second question rather than the first. But, by asking the more intrusive and uncomfortable-to-answer question first, the leader is setting the stage for a more constructive and fruitful dialogue once the conversation transitions to what can be done to reengage the team member.

When you strategically sequence your questions in this manner, your inquiries become less intimidating and foster a more candid exchange.